CN115368392A

CN115368392A - Polycyclic aromatic compound, reactive compound, material for organic device, ink composition, and organic electroluminescent element

Info

Publication number: CN115368392A
Application number: CN202210484380.5A
Authority: CN
Inventors: 畠山琢次; 近藤靖宏; 川角亮介
Original assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Current assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Priority date: 2021-05-20
Filing date: 2022-05-06
Publication date: 2022-11-22
Also published as: KR20220157312A

Abstract

The present invention provides a novel polycyclic aromatic compound, a reactive compound, a polymer compound or a crosslinked polymer, a pendant polymer compound or a crosslinked pendant polymer, a material for an organic device, an ink composition, an organic electroluminescent element, a display device or a lighting device, and a wavelength conversion filter, and provides an excellent element by producing an organic EL element using the novel material.

Description

Polycyclic aromatic compound, reactive compound, material for organic device, ink composition, and organic electroluminescent element

Technical Field

The present invention relates to a polycyclic aromatic compound, and an organic device such as an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, and a wavelength conversion filter, a display device, and a lighting device each using the polycyclic aromatic compound. In addition, in the present specification, the "organic electroluminescent element" may be sometimes expressed as an "organic EL (Electroluminescence) element" or simply an "element", and particularly relates to a polycyclic aromatic compound, a reactive compound, a material for an organic device, an ink composition, and an organic electroluminescent element.

Background

Conventionally, various studies have been made on display devices using light emitting elements that perform electroluminescence, because they can achieve power saving and reduction in thickness, and further, active studies have been made on organic electroluminescence elements including organic materials, because they are easy to reduce the weight and increase the size. In particular, active research has been conducted on the development of organic materials having light-emitting characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities (having the possibility of becoming semiconductors or superconductors) for holes, electrons, and the like, both of high molecular compounds and low molecular compounds.

The organic EL element has a structure including: a pair of electrodes including an anode and a cathode, and one or more layers which are disposed between the pair of electrodes and include an organic compound. Among the layers containing an organic compound, there are a light-emitting layer, a charge transport/injection layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

For example, as a material used for an organic EL device or an organic thin film solar cell, a material obtained by modifying a triphenylamine derivative has also been reported (international publication No. 2012/118164). The material is a material in which the aromatic rings constituting triphenylamine are connected to each other by referring to N, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1'-biphenyl-4,4' -diamine (N, N '-diphenyl-N, N' -bis (3-methylphenyl) -1,1'-biphenyl-4,4' -diamine, TPD) which has been put into practical use, thereby placing nitrogen at the center of the ring structure and improving the planarity thereof. In the above document, for example, the charge transport properties of an NO-linked compound (compound 1 on page 63) are evaluated, but there is NO description about a method for producing a material other than an NO-linked compound, and properties obtained from a material other than an NO-linked compound are unknown because the electron state of the entire compound differs depending on the elements to be linked.

The host material of an organic EL device is generally a molecule in which a plurality of conventional aromatic rings such as benzene and carbazole are connected by a single bond, a phosphorus atom, or a silicon atom. This is because a large Highest Occupied Molecular Orbital (HOMO) to Lowest Unoccupied Molecular Orbital (LUMO) gap (band gap Eg in the thin film) required for the host material is ensured by linking a plurality of conjugated smaller aromatic rings. Furthermore, high triplet excitation energy (E) is also required for the host material of an organic EL device using a phosphorescent material or a thermally active delayed fluorescence material _T ) However, by linking a donor or acceptor aromatic ring or a substituent to the molecule, the Single Occupied Molecular Orbital (SOMO) 1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, whereby the triplet excitation energy (E) can be increased _T ). However, the redox stability of the aromatic ring having a small conjugated system is insufficient, and the life of the device using a molecule connecting the conventional aromatic rings as a host material is insufficient. On the other hand, polycyclic aromatic compounds having extended pi-conjugated systems generally have excellent redox stability, but are formed due to the HOMO-LUMO gap (thin film) Middle band gap Eg) or triplet excitation energy (E) _T ) Low and therefore is considered unsuitable for the host material.

Under such circumstances, compounds in which a plurality of aromatic rings are condensed with boron or the like as a central atom have also been reported in recent years (international publication No. 2015/102118). In the above document, evaluation of an organic EL element using a compound obtained by condensing the above-mentioned plurality of aromatic rings as a dopant material of a light-emitting layer is carried out. Further, there have been reported examples of multimerization of such a compound (International publication No. 2018/212169) and examples of conjugation in which the molecule is extended by a linker (Korean patent laid-open Nos. 10-2020-0121228 and 2020/217229).

[ Prior art documents ]

[ patent document ]

[ patent document 1] International publication No. 2012/118164

[ patent document 2] International publication No. 2015/102118

[ patent document 3] International publication No. 2018/212169

[ patent document 4] Korean laid-open patent No. 10-2020-0121228

[ patent document 5] International publication No. 2020/217229

Disclosure of Invention

[ problems to be solved by the invention ]

As disclosed in patent documents 1 to 5, various materials have been developed as materials for organic EL devices, but in order to increase the options for materials for organic EL devices, it is desired to develop materials containing compounds different from those in the past. In particular, it is advantageous to search for organic EL characteristics obtained from a material other than an NO-linking compound in which nitrogen is arranged at the center of a ring structure, and a method for producing the same.

Further, patent documents 2 to 5 report polycyclic aromatic compounds containing boron and organic EL devices using the polycyclic aromatic compounds, but there are many compounds disclosed in the above documents, and it is useful to search for a material for a light-emitting layer, particularly a dopant material, which can improve organic EL characteristics such as light emission efficiency and device lifetime, in order to further improve device characteristics.

Further, since a wet film formation method is currently used as a method for forming an organic layer constituting an organic EL element in addition to a vacuum deposition method, development of an ink material for wet film formation for forming a hole injection layer, a hole transport layer, and a light emitting layer has been actively carried out particularly, and it is also advantageous to search for such an ink material.

[ means for solving problems ]

The present inventors have made extensive studies to solve the above problems, and as a result, have found that an excellent organic EL device can be obtained by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes, for example, to constitute an organic EL device, and have completed the present invention. That is, the present invention provides a polycyclic aromatic compound as described below, and a material for an organic device such as a material for an organic EL element containing a polycyclic aromatic compound as described below.

In the present specification, the chemical structure or the substituent is sometimes represented by a carbon number, but the carbon number in the case where the chemical structure is substituted with a substituent, the case where the substituent is substituted with a substituent, or the like means the carbon number of each of the chemical structure or the substituent, and does not mean the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent. For example, the "substituent B having a carbon number Y substituted by the substituent a having a carbon number X" means that the "substituent a having a carbon number X" is substituted on the "substituent B having a carbon number Y, and the carbon number Y is not the total carbon number of the substituent a and the substituent B. For example, the "substituent B having a carbon number Y substituted with the substituent a" means that the substituent a "(not limited to a carbon number) is substituted with the" substituent B having a carbon number Y "and the carbon number Y is not the total carbon number of the substituent a and the substituent B.

Item 1.

A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B).

[ solution 6]

In the formula (1A) or the formula (1B),

ring A and ring B are each independently an aryl or heteroaryl ring, at least one of which rings may be substituted,

R ^c each independently is hydrogen or a substituent group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

Y ¹ and Y ² Each independently is > B-, > P (= O) -, > P (= S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, wherein R of "> C (-R) -," > Si (-R) - ", and R of" > Ge (-R) - "are independently aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted,

X ¹ 、X ² 、X ³ and X ⁴ Are each independently > N-R, > O, > S, > C (-R) ₂ 、＞Si(-R) ₂ Or > Se, said "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "are each independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted,

further, as said X ¹ ～X ⁴ "> C (-R) ₂ "two R of each other and" > Si (-R) ₂ "two R's may be bonded to each other independently by a single bond or a linking group,

further, as said X ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may be independently bonded to at least one of the A ring and the B ring by a single bond or a linking group, respectively, as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may be independently bonded to at least one of the A ring and the c ring via a single bond or a linking group,

wherein, X is ¹ ～X ⁴ Is bonded to the a ring, the B ring, or the c ring through "-CR = CR-" as a linking group, each R of the "-CR = CR-" is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of the hydrogens may be substituted with alkyl or cycloalkyl, and in addition, two adjacent rs are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

at least one of the A ring, the B ring, the c ring, the aryl group, and the heteroaryl group in the compound represented by the formula (1A) or the formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one of the cycloalkanes — -CH ₂ - "may be substituted by" -O- ",

at least one hydrogen in the compound represented by formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen.

Item 2.

The polycyclic aromatic compound according to item 1, wherein in the formula (1A) or formula (1B),

the A ring and the B ring are each independently an aryl ring or a heteroaryl ring, at least one of which may be substituted by a substitutable aryl group, a substitutable heteroaryl group, a substitutable diarylamino group, a substitutable diheteroarylamino group, a substitutable arylheteroarylamino group, a substitutable diarylboron group (two aryl groups may be bonded via a single bond or a linking group), a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable alkoxy group, a substitutable aryloxy group, or a substituted silyl group,

R ^c Each independently is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboron (two aryl groups may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or optionally substituted silyl,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

Y ¹ and Y ² Each independently is > B-, > P (= O) -, > P (= S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of said "> C (-R) -," > Si (-R) - ", and R of said" > Ge (-R) - "are each independently aryl, heteroaryl, alkyl, or cycloalkyl, at least one of said R groups may be substituted with alkyl or cycloalkyl, X is ¹ 、X ² 、X ³ And X ⁴ Independently from each other > N-R, > O, > S, > C (-R) ₂ 、＞Si(-R) ₂ Or > Se, said "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ "each R of which is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl,

In addition, as the X ¹ ～X ⁴ "> C (-R) ₂ "two R of each other and" > Si (-R) ₂ "two R' S may each independently of one another be bound by a single bond, -CH = CH-, -CR = CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ a-or-Se-bond, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ - "R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

in addition, as the X ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may each independently be a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the A ring and the B ring as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may each independently be a single bond, -CH =CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the A ring and the C ring, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ - "R, and" -Si (-R) ₂ - "R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

wherein, X is ¹ ～X ⁴ Is bonded to the a ring, the B ring, or the c ring through the "-CR = CR-" as a linking group, and in addition, two adjacent R in the "-CR = CR-" are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

at least one of the A ring, the B ring, the c ring, the aryl group, and the heteroaryl group in the compound represented by the formula (1A) or the formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, and at least one "-CH" in the cycloalkane ₂ - "may be substituted by" -O- ",

at least one hydrogen in the compound represented by the formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen.

Item 3.

The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2A) or general formula (2B).

[ solution 7]

In the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino a diarylboron group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a,Cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl, R ^a 、R ^b And R ^c Wherein at least one hydrogen is substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and further, R is ^a And R ^b Wherein adjacent groups in (a) may be bonded to each other and form, together with the a-ring and the b-ring, an aryl ring or a heteroaryl ring, at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl group, at least one of these substituents may be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any of the rings a and b "-C (-R) =" (where R is R) ^a Or R ^b ) May be substituted with "-N =", optionally "-C (-R) = C (-R) -" (where R is R) ^a Or R ^b ) May be substituted with "-N (-R) -", "-O-", "-S-", "-C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", R," -C (-R) of said "-N (-R) -" ₂ - "R, and" -Si (-R) ₂ - "R is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of said R hydrogen being substituted with alkyl or cycloalkyl, said" -C (-R) ₂ Two R of- "are each other and" -Si (-R) ₂ Two R of- "may each independently of one another be bound by a single bond, -CH = CH-, -CR = CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ - "R, and" -Si (-R) ₂ - "R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkylTwo adjacent R's may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

Y ¹ and Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

X ¹ 、X ² 、X ³ And X ⁴ Each independently > N-R, > O, > S, or > C (-R) ₂ R of "> N-R" and "> C (-R) ₂ "each R of which is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl,

further, as said X ¹ ～X ⁴ "> C (-R) ₂ "two R' S may be bonded to each other by a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ - "R, and" -Si (-R) ₂ R of-each independently is hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

in addition, as the X ¹ Or said X ³ R > N-R and C (-R) ₂ R of "may each independently be a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded to at least one of the a ring and the b ring as the X ² Or said X ⁴ R > N-R and C (-R) ₂ R of "may each independently be a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the a-ring and the C-ring, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ - "R, and" -Si (-R) ₂ Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of said RHydrogen may be substituted with alkyl or cycloalkyl, two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

at least one of the a-ring, B-ring, c-ring, the formed ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or (2B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, and at least one "-CH-in the cycloalkane ₂ - "may be substituted by" -O- ",

at least one hydrogen in the compound represented by the formula (2A) or the formula (2B) may be substituted with deuterium, cyano, or halogen.

Item 4.

The polycyclic aromatic compound according to item 3, wherein in the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently represents hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and both aryl groups may be bonded by a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and R represents a group represented by the formula ^a 、R ^b And R ^c Wherein at least one hydrogen in the (A) is substituted by an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and R is ^a And R ^b Wherein adjacent groups in (A) are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a-ring and the b-ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), or a diarylboron group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms)Two aryl groups may be bonded via a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, at least one hydrogen of these substituents may be substituted with an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any of the rings a and b "-C (-R) =" (where R is R) ^a Or R ^b ) May be substituted with "-N =", optionally "-C (-R) = C (-R) -" (where R is R) ^a Or R ^b ) May be substituted by "-N (-R) -", "-O-", "-S-", "-C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", the R of" -N (-R) - ", the" -C (-R) ₂ - "R, and" -Si (-R) ₂ R represents hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein at least one of the groups in R may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the formula, -C (-R) ₂ - "two R of each other and" -Si (-R) ₂ Two R of- "may each independently of one another be bound by a single bond, -CH = CH-, -CR = CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ R in the formula (I) represents hydrogen, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an alkynyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one hydrogen in the R group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and two adjacent R groups may be bonded to each other to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms or a heteroarylene ring having 2 to 15 carbon atoms,

Y ¹ And Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

X ¹ 、X ² 、X ³ and X ⁴ Each independently > N-R, > O, or > S, toR > N-R "is hydrogen, 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, at least one of the hydrogens in R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

in addition, as the X ¹ Or said X ³ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded to at least one of the a ring and the b ring as the X ² Or said X ⁴ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-) -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the a-ring and the C-ring, R of the "-CR = CR-", "-R of the" -N (-R) - "," -C (-R) ₂ R of- "and" -Si (-R) ₂ R in the formula- "is independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, at least one of the hydrogens in the R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs may be bonded to each other to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms or a heteroarylene ring having 2 to 15 carbon atoms,

Wherein, X is ¹ ～X ⁴ Wherein at least one of the a ring, the b ring, and the c ring is bonded via the aforementioned "-CR = CR-" as a linking group, and wherein two adjacent R's in the aforementioned "-CR = CR-" are bonded to each other to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms,

at least one of the a-ring, B-ring, c-ring, the formed ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or (2B) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, wherein at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms,

at least one hydrogen in the compound represented by formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.

Item 5.

R ^a 、R ^b and R ^c Each independently represents hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and both aryl groups may be bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and R represents ^a 、R ^b And R ^c Wherein at least one hydrogen in the (A) is substituted by an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R is ^a And R ^b Wherein adjacent groups in (b) are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring and the b ring, at least one of hydrogens in the formed ring may be substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and both of the aryl groups may be bonded via a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and at least one of these substituents may be substituted with an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any of the rings a and b "-C (-R) =" (where R is R) ^a Or R ^b ) May be substituted with "-N =", optionally "-C (-R) = C (-R) -" (where R is R) ^a Or R ^b ) May be substituted with "-N (-R) -", "-O-", "-S-", or "-C (-R) ₂ - ", the R and" -C (-R) of "-N (-R) -" ₂ R represents hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen atom in the R is a hydrogen atomSubstituted by C1-C6 alkyl or C3-C14 cycloalkyl,

Y ¹ and Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

X ¹ 、X ² 、X ³ and X ⁴ Each independently represents > N-R, > O, or > S, wherein R > N-R' represents hydrogen, 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, at least one hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

in addition, as the X ¹ Or said X ³ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-) -N (-R) -, -O-, -S-, or-C (-R) ₂ -and is bonded to said b ring as said X ² Or said X ⁴ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-, -N (-R) -, -O-, -S-, or-C (-R) ₂ -R of "-CR = CR-", R of "-N (-R) -", and "-C (-R) bonded to said a-ring ₂ R in the formula (I) represents hydrogen, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an alkynyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one hydrogen in the R group may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and two adjacent R groups may be bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

Wherein, X is ¹ And X ³ Wherein at least one of the above-mentioned groups is bonded to the b ring through the above-mentioned "-CR = CR-" as a linking group, and wherein two adjacent R groups in the "-CR = CR-" are bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

at least one of the a-ring, B-ring, c-ring, the formed ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or (2B) may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, wherein at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms,

Item 6.

R ^a 、R ^b and R ^c Independently represents 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), diarylboron (wherein aryl is aryl having 6 to 10 carbon atoms, and both aryl groups may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and R is ^a 、R ^b And R ^c Wherein at least one hydrogen in the above-mentioned group is substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any of the rings a and b "-C (-R) =" (where R is R) ^a Or R ^b ) May be substituted with "-N =", optionally "-C (-R) = C (-R) -" (where R is R ^a Or R ^b ) Can be substituted by "-N (-R) -", "-O-", or "-S-", wherein R of the "-N (-R) -" is aryl with 6-10 carbon atoms, heteroaryl with 2-10 carbon atoms, alkyl with 1-5 carbon atoms, or cycloalkyl with 5-10 carbon atoms,

Y ¹ and Y ² Is more than B-,

X ¹ 、X ² 、X ³ and X ⁴ Each independently represents > N-R or > O, wherein R > N-R' represents an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, at least one hydrogen in R may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

in addition, as the X ¹ Or said X ³ R of "> N-R" may be bonded to the b ring by a single bond or-CR = CR-, as the X ² Or said X ⁴ R of "> N-R" may be represented by a single bond or-CR =CR-and bonded to the a ring, wherein R of the formula "-CR = CR-" is independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, at least one hydrogen of the R is substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and two adjacent R's may be bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

Wherein, X is ¹ And X ³ Wherein at least one of the above-mentioned groups is bonded to the b ring through the aforementioned "-CR = CR-" as a linking group, and wherein two adjacent R's in the aforementioned "-CR = CR-" are bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

Item 7.

The polycyclic aromatic compound according to claim 1, represented by any one of the following structural formulae.

[ solution 8]

The benzene rings in the structural formula can be respectively and independently substituted by aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diarylamino (wherein the aryl is aryl with 6 to 10 carbon atoms), diarylboron (wherein the aryl is aryl with 6 to 10 carbon atoms, two aryl can be bonded through a single bond or a connecting group), alkyl with 1 to 12 carbon atoms or cycloalkyl with 3 to 16 carbon atoms, at least one hydrogen in the substituent can be substituted by alkyl with 1 to 5 carbon atoms or cycloalkyl with 5 to 10 carbon atoms,

at least one hydrogen in the compounds represented by the structural formula may be substituted with deuterium, cyano, or halogen.

Item 8.

[ solution 9]

Item 9.

A reactive compound obtained by substituting a reactive substituent in the polycyclic aromatic compound according to any one of items 1 to 8.

Item 10.

A polymer compound obtained by polymerizing the reactive compound according to item 9 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

Item 11.

A pendant type polymer compound obtained by substituting the reactive compound according to item 9 in a main chain type polymer or a pendant type crosslinked polymer obtained by further crosslinking the pendant type polymer compound.

Item 12.

A material for organic devices, comprising the polycyclic aromatic compound according to any one of items 1 to 8.

Item 13.

A material for organic devices, comprising the reactive compound according to item 9.

Item 14.

A material for organic devices, which comprises the polymer compound or the crosslinked polymer according to item 10.

Item 15.

A material for organic devices, which comprises the pendant type polymeric compound or the pendant type crosslinked polymeric compound according to item 11.

Item 16.

The material for an organic device according to any one of claims 12 to 15, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field-effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

Item 17.

The material for an organic device according to item 16, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

Item 18.

An ink composition comprising the polycyclic aromatic compound according to any one of items 1 to 8, and an organic solvent.

Item 19.

An ink composition comprising the reactive compound according to item 9, and an organic vehicle.

Item 20.

An ink composition comprising a main chain polymer, the reactive compound according to item 9, and an organic solvent.

Item 21.

An ink composition comprising the polymer compound or the polymer crosslinked body according to item 10 and an organic solvent.

Item 22.

An ink composition comprising the pendant polymer compound or the pendant crosslinked polymer according to item 11 and an organic solvent.

Item 23.

An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode; and an organic layer disposed between the pair of electrodes, and containing the polycyclic aromatic compound according to any one of items 1 to 8, the reactive compound according to item 9, the polymer compound or the crosslinked polymer according to item 10, or the pendant polymer compound or the crosslinked polymer according to item 11.

Item 24.

The organic electroluminescent element according to item 23, wherein the organic layer is a light-emitting layer.

Item 25.

The organic electroluminescent element according to item 24, wherein the light-emitting layer comprises a host, and the polycyclic aromatic compound, the reactive compound, the polymer compound, the crosslinked polymer, the pendant polymer compound, or the crosslinked pendant polymer as a dopant.

Item 26.

The organic electroluminescent element according to item 25, wherein the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a Thermally Activated Delayed Fluorescence (TADF) material.

[ solution 10]

In the general formula (H1), L ¹ Is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms,

in the general formula (H2), L ² And L ³ Each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms,

in the general formula (H3), MU is a divalent group represented by removing any two hydrogen atoms from an aromatic compound, EC is a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogens in MU are replaced by EC or MU, k is an integer of 2-50000,

In the general formula (H4), G is = C (-H) -or = N-, respectively, H in the = C (-H) -may be substituted by a substituent or a structure represented by another formula (H4),

in the general formula (H5) described above,

R ¹ ～R ¹¹ each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and R is ¹ ～R ¹¹ At least one hydrogen in (a) may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

R ¹ ～R ¹¹ may be bonded to each other and together with the a-, b-or c-ring form an aryl or heteroaryl ring, at least one hydrogen of the ring formed may be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of these substituents may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

any of the rings a, b and C "-C (-R) =" (where R is R) ¹ ～R ¹¹ ) May be substituted by "-N =",

in the general formula (H6), the compound (A) is,

R ¹ ～R ¹⁶ each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and R is ¹ ～R ¹⁶ At least one hydrogen in (a) may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

R ¹ ～R ¹⁶ Can be bonded to one another and together with the a-, b-, c-or d-ring form an aryl or heteroaryl ring, at least one hydrogen in the ring formed can be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen in these substituents can in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, and

at least one hydrogen in the compound or structure represented by each formula may be substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen or deuterium.

Item 27.

The organic electroluminescent element according to any one of items 23 to 26, which comprises at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein the at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, a hydroxyquinoline-based metal complex, a thiazole derivative, a benzothiazole derivative, a thiaole derivative, and an oxazoline derivative.

Item 28.

The organic electroluminescent element according to claim 27, 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.

Item 29.

The organic electroluminescent element according to any one of items 23 to 28, wherein at least one of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer comprises: the polymer compound is formed by polymerizing a low-molecular compound capable of forming each layer as a monomer, or a crosslinked polymer formed by further crosslinking the polymer compound, or a pendant-type polymer compound formed by further crosslinking the pendant-type polymer compound and a main chain-type polymer.

Item 30.

A display device or a lighting device, comprising the organic electroluminescent element according to any one of items 23 to 29.

Item 31.

A wavelength conversion filter comprising the material for a wavelength conversion filter according to item 16.

[ Effect of the invention ]

According to a preferred embodiment of the present invention, there is provided a polycyclic aromatic compound having a novel structure which is useful as a material for an organic device such as a material for an organic EL element, for example, and by using the polycyclic aromatic compound, there can be provided an excellent organic device such as an organic EL element.

Specifically, the present inventors have found that a polycyclic aromatic compound in which aromatic rings are linked by a heterogeneous element such as boron, phosphorus, oxygen, nitrogen, or sulfur has a large HOMO-LUMO gap or a small HOMO-LUMO gap (a band gap Eg in a thin film) depending on the linking method of the heterogeneous element. The reason is considered to be that: since the 6-membered ring containing a hetero element has low aromaticity, the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system and the localization or non-localization of each orbital is suppressed or promoted. These polycyclic aromatic compounds have a strong skeleton in which 5-or 6-membered rings are condensed or connected, and therefore have a narrow half-value width of a fluorescence emission peak, and when used as an emitter of an organic EL element, light emission with high color purity can be obtained. Further, by selecting a method of bonding heterogeneous elements, thermally active delayed fluorescence is exhibited, and high efficiency can be obtained when the compound is used as an emitter of an organic EL element. Furthermore, since the energies of HOMO and LUMO can be arbitrarily changed by introducing a substituent, ionization potential (ionization potential) and electron affinity (electron affinity) can be optimized according to the surrounding material. The present invention is not particularly limited to these principles.

Drawings

Fig. 1 is a schematic sectional view showing an organic EL device according to the present embodiment.

FIG. 2 shows the results of fluorescence lifetime measurement of Compound (1A-1).

[ description of symbols ]

100: organic electroluminescent element

101: substrate board

102: anode

103: hole injection layer

104: hole transport layer

105: luminescent layer

106: electron transport layer

107: electron injection layer

108: cathode electrode

Detailed Description

1. Polycyclic aromatic compound

< description of the overall Structure of the Compound >

The present invention is a polycyclic aromatic compound represented by the following general formula (1A) or (1B), and preferably a polycyclic aromatic compound represented by the following general formula (2A) or (2B). The symbols in each structural formula are defined as described above, and the symbols in all structural formulae shown below are also defined as described above.

[ solution 11]

[ solution 12]

Any of the compounds has a ring-shared condensation structure including two unit structures in which a ring a, a ring B, and a ring c are condensed in a condensed bicyclic structure, and the two unit structures are condensed so as to share the ring c. The condensed bicyclic structure is a structure in which two 6-membered saturated hydrocarbon rings are condensed with each other, and in the structural formula, Y is contained ¹ And X ¹ And X ² And a decahydronaphthalene-type structure on the left side, and Y ² And X ³ And X ⁴ And the right decalin type structure.

The compound has an meta-type and a para-type, and the meta-type compound has a structure represented by Y ¹ And Y ² A structure obtained by condensing two unit structures so as to be positioned at meta positions of the c ring, and a para-type compound having a structure represented by Y ¹ And Y ² A structure obtained by condensing two unit structures so as to be positioned at the para-position of the c-ring.

< description of the Ring Structure and substituents thereof in the Compound >

Wherein each of the A and B rings is independently an aryl or heteroaryl ring, and at least one of the rings may be substituted with a substituent. The substituent is preferably an aryl group which may be substituted, a heteroaryl group which may be substituted, a diarylamino group which may be substituted, a diheteroarylamino group which may be substituted, an arylheteroarylamino group which may be substituted (an amino group having an aryl group and a heteroaryl group), a diarylboron group which may be substituted (two aryl groups may be bonded via a single bond or a linking group), an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or a substituted silane group. In the case where these substituents further have a substituent, as the substituent, there may be mentioned: aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. Further, details regarding the rings or substituents listed herein will be described together later.

R in the formulae ^a 、R ^b And R ^c Is hydrogen or a substituent, and specifically, is preferably hydrogen, an aryl group which may be substituted, a heteroaryl group which may be substituted, a diarylamino group which may be substituted, a diheteroarylamino group which may be substituted, an arylheteroarylamino group which may be substituted (an amino group having an aryl group and a heteroaryl group), a diarylboron group which may be substituted (two aryl groups may be bonded via a single bond or a linking group), an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or a substituted silyl group. In the case where these substituents further have a substituent, as the substituent, there may be mentioned: aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. Further, details regarding the rings or substituents enumerated herein will be described together later.

R in each formula ^a 、R ^b And R ^c Specific examples of (A) are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylaminoA group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, or an alkylbicycloalkylsilyl group, and R ^a 、R ^b And R ^c At least one hydrogen of (a) may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. Further, details regarding the substituents listed herein will be described together later.

The aryl or heteroaryl ring as the a and B rings is preferably a 5-or 6-membered ring having a bond common to the condensed bicyclic structure.

Here, the "6-membered ring bonded in common to the condensed bicyclic structure" means, for example, a ring a and a ring B (benzene ring (6-membered ring)) condensed in the condensed bicyclic structure as shown in the formula (2A) and the formula (2B). The expression "aryl ring or heteroaryl ring having the 6-membered ring" (as a ring a and a ring B) "means that the ring a and the ring B are formed only from the 6-membered ring, or that the ring a and the ring B are formed so as to include the 6-membered ring by further condensing another ring or the like on the 6-membered ring. In other words, the phrase "aryl ring or heteroaryl ring having 6-membered rings (as A ring and B ring)" as used herein means that 6-membered rings constituting all or part of A ring and B ring are condensed in a condensed bicyclic structure. The same explanation applies to "5-membered ring".

The A ring and the B ring in the formula (1A) and the formula (1B) correspond to the a ring and the substituent R thereof in the formula (2A) and the formula (2B), respectively ^a And ring b and substituents R thereof ^b . That is, the formulas (2A) and (2B) correspond to structures in which "a ring and B ring having 6-membered rings (as benzene rings)" are selected as the a ring and B ring of the formulas (1A) and (1B), respectively. In this sense, each ring in the formulae (2A) and (2B) is represented by a lower case letter "a" and "B".

< description of the Change in Ring Structure caused by the bond of substituents to each other >

Substituent R of ring a and ring b ^a And a substituent R ^b May be bonded to each other and form, together with the a-ring or the b-ring, an aryl ring or a heteroaryl ringAt least one hydrogen in the ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl, and at least one of these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. Further, details regarding the rings or substituents listed herein will be described together later.

Therefore, the polycyclic aromatic compound of the formula (2A) or the formula (2B) has a change in the ring structure of the compound as shown in the following formulae (2 AB-fr 1) to (2 AB-fr 3) depending on the bonding form of the substituents in the a-ring and the B-ring. The A 'ring and the B' ring in each formula correspond to the A ring and the B ring in formula (1A) and formula (1B), respectively. In addition, each formula simply shows only a part of the unit structures, two of which are condensed in a meta-type or a para-type to constitute a compound.

[ solution 13]

When the formulae (2A) and (2B) are used for the description, the A 'ring and the B' ring in the formulae (2 AB-fr 1) to (2 AB-fr 3) represent a plurality of substituents R ^a And R ^b The aryl ring or heteroaryl ring (may also be referred to as a condensed ring formed by condensing another ring structure in the a-ring or the b-ring) is formed by bonding adjacent groups in (a) to each other and forming together with the a-ring and the b-ring, respectively. Further, according to the above formula, for example, the substituent R of the a ring ^a With substituents R of ring b ^b It does not correspond to "adjacent radicals to each other", these are not bonded. That is, the term "adjacent groups" means groups adjacent to each other on the same ring.

Specific examples of the formulae (2 AB-fr 1) to (2 AB-fr 3) include a structure having an a 'ring or a B' ring formed by condensation of, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring or the like with respect to a benzene ring as the a ring or the B ring, and the formed condensed ring a 'or condensed ring B' is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring or the like.

For example, the following more specific examples of formulae (2 AB-fr 1) to (2 AB-fr 3) are shown.

[ solution 14]

The formula (2 AB-fr 1-ex) is a specific example of the formula (2 AB-fr 1), and is two adjacent R's in the a-ring of the formula (2A) or the formula (2B) ^a And bonded to and form an aryl ring (naphthalene ring) represented by A' together with the a ring (benzene ring). The aryl ring formed has a 6-membered ring (benzene ring a) bonded in common with the condensed bicyclic structure. Further, any substituent on the aryl ring A' (ring A of the formula (1A) or the formula (1B)) except R ^a In addition to the above, n is also represented by R, and the upper limit of n is the maximum number that can be substituted.

The formula (2 AB-fr 2-ex) is a specific example of the formula (2 AB-fr 2), and is two adjacent R's in the B-ring of the formula (2A) or the formula (2B) ^b And bonded to form a heteroaryl ring (carbazole ring) represented by B' together with the B ring (benzene ring). The heteroaryl ring formed has a 6-membered ring (phenyl ring b) that shares a bond with the condensed bicyclic structure. Further, any substituent on the aryl ring B' (ring B of formula (1A) or formula (1B)) except for R ^b In addition to the above, n is also represented by R, and the upper limit of n is the maximum number that can be substituted.

The formula (2 AB-fr 3-ex) is a specific example of the formula (2 AB-fr 3), and is two adjacent R's in the a-ring of the formula (2A) or the formula (2B) ^a Bonded to and taken together with the a ring (benzene ring) to form a heteroaryl ring (dibenzofuran ring) represented by A ', two adjacent R's in the b ring ^b And bonded to form an aryl ring (naphthalene ring) represented by B' together with the B ring (benzene ring). The heteroaryl and aryl rings formed have 6-membered rings (benzene ring a and benzene ring b) that are bonded in common with the condensed bicyclic structure. Further, any substituent on heteroaryl ring A '(ring A of formula (1A) or formula (1B)) and aryl ring B' (ring B of formula (1A) or formula (1B)) is divided by R ^a And R ^b In addition to the above, n is also represented by R, and the upper limit of n is the maximum number that can be substituted.

The above description is equally applicable to all the embodiments other than the specific examples.

< center element Y in Compound ¹ And a central element Y ² Description of (1) >

Y in each formula ¹ And Y ² R that is > B-, > P (= O) -, > P (= S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of "> C (-R) -," > Si (-R) - ", and" > Ge (-R) - "are independently aryl that may be substituted, heteroaryl that may be substituted, alkyl that may be substituted, or cycloalkyl that may be substituted, respectively. In the case of > P (= O) -, > P (= S) -, > C (-R) -, > Si (-R) -, or > Ge (-R) -, the atoms bonded to the A ring (a ring), the B ring (B ring), and the C ring are P, C, si, or Ge. Y is preferably > B-, > P (= O) -, > P (= S) -, > C (-R) -, or > Si (-R) -, more preferably > B-, > P (= O) -, or > P (= S) -, particularly preferably > B-. Further, details regarding the substituents listed herein will be described together later.

< linking element X in Compound ¹ A connecting element X ² A connecting element X ³ And a connecting element X ⁴ Description of (1) >

X in each formula ¹ 、X ² 、X ³ And X ⁴ Independently from each other > N-R, > O, > S, > C (-R) ₂ 、＞Si(-R) ₂ Or > Se, said "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ Each R of "is independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted.

As X ¹ 、X ² 、X ³ And X ⁴ From the viewpoint of stability, > N-R, > O, > S, or > C (-R) is preferred ₂ More preferably > N-R or > O. In addition, from the viewpoint of short-wavelength light emission, > N-R, > O, or > C (-R) is preferable ₂ More preferably > O or > C (-R) ₂ 。

Further, details regarding the substituents listed herein will be described together later.

In addition, as the X ¹ ～X ⁴ "> C (-R) ₂ "two R of each other and" > Si (-R) ₂ "two R's may be independently bonded to each other by a single bond or a linking group (these are also collectively referred to as a bonding group). Examples of the linking group include: -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ Examples of-Se-or-Se-include the following structures. Furthermore, the R, "-CR of the" -CHR- " ₂ -CR ₂ R of- "," -CR = CR- "," -R of N (-R) - "," -C (-R) ₂ - "R, and" -Si (-R) ₂ Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. Further, "-CHR-CHR-", "-CR ₂ -CR ₂ -”、“-CR＝CR-”、“-C(-R) ₂ - ", and" -Si (-R) ₂ Two adjacent R in the "may bond to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (refer to the rightmost structural formula in the following structural formulae). Further, details regarding the substituents listed herein will be described together later.

[ solution 15]

As a bonding group, a group having a group of a bond, preferably a single bond, a linking group of-CR = CR-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, and-Se-, more preferably a single bond, a linking group of-CR = CR-, -N (-R) -, -O-, -S-, and-C (-R) ₂ <xnotran> -, , -CR = CR-, -N (-R) -, -O-, -S-, -CR = CR-. </xnotran>

The position at which two R are bonded via a bonding group is not particularly limited as long as it is a position capable of bonding, and it is preferable that the two R are bonded at the most adjacent positions, and for example, when the two R are phenyl groups, they are bonded at the positions adjacent to each other (2-position) with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (see the structural formula).

< by X ¹ ～X ⁴ Description of the Change in Ring Structure caused by bond to Ring

As X ¹ Or X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "" may be independently bonded to at least one of the ring A (ring a) and the ring B (ring B) as X ² Or X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "" may be independently bonded to at least one of the rings of A (ring a) and c via a single bond or a linking group, respectively.

As X which can participate in a bond ¹ Preferably > N-R and > C (-R) ₂ More preferably, > N-R.

As a ring bound to X ¹ Or X ³ Preferably B ring (B ring), for X ² Or X ⁴ A ring (a ring) is preferred.

Examples of the linking group for bonding R to the ring include: -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ <xnotran> -, -Se-, -CH = CH-, -CR = CR-, -N (-R) -, -O-, -S-, -C (-R) </xnotran> ₂ <xnotran> -, -CH = CH-, -CR = CR-, -N (-R) -, -O-, -S-, -CR = CR-, -N (-R) -, -O-, -S-, -CR = CR-. </xnotran> Furthermore, the R, "-CR, of said" -CHR-CHR- " ₂ -CR ₂ R of- "," -CR = CR- "," -R of N (-R) - "," -C (-R) ₂ - "R, and" -Si (-R) ₂ Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of said R The hydrogen may be substituted with an alkyl or cycloalkyl group, and two adjacent R groups may be bonded to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. At least one hydrogen in these rings may also be substituted by alkyl or cycloalkyl groups.

"in the formulae (1A) and (1B)" as the X ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ "R of (A) is independently bonded to at least one of the ring A and the ring B as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ The definition of "R of (A) is bonded to at least one of the ring(s) of (A) and (c) independently by a single bond or a linking group" corresponds to the definition of "X" in the formulae (2A) and (2B) ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "are each independently a single bond, -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ -, and-Se-bonded to at least one of the a ring and the b ring as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "are each independently a single bond, -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ -, and-Se-bonded to at least one of the a ring and the c ring ".

In the meta-type, the specification can be expressed by, for example, the following structural formula. In addition, the substituent R in the structural formula ^a A substituent R ^b And a substituent R ^c The display is not performed, but actually exists. The alignment type will be similarly described.

[ solution 16]

The structural formula on the left represents the following compounds: in the formula (2A)

X ¹ (iii) a selection of (2) (> N-R, > C (-R) ₂ And > Si (-R) ₂ ) Wherein R is bonded to the b ring (benzene ring) through a single bond or a linking group, thereby introducing X ¹ While the other ring is condensed with respect to the B-ring (benzene ring) to form a B' ring,

X ² (iii) a selection of (2) (> N-R, > C (-R) ₂ And > Si (-R) ₂ ) Wherein R in (A) is bonded to the left a-ring (benzene ring) via a single bond or a linking group, thereby introducing X ² While the other rings are condensed with respect to the left a ring (benzene ring) to form a left A' ring,

X ³ (iii) a selection of (2) (> N-R, > C (-R) ₂ And > Si (-R) ₂ ) Wherein R is bonded to the right a-ring (benzene ring) via a single bond or a linking group, thereby introducing X ³ While the other rings are condensed with respect to the right a ring (benzene ring) to form the right a' ring.

The formed condensed ring B ', the left condensed ring A ', and the right condensed ring A ' are, for example, a ring having an azepine structure, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring. In addition, X is also present although not included in the structural formula ⁴ Examples of the bond to the ring, and examples of the c-ring bond.

The structural formula on the right represents a more specific example of the structural formula on the left and represents the following compounds:

as X ¹ R (phenyl group) of > N-R(s) is bonded to ring B (benzene ring) via "-CR = CR-" (two adjacent R's are bonded to each other to form an aryl ring as a phenylene ring) as a linking group to form a ring B' having an azepine structure surrounded by a dotted line,

as X ² R (phenyl) of > N-R (C) is bonded to the left a ring (benzene ring) through "O-" as a linking group to form a phenoxazine ring A' (left side) surrounded by a dotted line,

as X ³ R (phenyl) of > N-R is bonded to the right a-ring (benzene ring) by a single bond to form a carbazole ring A' (right side) surrounded by a dotted line.

Wherein X in each formula ¹ ～X ⁴ Is bonded to the a ring (a ring), the B ring (B ring), or the c ring through "-CR = CR-" as a linking group. Preferably X ¹ And X ³ Is bonded to the B ring (B ring) through said "-CR = CR-". In addition, two adjacent R's in the "-CR = CR-" are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring, at least one of which may be substituted with an alkyl or cycloalkyl group.

The description of the specific examples can be similarly applied to all the modes other than the specific examples.

< description of structural changes of ring a, ring b, and ring c >

In the description so far, the c-ring in the formula (1A) and the formula (1B), the a-ring, the B-ring, and the c-ring in the formula (2A) and the formula (2B) have been basically described as benzene rings, but examples in which these ring structures are changed to 5-or 6-membered aryl or heteroaryl rings other than benzene rings are described below. The description so far is understood similarly to the case where these rings are subjected to the following structural changes.

< structural Change of the c-Ring >

-C (-R) in C-Ring ^c ) And = h may be substituted by "— N =" to be a pyridine ring or a pyrazine ring. The following structural formula is a formula in which only a part of the c-ring and its peripheral structure is extracted.

[ chemical formula 17]

< structural changes of Ring a and Ring b (1) >)

any of the rings a and b "-C (-R) =" (where R is R) ^a Or R ^b ) May be substituted with "-N =". In addition, the following structural formula is such that only ring a or ring b is extractedAnd a part of the peripheral structure thereof.

[ solution 18]

As described above, the a-ring or B-ring represented by the benzene ring in the formula (2A) and the formula (2B) may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. In addition, as described above, when an adjacent group is present on the a-ring or the b-ring (two R's in the structural formula) ^a To each other and to both R ^b Each other), these may be bonded and form a heteroaryl ring (quinoline ring in the formula) together with the a-ring or the b-ring, and the formed ring may be further substituted (represented by n R).

The same applies to the case where the other site is substituted with "=" N ", or the case where adjacent substituents are bonded to each other to form another heteroaryl ring.

Structural change of < a Ring (2) >

any of the groups in the a ring-C (-R) ^a )＝C(-R ^a ) - "may be substituted with" -N (-R) - "," -O- "," -S- "," -C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", R," -C (-R) of said "-N (-R) -" ₂ - "R, and" -Si (-R) ₂ R of-is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. Further, details regarding the substituents listed herein will be described together later.

[ solution 19]

The above structural formula is a formula in which only a part of the a-ring and its peripheral structure is extracted, and the wavy line showing the partial structure is omitted in order to avoid complication.

As shown above, the a ring represented as a benzene ring in formula (2A) and formula (2B) may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, other nitrogen/oxygen/sulfur/silicon/selenium-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring).

Other sites are substituted with "-N (-R) -", "-O-", "-S-", "-C (-R) ₂ -”、“-Si(-R) ₂ The same applies to the case of- ", or" -Se- ".

“-C(-R) ₂ - "two R of each other and" -Si (-R) ₂ The two R groups of- "may be bonded to each other independently by a single bond or a linking group (these are also collectively referred to as a bonding group). Examples of the linking group include: -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ Examples of-Se-or-Se-include the following structures. Furthermore, the R, "-CR of the" -CHR- " ₂ -CR ₂ R of- "," -CR = CR- "," -R of N (-R) - ", and" -C (-R) ₂ R of- "and" -Si (-R) ₂ Each R of- "is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, "-CHR-", "-CR ₂ -CR ₂ -”、“-CR＝CR-”、“-C(-R) ₂ - ", and" -Si (-R) ₂ Two adjacent R's in the above-mentioned formula may be bonded to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (see the rightmost structural formula in the following structural formulae). Further, details regarding the substituents listed herein will be described together later.

[ solution 20]

As a bonding group, a group having a group of a bond, preferably a single bond, a linking group of-CR = CR-) -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, and-Se-, more preferably a single bond, a linking group of-CR = CR-, -N (-R) -, -O-, -S-, and-C (-R) ₂ -, more preferably a single bond, as a linking group-CR = CR-, -N (-R) -, -O-, and-S-, most preferably a single bond and-CR = CR-as a linking group.

The position at which two R are bonded via a bonding group is not particularly limited as long as it is a position capable of bonding, and it is preferable that the two R are bonded at the most adjacent positions, and for example, in the case where the two R are phenyl groups, they are bonded at the positions adjacent to each other (2-position) with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (see the structural formula).

Structural change of ring (2) > < b

Any of the rings of b "-C (-R) ^b )＝C(-R ^b ) - "may be substituted with" -N (-R) - "," -O- "," -S- "," -C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", the R of" -N (-R) - ", the" -C (-R) ₂ R of- "and" -Si (-R) ₂ R of the-is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. Further, details regarding the substituents listed herein will be described together later.

[ solution 21]

The above structural formula is a formula in which only a part of the b-ring and its peripheral structure is extracted.

As shown above, the B-ring represented by the benzene ring in formula (2A) and formula (2B) may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, other nitrogen/oxygen/sulfur/silicon/selenium-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). In addition, as described above, when there are adjacent groups on the b ring (the remaining two adjacent R's in the above formula) ^b ) These may be bonded and form together with the b ring a heteroaryl ring (in the formula, R-substituted indole, benzofuran, or benzothiophene rings, etc.) or an aryl ring, and the formed ring may be further substituted (represented by n R).

Further, there are also variations as described below.

[ solution 22]

Other sites are substituted with "-N (-R) -", "-O-", "-S-", "-C (-R) ₂ -”、“-Si(-R) ₂ The same applies to the cases of- ", or" -Se- ".

“-C(-R) ₂ - "two R of each other and" -Si (-R) ₂ The two R groups of- "may be bonded to each other independently by a single bond or a linking group (these are also collectively referred to as a bonding group). Examples of the linking group include: -CH ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ Examples of-Se-or-Se-include the following structures. Furthermore, the R, "-CR of the" -CHR- " ₂ -CR ₂ R of- "," -CR = CR- "," -R of N (-R) - "," -C (-R) ₂ - "R, and" -Si (-R) ₂ Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, "-CHR-", "-CR ₂ -CR ₂ -”、“-CR＝CR-”、“-C(-R) ₂ - ", and" -Si (-R) ₂ Two adjacent R's in the above-mentioned formula may be bonded to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (see the rightmost structural formula in the following structural formulae). Further, details regarding the substituents listed herein will be described together later.

[ solution 23]

As a bonding group, a group having a group of a bond, preferably a single bond, a linking group of-CR = CR-) -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, and-Se-, more preferably a single bond, a linking group of-CR = CR-, -N (-R) -),-O-, -S-, and-C (-R) ₂ <xnotran> -, , -CR = CR-, -N (-R) -, -O-, -S-, -CR = CR-. </xnotran>

< detailed description of the Ring or substituent >

Next, details of the ring or the substituent (including the second substituent further substituted on the first substituent) listed in the description so far will be described together.

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, an aryl ring having 6 to 10 carbon atoms or the like.

The "aryl ring" as the ring A and ring B in the formulae (1A) and (1B) corresponds to the "R" defined in the formulae (2A) and (2B) ^a And R ^b The "formed aryl ring" is an aryl ring in which adjacent groups in (b) are bonded to each other and which is formed together with the a-ring and the b-ring, and the a-ring or the b-ring already contains a benzene ring having 6 carbon atoms, so that the total carbon number of the condensed rings formed by condensing the smallest 5-membered ring on the benzene ring is 9 carbon atoms having the lower limit.

Specific "aryl rings" are for example: a benzene ring as a monocyclic system, a naphthalene ring as a condensed bicyclic system, an acenaphthene ring as a condensed tricyclic system, a fluorene ring, a phenalene ring, or a phenanthrene ring, an anthracene ring, a triphenylene ring, a pyrene ring, or a pentacene ring as a condensed tetracyclic system, or a perylene ring or a pentacene ring as a condensed pentacyclic system, and the like.

The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, a heteroaryl ring having 2 to 10 carbon atoms, or the like. The "heteroaryl ring" is, for example, a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Furthermore, the "heteroaryl ring" as the a ring and the B ring in the formulae (1A) and (1B) corresponds to the "R" defined in the formulae (2A) and (2B) ^a And R ^b The "heteroaryl ring formed" is a heteroaryl ring in which adjacent groups in (1) are bonded to each other and the a-ring and the b-ring are formed together, and the a-ring or the b-ring already contains a benzene ring having 6 carbon atoms, so that the total carbon number of 6 carbon atoms of a condensed ring formed by condensing the smallest 5-membered ring on the benzene ring is the lower limit. In the above-mentioned cases, the benzene rings, i.e., the a-ring and the b-ring, may be changed to a nitrogen-containing heteroaryl ring (6-or 5-membered ring), an oxygen/sulfur-containing heteroaryl ring (5-membered ring), or the like, and therefore the number of carbons in the lower limit is changed accordingly.

Specific "heteroaryl ring" is, for example, 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 ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring a phenothiazine ring, a phenazine silicon (phenazasidine) 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 benzindolocarbazole ring, a benzindoindolocarbazole ring, an imidazoline ring, or an oxazoline ring, and the like.

The "aryl group" is, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 16 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 10 carbon atoms or the like.

Specific "aryl" groups are for example: phenyl as monocyclic system, biphenyl (2-biphenyl, 3-biphenyl, or 4-biphenyl) as bicyclic system, naphthyl (1-naphthyl or 2-naphthyl) as condensed bicyclic system, terphenyl (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, or p-terphenyl-4-yl) as tricyclic condensed system, acenaphthylene- (1-, 3-, 4-, or 5-) as condensed tricyclic system, fluorene- (1-, 2-, 3-, 4-, or 9-) as terphenyl- (1-or 2-) or phenanthrene- (1-, 3-, 4-, or 9-) as terphenyl-3-, 5-, m-or phenanthrene-tetra-phenyl-3-, 5-or m-biphenyl (m-4 ' -yl), m-terphenyl-4-) as condensed tricyclic system, m-or m-biphenyl-4-phenyl-yl, triphenylene- (1-or 2-) group, pyrene- (1-, 2-, or 4-) group, or tetracene- (1-, 2-, or 5-) group as condensed four-ring system, perylene- (1-, 2-, or 3-) group, or pentacene- (1-, 2-, 5-, or 6-) group as condensed five-ring system, and the like.

In addition, among aryl groups as the second substituent, that is, aryl groups as the substituent (second substituent) which is further substituted on the substituent (first substituent), a structure in which at least one hydrogen in the aryl group is substituted with an aryl group such as a phenyl group (specifically, the above-mentioned group), an alkyl group such as a methyl group (specifically, the group described later), or a cycloalkyl group such as a cyclohexyl group or an adamantyl group (specifically, the group described later) is also included in the aryl group as the second substituent.

For example, when the second substituent is a fluorenyl group, the fluorenyl group may be one in which at least one hydrogen at the 9-position is substituted with an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group or an adamantyl group, and such a group is also included in the aryl group as the second substituent.

The "arylene group (ring)" is, for example, an arylene group having 6 to 30 carbon atoms, preferably an arylene group having 6 to 20 carbon atoms, an arylene group having 6 to 16 carbon atoms, an arylene group having 6 to 12 carbon atoms, an arylene group having 6 to 10 carbon atoms, or the like.

Specific examples of the "arylene group" include a structure in which one hydrogen is removed from the "aryl group" (monovalent group) to form a divalent group.

The "heteroaryl group" is, for example, a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms. The "heteroaryl group" is, for example, a monovalent group such as a heterocyclic ring containing, as a ring-constituting atom, one to five heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon.

<xnotran> " ", , , , , , , , , , , , , , , , , , , 1H- , , , , 1H- , , , , , , , , , , , , , , , , , (phenazasilinyl), , , , , , , , , , , , , , , , , , , , , , , . </xnotran>

In addition, in the heteroaryl group as the second substituent, that is, the heteroaryl group as the substituent (second substituent) further substituted on the substituent (first substituent), a structure in which at least one hydrogen in the heteroaryl group is substituted with an aryl group such as a phenyl group (specifically, the group described above), an alkyl group such as a methyl group (specifically, the group described below), or a cycloalkyl group such as a cyclohexyl group or an adamantyl group (specifically, the group described below) is also included in the heteroaryl group as the second substituent.

For example, when the second substituent is a carbazolyl group, the carbazolyl group is one in which at least one hydrogen at the 9-position is substituted with an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group or an adamantyl group, and such a group is also included in the heteroaryl group as the second substituent.

The "heteroarylene (ring)" is, for example, a heteroarylene group having 2 to 30 carbon atoms, preferably a heteroarylene group having 2 to 25 carbon atoms, a heteroarylene group having 2 to 20 carbon atoms, a heteroarylene group having 2 to 15 carbon atoms, a heteroarylene group having 2 to 10 carbon atoms, or the like. The "heteroarylene group" is a divalent group such as a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms, in addition to carbon.

Specific examples of the "heteroarylene group" include structures in which one hydrogen is removed from the "heteroaryl group" (monovalent group) to form a divalent group.

"diarylamino" is an amino group substituted with two aryl groups, and as to the details of the aryl groups, reference is made to the description of the "aryl groups".

"Diheteroarylamino" is an amino group substituted with two heteroaryl groups, and as to the details of the heteroaryl groups, reference may be made to the description of the "heteroaryl groups".

"Arylheteroarylamino" is an amino group substituted with an aryl or heteroaryl group, and as to the details of the aryl and heteroaryl groups, the descriptions of the "aryl" and "heteroaryl" groups may be cited.

"Diarylboron group" is a boron group in which two aryl groups are substituted, and as to the details of the aryl groups, the description of the "aryl groups" may be cited. In addition, the two aryl groups may be linked via a single bond or a linking group (e.g., -CH) ₂ -CH ₂ -、-CHR-CHR-、-CR ₂ -CR ₂ -、-CH＝CH-、-CR＝CR-、-C≡C-、＞N-R、＞O、＞S、＞C(-R) ₂ 、＞Si(-R) ₂ Or > Se). Here, the R, "-CR, of the" -CHR- "is described ₂ -CR ₂ R of- "," -CR = CR- "," > N-R "," > C (-R) ₂ R of "and R" > Si (-R) "are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, at least one of which may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. In addition, two adjacent R's may form a ring with each other to form a cycloalkylene, an arylene, and a heteroarylene. With regard to the details of the substituents listed herein, the descriptions of the "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" and the descriptions of the "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" described later may be cited.

The "alkyl group" may be either a straight-chain or branched chain, and is, for example, a straight-chain alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched chain alkyl group having 3 to 4 carbon atoms) or the like.

<xnotran> "" , , , ,1- -1- ,1,1- ,1,1,2- ,1,1,2,2- ,1- -1,2,2- , , , , ,2- ,1,1- ,3,3- ,1,1- ,1- -1- ,1- -1- ,1,1,3- ,1- -1,3- , , , , (t-pentyl) (t-amyl), 1- ,2- ,1,1- ,1- -1- ,1- -1- ,1- -1- ,1,1,4- , ,1- ,2- ,1,1- ,1- -1- ,1,1,5- ,3,5,5- , ,1- ,1- ,1,1- ,2,2- ,2,6- -4- , , (1,1,3,3- ), 1,1- , , ,1- , </xnotran> N-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, and the like.

As for the "alkenyl group", reference is made to the description of the "alkyl group" which is a group in which a C — C single bond in the structure of the "alkyl group" is substituted with a C = C double bond, and a group in which not only one but two or more single bonds are substituted with a double bond (also referred to as an alkadienyl group or alkatrienyl group) is also included.

With respect to the "alkynyl group", reference may be made to the description of said "alkyl group" which is a group in which a single C — C bond in the structure of the "alkyl group" is substituted with a triple C ≡ C bond, and a group in which not only one but two or more single bonds are substituted with a triple bond (also referred to as an alkanediyne-yl group or an alkanetriyne-yl group) is also included.

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

Specific examples of the "cycloalkyl group" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituents having 1 to 5 carbon atoms or 1 to 4 carbon atoms of these groups, norbornenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantanyl, decahydronaphthyl, and decahydroazulenyl groups.

The "cycloalkylene (ring)" is, for example, a cycloalkylene group having 3 to 24 carbon atoms, preferably a cycloalkylene group having 3 to 20 carbon atoms, a cycloalkylene group having 3 to 16 carbon atoms, a cycloalkylene group having 3 to 14 carbon atoms, a cycloalkylene group having 3 to 12 carbon atoms, a cycloalkylene group having 5 to 10 carbon atoms, a cycloalkylene group having 5 to 8 carbon atoms, a cycloalkylene group having 5 to 6 carbon atoms, a cycloalkylene group having 5 carbon atoms, or the like.

Specific examples of the "cycloalkylene group" include a structure in which one hydrogen is removed from the "cycloalkyl group" (monovalent group) to form a divalent group.

The "alkoxy group" may be either a linear or branched alkoxy group, and is, for example, a linear alkoxy group having 1 to 24 carbon atoms or a branched alkoxy group having 3 to 24 carbon atoms, preferably an alkoxy group having 1 to 18 carbon atoms (a branched alkoxy group having 3 to 18 carbon atoms), an alkoxy group having 1 to 12 carbon atoms (a branched alkoxy group having 3 to 12 carbon atoms), an alkoxy group having 1 to 6 carbon atoms (a branched alkoxy group having 3 to 6 carbon atoms), an alkoxy group having 1 to 5 carbon atoms (a branched alkoxy group having 3 to 5 carbon atoms), an alkoxy group having 1 to 4 carbon atoms (a branched alkoxy group having 3 to 4 carbon atoms), and the like.

<xnotran> "" , , , ,1- -1- ,1,1- ,1,1,2- ,1,1,2,2- ,1- -1,2,2- , , , , ,2- ,1,1- ,3,3- ,1,1- ,1- -1- ,1- -1- ,1,1,3- ,1- -1,3- , , , , (t-pentyloxy) (t-amyloxy), 1- ,2- ,1,1- ,1- -1- ,1- -1- ,1- -1- ,1,1,4- , ,1- ,2- ,1,1- ,1- -1- ,1,1,5- ,3,5,5- , ,1- ,1- ,1,1- ,2,2- ,2,6- -4- , </xnotran> N-octyloxy, t-octyloxy (1, 3-tetramethylbutoxy), 1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy, and the like.

The "aryloxy group" is a group represented by "Ar-O- (Ar is an aryl group)", and as for the details of the aryl group, the description of the "aryl group" can be cited.

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

"Triarylsilyl" is a silyl group substituted with three aryl groups, and for details of the aryl groups, reference may be made to the description of the "aryl group".

Specific "triarylsilyl group" is, for example, triphenylsilyl group, diphenylmononaphthylsilyl group, monophenyldinaphthylsilyl group, or trinaphthylsilyl group, etc.

"Trialkylsilyl" is a silyl group substituted with three alkyl groups, and for details of the alkyl groups, reference may be made to the description of the "alkyl groups".

Specific examples of the "trialkylsilyl group" include a trimethylsilyl group, a triethylsilyl group, a tri-n-propylsilyl group, a triisopropylsilyl group, a tri-n-butylsilyl group, a triisobutylsilyl group, a tri-sec-butylsilyl group, a tri-tert-butylsilyl group, an ethyldimethylsilyl group, an n-propyldimethylsilyl group, an isopropyldimethylsilyl group, an n-butyldimethylsilyl group, a methyldiethylsilyl group, an n-propyldiethylsilyl group, a sec-butyldiethylsilyl group, a tert-butyldiethylsilyl group, a methyldi-n-propylsilyl group, an ethyldi-n-propylsilyl group, an n-butyldi-n-propylsilyl group, a sec-butyldi-n-propylsilyl group, a tert-butyldi-n-propylsilyl group, a methyldiisopropylsilyl group, an ethyldiisopropylsilyl group, an n-butyldiisopropylsilyl group, a sec-butyldiisopropylsilyl group, a tert-butyldiisopropylsilyl group, and a tert-butyldiisopropylsilyl group.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups, and reference may be made to the description of the "cycloalkyl" for details of the cycloalkyl group.

Specific "tricycloalkylsilyl group" is, for example, tricyclopentylsilyl group, tricyclohexylsilyl group or the like.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyl groups and one cycloalkyl group, and for a detailed description of the alkyl and cycloalkyl groups, reference may be made to the descriptions of the "alkyl" and "cycloalkyl" groups.

"Alkylbicycloalkylsilyl" is a silyl group substituted with one alkyl group and two cycloalkyl groups, and for details of the alkyl and cycloalkyl groups, reference may be made to descriptions of the "alkyl" and "cycloalkyl" groups.

The substituent (including the first substituent and the second substituent) affects the emission wavelength of the polycyclic aromatic compound due to the steric resistance, electron donating property, and electron withdrawing property of the structure, and thus the emission wavelength can be adjusted by selecting the substituent. Preferred are groups represented by the following structural formulae, more preferred are methyl group, t-butyl group, bicyclooctyl group, cyclohexyl group, adamantyl group, phenyl group, o-tolyl group, p-tolyl group, 2, 4-xylyl group, 2, 5-xylyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, diphenylamino group, di-p-tolylamino group, bis (p- (t-butyl) phenyl) amino group, diphenylboron group, ditrimethylphenylboronyl group, dibenzooxyphenyl primary group, phenyldibenzodineoxyphenyl group, carbazolyl group, 3, 6-dimethylcarbazolyl group, 3, 6-di-t-butylcarbazolyl group, and phenoxy group, and further preferred are methyl group, t-butyl group, phenyl group, o-tolyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, diphenylamino group, di-p-tolylamino group, bis (p- (t-butyl) phenyl) amino group, carbazolyl group, 3, 6-dimethylcarbazolyl group, and 3, 6-di-t-butylcarbazolyl group. From the viewpoint of ease of synthesis, a group having a large steric hindrance is preferred for selective synthesis, and specifically, t-butyl group, o-tolyl group, p-tolyl group, 2, 4-xylyl group, 2, 5-xylyl group, 2, 6-xylyl group, 2,4, 6-mesitylyl group, di-p-tolylamino group, bis (p- (t-butyl) phenyl) amino group, 3, 6-dimethylcarbazolyl group, and 3, 6-di-t-butylcarbazolyl group are preferred.

In the following structural formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-pentyl group, "thoct" represents a tert-octyl group, and a bond site.

[ solution 24]

*-Me *-tBu *-tAm *-tOct

[ solution 25]

[ chemical 26]

[ solution 27]

[ solution 28]

[ solution 29]

[ solution 30]

[ solution 31]

[ chemical No. 32]

[ solution 33]

[ chemical 34]

[ solution 35]

[ solution 36]

[ solution 37]

[ solution 38]

[ chemical 39]

[ solution 40]

[ solution 41]

Description of Cycloalkane condensation

In addition, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

For example, aryl and heteroaryl rings as A-and B-rings, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy, or triarylsilyl) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as first and second substituents on these rings, aryl and heteroaryl rings as a-and B-rings, an aryl or heteroaryl ring formed by bonding adjacent substituents in a-and B-rings to each other, aryl (same as the above) and heteroaryl (same as the above) as first and second substituents on a-and B-rings, and a pharmaceutically acceptable carrier or diluent therefor as X-ring ¹ ～X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ At least one of the aryl or heteroaryl groups of R of "may be condensed with at least one cycloalkane.

Preferred are aryl and heteroaryl rings as the A and B rings, aryl (aryl moiety in aryl, diarylamino, diarylboron, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituent on these rings, aryl and heteroaryl rings as the a and B rings, an aryl or heteroaryl ring formed by bonding adjacent substituents in the a and B rings to each other, an aryl (same as described) and heteroaryl (same as described) as the first substituent on the a and B rings, and a heteroaryl (same as described) as the X ring ¹ ～X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ At least one of the aryl or heteroaryl groups of R of "may be condensed with at least one cycloalkane.

More preferred are aryl rings as the A ring and the B ring, aryl (aryl moiety of aryl or diarylamino) and heteroaryl (heteroaryl moiety of heteroaryl) as the first substituent on these rings, aryl rings as the a ring and the B ring, aryl rings formed by bonding adjacent substituents in the a ring and the B ring to each other, aryl (same as described above) and heteroaryl (same as described above) as the first substituent on the a ring and the B ring, and an aryl ring as the X ring ¹ ～X ⁴ At least one of the aryl groups of R of "> N-R" may be condensed with at least one cycloalkane.

Further preferred are aryl rings as the A ring and the B ring, an aryl group as a first substituent on these rings (aryl group or aryl moiety in diarylamino group), aryl rings as the a ring and the B ring, an aryl group as a first substituent on the a ring and the B ring (the same as described above), and X as X ¹ ～X ⁴ At least one of the aryl groups of R of "> N-R" may be condensed with at least one cycloalkane.

Examples of the "cycloalkane" include: cycloalkane having 3 to 24 carbon atoms, cycloalkane having 3 to 20 carbon atoms, cycloalkane having 3 to 16 carbon atoms, cycloalkane having 3 to 14 carbon atoms, cycloalkane having 5 to 10 carbon atoms, cycloalkane having 5 to 8 carbon atoms, cycloalkane having 5 to 6 carbon atoms, cycloalkane having 5 carbon atoms, and the like.

Specific examples of the cycloalkane include: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.1.0] butane, bicyclo [1.1.1] pentane, bicyclo [2.1.0] pentane, bicyclo [2.1.1] hexane, bicyclo [3.1.0] hexane, bicyclo [2.2.1] heptane, bicyclo [2.2.2] octane, adamantane, bisadamantane, decahydronaphthalene and decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substituents and deuterium substituents having 1 to 5 carbon atoms of these.

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

[ solution 42]

The number of cycloalkanes condensed in one aromatic ring or heteroaromatic ring is preferably one to three, more preferably one or two, and still more preferably one. For example, an example in which one or more cycloalkanes are condensed in one benzene ring (phenyl group) is shown below. In the respective structural formulae, the term "benzene ring" refers to a benzene ring contained in the skeleton structure of the compound, and the term "phenyl group" refers to a bond substituted on the skeleton structure of the compound. Cycloalkanes condensed as shown in the formulae (Cy-1-4) and (Cy-2-4) may be condensed with each other. The same applies to the case where the ring (group) to be condensed is an aromatic or heteroaromatic ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ solution 43]

At least one-CH in cycloalkanes ₂ -may be substituted by-O-. In which a plurality of-CH ₂ -when substituted by-O-, the adjacent-CH ₂ -is not substituted by-O-. For example, the following shows one or more-CH's of cycloalkanes condensed in one benzene ring (phenyl group) ₂ Examples of-O-substitution. In the respective structural formulae, the term "benzene ring" means a benzene ring contained in the skeleton structure of the compound, and the term "phenyl group" means a benzene ring contained in the skeleton structure of the compoundA bond to make a substitution. The same applies to the case where the ring (group) to be condensed is an aromatic or heteroaromatic ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ solution 44]

At least one hydrogen in the cycloalkane may be substituted, and as the substituent, for example: aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, the details of which may be cited in the description of the first substituent. Among these substituents, preferred are alkyl groups (for example, alkyl groups having 1 to 6 carbon atoms), cycloalkyl groups (for example, cycloalkyl groups having 3 to 14 carbon atoms), halogens (for example, fluorine), deuterium, and the like. In addition, when the cycloalkyl group is substituted, the substitution form may be a spiro structure, and for example, an example in which a spiro structure is formed on a cycloalkane condensed with one benzene ring (phenyl group) is shown below. In the respective structural formulae, the term "benzene ring" refers to a benzene ring contained in the skeleton structure of the compound, and the term "phenyl group" refers to a bond substituted on the skeleton structure of the compound.

[ solution 45]

Examples of other forms of the cycloalkane condensation include substitution of the polycyclic aromatic compound represented by formula (1A), formula (1B), formula (2A), or formula (2B) with, for example, a diarylamino group (condensed to the aryl moiety thereof) condensed with a cycloalkane, a carbazolyl group (condensed to the benzene ring moiety thereof) condensed with a cycloalkane, or a benzocarbazolyl group (condensed to the benzene ring moiety thereof) condensed with a cycloalkane. As the "diarylamino group", groups described as the "first substituent" can be cited.

More specific examples thereof include R in the polycyclic aromatic compound represented by the formula (2A) or (2B) ^a (especially with respect to Y) ¹ And Y ² And is para-to R ^a ) Are examples of diarylamino groups (condensed to the aryl portion thereof) condensed from cycloalkane or carbazolyl groups (condensed to the benzene ring portion thereof) condensed from cycloalkane.

< description of substitution with deuterium, cyano, or halogen >

At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine.

< description of specific examples of polycyclic aromatic Compounds of the present invention >

Specific examples of the polycyclic aromatic compound include compounds represented by the following structural formulae.

[ solution 46]

The benzene rings in the structural formula can be respectively and independently substituted by aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diarylamino (wherein the aryl is aryl with 6 to 10 carbon atoms), diarylboron (wherein the aryl is aryl with 6 to 10 carbon atoms, and two aryl can be bonded through a single bond or a connecting group), alkyl with 1 to 12 carbon atoms, or cycloalkyl with 3 to 16 carbon atoms, and at least one hydrogen in the substituent can be substituted by alkyl with 1 to 5 carbon atoms or cycloalkyl with 5 to 10 carbon atoms. Specific examples of such substituents can be found in the description. The number of the substituent groups to be substituted is one to the maximum number of substituents that can be substituted in each benzene ring, preferably one to two, more preferably one.

In addition, at least one hydrogen in the compound represented by the structural formula may be substituted with deuterium, cyano, or halogen.

More specific examples of the polycyclic aromatic compound include compounds represented by the following structural formulae. In the following structural formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, and "D" represents deuterium.

[ solution 47]

[ solution 48]

[ solution 49]

[ solution 50]

[ solution 51]

[ solution 52]

[ Hua 53]

[ solution 54]

[ solution 55]

[ chemical 56]

[ solution 57]

[ solution 58]

[ chemical 59]

< description of polycyclic aromatic Compound on molecular weight increase >

The polycyclic aromatic compound represented by the general formula (1A) or (1B) may be used as a polymer compound in which the polymer compound is further crosslinked, or a crosslinked polymer compound in which a main chain is reacted with the reactive polymer compound, or a suspended polymer compound in which the polymer compound is further crosslinked, or a suspended polymer compound in which the reactive compound having a reactive substituent is substituted in the polycyclic aromatic compound represented by the general formula (1A) or (1B) and which is further crosslinked with the suspended polymer compound, or a suspended polymer compound in which the suspended polymer compound having a crosslinkable substituent is used in a material for an organic device, for example, a material for an organic electroluminescent element, a material for an organic transistor, a material for an organic thin-film solar cell, or a wavelength conversion filter.

The reactive substituent (including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant polymer, hereinafter also simply referred to as "reactive substituent") is not particularly limited as long as it is a substituent capable of imparting a high molecular weight to the polycyclic aromatic compound, a substituent capable of further crosslinking the polymer compound obtained in this manner, or a substituent capable of undergoing a pendant reaction with a main chain polymer, but is preferably a substituent having the following structure. Each structural formula indicates a bonding position.

[ chemical formula 60]

L is independently a single bond, -O-, -S-, C = O, -O-C (= O) -, or alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms and polyoxyalkylene having 1 to 12 carbon atoms. Among the substituents, preferred are those represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17), and more preferred are those represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17).

Such a polymer compound, a polymer crosslinked body, a pendant polymer compound, and a pendant polymer crosslinked body may contain, in addition to the repeating unit of the polycyclic aromatic compound represented by formula (1A) or formula (1B), at least one selected from the group consisting of compounds containing a substituted or unsubstituted triarylamine, a substituted or unsubstituted fluorene, a substituted or unsubstituted anthracene, a substituted or unsubstituted tetracene, a substituted or unsubstituted triazine, a substituted or unsubstituted carbazole, a substituted or unsubstituted tetraphenylsilane, a substituted or unsubstituted spirofluorene, a substituted or unsubstituted triphenylphosphine, a substituted or unsubstituted dibenzothiophene, and a substituted or unsubstituted dibenzofuran, as a repeating unit.

Examples of the substituent in these repeating units include: aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl groups, and the like. As for the details of the "aryl group" of the triarylamine or the substituents, the description of the polycyclic aromatic compound represented by the formula (1A) or the formula (1B) can be cited.

The use of such a polymer compound, crosslinked polymer, pendant polymer compound and crosslinked pendant polymer (hereinafter, also simply referred to as "polymer compound and crosslinked polymer") will be described in detail later.

2. Method for producing polycyclic aromatic compound

The polycyclic aromatic compounds of the present invention are basically prepared by first utilizing a bonding group (containing X) ¹ ～X ⁴ The a ring (a ring) is bonded to the B ring (B ring) and the c ring, thereby producing an intermediate (first reaction), followed by the utilization of a bonding group (including the central element Y) ¹ And a central element Y ² A group of (A) is as follows "Y ¹ And Y ² "abbreviated as" Y ") to bond the A ring (ring a), the B ring (ring B) and the c ring, thereby producing a final product (second reaction). Reference is made to the production method described in International publication No. 2015/102118.

In the first Reaction, for example, in the case of etherification, a typical Reaction such as nucleophilic substitution Reaction or Ullmann Reaction (Ullmann Reaction) may be used, and in the case of amination, a typical Reaction such as Buchwald-Hartwig Reaction (Buchwald-Hartwig Reaction) may be used. In the second Reaction, a Tandem Hetero-Friedel-Crafts Reaction (consecutive aromatic electrophilic substitution Reaction, the same applies hereinafter) can be used.

As shown in the following scheme (1), the second reaction is a reaction in which a central element Y is introduced to bond the a ring (a ring), the B ring (B ring), and the c ring. First, X is treated with n-butyllithium, sec-butyllithium, tert-butyllithium or the like ¹ And X ² Hydrogen atom and X in between ³ And X ⁴ The hydrogen atoms in between undergo ortho-metallation. Subsequently, a halide of Y such as boron trichloride or boron tribromide is added to carry out metal exchange of lithium-boron, and then a Bronsted base (Bronsted base) such as N, N-diisopropylethylamine is added to carry out a Tandem boro-Friedel-Crafts Reaction (Tandem Bora-Crafts Reaction), whereby a target product can be obtained. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. Note that the symbols in each structural formula in the following flowchart (1) and the subsequent flowcharts are defined as described above.

[ solution 61]

In the above-mentioned scheme, lithium is introduced to a desired position by ortho-metallation, but lithium may be introduced to a desired position by introducing a bromine atom or the like to a position to which lithium is to be introduced and also by halogen-metal exchange as in the following scheme (2). According to the above method, even when the ortho-metalation cannot be performed due to the influence of the substituent, the target product can be produced and is useful.

[ solution 62]

The above-mentioned flow (1) and flow (2) are typical production methods in which Y is boron (> B-) or the like.

Next, the following schemes (3) and (4) are shown by way of example in the case where Y is a phosphine sulfide, phosphine oxide, or phosphorus atom. As described above, first, X is treated with n-butyllithium or the like ¹ And X ² Hydrogen atom and X in between ³ And X ⁴ The hydrogen atoms in between undergo ortho-metallation. Then, phosphorus trichloride and sulfur are sequentially added, and finally, a lewis acid such as aluminum trichloride and a bronsted base such as N, N-diisopropylethylamine are added, whereby a Tandem Phospha-Friedel-Crafts Reaction (Tandem Phospha-Friedel-Crafts Reaction) can be performed, and a compound in which Y is a phosphine sulfide can be obtained. The obtained phosphine sulfide compound was treated with m-Chloroperbenzoic acid (m-CPBA) to obtain a compound in which Y is a phosphine oxide, and treated with triethylphosphine to obtain a compound in which Y is a phosphorus atom.

[ solution 63]

[ solution 64]

In the above-mentioned schemes, examples are mainly described in which Y is > B-, > P (= O) -, or > P (= S) -, etc., and other compounds can be produced by appropriately changing the raw materials.

The following example is shown in the flow: using butyl lithium or the like for X before adding a halide of Y such as boron trichloride or boron tribromide or the like ¹ And X ² Hydrogen atom (or halogen atom) and X in between ³ And X ⁴ In-line friedel-crafts reaction is performed by subjecting the hydrogen atom (or halogen atom) in between to ortho-metalation, but the reaction may be performed by adding a halide of Y such as boron trichloride or boron tribromide without subjecting to ortho-metalation using butyl lithium or the like.

The solvent used in the above-mentioned process may be, for example, tert-butyl benzene or xylene.

Examples of the ortho-metalation reagent used in the above-mentioned process include: an alkali metal is dispersed in an organic solvent such as alkyllithium (e.g., methyllithium, n-butyllithium, sec-butyllithium, and tert-butyllithium), an organic basic compound (e.g., lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide).

Examples of the metal-Y metal exchange reagent used in the above-mentioned process include: halide of Y such as Y-trifluoride, Y-trichloride, Y-tribromide, Y-triiodide, CIPN (NEt) ₂ ) ₂ And the like, an aminated halide of Y, an alkoxylate of Y, an aryloxide of Y, and the like.

Examples of the bransted base used in the above-mentioned scheme include: n, N-diisopropylethylamine, triethylamine, 2, 6-tetramethylpiperidine, 1,2, 6-pentamethylpiperidine, N-dimethylaniline, N, N-dimethyltoluidine, 2, 6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, ar ₄ BNa、Ar ₄ BK、Ar ₃ B、Ar ₄ Si (Ar represents an aryl group such as a phenyl group), and the like.

As lewis acids used in the above-mentioned scheme, there can be mentioned: alCl ₃ 、AlBr ₃ 、AlF ₃ 、BF ₃ ·OEt ₂ 、BCl ₃ 、BBr ₃ 、GaCl ₃ 、GaBr ₃ 、InCl ₃ 、InBr ₃ 、In(OTf) ₃ 、SnCl ₄ 、SnBr ₄ 、AgOTf、ScCl ₃ 、Sc(OTf) ₃ 、ZnCl ₂ 、ZnBr ₂ 、Zn(OTf) ₂ 、MgCl ₂ 、MgBr ₂ 、Mg(OTf) ₂ 、LiOTf、NaOTf、KOTf、Me ₃ SiOTf、Cu(OTf) ₂ 、CuCl ₂ 、YCl ₃ 、Y(OTf) ₃ 、TiCl ₄ 、TiBr ₄ 、ZrCl ₄ 、ZrBr ₄ 、FeCl ₃ 、FeBr ₃ 、CoCl ₃ 、CoBr ₃ And so on.

In the scheme, in order to promote the cascade of hybrid Friedel-crafts reaction, a Bransted base or Lewis acid can also be used. Among them, when a halide of Y such as Y trifluoride, Y trichloride, Y tribromide, or Y triiodide is used, an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated as the aromatic electrophilic substitution reaction proceeds, and therefore it is effective to use a bransted base which captures the acid. On the other hand, in the case of using an aminated halide of Y or an alkoxylate of Y, since an amine or an alcohol is produced as the aromatic electrophilic substitution reaction proceeds, it is not necessary to use a bronsted base in many cases, but since the ability to remove an amino group or an alkoxy group is low, it is effective to use a lewis acid for accelerating the removal thereof.

The polycyclic aromatic compound of the present invention further contains a compound in which at least a part of hydrogen is substituted with deuterium, cyano group, or halogen, and such a compound can be produced in the same manner as described above by using a raw material in which a desired position is halogenated with deuteration, cyanation, fluorination, chlorination, or the like.

3. Organic device

In the chemical structural formulae exemplified below, "Me" represents a methyl group, and "tBu" represents a tert-butyl group.

The polycyclic aromatic compound of the invention is useful as a material for organic devices. Examples of the organic device include: an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, or the like.

3-1. Organic electroluminescent element

The polycyclic aromatic compound of the present invention is useful, for example, as a material for an organic electroluminescent element. Hereinafter, the organic EL device of the present embodiment will be described in detail with reference to the drawings. Fig. 1 is a schematic sectional view showing an organic EL element according to the present embodiment.

< Structure of organic electroluminescent element >

The organic EL element 100 shown in fig. 1 includes: the light-emitting device comprises a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

In addition, the organic EL element 100 may be formed by reversing the manufacturing procedure to have, for example, a structure including: the organic light emitting diode comprises a substrate 101, a cathode 108 arranged on the substrate 101, an electron injection layer 107 arranged on the cathode 108, an electron transport layer 106 arranged on the electron injection layer 107, a light emitting layer 105 arranged on the electron transport layer 106, a hole transport layer 104 arranged on the light emitting layer 105, a hole injection layer 103 arranged on the hole transport layer 104, and an anode 102 arranged on the hole injection layer 103.

All of the layers are not indispensable, and the minimum structural unit is configured to include the anode 102, the light-emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be arbitrarily provided. In addition, each of the layers may include a single layer, or may include a plurality of layers.

As the form of the layers constituting the organic EL element, in addition to the structural form of the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", the material may be in the structural form of "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/light-emitting layer/hole injection layer/light-emitting layer/electron injection layer/cathode", "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 injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/light-emitting layer/electron injection layer/cathode".

< substrate in organic electroluminescent element >

The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, or the like is generally used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape according to the purpose, and for example, a glass plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate and polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, or the like can be used, and the thickness is sufficient to maintain the mechanical strength, and therefore, for example, the thickness may be 0.2mm or more. The upper limit of the thickness is, for example, 2mm or less, preferably 1mm or less. The material of the glass is preferably alkali-free glass because it is preferable that the amount of eluted ions from the glass is small, and SiO is added ₂ Etc. of barrier coating (barrier coat) are also commercially available, and therefore the soda-lime glass can be used. In order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film may be provided on at least one surface of the substrate 101, and particularly, when a synthetic resin plate, film or sheet having low gas barrier property is used as the substrate 101, it is preferable to provide a gas barrier film.

< Anode in organic electroluminescent element >

The anode 102 functions 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 through these layers.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound 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, or NESA glass, etc. Examples of the organic compound include: polythiophene such as poly (3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. Further, it can be suitably selected from substances used as an anode of an organic EL element.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light-emitting element, but is preferably low in terms of power consumption of the light-emitting element. For example, an ITO substrate of 300 Ω/γ or less functions as an element electrode, but now it is possible to provide a substrate of about 10 Ω/γ, and therefore, it is particularly preferable to use a low-resistance product of, for example, 100 Ω/γ to 5 Ω/γ, preferably 50 Ω/γ to 5 Ω/γ. The thickness of ITO can be arbitrarily selected depending on the resistance value, but is usually used in a range of 50nm to 300nm in many cases.

< hole injection layer, hole transport layer in organic electroluminescent element >

The hole injection layer 103 functions to efficiently inject holes transferred from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 functions to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by laminating and mixing one or two or more kinds of hole injection/transport materials, or are formed by mixing a hole injection/transport material and a polymer binder. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

As the hole injecting/transporting substance, it is necessary to efficiently inject/transport holes from the positive electrode between the electrodes to which an electric field is applied, and it is desirable that the hole injecting efficiency is high and the injected holes are efficiently transported. Therefore, a substance having a small ionization potential, a large hole mobility, and excellent stability, and in which impurities serving as traps are not easily generated during production and use, is preferable. In the present invention, as the material for the hole injection layer and the hole transport layer, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used.

As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected and used 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 devices.

Specific examples of these compounds include carbazole derivatives (e.g., N-phenylcarbazole, polyvinylcarbazole, etc.), bis-carbazole derivatives such as bis (N-arylcarbazole) and bis (N-alkylcarbazole), triarylamine derivatives (e.g., polymers having an aromatic tertiary amino group in the main chain or side chain, 1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N '-diphenyl-N, N' -di (3-methylphenyl) -4,4 '-diaminobiphenyl, N' -diphenyl-N, N '-dinaphthyl-4, 4' -diaminobiphenyl, N '-diphenyl-N, N' -di (3-methylphenyl) -4,4 '-diphenyl-1, 1' -diamine, N '-dinaphthyl-N, N' -diphenyl-4, 4 '-diphenyl-1, 1' -diamine, N ⁴ ,N ⁴ ' -Diphenyl-N ⁴ ,N ⁴ '-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]4,4' -diamine, N ⁴ ,N ⁴ ,N ⁴ ',N ⁴ '-tetrakis ([ 1,1' -biphenyl group)]-4-yl) - [1,1' -biphenyl]Triphenylamine derivatives such as-4, 4 '-diamine, 4' -tris (3-methylphenyl (phenyl) amino) triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9, 12-hexaazatriphenylene-2, 3,6,7,10, 11-hexachloronitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, a polycarbonate or a styrene derivative, polyvinylcarbazole, polysilane, or the like having the monomer in the side chain is preferable, but there is no particular limitation as long as it is a compound which can form a thin film necessary for manufacturing a light-emitting element, can inject holes from an anode, and can further transport holes.

Further, it is also known that the conductivity of an organic semiconductor is strongly affected by doping. Such an organic semiconductor matrix material contains a compound having a good electron donating property or a compound having a good electron accepting property. For the doping of electron donor substances, strong electron acceptors such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluorotetracyanoquinodimethane-1, 4-benzoquinodimethane (2, 3,5, 6-tetrafluorotetracyanotetracyano-1, 4-benzoquinodimethane (2, 3,5, 6-tetrafluoro-1, 4-benzoquinodimethane, F4 TCNQ) are known (see, for example, documents "m. Faffy, a. Bayer, t. Floritz, k. Rio (m.pfeiffer, a.beyer, t.fritz, k.leo)," applied physics letters (app. Phys. Lett.), 73 (22), 3202-3204 (1998) "and documents" j. Brewhortz, m. Faffy, t. Flor, k. Blowwitz), "applied physics (j.p. Pfewi, m.p., t., t.p. Pfitwin.)," applied physics (r, k.p. Tweez), "applied physics (r, k.p. Fti, k.3, k.p., t.p., t.3, r., t.: pp. Brity (1998)" and "applied electronics (r, k.p., t.12, p.p., l.p., etc.). These generate so-called holes by an electron transfer process in an electron-donating base substance (hole-transporting substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. As a matrix material having a hole transporting property, for example, a benzidine derivative (N, N ' -bis (3-methylphenyl) -N, N ' -bis (phenyl) benzidine (N, N ' -bis (3-methylphenylamino) -N, N ' -bis (phenyl) benzidine, TPD), etc.) or a starburst amine derivative (4,4 ',4 ″ -tris (N, N-diphenylamino) triphenylamine, TDATA, etc.), or a specific metal phthalocyanine (particularly zinc phthalocyanine (ZnPc), etc.) is known (japanese patent laid-open No. 2005-167175).

The hole injection layer material and the hole transport layer material may be used as a hole layer material as a polymer compound obtained by polymerizing, as a monomer, a reactive compound obtained by substituting a reactive substituent in the hole injection layer material and the hole transport layer material, or as a polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked polymer compound thereof, or as a pendant polymer compound obtained by substituting a reactive substituent in the hole injection layer material and the hole transport layer material, or as a crosslinked pendant polymer compound thereof. As the reactive substituent in such a case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

The use of such a polymer compound and a crosslinked polymer will be described in detail later.

< light-emitting layer in organic electroluminescent element >

The light-emitting layer 105 emits light by recombination of 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) which emits light by being excited by recombination of holes and electrons, and is preferably a compound which can be formed into a stable thin film shape and which exhibits strong light emission (fluorescence) efficiency in a solid state. In the present invention, as a material for the light-emitting layer, a host material and, for example, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) as a dopant material can be used.

The light-emitting layer may be a single layer or may include a plurality of layers, and each of the layers is formed of a material (host material or dopant material) for the light-emitting layer. The host material and the dopant material may be one kind or a combination of two or more kinds, respectively. Further, a material for a hole transport layer or a material for an electron transport layer may be mixed in the host material, or a combination of these materials may be used. The dopant material may be included in the bulk of the host material, or may be included in a portion of the host material, either. The doping method may be a co-evaporation method with the host material, a simultaneous evaporation method in which the host material is mixed in advance, or a wet film-forming method in which the host material is mixed with an organic solvent in advance.

The amount of the host material to be used differs depending on the type of the host material, and may be determined in accordance with the characteristics of the host material. The amount of the host material used is preferably 50 to 99.999 wt%, more preferably 80 to 99.95 wt%, and still more preferably 90 to 99.9 wt% of the total amount of the light-emitting layer material.

The amount of the dopant material used varies depending on the kind of the dopant material, and may be determined by matching the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50 wt%, more preferably 0.05 to 20 wt%, and still more preferably 0.1 to 10 wt% of the total material for the light-emitting layer. The above range is preferable, for example, in terms of preventing the concentration quenching phenomenon. In addition, from the viewpoint of durability, it is also preferable that a part or all of hydrogen atoms of the dopant material be deuterated.

On the other hand, in the organic EL element using the thermally activated delayed fluorescence dopant material, the amount of the dopant material used is preferably low in terms of preventing the concentration quenching phenomenon, but is preferably high in terms of the efficiency of the thermally activated delayed fluorescence mechanism. In an organic EL device using a thermally activated delayed fluorescence auxiliary dopant material, it is preferable that the amount of the dopant material used is lower than the amount of the auxiliary dopant material used in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the auxiliary dopant material.

When the auxiliary dopant material is used, the amounts of the host material, the auxiliary dopant material, and the dopant material used are, based on 40 to 99.999 wt%, 59 to 1 wt%, and 20 to 0.001 wt%, respectively, of the entire light-emitting layer material, preferably 60 to 99.99 wt%, 39 to 5 wt%, and 10 to 0.01 wt%, more preferably 70 to 99.95 wt%, 29 to 10 wt%, and 5 to 0.05 wt%, respectively. The polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) and the polymer compound thereof can also be used as an auxiliary dopant material.

As the host material, anthracene, pyrene, dibenzo known as a light-emitting body from the past can be mentioned

Or a condensed ring derivative such as fluorene, a bisstyryl derivative such as a bisstyrylanthracene derivative or a distyrylbenzene derivative, a tetraphenylbutadiene derivative, a cyclopentadiene derivative, and the like. Particularly, an anthracene compound, a fluorene compound or a dibenzo

Is a compound of the formula (I). In particular, from the viewpoint of durability, it is also preferable that a part or all of the hydrogen atoms of the host material be deuterated.Further, it is also preferable that the light-emitting layer is formed by combining a host compound in which a part or all of hydrogen atoms are deuterated and a dopant compound in which a part or all of hydrogen atoms are deuterated.

From the viewpoint of promoting but not inhibiting the generation of TADF in the light-emitting layer, the triplet energy of the host material is preferably higher than the triplet energy of the dopant or the assist dopant having the highest triplet energy in the light-emitting layer, and specifically, the triplet energy of the host material is preferably 0.01eV or more, more preferably 0.03eV or more, and further preferably 0.1eV or more. In addition, a compound having TADF activity may also be used in the host material.

Examples of the host material include a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. Preferred is a compound represented by the general formula (H1).

[ solution 65]

< Compound represented by the general formula (H1) >

[ solution 66]

In the formula (H1), L ¹ Is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms, preferably an arylene group having 6 to 24 carbon atoms, more preferably an arylene group having 6 to 16 carbon atoms, further preferably an arylene group having 6 to 12 carbon atoms, particularly preferably an arylene group having 6 to 10 carbon atoms, further preferably a heteroarylene group having 2 to 25 carbon atoms, more preferably a heteroarylene group having 2 to 20 carbon atoms, further preferably a heteroarylene group having 2 to 15 carbon atoms, and particularly preferably a heteroarylene group having 2 to 10 carbon atoms. Specific examples of the arylene group include: benzene and its derivativesA divalent group such as a ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring. Specific examples of the heteroarylene group include: divalent groups of the heterocyclic 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 phthalein ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenothiazine ring, a phenazine azine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazane ring, an indole-carbazole ring, a benzindole-carbazole ring, a benzindolino-indole-carbazole ring, a benz ring, a benzndole-and benz-carbazole ring.

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

< Compound represented by the general formula (H2) >)

[ formula 67]

In the formula (H2), L ² And L ³ Each independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. The aryl group is preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 16 carbon atoms, still more preferably an aryl group having 6 to 12 carbon atoms, particularly preferably an aryl group having 6 to 10 carbon atoms, and specifically, there may be mentioned: a monovalent group such as a benzene ring, a biphenyl ring, a naphthalene ring, a tribiphenyl ring, an acenaphthene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a tetracene ring, a perylene ring, and a pentacene ring. The heteroaryl group is preferably a carbon number2 to 25, more preferably 2 to 20, still more preferably 2 to 15, particularly preferably 2 to 10, and specifically: a monovalent benzfuran ring, e.g., 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 oxazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxazine ring, a phenothiazine ring, a phenazine azsilicon ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a furazan ring, an anthracene ring, an indolocarbazole ring, a benzazolo carbazole ring, a naphthocarbazole ring, and the like.

At least one hydrogen in the compound represented by the formula (H2) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen or deuterium.

< Compound represented by the general formula (H3) > (an example of a Polymer host Material)

[ solution 68]

In the formula (H3), the compound represented by the formula,

each MU is independently a divalent group represented by removing any two hydrogen atoms from the aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from the aromatic compound, two hydrogens in the MU are replaced with EC or MU, and k is an integer of 2 to 50000.

More specifically, the present invention is to provide a novel,

MU is independently arylene, heteroarylene, diarylenearylamino, diarylenearylboranyl, oxaborane-diyl, azaborine-diyl,

EC are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy,

at least one hydrogen in MU and EC may in turn be substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl groups,

k is an integer of 2 to 50000.

k is preferably an integer of 20 to 50000, more preferably an integer of 100 to 50000.

At least one hydrogen of MU and EC in the formula (H3) may be substituted by an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or deuterium, and further any-CH in the alkyl group ₂ May be-O-or-Si (CH) ₃ ) ₂ -substitution, of the alkyl radical, directly bonded to the-CH of EC in formula (H3) ₂ Any other than-CH ₂ -optionally substituted by an arylene group having 6 to 24 carbon atoms, any hydrogen of the alkyl group being optionally substituted by fluorine.

Examples of the MU include divalent groups represented by removing any two hydrogen atoms from any of the following compounds.

[ solution 69]

More specifically, divalent groups represented by any one of the following structures are included. In these, MUs are bonded to other MUs or ECs at one site.

[ solution 70]

[ solution 71]

[ chemical 72]

[ chemical 73]

[ chemical formula 74]

[ solution 75]

[ 76]

[ solution 77]

[ solution 78]

Examples of EC include monovalent groups represented by any of the following structures. In these, EC is bound to MU at x.

[ solution 79]

[ solution 80]

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

< Compound having a structure represented by the general formula (H4) >

The compound is a compound including a structure represented by the following formula (H4), and includes a plurality of the structures, preferably one to five, more preferably one to three, further preferably one to two, most preferably one, and in the case of including a plurality of the structures, the structures are bonded to each other directly by a single bond or by a specific linking group.

[ solution 81]

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

Compounds having a structure represented by general formula (H4) can be produced, for example, by using compounds described in international publication No. 2012/153780, international publication No. 2013/038650, and the like, according to the methods described in the above documents.

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

Specific examples of the "aryl" as the substituent include: phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl,

Radical, benzo [ c ]]Phenanthryl, benzo [ g ] ]

Examples of the group include a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a 9, 9-dimethylfluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and a fluoranthenyl group. As the aryl group having a substituent, there may be mentioned: tolyl group, xylyl group, and 9, 9-dimethylfluorenyl group. As shown in the specific examples, the aryl group includes both a condensed aryl group and a non-condensed aryl group.

Specific examples of the "heteroaryl" as the substituent include: pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo [1,2-a ] pyridyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azabenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azabenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl and the like, and preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azabenzofuranyl and azabenzothienyl and the like. Further preferred is a dibenzofuranyl group, a dibenzothienyl group, an azabenzofuranyl group, or an azabenzothienyl group.

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

Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group. Specific examples of the substituted or unsubstituted arylalkylsilyl group include: diphenylmethylsilyl, ditolymethylsilyl, and phenyldimethylsilyl groups. Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl group and tritolylsilyl group.

The "substituted phosphinoxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphinoxide group. Specific examples of the substituted or unsubstituted diarylphosphinoxide group include diphenylphosphine oxide and xylylphosphine oxide.

Examples of the "substituted carboxyl group" as a substituent include benzoyloxy and the like.

Examples of the linking group for bonding the structures represented by the formula (H4) to each other include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the aryl group or the heteroaryl group.

Specific examples of the compound having a structure represented by general formula (H4) are shown below.

[ chemical 82]

[ solution 83]

< Compound represented by the general formula (H5) >)

[ solution 84]

In the formula (H5), the reaction mixture is,

R ¹ ～R ¹¹ each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above is the first substituent), and R is ¹ ～R ¹¹ At least one hydrogen in (a) may further be substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group (above which is a second substituent),

R ¹ ～R ¹¹ wherein at least one hydrogen in the ring formed may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl group (first substituents above), which in turn may be substituted with an aryl, heteroaryl, diarylamino, alkyl or cycloalkyl group (second substituents above),

any of the rings a, b, and C "-C (-R) =" (where R is R) ¹ ～R ¹¹ ) May be substituted by "-N =",

at least one hydrogen in the compound represented by formula (H5) may be independently substituted with halogen or deuterium, respectively.

Any of the a ring, the b ring, and the C ring in the formula (H5) — C (-R) = "(where R is R) ¹ ～R ¹¹ ) Substituted with "-N =", and may be changed to a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, other nitrogen-containing heteroaryl ring. The details of the description may refer to the descriptions in the general formula (2A) and the formula (2B).

Preferably in the formula (H5) mentioned above,

R ¹ ～R ¹¹ each independently represents 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), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, and R is ¹ ～R ¹¹ At least one hydrogen in the (C) may be further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms or a diarylamino group (wherein the aryl group is a carbon atom)6-12 aryl), C1-12 alkyl or C3-16 cycloalkyl,

R ¹ ～R ¹¹ in the (b) ring, or the (c) ring, at least one hydrogen in the ring may be substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and at least one hydrogen in these substituents may be further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

Still more preferably, in the formula (H5),

R ¹ ～R ¹¹ independently represents hydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 15 carbon atoms, diarylamino group (wherein the aryl group is aryl group having 6 to 10 carbon atoms), alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 14 carbon atoms, and R ¹ ～R ¹¹ At least one hydrogen in the (C) group may be further substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

R ¹ ～R ¹¹ wherein adjacent groups in (a) may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a, b or c ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen in these substituents may further be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

In the first substituent and the second substituent, the "aryl" or the "heteroaryl" in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino may be exemplified as follows.

Specific examples of the "aryl group" include aryl groups having 6 to 30 carbon atoms, preferably 6 to 24 carbon atoms, more preferably 6 to 20 carbon atoms, still more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, and most preferably 6 to 10 carbon atoms. Examples thereof include: phenyl as monocyclic aryl, (2-, 3-, 4-) biphenyl as bicyclic aryl, (1-, 2-) naphthyl as condensed bicyclic aryl, (m-terphenyl-2 ' -yl, m-terphenyl-4 ' -yl, m-terphenyl-5 ' -yl, o-terphenyl-3 ' -yl, o-terphenyl-4 ' -yl, p-terphenyl-2 ' -yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) as tricyclic aryl, (1-, 3-, 4-, 5-) acenaphthylene- (1-, 2-, 3-, 4-, 9-) non-terphenyl- (1-, 2-) terphenyl, (1-, 2-, 3-, 4-, 9-, tetracyclic aryl as condensed tricyclic aryl, (5 ' -tetra (1-, 3-, 5' -tetra-terphenyl) biphenyl, m-2 ' -yl, m-terphenyl-4 ' -yl, m-terphenyl-5 ' -yl, m-terphenyl-2 ' -yl, p-2-, 3-, 4' -phenanthrenyl, m-terphenyl-3-, 5' -tetra-yl, and m-terphenyl-4 ' -yl as condensed tricyclic aryl, and the like, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, pentacene- (1-, 2-, 5-, 6-) group, and the like.

Specific examples of the "heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples thereof 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, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphacyclopentadienyl, monovalent radicals of dibenzophosphole oxide ring, monovalent benzothiophenyl, thiadiazolyl, thiacarbazolyl, anthracenyl, benzindolinyl, and benzoxazolyl groups.

The "alkyl group" in the first substituent and the second substituent may be either a linear or branched one, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms), further preferably an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (a branched alkyl group having 3 to 5 carbon atoms) or an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms), and most preferably a methyl group. Examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1, 3-tetramethylbutyl), 1-methylheptyl 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 2, 6-dimethyl-4-heptyl group, 3, 5-trimethylhexyl group, n-decyl group, n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-eicosyl group and the like. Further, examples thereof include: <xnotran> 1- -1- ,1,1- ,1,1- ,1- -1- ,1,1,4- ,1,1,2- ,1,1- ,1,1- ,1,1- ,1,1,5- ,1- -1- ,1- -1,3- ,1,1,2,2- ,1- -1- ,1,1- ,1- -1- ,1,1,3- ,1- -1- ,1,1,2- ,1- -1,2,2- ,1- -1- ,1,1- . </xnotran>

In the first substituent and the second substituent, as the "cycloalkyl group", there may be mentioned: cycloalkyl group having 3 to 24 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 16 carbon atoms, cycloalkyl group having 3 to 14 carbon atoms, cycloalkyl group having 5 to 10 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, cycloalkyl group having 5 to 6 carbon atoms, cycloalkyl group having 5 carbon atoms and the like. Examples thereof include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and a substituent of an alkyl group (particularly, methyl) having 1 to 4 carbon atoms of these groups, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantanyl, decahydronaphthyl, decahydroazulenyl, and the like.

The substitution position when the first substituent is an aryl group is preferably R ¹ 、R ³ 、R ⁴ 、R ⁵ 、R ¹⁰ And R ¹¹ More preferably, for example, to R ¹ And R ³ Substituted with respect to R ⁵ And R ¹⁰ Substituted with respect to R ⁴ And R ¹¹ Aryl is preferably phenyl.

The substitution position when the first substituent is heteroaryl is preferably R ¹ 、R ² 、R ³ 、R ⁴ 、R ⁵ 、R ⁶ 、R ⁹ 、R ¹⁰ And R ¹¹ More preferably, for example, to R ¹ Substituted with respect to R ² Substituted with respect to R ³ Substituted with respect to R ¹ And R ³ Substituted with respect to R ⁴ And R ¹¹ Substituted with respect to R ⁵ And R ¹⁰ Substituted with respect to R ⁶ And R ⁹ The heteroaryl group is preferably a carbazolyl group. The heteroaryl (e.g., carbazolyl) may be substituted at that position via a phenylene group.

Specific examples of the compound represented by the formula (H5) include compounds represented by the following structural formulae. Further, "Me" in the formula is methyl.

[ solution 85]

[ solution 86]

The compound represented by formula (H5) can be produced by first bonding the a-rings to c-rings with a bonding group (-O-) to produce an intermediate (first reaction), and then bonding the a-rings to c-rings with B (boron) to produce a final product (second reaction). In the first reaction, for example, a nucleophilic substitution reaction, an ullmann reaction, or other general etherification reaction can be used. In the second reaction, a cascade-type hetero Friedel-crafts reaction (a sequential aromatic electrophilic substitution reaction) can be used. The details of the first reaction and the second reaction can be found in the description of International publication No. 2015/102118.

< Compound represented by the general formula (H6) >

[ solution 87]

In the formula (H6), the compound represented by the formula (H6),

R ¹ ～R ¹⁶ each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above is the first substituent), and R is ¹ ～R ¹⁶ Which in turn may be substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group (the second substituent above),

R ¹ ～R ¹⁶ adjacent groups in (1) may be bonded to each other and to the a-ringThe b, c, or d rings together form an aryl or heteroaryl ring, at least one hydrogen in the ring formed may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl group (first substituents above), at least one hydrogen of which may in turn be substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group (second substituents above),

at least one hydrogen in the compound represented by formula (H6) may be independently substituted with halogen or deuterium, respectively.

Preferably in the formula (H6),

R ¹ ～R ¹⁶ each independently represents 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), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, and R is ¹ ～R ¹⁶ At least one hydrogen in the (C) group may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

R ¹ ～R ¹⁶ In (b), adjacent groups in (c) may be bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a, b, c, or d ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and at least one hydrogen in these substituents may be further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

Still more preferably, in the formula (H6),

R ¹ ～R ¹⁶ each independently represents hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and R is ¹ ～R ¹⁶ At least one hydrogen in (1)Further substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

R ¹ ～R ¹⁶ in (b), adjacent groups in (c) may be bonded to each other and form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a, b, c, or d ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen in these substituents may be further substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms.

Specific examples of the "aryl group" include aryl groups having 6 to 30 carbon atoms, preferably 6 to 24 carbon atoms, more preferably 6 to 20 carbon atoms, still more preferably 6 to 16 carbon atoms, particularly preferably 6 to 12 carbon atoms, and most preferably 6 to 10 carbon atoms. Examples thereof include: phenyl as monocyclic aryl group, (2-, 3-, 4-) biphenyl as bicyclic aryl group, (1-, 2-) naphthyl as condensed bicyclic aryl group, (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) as tricyclic aryl group of tricyclic ring system, acenaphthene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl as condensed tricyclic aryl, quaterphenyl (5 ' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl, m-quaterphenyl) as tetracyclic aryl, triphenylene- (1-, acenaphthylene- (3-), acenaphthylene- (4-), and acenaphthylene- (1-), 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, pentacene- (1-, 2-, 5-, 6-) group, and the like.

Specific examples of the "heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, further preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples thereof 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, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphacyclopentadienyl, monovalent radicals of dibenzophosphole oxide ring, monovalent benzothiophenyl, thiadiazolyl, thiacarbazolyl, anthracenyl, benzindolinyl, and benzoxazolyl groups.

The compound represented by formula (H6) can be produced by referring to the description described in international publication No. 2014/042197.

< TADF Material >

By reducing the energy difference between the excited singlet state and the excited triplet state, reverse energy transfer from the excited triplet state to the excited singlet state, which is generally low in transition probability, occurs efficiently, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) appears. In normal fluorescence emission, 75% of triplet excitons generated by current excitation pass through a thermal deactivation path, and thus cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL device can be realized.

Examples of the TADF material that can be used for such a purpose include a compound represented by the following general formula (H7) and a compound having the following general formula (H7) as a partial structure.

[ 88]

ED-Ln-EA (H7)

In the formula (H7), ED is an electron donating group, ln is a bonding group, EA is an electron accepting group, and the singlet energy (S) of the compound represented by the formula (H7) ¹ ) And triplet energy (T) ¹ ) Energy difference (Δ S) of ¹ T ¹ ) Is below 0.2eV (Hiroki UOyama, xinzhijian (Kenichi Goushi), zhijin Kazuki (Katsuyuki Shizu), wild village Haozi (Hiroko Nomura), chihaya Adachi (Chihaya Adachi), & ltNature & gt, nature & lt 492, 234-238 (2012)). Energy difference (Δ S) ¹ T ¹ ) Preferably 0.15eV or less, more preferably 0.10eV or less, and still more preferably 0.08eV or less.

The TADF material is preferably a donor-acceptor type TADF compound (a D-a type TADF compound) designed to locally present HOMO and LUMO in the molecule using an electron donating substituent called a donor and an electron accepting substituent called an acceptor to produce efficient reverse intersystem crossing.

In the present specification, "electron donating substituent" (donor) refers to a substituent and a partial structure locally existing in the LUMO orbital of a TADF compound molecule, and "electron accepting substituent" (acceptor) refers to a substituent and a partial structure locally existing in the HOMO orbital of a TADF compound molecule.

Generally, TADF compounds using donors or acceptors have large Spin Orbit Coupling (SOC: spin Orbit Coupling) and small exchange interaction between HOMO and LUMO and small Δ E (ST) due to structural reasons, and thus can achieve very fast reverse intersystem crossing speed. On the other hand, a TADF compound using a donor or an acceptor has a large structural relaxation in an excited state (in a molecule, since a stable structure is different between a ground state and an excited state, when a transition from the ground state to the excited state occurs by an external stimulus, the structure is changed to the stable structure in the excited state thereafter), and a wide emission spectrum is provided, and thus when it is used as a light emitting material, there is a possibility that color purity may be lowered.

When the color purity is lowered by the TADF material, a fluorescent compound may be added as another component to the light-emitting layer or a layer adjacent to the light-emitting layer. The TADF material functions as an auxiliary dopant, and the other components function as an emitting dopant. The other component may be a compound whose absorption spectrum overlaps at least a part of the emission peak of the auxiliary dopant.

As the structure of the donor and the acceptor used in the TADF material, for example, the structure described in "Materials Chemistry of Materials", 2017, 29, 1946-1963, can be used. The ED may contain sp ³ More specifically, the nitrogen functional group includes, for example, carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothiophenocarbazole, phenylindolinocarbazole, phenylbicarbazole, bicarbazole, tercarbazole (tercarbazole), diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethylacridine, diphenylamine, bis (t-butylphenyl) amine, N1- (4- (diphenylamino) phenyl) -N4, N4-diphenylbenzene-1, 4-diamine, dimethylacridinediamine, tetramethyl-dihydro-indenylacridine and dibutyrylPhenyl-dihydrodibenzoazacillin and the like. Further, the EA includes, for example, an sp-containing compound ² Nitrogen aromatic rings, CN-substituted aromatic rings, ketone-containing rings, and cyano groups, and more specifically, there may be mentioned compounds selected from sulfonylbenzophenones, benzophenones, phenylenebis (phenylmethanones), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthrone, anthracenedione, pyridine, 5H-cyclopentyl [1,2-b:5,4-b' ]Bipyridine, benzenetricarboxylic acid nitrile, fluorenedicarbonitrile, pyrazinedicarboxylic acid nitrile, pyridinedicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis (phenylsulfonyl) benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, tris (dimethylphenyl) borane, and the like. Examples of Ln include a single bond and an arylene group, and more specifically, include: phenylene, biphenylene, naphthylene, and the like. In either structure, hydrogen may be substituted with alkyl, cycloalkyl, and aryl groups. Particularly preferred are compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone as a partial structure.

More specifically, the compound represented by the general formula (H7) is a compound represented by any one of the following general formulae (H7-1), (H7-2) and (H7-3).

[ solution 89]

In the general formula (H7-1), the formula (H7-2) and the formula (H7-3),

m is each independently a single bond, -O-, > N-Ar or > C (-Ar) ₂ From the viewpoint of the depth of the HOMO of the partial structure to be formed and the heights of the excited singlet level and the excited triplet level Preferably a single bond, -O-or > N-Ar,

j is a spacer structure for separating a donor partial structure and a receptor partial structure, and is each independently an arylene group having 6 to 18 carbon atoms, and is preferably an arylene group having 6 to 12 carbon atoms from the viewpoint of the size of conjugate bleeding from the donor partial structure and the receptor partial structure, and more specifically, includes: phenylene, methylphenylene and dimethylphenylene,

q is independently = C (-H) -or = N-, and preferably = N-from the viewpoint of the shallowness of the LUMO of the partial structure to be formed and the heights of the excited singlet level and the excited triplet level,

ar is independently hydrogen, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 18 carbon atoms, and from the viewpoints of the depth of the HOMO of the partial structure to be formed and the heights of the excited singlet level and excited triplet level, it is preferably hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 14 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesitylyl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl or phenylbenzimidazolyl, further preferably hydrogen, phenyl or carbazolyl,

m is 1 or 2, and m is,

n is an integer of 2 to (6-m), and preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance.

Further, at least one hydrogen in the compounds represented by each of the formulae may be substituted with halogen or deuterium.

Examples of the compound represented by the formula (H7) include compounds represented by the following structures. In the structural formula, ". Indicates a bonding position,". Me "indicates a methyl group, and" tBu "indicates a tert-butyl group.

[ solution 90]

[ solution 91]

[ chemical No. 92]

[ solution 93]

[ chemical 94]

[ solution 95]

[ solution 96]

[ chemical 97]

[ solution 98]

As the compound represented by the general formula (H7), among the specific compounds, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiro AC-TRZ, ac-HPM, ac-PPM, ac-MPM, TCzTrz, tmCzTrz and DCzmCZTrz are particularly preferable.

As the dopant material, in addition to the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B), known compounds can be used, and the dopant material can be selected from various materials according to a desired luminescent color. Specific examples thereof include: phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and

Bisbenylene derivatives such as isocondensated ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives or distyrylbenzene derivatives (Japanese patent laid-open No. Hei 1-24087), bisstyrylarylene derivatives (Japanese patent laid-open No. Hei 2-247278), diazabenzodiindene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, ditrimethylphenylisobenzofuran, bis (2-methylphenyl) isobenzofuran, bis (2-trifluoromethylphenyl) isobenzofuran, phenylisobenzofuran and the like, dibenzofuran derivatives, coumarin derivatives such as 7-dialkylaminocoumarin derivatives, 7-piperidylcoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolyl coumarin derivatives and the like, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinolone derivatives Examples of the organic compound include an organic compound, an acridine derivative, an oxazine derivative, a phenylate derivative, a quinacridone derivative, a quinazoline derivative, a pyrrolopyridine derivative, a furopyridine derivative, a 1,2, 5-thiadiazolopyridine derivative, a pyrromethene derivative, a perinone derivative, a pyrrolopyrrole derivative, a squarylium salt derivative, an anthrone derivative, a phenazine derivative, an acridone derivative, a deazaflavin derivative, a fluorene derivative, and a benzofluorene derivative.

When the color-developed light is exemplified, examples of the blue dopant material to the blue-green dopant material include: naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene,

And aromatic hydrocarbon compounds or derivatives thereof, such as furan, pyrrole, thiophene, silole, 9-silafluorene (9-silafluorene), 9' -spirodisilylfluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene and other aromatic heterocyclic compounds or derivatives thereof, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and other azole derivatives and metal complexes thereof, and aromatic amine derivatives represented by N, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -4,4' -diphenyl-1, 1' -diamine.

Further, examples of the green to yellow dopant materials include: coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and tetracene derivatives such as rubrene, and the like, and further, the following compounds are preferable examples: examples of the blue-green dopant material include compounds obtained by introducing a substituent capable of increasing the wavelength of light, such as an aryl group, a heteroaryl group, an arylvinyl group, an amino group, or a cyano group, into a compound exemplified as the blue-green dopant material to the blue-green dopant material.

Further, the orange dopant material to the red dopant material include: naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes in which acetylacetone or benzoylacetone and phenanthroline are used as ligands, 4- (dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran or the like, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium salt derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyridine derivatives, and the like, and further, the following compounds are exemplified as preferable examples: a compound obtained by introducing a substituent capable of increasing the wavelength of light, such as an aryl group, a heteroaryl group, an arylvinyl group, an amino group, or a cyano group, into the compounds exemplified as the blue-to cyan-and yellow-dopant materials.

The dopant may be suitably selected from compounds described in 2004, 6/13, and references cited therein, and the like.

Among the dopant materials, an amine having a stilbene structure, a perylene derivative, a borane derivative, an aromatic amine derivative, a coumarin derivative, a pyran derivative, or a pyrene derivative is particularly preferable.

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

[ solution 99]

In the formula, ar ¹ Is an m-valent group derived from an aryl group having 6 to 30 carbon atoms, ar ² And Ar ³ Are each independently an aryl group having 6 to 30 carbon atoms, ar ¹ ～Ar ³ At least one of (A) has a stilbene structure, ar ¹ ～Ar ³ May be substituted with an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a trisubstituted silyl group (a silyl group trisubstituted with at least one of an aryl group, an alkyl group and a cycloalkyl group), or a cyano group, and m is an integer of 1 to 4.

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

[ solution 100]

In the formula, ar ² And Ar ³ Each independently an aryl group having 6 to 30 carbon atoms, ar ² And Ar ³ May be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl and cycloalkyl) or cyano.

Specific examples of the aryl group having 6 to 30 carbon atoms include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl anthryl, fluoranthryl triphenylene, pyrenyl,

Mesityl, tetracenyl, perylenyl, distyryl, distyrylphenyl, distyrylbiphenyl, distyrylfluorenyl, and the like.

Specific examples of the amines having a stilbene structure include: n, N, N ', N' -tetrakis (4-biphenyl) -4,4 '-diaminostilbene, N, N, N', N '-tetrakis (1-naphthyl) -4,4' -diaminostilbene, N, N ', N' -tetrakis (2-naphthyl) -4,4 '-diaminostilbene, N, N' -bis (2-naphthyl) -N, N '-diphenyl-4, 4' -diaminostilbene, N, N '-bis (9-phenanthryl) -N, N' -diphenyl-4, 4 '-diaminostilbene, 4' -bis [4 "-bis (diphenylamino) styryl ] -biphenyl, 1, 4-bis [4 '-bis (diphenylamino) styryl ] -benzene, 2, 7-bis [4' -bis (diphenylamino) styryl ] -9, 9-dimethylfluorene, 4 '-bis (9-ethyl-3-carbazolylidene) -biphenyl, 4' -bis (9-phenyl-3-carbazolylidene) -biphenyl and the like.

Further, amines having a stilbene structure described in Japanese patent laid-open Nos. 2003-347056 and 2001-307884 may be used.

Examples of perylene derivatives include: 3, 10-bis (2, 6-dimethylphenyl) perylene, 3, 10-bis (2, 4, 6-trimethylphenyl) perylene, 3, 10-diphenyl perylene, 3, 4-diphenyl perylene, 2,5,8, 11-tetra-tert-butylperylene, 3,4,9, 10-tetraphenylperylene, 3- (1 ' -pyrenyl) -8, 11-di (tert-butyl) perylene, 3- (9 ' -anthryl) -8, 11-di (tert-butyl) perylene, 3' -bis (8, 11-di (tert-butyl) perylenyl), and the like.

Further, perylene derivatives described in Japanese patent laid-open No. 11-97178, japanese patent laid-open No. 2000-133457, japanese patent laid-open No. 2000-26324, japanese patent laid-open No. 2001-267079, japanese patent laid-open No. 2001-267078, japanese patent laid-open No. 2001-267076, japanese patent laid-open No. 2000-34234, japanese patent laid-open No. 2001-267075, japanese patent laid-open No. 2001-217077, and the like can also be used.

Examples of the borane derivatives include: 1, 8-diphenyl-10- (ditrimethylphenylboronyl) anthracene, 9-phenyl-10- (ditrimethylphenylboronyl) anthracene, 4- (9 ' -anthryl) ditrimethylphenylboronyl naphthalene, 4- (10 ' -phenyl-9 ' -anthryl) ditrimethylphenylboronyl naphthalene, 9- (ditrimethylphenylboronyl) anthracene, 9- (4 ' -biphenyl) -10- (ditrimethylphenylboronyl) anthracene, 9- (4 ' - (N-carbazolyl) phenyl) -10- (ditrimethylphenylboronyl) anthracene, and the like.

Further, borane derivatives described in International publication No. 2000/40586, for example, can also be used.

The aromatic amine derivative is represented by the following formula, for example.

[ solution 101]

In the formula, ar ⁴ Is an n-valent group derived from an aryl group having 6 to 30 carbon atoms, ar ⁵ And Ar ⁶ Are each independently an aryl group having 6 to 30 carbon atoms, ar ⁴ ～Ar ⁶ Can be substituted by aryl, heteroaryl, alkyl, cycloalkaneA group, a trisubstituted silyl group (a silyl group trisubstituted by at least one of an aryl group, an alkyl group and a cycloalkyl group) or a cyano group, and n is an integer of 1 to 4.

Particularly, the following aromatic amine derivatives are more preferable: ar (Ar) ⁴ Is derived from anthracene,

Divalent radicals of fluorene, benzofluorene or pyrene, ar ⁵ And Ar ⁶ Are each independently an aryl group having 6 to 30 carbon atoms, ar ⁴ ～Ar ⁶ May be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 2.

Mesityl, tetracenyl, perylenyl, pentacenyl, and the like.

As aromatic amine derivatives, as

Examples of the system include: n, N, N ', N' -tetraphenyl

6,12-diamine, N, N, N ', N' -tetra (p-tolyl)

6,12-diamine, N, N, N ', N' -tetra (m-tolyl)

6,12-diamine, N, N, N ', N' -tetrakis (4-isopropylphenyl)

6, 12-diamine, N, N, N ', N' -tetrakis (naphthalen-2-yl)

6, 12-diamine, N '-diphenyl-N, N' -di (p-tolyl)

6, 12-diamine, N '-diphenyl-N, N' -bis (4-ethylphenyl)

6, 12-diamine, N '-diphenyl-N, N' -bis (4-isopropylphenyl)

6, 12-diamine, N '-diphenyl-N, N' -bis (4-tert-butylphenyl)

6, 12-diamine, N '-bis (4-isopropylphenyl) -N, N' -di (p-tolyl)

6, 12-diamine, and the like.

Examples of pyrene-based compounds include: <xnotran> N, N, N ', N' - -1,6- , N, N, N ', N' - ( ) -1,6- , N, N, N ', N' - ( ) -1,6- , N, N, N ', N' - (4- ) -1,6- , N, N, N ', N' - (3,4- ) -1,6- , N, N '- -N, N' - ( ) -1,6- , N, N '- -N, N' - (4- ) -1,6- , N, N '- -N, N' - (4- ) -1,6- , N, N '- -N, N' - (4- ) -1,6- , N, N '- (4- ) -N, N' - ( ) -1,6- , N, N, N ', N' - (3,4- ) -3,8- -1,6- , N, N, N, N- -1,8- , N, N '- ( -4- ) -N, N' - -1,8- , </xnotran> N is a radical of ¹ ,N ⁶ -diphenyl-N ¹ ,N ⁶ -bis- (4-trimethylsilyl-phenyl) -1H, 8H-pyrene-1, 6-diamine, and the like.

Further, examples of anthracene series include: n, N, N, N-tetraphenylanthracene-9, 10-diamine, N, N, N ', N' -tetra (p-tolyl) anthracene-9, 10-diamine, N, N, N ', N' -tetra (m-tolyl) anthracene-9, 10-diamine, N, N, N ', N' -tetra (4-isopropylphenyl) anthracene-9, 10-diamine, N, N '-diphenyl-N, N' -di (p-tolyl) anthracene-9, 10-diamine, N, N '-diphenyl-N, N' -di (m-tolyl) anthracene-9, 10-diamine, N, N '-diphenyl-N, N' -bis (4-ethylphenyl) anthracene-9, 10-diamine, N, N '-diphenyl-N, N' -bis (4-isopropylphenyl) anthracene-9, 10-diamine, N, N '-diphenyl-N, N' -bis (4-t-butylphenyl) anthracene-9, 10-diamine, N, N '-bis (4-isopropylphenyl) -N, N' -di (p-tolyl) anthracene-9, 10-diamine, 2, 6-di-t-butyl-N, N, N ', N' -tetra (p-tolyl) anthracene-9, 10-diamine, 2, 6-di-t-butyl-N, N '-diphenyl-N, N' -bis (4-isopropylphenyl) anthracene-9, 10-diamine, a salt thereof, a base material thereof, and a binder, 2, 6-di-t-butyl-N, N '-bis (4-isopropylphenyl) -N, N' -di (p-tolyl) anthracene-9, 10-diamine, 2, 6-dicyclohexyl-N, N '-bis (4-isopropylphenyl) -N, N' -bis (4-t-butylphenyl) anthracene-9, 10-diamine, 9, 10-bis (4-diphenylamino-phenyl) anthracene, 9, 10-bis (4-di (1-naphthylamino) phenyl) anthracene, 9, 10-bis (4-di (2-naphthylamino) phenyl) anthracene, 10-di-p-tolylamino-9- (4-di-p-tolylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (4-diphenylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (6-diphenylamino-2-naphthyl) anthracene, and the like.

In addition, there may be mentioned: [4- (4-diphenylamino-phenyl) naphthalen-1-yl ] -diphenylamine [6- (4-diphenylamino-phenyl) naphthalen-2-yl ] -diphenylamine, 4 '-bis [ 4-diphenylaminonaphthalen-1-yl ] biphenyl 4,4' -bis [ 6-diphenylaminonaphthalene-2-yl ] biphenyl, 4 "-bis [ 4-diphenylaminonaphthalene-1-yl ] -p-terphenyl, 4" -bis [ 6-diphenylaminonaphthalene-2-yl ] -p-terphenyl, and the like.

Further, aromatic amine derivatives described in Japanese patent laid-open publication No. 2006-156888 and the like can also be used.

Examples of the coumarin derivatives include coumarin-6 and coumarin-334.

Furthermore, coumarin derivatives described in, for example, japanese patent laid-open Nos. 2004-43646, 2001-76876, and Hei 6-298758 can also be used.

Examples of the pyran derivative include pyranecarbonitrile Derivatives (DCM) and (E) -4- (Dicyanomethylene) -2-tert-butyl-6- (1, 7-tetramethyljulolidinyl vinyl) pyran (4- (Dicyanomethylene) -2-tert-butyl-6- (1, 7-tetramethyljuolidin-4-yl-vinyl) -4H-pyran, DCJTB) described below.

[ solution 102]

Further, pyran derivatives described in Japanese patent laid-open Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, 2001-052869, and the like can also be used.

The material for the light-emitting layer (host material and dopant material) may be used as a polymer compound obtained by polymerizing a reactive compound obtained by substituting a reactive substituent in the material for the light-emitting layer (host material and dopant material) as a monomer, or a crosslinked polymer thereof obtained by reacting a main chain polymer with the reactive compound, or a pendant polymer compound obtained by substituting a reactive substituent in the material for the light-emitting layer (host material and dopant material) or a crosslinked pendant polymer thereof. As the reactive substituent in such a case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

< Electron injection layer, electron transport layer of organic electroluminescent element >

The electron injection layer 107 functions to efficiently inject electrons transferred from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 functions to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light-emitting layer 105. The electron transporting layer 106 and the electron injecting layer 107 are formed by laminating and mixing one or more kinds of electron transporting/injecting materials, or are formed by mixing an electron transporting/injecting material and a polymer binder.

The electron injection/transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons, and is preferably high in electron injection efficiency and capable of transporting the injected electrons efficiently. Therefore, a substance having a high electron affinity, a high electron mobility, and excellent stability is preferable, and impurities that become traps are less likely to be generated during production and use. However, when the balance between the transport of holes and electrons is considered, if the effect of efficiently blocking the flow of holes from the anode to the cathode side without being recombined is mainly exerted, the effect of improving the light emission efficiency is obtained as in the case of a material having a high electron transport ability even if the electron transport ability is not so high. Therefore, the electron injection/transport layer in this embodiment mode may also have a function of a layer that can efficiently block the transfer of holes.

The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be selected from any of compounds conventionally used as electron transport compounds in photoconductive materials, and known compounds used in electron injection layers and electron transport layers of organic EL devices. In the present invention, as the electron transporting material, a polycyclic aromatic compound represented by the general formula (1A) or (1B) may be used.

The material used for the electron transport layer or the electron injection layer preferably contains at least one compound selected from the following compounds: a compound containing an aromatic ring or a heteroaromatic ring containing at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and condensed ring derivatives thereof; and a metal complex having electron-accepting nitrogen. Specifically, there may be mentioned: aromatic ring derivatives having condensed ring systems such as naphthalene and anthracene, styrene-based aromatic ring derivatives represented by 4,4' -bis (diphenylvinyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, carbazole derivatives, indole derivatives, and the like. Examples of the metal complex having electron-accepting nitrogen include: and hydroxyoxazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials may be used alone or in combination with different materials.

Specific examples of the other electron transport compound 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 (1, 3-bis [ (4-tert-butylphenyl) 1,3, 4-oxadiazolyl ] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2, 5-diphenyl-1, 3, 4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2, 2 '-bis (benzo [ h ] quinolin-2-yl) -9,9' -spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris (N-phenylbenzimidazol-2-yl) benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, oligomeric pyridine derivatives (tris (2 '- (2-terpyridyl) derivatives, 3, 4' - (2-terpyridyl) derivatives, etc.: 6', 2' -terpyridyl)) benzene, naphthyridine derivatives (bis (1-naphthyl) -4- (1, 8-naphthyridin-2-yl) phenylphosphine oxide, etc.)), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, and the like.

In addition, a metal complex having electron-accepting nitrogen may also be used, and examples thereof include: hydroxyoxazole complexes such as hydroxyquinoline metal complexes and hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The materials can be used alone or in admixture with different materials.

Among the above materials, preferred are 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 hydroxyquinoline-based metal complexes.

Borane derivatives

The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in Japanese patent application laid-open No. 2007-27587.

[ solution 103]

In the formula (ETM-1), R ¹¹ And R ¹² Each independently at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R ¹³ ～R ¹⁶ Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, X is an arylene group which may be substituted, Y is an aryl group having 16 or less carbon atoms which may be substituted, a substituted boron group, or a substituted carbazolyl group, and n is each independently an integer of 0 to 3. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Among the compounds represented by the general formula (ETM-1), a compound represented by the following general formula (ETM-1-1) or a compound represented by the following general formula (ETM-1-2) is preferable.

[ solution 104]

In the formula (ETM-1-1), R ¹¹ And R ¹² Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R ¹³ ～R ¹⁶ Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, R ²¹ And R ²² Each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X ¹ Is an arylene group having 20 or less carbon atoms which may be substituted, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 4. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

[ solution 105]

In the formula (ETM-1-2), R ¹¹ And R ¹² Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R ¹³ ～R ¹⁶ Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X ¹ Is an arylene group having 20 or less carbon atoms which may be substituted, and n is an integer of 0 to 3 independently. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

As X ¹ Specific examples of (B) include divalent groups represented by any one of the following formulae (X-1) to (X-9). Each structural formula indicates a bonding position.

[ chemical 106]

(in the formulae, R ^a Each independently is alkyl, cycloalkyl or optionally substituted phenyl)

Specific examples of the borane derivative include the following compounds.

[ solution 107]

The borane derivative can be produced using a known raw material and a known synthesis method.

< pyridine derivatives >

The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).

[ solution 108]

Phi- (pyridine substituent) n (ETM-2)

Phi 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.

In the formula (ETM-2-1), R ¹¹ ～R ¹⁸ Each independently is hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms).

In the formula (ETM-2-2), R ¹¹ And R ¹² Each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), R ¹¹ And R ¹² May be bonded to form a ring.

In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15), and the pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. In addition, the pyridine substituent may be bonded to phi, anthracene ring or fluorene ring in the various formulae via phenylene or naphthylene. Each structural formula represents a bonding site.

[ chemical 109]

The pyridine 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. Each structural formula represents a bonding site.

[ solution 110]

At least one hydrogen of each pyridine derivative may be substituted with deuterium, and in addition, one of the two "pyridine-based substituents" in the formula (ETM-2-1) and the formula (ETM-2-2) may be substituted with an aryl group.

As R ¹¹ ～R ¹⁸ The "alkyl group" in (1) may be either a straight-chain or branched one, and examples thereof include a straight-chain alkyl group having 1 to 24 carbon atoms and a branched-chain alkyl group having 3 to 24 carbon atoms. The "alkyl group" is preferably an alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms). Further, the "alkyl group" is preferably an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms). Particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms).

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

Further, examples thereof include: <xnotran> 1- -1- ,1,1- ,1,1- ,1- -1- ,1,1,4- ,1,1,2- ,1,1- ,1,1- ,1,1- ,1,1,5- ,1- -1- ,1- -1,3- ,1,1,2,2- ,1- -1- ,1,1- ,1- -1- ,1,1,3- ,1- -1- ,1,1,2- ,1- -1,2,2- ,1- -1- ,1,1- . </xnotran>

As the alkyl group having 1 to 4 carbon atoms substituted in the pyridine substituent, the description of the alkyl group can be cited.

As R ¹¹ ～R ¹⁸ Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. Preferred "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferred "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further, a more preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms.

Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As the cycloalkyl group having 5 to 10 carbon atoms substituted in the pyridine substituent, the description of the cycloalkyl group can be cited.

As R ¹¹ ～R ¹⁸ The "aryl group" in (1) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl group having 6 to 30 carbon atoms" include: phenyl as monocyclic aryl, (1-, 2-) naphthyl as condensed bicyclic aryl, acenaphthene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) group, phenalene- (1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrene group, triphenylene- (1-, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group as condensed tetracyclic aryl, perylene- (1-, 2-, 3-) group, pentacene- (1-, 2-, 5-, 6-) group as condensed pentacyclic aryl, and the like.

Preferred "aryl group having 6 to 30 carbon atoms" include: phenyl, naphthyl, phenanthryl,

Examples of the group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group and a phenanthryl group, and examples of the group include a phenyl group, a 1-naphthyl group and a 2-naphthyl group.

R in the formula (ETM-2-2) ¹¹ And R ¹² The bond may form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

Specific examples of the pyridine derivative include the following compounds.

[ solution 111]

The pyridine derivative can be produced using a known raw material and a known synthesis method.

< fluoranthene derivative >

The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in international publication No. 2010/134352.

[ chemical 112]

In the formula (ETM-3), X ¹² ～X ²¹ Represents hydrogen, halogen, straight chainA branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Here, as the substituent at the time of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Specific examples of the fluoranthene derivative include the following compounds.

[ solution 113]

< BO series derivative >

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

[ chemical formula 114]

R ¹ ～R ¹¹ Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy ¹ ～R ¹¹ At least one hydrogen of (a) may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

In addition, R ¹ ～R ¹¹ May be bonded to each other and together with the a-, b-or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the ring formed may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy or aryloxy group, at least one of these substituents may be substituted by an aryl, heteroaryl, alkyl or cycloalkyl group.

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

As a description of the form in which the substituents or rings in formula (ETM-4) are formed, or of the multimer formed by combining the structures of a plurality of formulae (ETM-4), the description described in International publication No. 2015/102118 or the description of the polycyclic aromatic compound represented by formula (1A) or formula (1B) can be cited.

Specific examples of the BO-based derivative include the following compounds.

[ solution 115]

The BO-based derivative can be produced using a known raw material and a known synthesis method.

< Anthracene derivatives >

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

[ solution 116]

Ar is each independently divalent benzene or naphthalene, R ¹ ～R ⁴ Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms.

Each Ar may be appropriately selected independently from divalent benzene or naphthalene, and the two Ar may be different or the same, and are preferably the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form "a site including Ar and pyridine", and the site is bonded to anthracene as a group represented by any one of the following formulae (Py-1) to (Py-12), for example. Each structural formula represents a bonding site.

[ solution 117]

Among these groups, the group represented by any one of the formulae (Py-1) to (Py-9) is preferable, and the group represented by any one of the formulae (Py-1) to (Py-6) is more preferable. The two "sites containing Ar and pyridine" bonded to anthracene may be the same or different in structure, and the same structure is preferable from the viewpoint of ease of synthesis of the anthracene derivative. In view of device characteristics, the two "sites containing Ar and pyridine" preferably have the same or different structures.

With respect to R ¹ ～R ⁴ The alkyl group having 1 to 6 carbon atoms in the group (b) may be either a straight chain or branched chain. Namely, a straight-chain alkyl group having 1 to 6 carbon atoms or a branched-chain alkyl group having 3 to 6 carbon atoms. More preferably an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). Specific examples include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3-dimethylbutyl, or 2-ethylbutyl, and the like, preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, or tert-butyl.

As R ¹ ～R ⁴ Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in (b) include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

With respect to R ¹ ～R ⁴ The aryl group having 6 to 20 carbon atoms in (b) is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

Specific examples of the "aryl group having 6 to 20 carbon atoms" include: phenyl, (o, m, p) tolyl, (2, 3-, 2,4-, 2,5-, 2,6-, 3,4-, 3, 5-) xylyl, mesityl (2, 4, 6-trimethylphenyl), (o, m, p) cumenyl, as bicyclic aryl, (2-, 3-, 4-) biphenyl, as condensed bicyclic aryl, (1-, 2-) naphthyl, terphenyl group (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) as the tricyclic aryl group, anthracene- (1-, 2-, 9-) yl, acenaphthene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, (1-, 9-) -aryl group as the condensed tricyclic aryl group, 4-, 9-) phenanthrene group, triphenylene- (1-, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group as condensed four-ring system aryl group, perylene- (1-, 2-, 3-) group as condensed five-ring system aryl group, and the like.

The "aryl group having 6 to 20 carbon atoms" is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group or an m-terphenyl-5' -yl group, further preferably a phenyl group, a biphenyl group, a 1-naphthyl group or a 2-naphthyl group, and most preferably a phenyl group.

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

[ chemical formula 118]

Ar ¹ Each independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar ² As the aryl group having 6 to 20 carbon atoms, the same explanation as in the "aryl group having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

R ¹ ～R ⁴ 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,the description in said formula (ETM-5-1) can be cited.

Specific examples of the anthracene derivative include the following compounds.

[ solution 119]

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

< benzofluorene derivative >

The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

[ chemical formula 120]

Ar ¹ As the aryl group having 6 to 20 carbon atoms, the same explanation as in the "aryl group having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples thereof include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenaenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

Ar ² Each independently represents hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms) or an aryl group (preferably an aryl group having 6 to 30 carbon atoms), two Ar groups ² May be bonded to form a ring.

As Ar ² The "alkyl group" in (1) may be either a straight-chain or branched one, and examples thereof include a straight-chain alkyl group having 1 to 24 carbon atoms and a branched-chain alkyl group having 3 to 24 carbon atoms. The "alkyl group" is preferably an alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms). Further, the "alkyl group" is preferably an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms). In particular The "alkyl group" is preferably an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). Specific examples of the "alkyl group" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

As Ar ² Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The "cycloalkyl group" is preferably a cycloalkyl group having 3 to 10 carbon atoms. More preferred "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further, a more preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As Ar ² The "aryl group" in (1) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl group having 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, pentacenyl, and the like.

Two Ar ² The bond may form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

Specific examples of the benzofluorene derivative include the following compounds.

[ solution 121]

The benzofluorene derivative can be produced using a known raw material and a known synthesis method.

< phosphine oxide derivative >

The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International publication No. 2013/079217.

[ chemical formula 122]

R ⁵ Is substituted or unsubstituted alkyl with 1 to 20 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, aryl with 6 to 20 carbon atoms or heteroaryl with 5 to 20 carbon atoms,

R ⁶ CN, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, heteroalkyl group with 1 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, heteroaryl group with 5 to 20 carbon atoms, alkoxy group with 1 to 20 carbon atoms or aryloxy group with 6 to 20 carbon atoms,

R ⁷ and R ⁸ Each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R ⁹ is oxygen or sulfur, and is selected from the group consisting of,

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.

Here, as the substituent at the time of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

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

[ 123]

R ¹ ～R ³ May be the same or different and is selected from the group consisting of hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, arylthioether, aryl, heterocyclic, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silane, and condensed rings formed between adjacent substituents。

Ar ¹ May be the same or different and is an arylene or heteroarylene group. Ar (Ar) ² Which may be the same or different, and is aryl or heteroaryl. Wherein Ar is ¹ And Ar ² Has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer of 0 to 3, and when n is 0, no unsaturated moiety is present, and when n is 3, no R is present ¹ 。

Among these substituents, the alkyl group means, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and the alkyl group may be unsubstituted or substituted. The substituent to be substituted is not particularly limited, and examples thereof include: alkyl groups, aryl groups, heterocyclic groups, and the like, which are also common in the following description. The number of carbon atoms of the alkyl group is not particularly limited, and is usually in the range of 1 to 20 in terms of easiness of obtaining and cost.

The cycloalkyl group means a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group and the like, and the cycloalkyl group may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, and is usually in the range of 3 to 20.

The aralkyl group means an aromatic hydrocarbon group such as a benzyl group or a phenylethyl group through which an aliphatic hydrocarbon is interposed, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, and is usually in the range of 1 to 20.

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

The cycloalkenyl group means an unsaturated alicyclic hydrocarbon group having a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, and the cycloalkenyl group may be unsubstituted or substituted.

The alkynyl group means an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, and the alkynyl group may be unsubstituted or substituted. The carbon number of the alkynyl group is not particularly limited, and is usually in the range of 2 to 20.

The alkoxy group means, for example, an aliphatic hydrocarbon group such as a methoxy group through an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the alkoxy group is not particularly limited, and is usually in the range of 1 to 20.

The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.

The cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.

The aryl ether group means, for example, an aromatic hydrocarbon group such as phenoxy group, which is separated by an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the aryl ether group is not particularly limited, and is usually in the range of 6 to 40.

The arylthioether group is a group in which an oxygen atom of an ether bond of an arylether group is substituted with a sulfur atom.

The aryl group represents, for example, 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 of the aryl group is not particularly limited, and is usually in the range of 6 to 40.

The heterocyclic group means a cyclic structural group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, and a carbazolyl group, and the heterocyclic group may be unsubstituted or substituted. The number of carbon atoms of the heterocyclic group is not particularly limited, and is usually in the range of 2 to 30.

Halogen means fluorine, chlorine, bromine and iodine.

The aldehyde group, carbonyl group, or amino group may contain a group substituted with an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocyclic ring, or the like.

Further, the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocyclic ring may be unsubstituted or substituted.

The silyl group means, for example, a silicon compound group such as a trimethylsilyl group, and the silyl group may be unsubstituted or substituted. The number of carbon atoms of the silane group is not particularly limited, and is usually in the range of 3 to 20. The number of silicon is usually 1 to 6.

The condensed ring formed between the adjacent substituent 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. to form conjugated or non-conjugated condensed rings therebetween. Here, in the case where n is 1, two R' s ¹ May form conjugated or non-conjugated condensed rings with each other. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring inner structure, and may further be condensed with other rings.

Specific examples of the phosphine oxide derivative include the following compounds.

[ solution 124]

The phosphine oxide derivatives can be produced using known starting materials and known synthesis methods.

[ pyrimidine derivatives ]

The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in international publication No. 2011/021689.

[ 125]

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. n is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3.

Examples of the "aryl group" of the "aryl group which may be substituted" include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and further preferably aryl groups having 6 to 12 carbon atoms.

Specific "aryl" groups include: phenyl as monocyclic aryl, (2-, 3-, 4-) biphenyl as bicyclic aryl, (1-, 2-) naphthyl as condensed bicyclic aryl, (m-terphenyl-2 ' -yl, m-terphenyl-4 ' -yl, m-terphenyl-5 ' -yl, o-terphenyl-3 ' -yl, o-terphenyl-4 ' -yl, p-terphenyl-2 ' -yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) as tricyclic aryl, (1-, 3-, 4-, 5-) acenaphthylene- (1-, 2-, 3-, 4-, 9-) non-terphenyl- (1-, 2-) terphenyl, (1-, 2-, 3-, 4-, 9-, tetracyclic aryl as condensed tricyclic aryl, (5 ' -tetra (1-, 3-, 5' -tetra-terphenyl) biphenyl, m-2 ' -yl, m-terphenyl-4 ' -yl, m-terphenyl-5 ' -yl, m-terphenyl-2 ' -yl, p-2-, 3-, 4' -phenanthrenyl, m-terphenyl-3-, 5' -tetra-yl, and m-terphenyl-4 ' -yl as condensed tricyclic aryl, and the like, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, pentacene- (1-, 2-, 5-, 6-) group and the like.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocyclic rings containing one to five heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific examples of the heteroaryl group 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, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphoazanyl, the monovalent benzazanyl of dibenzophosphole oxide ring, dibenzophospholyl, furanyl, indolyl, benzazolyl, and the like.

Additionally, at least one hydrogen of the aryl and heteroaryl groups may be substituted, e.g., by the aryl or heteroaryl group, respectively.

Specific examples of the pyrimidine derivative include the following compounds.

[ solution 126]

The pyrimidine derivative can be produced using a known raw material and a known synthesis method.

< carbazole derivative >

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 by a single bond or the like. Details are described in U.S. patent application publication No. 2014/0197386.

[ solution 127]

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. Each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

Examples of the "aryl group" of the "aryl group which may be substituted" include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and still more preferably aryl groups having 6 to 12 carbon atoms.

Specific "aryl" groups include: phenyl as a monocyclic aryl group, (2-, 3-, 4-) biphenyl as a bicyclic aryl group, (1-, 2-) naphthyl as a condensed bicyclic aryl group, (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) as a tricyclic aryl group, acenaphthene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) as non- (1-, 2-) as well as (1-, 2-, 3-, 4-, 9-) phenanthrene as well as tetrabiphenyl (5 ' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl and m-tetrabiphenyl) as tetracyclic aryl, triphenylene- (1-, as condensed tricyclic aryl, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, pentacene- (1-, 2-, 5-, 6-) group, and the like.

Specific examples of the heteroaryl group 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, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, naphthobenzothienyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphole oxide ring, monovalent group of the dibenzophosphole oxide ring, furazanyl, thiazanyl, carbazolyl, benzazolyl, and benzindolinyl.

The carbazole derivative may be a polymer in which a plurality of compounds represented by the formula (ETM-9) are bonded to each other by a single bond or the like. In this case, the bond may be 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.

Specific examples of the carbazole derivative include the following compounds.

[ solution 128]

The carbazole derivative can be produced using a known raw material and a known synthesis method.

< triazine derivative >

The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). The details are described in U.S. patent publication 2011/0156013.

[ solution 129]

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. n is an integer of 1 to 3, preferably 2 or 3.

Specific examples of the triazine derivative include the following compounds.

[ chemical formula 130]

The triazine derivative can be produced using a known raw material and a known synthesis method.

< benzimidazole derivative >

The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

[ solution 131]

Phi- (benzimidazole substituent) n (ETM-11)

Phi 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, the "benzimidazole substituent" is a substituent in which a pyridyl group in the "pyridine substituent" of the above-mentioned formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is substituted with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium. In the following structural formula, a symbol indicates a bonding position.

[ solution 132]

R in the benzimidazolyl group ¹¹ As the hydrogen, alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms or aryl group having 6 to 30 carbon atoms, R in the above-mentioned formulas (ETM-2-1) and (ETM-2-2) can be cited ¹¹ And (4) description.

φ is further preferably an anthracycline or fluorene ring, and the structure in this case can be referred to the description in said formula (ETM-2-1) or formula (ETM-2-2), R in each formula ¹¹ ～R ¹⁸ Reference may be made to the description in said formula (ETM-2-1) or formula (ETM-2-2). In addition, in the formula (ETM-2-1) or (ETM-2-2) described above, two pyridine substituents are bonded, but when these are substituted with benzimidazole substituents, two pyridine substituents may be substituted with benzimidazole substituents (i.e., n = 2), or one pyridine substituent may be substituted with benzimidazole substituents and R may be substituted with benzimidazole substituents ¹¹ ～R ¹⁸ Substituted with another pyridine substituent (i.e., n = 1). Further, R in the formula (ETM-2-1) may be substituted with a benzimidazole substituent ¹¹ ～R ¹⁸ And R is ¹¹ ～R ¹⁸ Substituted "pyridine-based substituent".

Specific examples of the benzimidazole derivative include: 1-phenyl-2- (4- (10-phenylanthren-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, 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.

[ solution 133]

The benzimidazole derivative can be produced using a known raw material and a known synthesis method.

[ phenanthroline derivative ]

The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details thereof are disclosed in International publication No. 2006/021982.

[ solution 134]

R of the formulae ¹¹ ～R ¹⁸ Each independently is hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group (preferably an aryl group having 6 to 30 carbon atoms). In addition, R in the formula (ETM-12-1) ¹¹ ～R ¹⁸ Is bonded to phi as the aryl ring.

At least one hydrogen in each phenanthroline derivative may be substituted by deuterium.

As R ¹¹ ～R ¹⁸ Alkyl, cycloalkyl and aryl in (1), R in said formula (ETM-2) can be cited ¹¹ ～R ¹⁸ And (4) description. Further, phi is represented by the following structural formula, for example, in addition to the above examples. In addition, R in the following structural formula is hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl or terphenyl independently. In addition, in each structural formula, a indicates a bonding position.

[ solution 135]

Specific examples of the phenanthroline derivative include: 4, 7-diphenyl-1, 10-phenanthroline, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline, 9, 10-bis (1, 10-phenanthroline-2-yl) anthracene, 2, 6-bis (1, 10-phenanthroline-5-yl) pyridine, 1,3, 5-tris (1, 10-phenanthroline-5-yl) benzene, 9' -difluoro-bis (1, 10-phenanthroline-5-yl), 2, 9-dimethyl-4, 7-biphenyl-1, 10-phenanthroline (bathocoupprine), 1, 3-bis (2-phenyl-1, 10-phenanthroline-9-yl) benzene, or a compound represented by the following structural formula.

[ solution 136]

The phenanthroline derivative can be produced using a known raw material and a known synthesis method.

< hydroxyquinoline-based metal complex >

The hydroxyquinoline metal complex is, for example, a compound represented by the following general formula (ETM-13).

[ solution 137]

In the formula, R ¹ ～R ⁶ Each independently is 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.

Specific examples of the hydroxyquinoline metal complex include: lithium 8-quinolinolate, aluminum tris (8-quinolinolate), aluminum tris (4-methyl-8-quinolinolate), aluminum tris (5-methyl-8-quinolinolate), aluminum tris (3, 4-dimethyl-8-quinolinolate), aluminum tris (4, 5-dimethyl-8-quinolinolate), aluminum tris (4, 6-dimethyl-8-quinolinolate), aluminum bis (2-methyl-8-quinolinolate) (phenol), aluminum bis (2-methyl-8-quinolinolate) (2-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (3-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (4-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (2-phenylphenol), aluminum bis (2-methyl-8-quinolinolate) (3-phenylphenol), aluminum bis (2-methyl-8-quinolinolate) (4-phenylphenol), aluminum bis (2-methyl-8-quinolinolate) (2, 3-xylenolate), aluminum bis (2-methyl-8-quinolinolate) (2, aluminum bis (2-dimethyl-8-quinolinolate) (2, 8-quinolinolate) (3-xylenol, aluminum bis (2, 6-dimethyl-8-quinolinolate) (2 Aluminum, aluminum bis (2-methyl-8-quinolinol) (3, 5-dimethylphenol), aluminum bis (2-methyl-8-quinolinol) (3, 5-di-tert-butylphenol), aluminum bis (2-methyl-8-quinolinol) (2, 6-diphenylphenol), aluminum bis (2-methyl-8-quinolinol) (2, 4, 6-triphenylphenol), aluminum bis (2-methyl-8-quinolinol) (2, 4, 6-trimethylphenol), aluminum bis (2-methyl-8-quinolinol) (2, 4,5, 6-tetramethylphenol), aluminum bis (2-methyl-8-quinolinol) (1-naphthol), aluminum bis (2-methyl-8-quinolinol) (2-naphthol), aluminum bis (2, 4-dimethyl-8-quinolinol) (2-phenylphenol), aluminum bis (2, 4-dimethyl-8-quinolinol) (3-phenylphenol), aluminum bis (2, 4-dimethyl-8-quinolinol) (4-dimethylphenol) (3, 5-dimethylphenol), aluminum bis (2, 4-dimethylquinolinol) (3, 4-dimethylphenol), aluminum bis (2, 4-8-hydroxyquinoline) (3, 5, 6-triphenylphenol), aluminum bis (2, bis (2-methyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2, 4-dimethyl-8-quinolinolato) aluminum- μ -oxo-bis (2, 4-dimethyl-8-quinolinolato) aluminum, bis (2-methyl-4-ethyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinato) aluminum- μ -oxo-bis (2-methyl-5-beryllium-8-quinolinolato) aluminum, bis (10-quinolinolato) aluminum, and the like.

The hydroxyquinoline metal complex can be produced using a known raw material and a known synthesis method.

Thiazole derivatives and benzothiazole derivatives

The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

[ 138]

Phi- (thiazole substituent) n (ETM-14-1)

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

[ solution 139]

Phi- (benzothiadiazole-based substituent) n (ETM-14-2)

Phi is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and the "thiazole-based substituent" or "benzothiazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" of the formula (ETM-2), the formula (ETM-2-1) or the formula (ETM-2-2) is substituted with the following thiazolyl group or benzothiazolyl group, and at least one of the thiazole derivative and the benzothiazole derivative may be substituted with deuterium. In the following structural formula, a symbol indicates a bonding position.

[ solution 140]

φ is further preferably an anthracycline or fluorene ring, and the structure in this case can be referred to the description in said formula (ETM-2-1) or formula (ETM-2-2), R in each formula ¹¹ ～R ¹⁸ The description in said formula (ETM-2-1) or formula (ETM-2-2) may be cited. In addition, although the above formula (ETM-2-1) or formula (ETM-2-2) has been described as a form in which two pyridine substituents are bonded, when these are substituted with a thiazole substituent (or a benzothiazole substituent), two pyridine substituents may be substituted with a thiazole substituent (or a benzothiazole substituent) (that is, n = 2), and either one of the pyridine substituents may be substituted with a thiazole substituent (or a benzothiazole substituent) and R may be substituted with R ¹¹ ～R ¹⁸ Another pyridine substituent (i.e., n = 1). Further, R in the formula (ETM-2-1) may be substituted with a thiazole-based substituent (or a benzothiazole-based substituent), for example ¹¹ ～R ¹⁸ And R is ¹¹ ～R ¹⁸ Substituted "pyridine-based substituents".

These thiazole derivatives and benzothiazole derivatives can be produced using known starting materials and known synthetic methods.

Silole derivatives

Examples of the silole derivative include compounds represented by the following formula (ETM-15). The details are described in Japanese patent laid-open No. 9-194487.

[ solution 141]

X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. As for details of these groups, the descriptions in the above general formula (1A) and general formula (1B) and the description in the above formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are each a group in which an alkyl moiety in an alkoxy group is substituted with an alkenyl group or an alkynyl group, and the details of these alkenyl group and alkynyl group can be referred to the description of the above formula (ETM-7-2).

In addition, X and Y may be bonded to form a cycloalkyl ring (and a partially unsaturated ring thereof), and details of the cycloalkyl ring may be referred to the description of the cycloalkyl group in the general formula (1A) and the general formula (1B).

R ¹ ～R ⁴ Each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl (sulfonyl), mercapto (sulfonyl), silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isocyanate, or cyano, which may be substituted with alkyl, cycloalkyl, aryl, or halogen, or may form a condensed ring with an adjacent substituent.

With respect to R ¹ ～R ⁴ Halogen in (1)Alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl, and alkynyl groups, the descriptions in the general formula (1A) and the general formula (1B) can be cited.

With respect to R ¹ ～R ⁴ In the above general formulae (1A) and (1B), the details of the alkyl group, the aryl group and the alkoxy group in the alkylcarbonyl group, arylcarbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylcarbonyloxy group, arylcarbonyloxy group, alkoxycarbonyloxy group and aryloxycarbonyloxy group are also cited.

Examples of the silane group include a silane group and a group in which at least one of the three hydrogens of the silane group is independently substituted with an aryl group, an alkyl group or a cycloalkyl group, preferably a trisubstituted silane group, and examples thereof include: triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, and the like. As details of the aryl group, the alkyl group and the cycloalkyl group, the descriptions in the general formula (1A) and the general formula (1B) can be cited.

The condensed ring formed between the adjacent substituent is, for example, R ¹ And R ² 、R ² And R ³ 、R ³ And R ⁴ Etc. to form conjugated or non-conjugated condensed rings therebetween. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring structure, and may further be condensed with other rings.

Among them, the compound is preferably represented by the formula R ¹ And R ⁴ In the case of phenyl, X and Y are not alkyl or phenyl. In addition, it is preferable not to satisfy R at the same time ¹ And R ⁴ In the case of thienyl, X and Y are alkyl and R ² And R ³ Is alkyl, aryl, alkenyl or R ² And R ³ A cycloalkyl group bonded to form a ring. In addition, it is preferable that when R is ¹ And R ⁴ When it is a silane group, R ² 、R ³ X and Y are each independently not hydrogen or alkyl of 1 to 6 carbon atoms. In addition, it is preferable that R is ¹ And R ² In the case of a structure in which a benzene ring is condensed, X and Y are not an alkyl group or a phenyl group.

These silole derivatives can be produced using known starting materials and known synthetic methods.

< oxazoline derivative >

The oxazoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in international publication No. 2017/014226.

[ solution 142]

In the formula (ETM-16),

phi is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, at least one hydrogen of phi may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 2 to 18 carbon atoms,

y is-O-, -S-or > N-Ar, ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, R is ¹ ～R ⁵ Each independently represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein Ar in the formula > N-Ar and R are ¹ ～R ⁵ Any of which is a site bonded to L,

l is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

[ solution 143]

In the formula (L-1), X ¹ ～X ⁶ Are each independently = CR ⁶ -or = N-, X ¹ ～X ⁶ Is = CR ⁶ -，X ¹ ～X ⁶ Two of (2 = CR) ⁶ R in (a-C) ⁶ Is a site bonded to the phi or oxazoline ring, other than = CR ⁶ R in (a-C) ⁶ Is a hydrogen, and is,

in the formula (L-2), X ⁷ ～X ¹⁴ Are each independently = CR ⁶ -or = N-, X ⁷ ～X ¹⁴ Is = CR ⁶ -，X ⁷ ～X ¹⁴ Two of (2 = CR) ⁶ R in (A-C) ⁶ Is a site bonded to the phi or oxazoline ring, other than = CR ⁶ R in (a-C) ⁶ Is a hydrogen atom, and is,

at least one hydrogen of L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 10 carbon atoms,

m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the oxazoline ring and L may be the same or different, and,

at least one hydrogen in the compound represented by formula (ETM-16) may be substituted with deuterium.

The specific oxazoline derivative is a compound represented by the following general formula (ETM-16-1) or general formula (ETM-16-2).

[ solution 144]

In the formulae (ETM-16-1) and (ETM-16-2),

In the formula (ETM-16-1), Y is-O-, -S-or > N-Ar, ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms,

in the formula (ETM-16-1), R ¹ ～R ⁴ Each independently represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein R ¹ And R ² Are the same, and R ³ And R ⁴ In the same way, the first and second,

in the formula (ETM-16-2), R ¹ ～R ⁵ Each independently represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein R represents ¹ And R ² Are the same, and R ³ And R ⁴ Are identical to each other,

in the formulae (ETM-16-1) and (ETM-16-2),

[ solution 145]

In the formula (L-1), X ¹ ～X ⁶ Are each independently = CR ⁶ -or = N-, X ¹ ～X ⁶ Is = CR ⁶ -，X ¹ ～X ⁶ Two of (c = CR) ⁶ R in (A-C) ⁶ Is a site bonded to the phi or oxazoline ring, other than = CR ⁶ R in (A-C) ⁶ Is a hydrogen atom, and is,

in the formula (L-2), X ⁷ ～X ¹⁴ Each independently = CR ⁶ -or = N-, X ⁷ ～X ¹⁴ Is = CR ⁶ -，X ⁷ ～X ¹⁴ Two of (c = CR) ⁶ R in (A-C) ⁶ Is a site bonded to the phi or oxazoline ring, other than = CR ⁶ R in (a-C) ⁶ Is a hydrogen atom, and is,

at least one hydrogen of the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

Preferably: φ is selected from the group consisting of monovalent groups represented by the following formulas (φ 1-1) to (φ 1-18), divalent groups represented by the following formulas (φ 2-1) to (φ 2-34), trivalent groups represented by the following formulas (φ 3-1) to (φ 3-3), and tetravalent groups represented by the following formulas (φ 4-1) to (φ 4-2), wherein at least one hydrogen of φ is substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. In the following structural formula,. Indicates a bonding site.

[ solution 146]

[ solution 147]

[ solution 148]

Z in the formula is > CR ₂ N-Ar, > N-L, -O-or-S-, > CR ₂ Wherein R is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, R may be bonded to each other to form a ring, ar in > N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and L in > N-L is L in the general formula (ETM-16), the formula (ETM-16-1) or the general formula (ETM-16-2).

Preferably, the following components are used: l is a divalent group of a ring selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline and pteridine, and at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 10 carbon atoms.

Preferably, the following components are used: ar in > N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in > N-Ar as Y is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

Preferably, the following components are used: r ¹ ～R ⁴ Each independently represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein R represents ¹ And R ² Same as R ³ And R ⁴ Are identical to each other, and R ¹ ～R ⁴ All of them do not simultaneously form hydrogen, and when m is 1 or 2, the group formed by the oxazoline ring and L is the same.

Specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

[ 149]

[ chemical formula 150]

More preferably: φ is selected from the group consisting of divalent radicals represented by the following formulae (φ 2-1), (φ 2-31), formulae (φ 2-32), formulae (φ 2-33), and formulae (φ 2-34), at least one hydrogen of φ may be substituted with an aryl group having 6 to 18 carbon atoms, and a in each formula represents a bonding site,

[ solution 151]

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, at least one hydrogen of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 14 carbon atoms,

ar in > N-Ar as Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, at least one hydrogen of Ar may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms,

R ¹ ～R ⁴ each independently represents hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, wherein R represents ¹ And R ² Same as R ³ And R ⁴ Are identical to each other, and R ¹ ～R ⁴ Not all of them will be simultaneously converted to hydrogen, and,

m is 2 and the group formed by the oxazoline ring and L is the same.

Other specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

[ solution 152]

With respect to details of the alkyl group, cycloalkyl group, aryl group or heteroaryl group in the formulae for specifying the oxazoline derivative, the explanations in the general formula (1A) and the general formula (1B) may be cited.

The oxazoline derivative can be produced using a known raw material and a known synthesis method.

The electron transport layer or the electron injection layer may further contain a substance capable of reducing a 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 reducing property, 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 preferably used.

Preferable reducing substances include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), rb (work function 2.16 eV), and Cs (work function 1.95 eV), and alkaline earth metals such as Ca (work function 2.9 eV), sr (work function 2.0 to 2.5 eV), and Ba (work function 2.52 eV), and particularly preferable substances have a work function of 2.9eV or less. Among these, the reducing substance is more preferably K, rb or Cs as an alkali metal, further preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing power, and by adding a relatively small amount of the alkali metals to a material forming the electron transporting layer or the electron injecting layer, improvement in light emission luminance or prolongation in life in the organic EL element can be achieved. In addition, as the reducing substance having a work function of 2.9eV or less, a combination of two or more of these alkali metals is also preferable, and a combination including Cs, for example, a combination of Cs and Na, cs and K, cs and Rb, or Cs and Na and K is particularly preferable. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to a material for forming an electron transporting layer or an electron injecting layer, improvement in light emission luminance or prolongation in life of the organic EL element can be achieved.

The material for an electron injection layer and the material for an electron transport layer may be used as a polymer compound obtained by polymerizing a reactive compound obtained by substituting a reactive substituent in the material for an electron injection layer and the material for an electron transport layer with a main chain polymer as a monomer or a crosslinked polymer thereof, or as a suspended polymer compound obtained by reacting a reactive compound with a main chain polymer or a crosslinked polymer thereof. As the reactive substituent in the above case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

< cathode in organic electroluminescent element >

The cathode 108 functions to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it is a material capable of efficiently injecting electrons into the organic layer, and the same material as the material 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, and alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride and aluminum) are preferable. In order to improve the electron injection efficiency to improve the element characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, in general, these low work function metals are most often unstable in the atmosphere. In order to improve this, for example, a method of doping a small amount of lithium, cesium, or magnesium into an organic layer and using an electrode having high stability is known. As the other dopant, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can be used. However, the present invention is not limited to these examples.

Further, the following are preferable examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, alloys using these metals, and inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, and the like are laminated to protect the electrodes. The method for producing these electrodes is not particularly limited as long as conduction can be achieved by resistance heating, electron beam evaporation, sputtering, ion plating, coating, or the like.

< Binders usable in Each layer >

The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer may be used individually or may be 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, acrylonitrile-butadiene-styrene (ABS) resin, or 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, or silicone resin, which is a polymer binder.

< method for manufacturing organic electroluminescent element >

Each layer constituting the organic EL element can be formed by forming a material to be each layer 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, casting, or coating. The film thickness of each layer formed in the above-described manner is not particularly limited, and may be appropriately set according to the properties of the material, but is usually in the range of 2nm to 5000 nm. The film thickness can be measured by a crystal oscillation type film thickness measuring apparatus or the like. When a thin film is formed by a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the target crystal structure and the association structure of the film, and the like. The deposition conditions are preferably set to +50 ℃ to +400 ℃ in a boat heating temperature and 10 degrees of vacuum ^-6 Pa～10 ^-3 Pa, a deposition rate of 0.01nm/sec to 50nm/sec, a substrate temperature of-150 ℃ to +300 ℃, and a film thickness of 2nm to 5 μm.

When a dc voltage is applied to the organic EL element obtained as described above, the anode may be applied with a + polarity and the cathode may be applied with a-polarity, and when a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element emits light even when a pulse current or an alternating current is applied thereto. In addition, the waveform of the applied alternating current may be arbitrary.

Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element including an anode, a hole injection layer, a hole transport layer, a light-emitting layer including a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

< vapor deposition method >

An anode is formed by forming a thin film of an anode material on an appropriate substrate by an evaporation method or the like, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A target organic EL element is obtained by co-evaporating a host material and a dopant material on the thin film to form a thin film as a light-emitting layer, forming an electron transport layer and an electron injection layer on the light-emitting layer, and further forming a thin film containing a substance for a cathode as a cathode by an evaporation method or the like. In the production of the organic EL element, the order of production may be reversed, and the organic EL element may be produced by using a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode in this order.

< Wet film Forming method >

The low-molecular-weight compound capable of forming each organic layer of the organic EL element is prepared as a liquid composition for forming an organic layer, and a wet film-forming method is performed using the composition. In the case where an appropriate organic solvent for dissolving the low-molecular compound is not present, the composition for forming an organic layer may be prepared from a polymer compound which is polymerized together with another monomer or main chain polymer having a solubility function as a reactive compound obtained by substituting a reactive substituent in the low-molecular compound, or the like.

In general, a wet film forming method forms a coating film by passing through a coating step of coating a composition for forming an organic layer on a substrate and a drying step of removing a solvent from the coated composition for forming an organic layer. In the case where the polymer compound has a crosslinkable substituent (also referred to as a crosslinkable polymer compound), the polymer compound is further crosslinked by the drying step to form a crosslinked polymer. Depending on the coating process, a method using a spin coater is called a spin coating method, a method using a slit coater is called a slit coating method, a method using a plate is called a gravure, offset, reverse offset, or flexo printing method, a method using an ink jet printer is called an ink jet method, and a method of spraying mist is called a spray method. The drying step may be carried out by air drying, heating, drying under reduced pressure, or the like. The drying step may be performed only once, or may be performed a plurality of times by using different methods or conditions. Alternatively, for example, calcination under reduced pressure may be carried out in combination with different methods.

The wet film formation method is a film formation method using a solution, and examples thereof include a partial printing method (ink jet method), a spin coating method, a casting method, and a coating method. Unlike the vacuum deposition method, the wet film formation method can form a film under atmospheric pressure without using an expensive vacuum deposition apparatus. In addition, the wet film formation method can be used for large-area production or continuous production, which leads to reduction in production cost.

On the other hand, in comparison with the vacuum deposition method, there is a case where lamination by a wet film formation method is difficult. In the case of producing a laminated film by a wet film formation method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and to use a composition whose solubility is controlled, a cross-linking of the lower layer, an Orthogonal solvent (mutually insoluble solvent), and the like. However, even when these techniques are used, it is sometimes difficult to use the wet film formation method for coating all films.

Thus, in general, the following methods can be employed: only a plurality of layers were formed by a wet film formation method, and the remaining layers were formed by a vacuum evaporation method, thereby producing an organic EL element.

For example, a part of a process for producing an organic EL element by applying a wet film formation method is described below.

(procedure 1) deposition of Anode by vacuum deposition

(procedure 2) film formation by Wet film formation method of composition for Forming hole injection layer containing Material for hole injection layer

(program 3) film formation by Wet film formation method of composition for Forming hole transport layer containing Material for hole transport layer

(procedure 4) film formation by Wet film formation method of light-emitting layer-Forming composition containing host Material and dopant Material

(program 5) deposition of Electron transport layer by vacuum deposition

(procedure 6) film formation of the Electron injection layer by vacuum deposition

(program 7) film formation of cathode by vacuum vapor deposition

By passing through the procedure, an organic EL element including an anode/a hole injection layer/a hole transport layer/a light emitting layer containing a host material and a dopant material/an electron transport layer/an electron injection layer/a cathode can be obtained.

Of course, there is a means for preventing the light-emitting layer of the underlayer from dissolving, and a means for forming a film from the cathode side in reverse to the above procedure is used to prepare a composition for forming a layer containing a material for an electron-transporting layer or a material for an electron-injecting layer, and the composition can be formed into a film by a wet film-forming method.

< other film formation method >

For forming a film of the composition for forming an organic layer, a Laser Induced Thermal Imaging (LITI) method may be used. LITI is a method of performing thermal vapor deposition of a compound attached to a substrate by using a laser, and the organic layer forming composition can be used for a material to be coated on a substrate.

< optional Process >

Before and after each step of film formation, an appropriate treatment step, cleaning step and drying step may be added as appropriate. Examples of the treatment step include: exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment with an appropriate solvent, heat treatment, and the like. Further, a series of steps for producing the bank may be mentioned.

Photolithography techniques may be used in the fabrication of the banks. As the bank material that can be used for photolithography, a positive resist material and a negative resist material can be used. Further, a printing method capable of forming a pattern, such as an ink jet method, gravure offset printing, reverse offset printing, or screen printing, may be used. At this time, a permanent resist material may also be used.

As materials for the bank, there can be mentioned: polysaccharides and derivatives thereof, homopolymers and copolymers of vinyl monomers having hydroxyl groups, biopolymer compounds, polyacryl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polythioethers, polysulfones, polyphenylenes, polyphenylethers, polyurethanes, epoxy (meth) acrylates, melamine (meth) acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymer (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornenes, synthetic rubbers, polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, fluoroolefin-hydrocarbon olefin copolymer polymers, and fluorocarbon polymers, but the present invention is not limited thereto.

< composition for forming organic layer used in Wet film Forming method >

The composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL element or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light-emitting layer contains a polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is at least one 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 light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent for dissolving the first component and the second component in the composition, and a smooth and uniform surface shape is obtained by a controlled evaporation rate of the third component itself at the time of coating.

< organic solvent >

The composition for forming an organic layer contains at least one organic solvent. The film forming property, the presence or absence of defects in the film, the surface roughness, and the smoothness can be controlled and improved by controlling the evaporation rate of the organic solvent during film formation. In addition, when the film formation is performed by using the ink jet method, the meniscus (meniscus) stability at the pin hole of the ink jet head can be controlled, and the ejection property can be controlled/improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light emission characteristics, efficiency, and lifetime of the organic EL element having the organic layer obtained from the composition for forming an organic layer can be improved.

(1) Physical Properties of organic solvent

The boiling point of the at least one organic solvent is 130 to 300 ℃, more preferably 140 to 270 ℃, and still more preferably 150 to 250 ℃. From the viewpoint of the ejection property of the inkjet, the boiling point is preferably higher than 130 ℃. In addition, from the viewpoint of defects, surface roughness, residual solvent and smoothness of the coating film, the boiling point is preferably less than 300 ℃. The organic solvent is more preferably a composition containing two or more organic solvents from the viewpoint of good ink jet ejection properties, film formation properties, smoothness, and a small amount of residual solvent. On the other hand, the composition may be made into a solid state by removing the solvent from the organic layer-forming composition in consideration of the transportability and the like.

The organic solvent further 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 particularly preferred _GS ) Lower than the Boiling Point (BP) of the Poor Solvent (PS) _PS ) The composition of (1).

By adding poor solvent with high boiling point, the good solvent with low boiling point volatilizes first during film forming, the concentration of the content in the composition and the concentration of the poor solvent are increased, and the rapid film forming is promoted. Thus, a coating film having few defects, small surface roughness, and high smoothness can be obtained.

Difference in solubility (S) _GS -S _PS ) Preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. Difference of Boiling Points (BP) _PS -BP _GS ) Preferably 10 ℃ or higher, more preferably 30 ℃ or higher, and still more preferably 50 ℃ or higher.

The organic solvent is removed from the coating film by a drying step such as vacuum, reduced pressure, or heating after film formation. In the case of heating, from the viewpoint of improving coating film formability, it is preferable to perform the heating at a glass transition temperature (Tg) of at least one of the solutes) +30 ℃. From the viewpoint of reducing the residual solvent, it is preferable to heat at least one solute at a glass transition temperature (Tg) of-30 ℃. 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. Further, the drying may be performed a plurality of times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific examples of organic solvents

Examples of the organic solvent used in the composition for forming an organic layer include: an alkylbenzene solvent, a phenyl ether solvent, an alkyl ether solvent, a cyclic ketone solvent, an aliphatic ketone solvent, a monocyclic ketone solvent, a solvent having a diester skeleton, and a fluorine-containing solvent, and specific examples thereof include: pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecane-2-ol, cyclohexanol, α -terpineol, β -terpineol, γ -terpineol, δ -terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol 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-trifluoromethylanisole, mesitylene, 1,2, 4-trimethylbenzene, tert-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, sec-butylbenzene, 3-methylanisole, <xnotran> 4- -3- , (cymene), 1,2,3- , 1,2- ,2- ,4- (4-fluoroveratrole), 2,6- , ,3- , (decalin) ( (decahydronaphthalene)), ,2,5- ,2,4- , ,3,5- , , 1- -3,5- , , ,3,4- , (o-tolunitrile), , (veratrole), 1,2,3,4- , , , , , 1- , ,2- ,3- ,2,2 '- (2,2' -bitolyl), , , , , ,2,3- , 1- -4- ( ) , 1- -4- ( ) , 1- -4- ( ) , 1- -4- ( ) , 1- -4- ( ) , , , , </xnotran> Benzyl heptyl ether, benzyl octyl ether, and the like, but are not limited thereto. The solvents may be used alone or in combination.

< optional component >

The composition for forming an organic layer may contain any component within a range not impairing the properties thereof. Examples of the optional component include a binder and a surfactant.

(1) Adhesive agent

The composition for forming an organic layer may contain a binder. As for the binder, the obtained film is joined to the substrate while forming the film at the time of film formation. In addition, the organic layer forming composition plays a role in dissolving, dispersing, and binding other components.

Examples of the binder used in the organic layer-forming composition include: acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, ionomer (ionomer), chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, teflon (Teflon), acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile-styrene copolymer (AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the resins and polymers, but is not limited thereto.

The binder used in the composition for forming an organic layer may be only one type, or may be used in combination of two or more types.

(2) Surface active agent

The organic layer forming composition may contain a surfactant, for example, in order to control the film surface uniformity of the organic layer forming composition, and the solvent affinity and liquid repellency of the film surface. Surfactants are classified into ionic and nonionic surfactants according to the structure of hydrophilic groups, and further classified into alkyl surfactants, silicon surfactants, and fluorine surfactants according to the structure of hydrophobic groups. Further, the molecular structure is classified into a simple molecular system having a relatively small molecular weight and a high molecular system having a side chain or branch having a large molecular weight. Further, the compositions are classified into a single system and a mixed system in which two or more surfactants and a base material are mixed. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include: polyflow No.45, polyflow KL-245, polyflow No.75, polyflow No.90, polyflow No.95 (trade name, manufactured by Kyoeisha chemical industries, ltd.); disperbyk 161, disperbyk 162, disperbyk 163, disperbyk 164, disperbyk 166, disperbyk 170, disperbyk 180, disperbyk 181, disperbyk 182, BYK 300, BYK 306, BYK 310, BYK 320, BYK 330, BYK 342, BYK 344, BYK 346 (trade name, manufactured by Japan bischem (BYK-Chemie) (stock); KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by shin-Etsu chemical industries, ltd.); safflon (Surflon) SC-101, safflon (Surflon) KH-40 (trade name, manufactured by Qingmei Chemical Co., ltd.); forgertet (Ftergent) 222F, forgertet (Ftergent) 251, FTX-218 (trade name, manufactured by Nees (NEOS) (stock)); avotuo (EFTOP) EF-351, avotuo (EFTOP) EF-352, avotuo (EFTOP) EF-601, avotuo (EFTOP) EF-801, avotuo (EFTOP) EF-802 (trade name, manufactured by Mitsubishi Material, ltd.); meijia method (Megafac) F-470, meijia method (Megafac) F-471, meijia method (Megafac) F-475, meijia method (Megafac) R-08, meijia method (Megafac) F-477, meijia method (Megafac) F-479, meijia method (Megafac) F-553, meijia method (Megafac) F-554 (trade name, manufactured by Diesen (DIC) (Strand)); fluoroalkyl benzenesulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglyceryl tetrakis (fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl sulfamate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene naphthyl ether, alkylbenzenesulfonate, and alkyldiphenyl ether disulfonate.

One kind of surfactant may be used, or two or more kinds thereof may be used in combination.

< composition and physical Properties of composition for Forming organic layer >

The content of each component in the composition for forming an organic layer is determined in consideration of good solubility, storage stability and film forming property of each component in the composition for forming an organic layer, good film quality of a coating film obtained from the composition for forming an organic layer, good ejection property in the case of using an inkjet method, and good electrical characteristics, light emitting characteristics, efficiency and lifetime of an organic EL element having an organic layer formed using the composition. For example, in the case of the composition for forming a light-emitting layer, it is preferable that: the first component is 0.0001 to 2.0 wt% based on the total weight of the composition for forming a light-emitting layer, the second component is 0.0999 to 8.0 wt% based on the total weight of the composition for forming a light-emitting layer, and the third component is 90.0 to 99.9 wt% based on the total weight of the composition for forming a light-emitting layer.

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

The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by a known method and stirring, mixing, heating, cooling, dissolving, dispersing, or the like. After the preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas replacement/encapsulation treatment, and the like may be optionally performed.

As the viscosity of the organic layer forming composition, a good film forming property and a good ejection property when the ink jet method is used can be obtained when the viscosity is high. On the other hand, when the viscosity is low, a film can be easily formed. Therefore, the viscosity of the organic layer forming composition is preferably 0.3 to 3 mPas, more preferably 1 to 3 mPas at 25 ℃. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

When the surface tension of the composition for forming an organic layer is low, a coating film having good film formability and no defects can be obtained. On the other hand, when the surface tension is high, good ink ejection properties can be obtained. Therefore, the surface tension of the organic layer forming composition is preferably 20 to 40mN/m, more preferably 20 to 30mN/m, at 25 ℃. In the present invention, the surface tension is a value measured using a pendant drop method.

< crosslinkable Polymer: a compound represented by the general formula (XLP-1) >

Next, a case where the polymer compound has a crosslinkable substituent will be described. The crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

[ solution 153]

In the formula (XLP-1),

MUx, ECx and k have the same meanings as MU, EC and k in the formula (H3), wherein the compound represented by the 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 wt% in the molecule.

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

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the polymer compound, and is preferably a substituent having the following structure. Each structural formula represents a bonding site.

[ solution 154]

<xnotran> L , -O-, -S-, ＞ C = O, -O-C (= O) -, 1 ～ 12 , 1 ～ 12 1 ～ 12 . </xnotran> Among the substituents, preferred is a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17), and more preferred is a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17).

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures. In the following structural formula,. Indicates a bonding site.

[ solution 155]

[ solution 156]

[ chemical 157]

[ solution 158]

< method for producing Polymer Compound and crosslinkable Polymer Compound

The production method of the polymer compound and the crosslinkable polymer compound will be described by taking the compound represented by the above formula (H3) and the compound represented by the above formula (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include an aromatic solvent, a saturated/unsaturated hydrocarbon solvent, an alcohol solvent, and an ether solvent, and examples thereof include: dimethoxyethane, 2- (2-methoxyethoxy) ethane, 2- (2-ethoxyethoxy) ethane, and the like.

Alternatively, the reaction may be carried out as a two-phase system. In the case of carrying out the reaction in a two-phase system, a phase transfer catalyst such as quaternary ammonium salt may be added as required.

When the compound of the formula (H3) and the compound of the formula (XLP-1) are produced, they can be produced in one stage or through multiple stages. The synthesis may be carried out by an all-round polymerization method in which the reaction is started after all the raw materials are placed in the reaction vessel, by a dropping polymerization method in which the raw materials are dropped into the reaction vessel, by a precipitation polymerization method in which the product precipitates as the reaction proceeds, and by a combination of these methods as appropriate. For example, when the compound represented by formula (H3) is synthesized in one stage, the target compound is obtained by performing the reaction in a state where the Monomer Unit (MU) and the end-capping unit (EC) are added to the reaction vessel. In addition, when the compound represented by the general formula (H3) is synthesized in multiple stages, the target compound is obtained by adding and reacting the end-capping unit (EC) after polymerizing the Monomer Unit (MU) to a target molecular weight. When different types of Monomer Units (MU) are added in multiple stages to carry out the reaction, a polymer having a concentration gradient with respect to the structure of the monomer units can be produced. In addition, after the precursor polymer is prepared, a polymer as a target can be obtained by a subsequent reaction.

Further, when the polymerizable group of the Monomer Unit (MU) is selected, the primary structure of the polymer can be controlled. For example, as shown in 1 to 3 of the synthesis flow, a polymer having a random primary structure (1 of the synthesis flow), a polymer having a regular primary structure (2 and 3 of the synthesis flow), and the like can be synthesized, and can be used in combination as appropriate depending on the target. Further, when a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer (hyperbranched polymer) or a dendrimer (dendrimer) can be synthesized.

[ chemical 159]

a. b = MU or MUx

Polymerizable group = x, y (x and y bond, respectively)

1) Polymers synthesized using two monomers (x-a-y) and (x-b-y)

2) Polymers synthesized using two monomers (x-a-x) and (y-b-y)

3) Polymers synthesized using two monomers (x-a-y) and (y-b-y)

The monomer unit usable in the present invention can be synthesized by the methods described in Japanese patent laid-open publication No. 2010-189630, international publication No. 2012/086671, international publication No. 2013/191088, international publication No. 2002/045184, international publication No. 2011/049241, international publication No. 2013/146806, international publication No. 2005/049546, international publication No. 2015/145871, japanese patent laid-open publication No. 2010-215886, japanese patent laid-open publication No. 2008-106241, international publication No. 2016/031639, and Japanese patent laid-open publication No. 2011-174062.

Further, specific polymer synthesis procedures can be synthesized by methods described in japanese patent laid-open nos. 2012-036388, 2015/008851, 2012-36381, 2012-144722, 2015/194448, 2013/146806, 2015/145871, 2016/031639, 2016/125560, and 2011/049241.

< application example of organic electroluminescent element >

In addition, the present invention is also applicable to a display device including an organic EL element, an illumination device including an organic EL element, or the like.

A display device or an illumination device including an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known driving device, and can be driven by a known driving method such as dc driving, pulse driving, or ac driving.

Examples of the display device include: a panel display such as a color flat panel display, a flexible display such as a flexible color organic Electroluminescence (EL) display, and the like (for example, refer to japanese patent laid-open No. 10-335066, japanese patent laid-open No. 2003-321546, and japanese patent laid-open No. 2004-281086). Examples of the display mode of the display include a matrix mode and a segment mode. Furthermore, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are two-dimensionally arranged in a lattice shape, a mosaic shape, or the like, and characters or images are displayed by a set of pixels. The shape or size of the pixel is determined according to the application. For example, in image and character display of a personal computer, a monitor, and a television, a rectangular pixel having a side of 300 μm or less is generally used, and in the case of a large-sized display such as a display screen, a pixel having a side of mm level is used. In the case of monochrome display, pixels of the same color may be arranged, and in the case of color display, pixels of red, green, and blue are arranged in parallel to perform display. In this case, a triangular shape and a striped shape are typical. Also, as a driving method of the matrix, any one of a line-sequential (line-sequential) driving method or an active matrix may be used. The line sequential driving has an advantage of a simple structure, but when the operation characteristics are taken into consideration, the active matrix is sometimes more excellent, and therefore the driving method needs to be used separately depending on the application.

In the segmentation method (type), a pattern is formed so as to display information determined in advance, and the determined region is caused to emit light. Examples thereof include: time and temperature display in a digital clock or a thermometer, operation state display of an audio device or an induction cooker, panel display of an automobile, and the like.

Examples of the illumination device include an illumination device such as an indoor illumination, and a backlight of a liquid crystal display device (see, for example, japanese patent laid-open nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are used mainly for improving visibility of display devices that do not emit light, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display panels, signs, and the like. In particular, as a backlight for personal computers, which is a problem in thinning of liquid crystal display devices, the backlight using the light emitting element of the present embodiment has characteristics of thinness and light weight, when considering that thinning is difficult due to the inclusion of a fluorescent lamp or a light guide plate in the conventional system.

3-2. Other organic devices

The polycyclic aromatic compound of the present invention can be used for the production of an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, or the like, in addition to the organic electroluminescent element.

An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and includes a gate electrode in addition to an active electrode and a drain electrode. The organic field effect transistor is a transistor as follows: 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 is arbitrarily blocked to control the current. A field effect transistor is easy to be miniaturized compared with a single transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.

In general, the organic field effect transistor may be configured 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 of the present invention, and a gate electrode is provided through an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structures.

(1) Substrate, gate electrode, insulator layer, source electrode, drain electrode, and organic semiconductor active layer

(2) Substrate, gate electrode, insulator layer, organic semiconductor active layer, source electrode and drain electrode

(3) Substrate/organic semiconductor active layer/source electrode and drain electrode/insulator layer/gate electrode

(4) Substrate/source electrode and drain electrode/organic semiconductor active layer/insulator layer/gate electrode

The organic field effect transistor configured as described above can be applied to a pixel driving switching element of an active matrix driving type liquid crystal display or an organic electroluminescence display, and the like.

An 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 stacked 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 of 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 the physical properties thereof. In the organic thin film solar cell, the polycyclic aromatic compound of the present invention can function as a hole transport material or an electron transport material. The organic thin-film solar cell may suitably include a hole blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like, in addition to the above. In the organic thin film solar cell, known materials used in the organic thin film solar cell can be appropriately selected and used in combination.

Quantum dots having a narrow emission half-value width are used as phosphors for wavelength conversion filters for the purpose of a wide color gamut of a display. On the other hand, there are problems as follows: the instability to oxidation is high due to the high aggregation caused by the nano-sized fine particles, and the metal used is limited to a contaminant. The polycyclic aromatic compound of the present invention is useful as a phosphor for a wavelength conversion filter. The matrix in which the polycyclic aromatic compound is dispersed is preferably a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability, and examples thereof include (meth) acrylic polymers such as polymethyl (meth) acrylate and cycloolefin polymers such as Zeonex.

[ examples ]

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. First, a synthesis example of the polycyclic aromatic compound will be described below.

Synthesis example (1): synthesis of Compound (1A-1)

[ solution 160]

Iodine tribromide (2.35g, 6.0mmol,6.0 eq.) was added to a flask containing compound (Int-1A-1) (1.39g, 1.0mmol,1.0 eq.) 2, 6-di-tert-butylpyridine (0.57g, 3.0mmol,3.0 eq.) and 1,2, 4-trichlorobenzene (50 ml) at room temperature under nitrogen atmosphere. Then, the mixture was heated and stirred at 60 ℃ for 4 hours. The reaction was cooled to room temperature. To the reaction solution was added a phosphate buffer (30 ml), and the organic layer was recovered by liquid separation and concentrated under reduced pressure. For the obtained crude product, purification by a silica gel column (eluent: hexane/dichloromethane =1/1 (volume ratio)) and washing with methanol were performed, whereby compound (1A-1) (10.1 mg) was obtained as a yellow solid.

[ chemical 161]

The compound (1A-1) as a target was confirmed at m/z =1413.6820 by Matrix-assisted laser desorption/ionization-time of flight/Mass Spectrometer (MALDI-TOF/MS).

Synthesis example (2): synthesis of Compound (1A-2)

[ chemical 162]

Compound (1A-2) (0.18 g) was synthesized according to the same procedure except that compound (Int-1A-1) (1.39g, 1.0mmol,1.0 eq.) was changed to compound (Int-1A-2) (1.45g, 1.0mmol,1.0 eq.) in the synthesis method described in Synthesis example (1).

[ chemical 163]

The compound (1A-2) as the target substance was confirmed at m/z =1479.7441 by MALDI-TOF/MS.

Synthesis example (3): synthesis of Compound (1A-19)

[ 164]

Compound (1A-19) (0.18 g) was synthesized according to the same procedure except that compound (Int-1A-1) (1.39g, 1.0mmol,1.0 eq.) was changed to compound (Int-1A-19) (1.35g, 1.0mmol,1.0 eq.) in the synthesis method described in synthetic example (1).

[ solution 165]

The compound (1A-19) as the target was confirmed at m/z =1367.4118 by MALDI-TOF/MS.

Synthesis example (4): synthesis of Compound (1A-33)

[ solution 166]

Compound (1A-33) (0.11 g) was synthesized according to the same procedure except that compound (Int-1A-1) (1.39g, 1.0mmol,1.0 eq.) was changed to compound (Int-1A-33) (1.32g, 1.0mmol,1.0 eq.) in the synthesis method described in synthetic example (1).

[ 167]

The compound (1A-33) as the target was confirmed at m/z =1337.6576 by MALDI-TOF/MS.

Synthesis example (5): synthesis of Compound (1A-88)

[ solution 168]

Compound (Int-1A-88) (138mg, 0.10 mmol), 2, 6-di-t-butylpyridine (64.9. Mu.L, 0.30 mmol) and 1,2, 4-trichlorobenzene (1.0 mL) were added to boron triiodide (313mg, 0.80mmol) under a nitrogen atmosphere, and the mixture was stirred at 60 ℃ for 4 hours. After the reaction solution was cooled to room temperature, a phosphate buffer (pH = 7) was added, extraction was performed three times with dichloromethane, and the solvent was distilled off under reduced pressure, thereby obtaining a crude product. The obtained crude product was subjected to washing with hexane, whereby compound (1A-88) (12.4 mg, yield 8.9%) was obtained as a yellow solid.

[ 169]

The target compound (1A-88) was confirmed by Nuclear Magnetic Resonance (NMR) and MALDI-TOF/MS.

¹ H-NMR(500MHz,CDCl ₃ )：δ＝1.08(s,36H),5.42(d,1H),5.62(dd,2H),5.69(s,1H),6.71-6.75(m,5H),6.79-6.85(m,2H),6.88-6.96(m,10H),7.01-7.17(m,14H),7.33-7.48(m,12H),7.56-7.58(m,1H),7.67(dd,1H),8.77(dd,1H),9.14(dd,1H),10.30(s,1H).

¹¹ B-NMR(128MHz,CDCl ₃ )：δ＝36.9

MALDI-TOF/MS：m/z＝1394.73

The other polycyclic aromatic compound of the present invention can be synthesized by the method according to the above synthesis example by appropriately changing the compound as a raw material.

Next, examples of the organic EL device using the compound of the present invention are shown in order to explain the present invention in more detail, but the present invention is not limited to these examples.

Evaluation of basic Properties >

Preparation of samples

When the absorption characteristics and the emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated are evaluated, there are a case where the compound to be evaluated is dissolved in a solvent and evaluated in the solvent and a case where the compound to be evaluated is evaluated in a thin film state. Further, when the evaluation is performed in a thin film state, there are a case where only the compound to be evaluated is made thin and evaluated depending on the use form of the compound to be evaluated in the organic EL element, and a case where the compound to be evaluated is dispersed in an appropriate matrix material and made thin and evaluated.

As the matrix material, commercially available polymethyl methacrylate (PMMA) or the like can be used. In this example, a thin film sample was prepared by dissolving PMMA and a compound to be evaluated in toluene and then forming a thin film on a transparent support substrate (10 mm × 10 mm) made of quartz by a spin coating method.

Further, a film sample in the case where the host compound is the matrix material was produced as follows. A quartz transparent support substrate (10 mm. Times.10 mm. Times.1.0 mm) was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Changzhou industry, ltd.), a molybdenum vapor deposition boat containing a host compound and a molybdenum vapor deposition boat containing a dopant compound were set, and then a vacuum vessel was depressurized to 5X 10 ^-4 Pa is up to. Next, the two evaporation boats were heated simultaneously, and the two compounds were co-evaporated to have an appropriate film thickness, thereby forming a mixed thin film (sample) of the host compound and the dopant compound. Here, the evaporation speed is controlled according to the set mass ratio of the host compound to the dopant compound.

Evaluation of absorption characteristics and luminescence characteristics

The absorption spectrum of the sample was measured using an ultraviolet-visible near-infrared spectrophotometer (Shimadzu corporation, UV-2600). The measurement of the fluorescence spectrum or phosphorescence spectrum of the sample was performed using a spectrofluorometer (Hitachi High-Tech, manufactured by Hitachi technologies, ltd., F-7000).

For measurement of fluorescence spectrum, photoluminescence was measured by excitation at room temperature at an appropriate excitation wavelength. For the measurement of the phosphorescence spectrum, the measurement was performed in a state in which the sample was immersed in liquid nitrogen (temperature 77K) using an attached cooling unit. In order to observe the phosphorescence spectrum, the delay time from the irradiation of the excitation light until the start of measurement was adjusted using a chopper. With respect to the sample, photoluminescence was measured by excitation at an appropriate excitation wavelength.

In addition, the fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring apparatus (manufactured by Hamamatsu photonics, inc., C9920-02G).

Evaluation of fluorescence lifetime (delayed fluorescence)

The fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring apparatus (manufactured by Hamamatsu photonics (Strand), C11367-01). Specifically, a light-emitting component having a fast fluorescence lifetime and a light-emitting component having a slow fluorescence lifetime at a maximum light-emitting wavelength measured at an appropriate excitation wavelength are observed. In a fluorescence lifetime measurement at room temperature of a general organic EL material emitting fluorescence, a triplet component is deactivated by heat, and thus a slow light emitting component in which a triplet component derived from phosphorescence participates is hardly observed. In the case where a slow light-emitting component is observed in a compound to be evaluated, triplet energy indicating a long excitation lifetime is transferred to singlet energy by thermal activation, and is observed as delayed fluorescence.

Calculation of energy gap (Eg)

From the long wavelength end a (nm) of the absorption spectrum obtained by the method, it was calculated by Eg = 1240/a.

Calculation of E (S, sh), E (T, sh) and Δ E (ST)

Singlet excitation level E (S, sh) is determined by wavelength B at the intersection of the tangent line passing through the inflection point on the short wavelength side of the peak of the fluorescence spectrum and the base line _Sh (nm) by using E (S, sh) =1240/B _Sh To calculate. The triplet excitation level E (T, sh) is defined by the inflection point on the short wavelength side of the peak passing through the phosphorescence spectrumC at the intersection of the tangent line of (a) and the base line _Sh (nm) by E (T, sh) =1240/C _Sh To calculate.

Δ E (ST) is defined by the energy difference between E (S, sh) and E (T, sh), i.e., Δ E (ST) = E (S, sh) -E (T, sh). In addition, Δ E (ST) can also be calculated by using, for example, a method described in "pure organic electroluminescent material (100% conversion from electroluminescence to light) that realizes 100% electro-optical conversion", h. Kache, h. Suzuki, t. Fornia, k. Zhijin, k. Clarin, s. Jubao, t. Small mei, h. Large rock, f. Suzuki, a. Ju, y. Village, c. Andea (h.kaji, h.suzuki, t.fukushima, k.shizu, k.katsuaki, s.kubo, t.komino, h.oiwa, f.suzuki, a.wakamiya, y.mua, c.adachi, and com (nat. Communication), 8476.

< example A1 >

Evaluation of basic physical Properties of Compound (1A-1)

[ absorption characteristics ]

A thin film-formed substrate (made of glass) in which the compound (1A-1) was dispersed in PMMA at a concentration of 1 mass% was prepared, and the absorption spectrum was measured. As a result, the maximum absorption wavelength λ (Abs) was 449nm. The Eg obtained from the intersection of the tangent passing through the inflection point on the long wavelength side of the absorption peak and the base line was 2.78eV.

[ luminescence characteristics ]

A thin film-formed substrate (made of glass) in which the compound (1A-1) was dispersed in PMMA at a concentration of 1 mass% was prepared, and the substrate was excited at an excitation wavelength of 360nm at room temperature and 77K, and the fluorescence spectrum was observed. As a result, the maximum light emission wavelength λ (PL) was 459nm, the full width at half maximum FWHM was 19nm, and the maximum light emission wavelength λ (PL, 77K) was 460nm at 77K. E (S1) obtained from the intersection of the tangent of the inflection point on the short-wavelength side of the light peak at 77K and the base line was 2.76eV.

Further, a thin film-formed substrate (made of quartz) in which the compound (1A-1) was dispersed in PMMA at a concentration of 1 mass% was prepared, and excitation was performed at an excitation wavelength of 340nm to measure a fluorescence quantum yield PLQY, and the result was 85%, which was a very high value.

Further, a thin film-formed substrate (made of glass) in which the compound (1A-1) was dispersed in PMMA at a concentration of 1 mass% was prepared, and the substrate was excited at an excitation wavelength of 340nm at 77K to observe a phosphorescence spectrum. As a result, the maximum light emission wavelength λ (Phos) was 461nm. E (T1) obtained from the intersection of the base line and the tangent line passing through the inflection point on the short-wavelength side of the phosphorescence peak was 2.75eV.

When Δ E (ST) was calculated, it was 0.01eV.

The lifetime of the delayed fluorescence component was measured using a fluorescence lifetime measuring apparatus using a thin film-formed substrate (made of quartz) in which the compound (1A-1) was dispersed in PMMA at a concentration of 1 mass%, and was 3.0 μ sec (fig. 2). In the fluorescence lifetime measurement, fluorescence having an emission lifetime of 100ns or less is determined as immediate fluorescence, fluorescence having an emission lifetime of 0.1 μ sec or more is determined as delayed fluorescence, and data in a range of 10 or more photon count numbers from 5 μ sec is used for calculating the fluorescence lifetime.

< example A2 to example A4, and example A5 >

Evaluation was performed under the same conditions as in example A1 except that the compound (1A-1) was changed to the compound (1A-2), the compound (1A-19), the compound (1A-33), or the compound (1A-88). The results are summarized in table A1.

< comparative example RA1 and comparative example RA2 >

Evaluation was performed under the same conditions as those used for the evaluation of example A1 except that the compound (1A-1) was changed to R-BD1 or R-BD 2. The results are summarized in table A1.

[ Table A1]

R-BD1 and R-BD2 in Table A1 are the following compounds.

[ solution 170]

Evaluation of vapor deposition organic EL element

< example B1 >

On a glass substrate (26 mm. Times.28 mm. Times.0.7 mm) on which an anode comprising indium-tin oxide (ITO) having a thickness of 50nm was formed, a vacuum deposition method was used to control the degree of vacuum to 5X 10 ^-4 Pa the films were laminated.

First, NPD was deposited on ITO to a film thickness of 40nm, and TcTa was deposited thereon to a film thickness of 15nm, thereby forming a hole layer including two layers. Then, the mCP was vapor-deposited to a film thickness of 15nm to form an electron blocking layer. Then, DOBNA1 as a host and 1A-1 as a dopant were co-evaporated from different evaporation sources to form a light-emitting layer having a thickness of 20 nm. At this time, the mass ratio of the host and the emitting dopant was set to 99:1. next, 2CzBN was deposited to a film thickness of 10nm, and BPy-TP2 was deposited to a film thickness of 20nm, thereby forming an electron transport layer including two layers. Then, liF was deposited to have a film thickness of 1nm, and aluminum was deposited thereon to have a film thickness of 100nm to form a cathode, thereby obtaining an organic EL device (table B1).

< example B2 to example B4, and example B8 >

Elements were produced under the same conditions except that compound (1A-1) was changed to compound (1A-2), compound (1A-19), compound (1A-33), or compound (1A-88) in the step of producing the element in example B1 (table B1).

< comparative examples RB1 and RB2 >

Elements were produced under the same conditions except that the compound (1A-1) was changed to R-BD1 or R-BD2 in the element production step of example B1 (Table B1).

[ Table B1]

"NPD" in said Table B1 is N, N ' -diphenyl-N, N ' -dinaphthyl-4, 4' -diaminobiphenyl, "TcTa" is 4,4',4 "-tris (N-carbazolyl) triphenylamine," mCP "is 1, 3-bis (N-carbazolyl) benzene," DOBNA "is 3, 11-di-o-tolyl-5, 9-dioxa-13B-boranonaphtho [3,2,1-de ] anthracene," 2CZBN "is 3, 4-di (9H-carbazol-9-yl) benzonitrile," BPy-TP2 "is 2, 7-di ([ 2,2' -bipyridyl ] -5-yl) triphenylene. The chemical structure is shown below.

[ solution 171]

Next, for each fabricated device, 1000cd/m was measured ² Characteristics in light emission, i.e., voltage (V) and current density (mA/cm) ² ) External quantum efficiency (EQE,%), and luminescence wavelength (nm), and then measured to be maintained at 10mA/cm ² The current density of (3) is 50% or more of the initial luminance in the constant current driving.

[ Table B2]

< example B5 >

First, NPD was deposited on ITO to a film thickness of 40nm, and TcTa was deposited thereon to a film thickness of 15nm, thereby forming a hole layer including two layers. Then, the mCP was vapor-deposited to a film thickness of 15nm to form an electron blocking layer. Then, mCBP as a host, 4CzIPN as an Auxiliary Dopant (AD), and a compound (1A-1) as a dopant were co-evaporated from different evaporation sources to form a light-emitting layer with a thickness of 20 nm. At this time, the mass ratio of the host, the auxiliary dopant, and the dopant was set to 82:17:1. next, 2CzBN was vapor-deposited so that the film thickness became 10nm, and then BPy-TP2 was vapor-deposited so that the film thickness became 20nm, thereby forming an electron transport layer including two layers. Then, liF was deposited to have a film thickness of 1nm, and aluminum was deposited thereon to have a film thickness of 100nm to form a cathode, thereby obtaining an organic EL device (table B3).

< embodiments B6 and B7 >

In the element fabrication step of example B5, elements were fabricated under the same conditions except that the constituent material of the light-emitting layer was changed to the material described in table B3 (table B3).

< comparative example RB3 >

[ Table B3]

The host material for the respective example B7 is Tris-PCz:3Cz-TRZ =1:1 (mass ratio).

The chemical structures of "mCBP", "Tris-PCz", "3Cz-TRZ", "4CzIPN" and "Firpic" in the above-mentioned Table B3 are shown below.

[ chemical 172]

Next, for each fabricated device, 1000cd/m was measured ² Characteristics in light emission, i.e., voltage (V) and current density (mA/cm) ² ) External quantum efficiency (EQE,%), and emission wavelength (nm), and then measured to be maintained at 10mA/cm ² The current density of (3) is 50% or more of the initial luminance in the constant current driving.

[ Table B4]

< C. evaluation of coating type organic EL element >

Next, an organic EL device obtained by forming an organic layer by coating will be described.

< macromolecular host compound: synthesis of SPH-101

SPH-101 was synthesized according to the method described in International publication No. 2015/008851. A copolymer in which M2 or M3 is bonded to the adjacent site of M1 is obtained, and each unit is estimated to be 50:26:24 (molar ratio).

[ chemical 173]

< high molecular hole transport compound: synthesis of XLP-101

XLP-101 was synthesized according to the method described in Japanese patent laid-open publication No. 2018-61028. A copolymer in which M5 or M6 is bonded to a portion adjacent to M4 is obtained, and each unit is estimated to be 40:10:50 (molar ratio).

[ solution 174]

< examples C1 to C9 >

A coating solution of the material forming each layer was prepared to fabricate a coating-type organic EL element.

< production of organic EL element in embodiments C1 to C3 >

The material composition of each layer in the organic EL device is shown in table C1.

[ Table C1]

The chemical structure of "ET1" in table C1 is shown below.

[ chemical 175]

< preparation of composition (1) for Forming light-emitting layer >

The composition (1) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was obtained. The prepared light-emitting layer-forming composition was spin-coated on a glass substrate and heat-dried under reduced pressure, whereby a coating film free of film defects and excellent in smoothness was obtained.

The compound (X) is a polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (that is, the monomer has a reactive substituent), a crosslinked polymer obtained by further crosslinking the polymer compound, a pendant-type polymer compound obtained by substituting the monomer in a main chain-type polymer, or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer. The polymer compound or the suspended polymer compound used for obtaining the crosslinked polymer or the suspended polymer has a crosslinkable substituent.

Poly (3, 4-ethylenedioxythiophene) (poly (3, 4-ethylenedioxythiophene), PEDOT): poly (styrene sulfonate) (PSS) solution >

Commercially available PEDOT was used: PSS solution (Clevelos (TM) P VP AI4083, PEDOT: aqueous dispersion of PSS, manufactured by Heraeus Holdings).

[ solution 176]

< preparation of OTPD solution >

OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (a photo cation polymerization initiator, manufactured by sandapro, inc.) were dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7 wt% and an IK-2 concentration of 0.007 wt%.

[ solution 177]

< preparation of XLP-101 solution >

A 0.7 wt% XLP-101 solution was prepared by dissolving XLP-101 in xylene at a concentration of 0.6 wt%.

< preparation of PCz solution >

PCz (polyvinylcarbazole) was dissolved in dichlorobenzene to prepare a 0.7 wt% PCz solution.

[ solution 178]

< example C1 >

Spin-coating PEDOT: the PSS solution was calcined on a hot plate at 200 ℃ for 1 hour, thereby producing PEDOT: PSS film (hole injection layer). Then, the OTPD solution was spin-coated, dried on a hot plate at 80 ℃ for 10 minutes, and then exposed to light at an exposure intensity of 100mJ/cm using an exposure machine ² The film was exposed to light and calcined on a hot plate at 100 ℃ for 1 hour, whereby an OTPD film (hole transport layer) having a film thickness of 30nm, which was insoluble in the solution, was formed. Subsequently, the composition (1) for forming a light-emitting layer was spin-coated and calcined on a hot plate at 120 ℃ for 1 hour to form a light-emitting layer having a thickness of 20 nm.

The produced multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by showa vacuum (stock)), and a molybdenum-made evaporation boat containing ET1, a molybdenum-made evaporation boat containing LiF, and a tungsten-made evaporation boat containing aluminum were installed. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, heating ET1 to form a filmThe electron transport layer was formed by vapor deposition so as to have a thickness of 30 nm. The deposition rate in forming the electron transport layer was set to 1nm/sec. Then, liF is heated and vapor deposition is performed at a vapor deposition rate of 0.01 to 0.1nm/sec so that the film thickness becomes 1 nm. Then, aluminum was heated and vapor-deposited to a film thickness of 100nm to form a cathode. An organic EL element was obtained in the manner described.

< example C2 >

An organic EL element was obtained in the same manner as in example C1. Further, the hole transport layer was formed into a film having a thickness of 30nm by spin-coating an XLP-101 solution and calcining the solution on a hot plate at 200 ℃ for 1 hour.

< example C3 >

An organic EL element was obtained in the same manner as in example C1. Further, the hole transport layer was formed into a film having a thickness of 30nm by spin-coating a PCz solution and calcining the solution on a hot plate at 120 ℃ for 1 hour.

< production of organic EL elements in embodiments C4 to C6 >

The material composition of each layer in the organic EL device is shown in table C2.

[ Table C2]

< preparation of composition (2) for Forming light-emitting layer to composition (4) for Forming light-emitting layer >

The following components were stirred until a uniform solution was obtained, to prepare a composition (2) for forming a light-emitting layer.

mCBP 1.98 wt.%

Compound (X) 0.02% by weight

98.00% by weight of toluene

The following components were stirred until a uniform solution was obtained, to prepare a composition (3) for forming a light-emitting layer.

SPH-101.98% by weight

Compound (X) 0.02% by weight

98.00% by weight of xylene

The following components were stirred until a uniform solution was obtained, to prepare a composition (4) for forming a light-emitting layer.

DOBNA 1.98 wt%

Compound (X) 0.02% by weight

98.00% by weight of toluene

In Table C2, "mCBP" is 3,3 '-bis (N-carbazolyl) -1,1' -biphenyl, "DOBNA" is 3, 11-di-o-tolyl-5, 9-dioxa-13 b-boranaphtho [3,2,1-de ] anthracene, and "TSPO1" is diphenyl [4- (triphenylsilyl) phenyl ] phosphine oxide. The chemical structure is shown below.

[ chemical 179]

< example C4 >

An ND-3202 (manufactured by Nissan chemical industry) solution was spin-coated on a glass substrate on which ITO was formed to a thickness of 45nm, and then the substrate was heated at 50 ℃ for 3 minutes and 230 ℃ for 15 minutes in an atmospheric environment, thereby forming an ND-3202 film (hole injection layer) having a thickness of 50 nm. Then, the solution of XLP-101 was spin-coated and heated on a hot plate at 200 ℃ for 30 minutes under a nitrogen atmosphere, thereby forming an XLP-101 film (hole transport layer) with a film thickness of 20 nm. Subsequently, the composition (2) for forming a light-emitting layer was spin-coated and heated at 130 ℃ for 10 minutes in a nitrogen atmosphere to form a 20nm light-emitting layer.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (stock)), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were installed therein. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, TSPO1 was heated and vapor-deposited to a film thickness of 30nm, thereby forming an electron transport layer. Deposition rate at the time of forming an electron transport layerSet to 1nm/sec. Then, liF is heated and vapor deposition is performed at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness becomes 1 nm. Then, aluminum was heated and vapor-deposited to a film thickness of 100nm to form a cathode. An organic EL element was obtained in the manner described.

< embodiments C5 and C6 >

An organic EL device was obtained in the same manner as in example C4 using the composition (3) for forming a light-emitting layer or the composition (4) for forming a light-emitting layer.

< production of organic EL element in embodiments C7 to C9 >

The material composition of each layer in the organic EL device is shown in table C3.

[ Table C3]

< preparation of composition (5) for Forming light-emitting layer to composition (7) for Forming light-emitting layer >

The following components were stirred until a uniform solution was obtained, to prepare a composition (5) for forming a light-emitting layer.

The following components were stirred until a uniform solution was obtained, to prepare a composition (6) for forming a light-emitting layer.

The following components were stirred until a uniform solution was obtained, to prepare a composition (7) for forming a light-emitting layer.

In Table C3, "2PXZ-TAZ" is 10,10' - ((4-phenyl-4H-1, 2, 4-triazole-3, 5-diyl) bis (4, 1-phenyl)) bis (10H-phenoxazine). The chemical structure is shown below.

[ solution 180]

< example C7 >

An ND-3202 (manufactured by Nissan chemical industry) solution was spin-coated on a glass substrate on which ITO was formed to a thickness of 45nm, and then the substrate was heated at 50 ℃ for 3 minutes and 230 ℃ for 15 minutes in an atmospheric environment, thereby forming an ND-3202 film (hole injection layer) having a thickness of 50 nm. Then, the solution of XLP-101 was spin-coated and heated on a hot plate at 200 ℃ for 30 minutes under a nitrogen atmosphere, thereby forming an XLP-101 film (hole transport layer) with a film thickness of 20 nm. Subsequently, the composition (5) for forming a light-emitting layer was spin-coated and heated at 130 ℃ for 10 minutes in a nitrogen atmosphere to form a 20nm light-emitting layer.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (stock)), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were installed therein. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, TSPO1 was heated and vapor-deposited to a film thickness of 30nm, thereby forming an electron transport layer. The deposition rate in forming the electron transport layer was set to 1nm/sec. Then, liF is heated and vapor deposition is performed at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness becomes 1 nm. Then, aluminum was heated and vapor-deposited to a film thickness of 100nm to form a cathode. An organic EL element was obtained in the manner described.

< example C8 and example C9 >

An organic EL device was obtained in the same manner as in example C7 using the composition (6) for forming a light-emitting layer or the composition (7) for forming a light-emitting layer.

The above shows that: some of the compounds of the present invention were evaluated as excellent materials for organic EL devices, but other compounds not evaluated were also compounds having the same basic skeleton and similar structures as a whole, and it was understood by those skilled in the art that the compounds were also excellent materials for organic EL devices.

[ Industrial Applicability ]

According to a preferred aspect of the present invention, there is provided a polycyclic aromatic compound having a novel structure which is useful as a material for an organic device such as a material for an organic EL element, and an excellent organic device such as an organic EL element can be provided by using the polycyclic aromatic compound.

Claims

1. A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B),

in the formula (1A) or the formula (1B),

R ^c each independently of the other is hydrogen or a substituent,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

X ¹ 、X ² 、X ³ and X ⁴ Are each independently > N-R, > O, > S, > C (-R) ₂ 、＞Si(-R) ₂ Or > Se, said "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "are each independentlyHydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted,

In addition, as the X ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may be independently bonded to at least one of the A ring and the B ring by a single bond or a linking group, respectively, as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "" may be bonded to at least one of the A ring and the c ring independently through a single bond or a linking group,

wherein, X is ¹ ～X ⁴ Is bonded to the a ring, the B ring, or the c ring through "-CR = CR-" as a linking group, each R of the "-CR = CR-" is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of the hydrogens may be substituted with an alkyl or cycloalkyl group, and in addition, two adjacent rs are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

2. The polycyclic aromatic compound according to claim 1, wherein in the formula (1A) or the formula (1B),

the A ring and the B ring are each independently an aryl ring or a heteroaryl ring, at least one hydrogen in these rings may be substituted by an aryl group which may be substituted, a heteroaryl group which may be substituted, a diarylamino group which may be substituted, a diheteroarylamino group which may be substituted, an arylheteroarylamino group which may be substituted, a diarylboron group which may be substituted, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, or a substituted silyl group, two aryl groups of the diarylboron group which may be substituted may be bonded via a single bond or a linking group,

R ^c independently of one another hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboron, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or optionally substituted silyl, the two aryl radicals of the optionally substituted diarylboron being able to be bonded via a single bond or a connecting group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

Y ¹ and Y ² Each independently is > B-, > P (= O) -, > P (= S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of said "> C (-R) -," > Si (-R) - ", and R of said" > Ge (-R) - "are each independently aryl, heteroaryl, alkyl, or cycloalkyl, at least one of said R may be substituted with alkyl or cycloalkyl,

X ¹ 、X ² 、X ³ and X ⁴ Independently from each other > N-R, > O, > S, > C (-R) ₂ 、＞Si(-R) ₂ Or > Se, said "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ "each R of which is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl,

in addition, as the X ¹ ～X ⁴ "> C (-R) ₂ "two R of each other and" > Si (-R) ₂ "two R's may each independently be represented by a single bond-CH = CH-, -CR = CR-, -C ≡ C-, -N (-R)-、-O-、-S-、-C(-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ - "R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

In addition, as the X ¹ Or said X ³ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may be independently a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded to at least one of the A ring and the B ring as the X ² Or said X ⁴ "> R of N-R" > C (-R) ₂ "R, and" > Si (-R) ₂ R of "may each independently be a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the A ring and the C ring, R of the "-CR = CR-", "-R of the" -N (-R) - "," -C (-R) ₂ R of- "and" -Si (-R) ₂ - "R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

At least one of the A ring, the B ring, the c ring, the aryl group, and the heteroaryl group in the compound represented by the formula (1A) or the formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted with an aryl group, a heteroaryl group, an alkaneSubstituted by radicals, or cycloalkyl radicals, at least one of said cycloalkanes being "-CH ₂ - "may be substituted by" -O- ",

3. The polycyclic aromatic compound according to claim 1, which is represented by the following general formula (2A) or general formula (2B),

in the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl, and R is ^a 、R ^b And R ^c At least one hydrogen in (a) may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and further, R is ^a And R ^b Wherein adjacent groups in (a) may be bonded to each other and form, together with the a-ring and the b-ring, an aryl ring or a heteroaryl ring, at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl group, at least one of these substituents may be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group, two aryl groups of the diarylboryl group may be bonded via a single bond or a linking group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any "-C (-R) =" in the a ring and the b ring may be substituted with "-N =", any "-C (-R) = C (-R) - "may be substituted" -N (-R) - "," -O- "," -S- "," -C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", and R of said any" -C (-R) = "is R ^a Or R ^b R of said arbitrary "-C (-R) = C (-R) -" is R ^a Or R ^b R, "-C (-R) of said" -N (-R) - " ₂ R of- "and" -Si (-R) ₂ R of- "is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted by alkyl or cycloalkyl, the" -C (-R) ₂ Two R of- "are each other and" -Si (-R) ₂ Two R' S of-independently of one another may each be bound by a single bond, -CH = CH-, (R-H-) -CR = CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ a-or-Se-bond, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ R of-each independently is hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

Y ¹ And Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

in addition, as the X ¹ ～X ⁴ "> C (-R) ₂ "two R' S may be bonded to each other by a single bond, -CH = CH-, -CR = CR-) -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ a-or-Se-bond, R of the "-CR = CR-", "-R of the" -N (-R) - "," -C (-R) ₂ R of- "and" -Si (-R) ₂ R of-are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and R isWherein at least one hydrogen in the group is substituted with an alkyl or cycloalkyl group, and two adjacent R groups may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

further, as said X ¹ Or said X ³ R > N-R and C (-R) ₂ R of "may each independently be a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded to at least one of the a ring and the b ring as the X ² Or said X ⁴ R > N-R and C (-R) ₂ R of "may be independently a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the a ring and the C ring, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ R of-each independently is hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and two adjacent R's may be bonded to each other to form a cycloalkylene, arylene, or heteroarylene ring,

wherein, X is ¹ ～X ⁴ Is bonded to the a ring, the b ring, or the c ring through the "-CR = CR-" as a linking group, and in addition, two adjacent R's in the "-CR = CR-" are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

4. The polycyclic aromatic compound according to claim 3, wherein in the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently represents hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, wherein R is ^a 、R ^b And R ^c Wherein at least one hydrogen in the (A) is substituted by an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and R is ^a And R ^b Wherein adjacent groups in (b) are 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 the a-ring and the b-ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, at least one hydrogen in these substituents may be substituted by an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, the aryl group of the diarylamino group is an aryl group having 6 to 12 carbon atoms, the aryl group of the diarylboron group is an aryl group having 6 to 12 carbon atoms, and both aryl groups of the diarylboron group may be bonded via a single bond or a connecting group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any "-C (-R) =" in the a-ring and the b-ring may be substituted with "-N =", and any "-C (-R) = C (-R) -" may be substituted with "-N (-R) -", "-O-", "-S-", "-C (-R) ₂ -”、“-Si(-R) ₂ - ", or" -Se- ", and R of any of" -C (-R) = "is R ^a Or R ^b R of said arbitrary "-C (-R) = C (-R) -" is R ^a Or R ^b R of the "-N (-R) -", "-C (-R) ₂ - "R, and" -Si (-R) ₂ R represents hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein at least one of the groups in R may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the formula, -C (-R) ₂ Two ofR and-Si (-R) ₂ Two R' S of-independently of one another may each be bound by a single bond, -CH = CH-, (R-H-) -CR = CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-is bonded, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ R in the formula (I) represents hydrogen, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an alkynyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one hydrogen in the R group may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and two adjacent R groups may be bonded to each other to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms or a heteroarylene ring having 2 to 15 carbon atoms,

Y ¹ And Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

X ¹ 、X ² 、X ³ and X ⁴ Each independently represents > N-R, > O, or > S, wherein R > N-R "represents hydrogen, 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, at least one hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

in addition, as the X ¹ Or said X ³ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-) -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the a ring and the b ring as the X ² Or said X ⁴ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R) ₂ -、-Si(-R) ₂ -, or-Se-bonded to at least one of the a-ring and the C-ring, R of the "-CR = CR-", "-N (-R) -", and "-C (-R) ₂ R of- "and" -Si (-R) ₂ R is independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and at least one of R isOne hydrogen may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and two adjacent R's may be bonded to each other to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms,

5. The polycyclic aromatic compound according to claim 3, wherein in the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently represents hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and R ^a 、R ^b And R ^c Wherein at least one hydrogen in the (A) is substituted by an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R is ^a And R ^b Wherein adjacent groups in (a) 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 the a-ring and the b-ring, at least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atomsAt least one hydrogen in the substituent may be substituted by an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, the aryl group of the diarylamino group is an aryl group having 6 to 10 carbon atoms, the aryl group of the diarylboron group is an aryl group having 6 to 10 carbon atoms, and both aryl groups of the diarylboron group may be bonded via a single bond or a linking group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any "-C (-R) =" in the a-ring and the b-ring may be substituted with "-N =", and any "-C (-R) = C (-R) -" may be substituted with "-N (-R) -", "-O-", "-S-", or "-C (-R) ₂ - ", and R of said arbitrary" -C (-R) = "is R ^a Or R ^b R of said arbitrary "-C (-R) = C (-R) -" is R ^a Or R ^b R and "-C (-R) of said" -N (-R) - " ₂ - "R is hydrogen, 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, at least one hydrogen in the R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

Y ¹ and Y ² Each independently > B-, > P (= O) -, or > P (= S) -,

further, as said X ¹ Or said X ³ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-, -N (-R) -, -O-, -S-, or-C (-R) ₂ -and is bonded to the b ring as the X ² Or said X ⁴ R of "> N-R" may be represented by a single bond, -CH = CH-, -CR = CR-, -N (-R) -, -O-, -S-, or-C (-R) ₂ -and bonded to said a-ring, R of "-CR = CR-", R of "-N (-R) -", and "-C (-R) ₂ R of- "are each independently hydrogenAn aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an alkynyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one hydrogen in R may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and two adjacent R's may be bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

6. The polycyclic aromatic compound according to claim 3, wherein in the formula (2A) or the formula (2B),

R ^a 、R ^b and R ^c Each independently represents hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and R ^a 、R ^b And R ^c Wherein at least one hydrogen in the diarylamino group is substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, the aryl group of the diarylamino group is an aryl group having 6 to 10 carbon atoms, the aryl group of the diarylboron group is an aryl group having 6 to 10 carbon atoms, and both aryl groups of the diarylboron group may be bonded via a single bond or a linking group,

-C (-R) in C-Ring ^c ) = "may be substituted for" -N = ",

any "-C (-R) =" in the a-ring and the b-ring may be substituted with "-N =", any "-C (-R) = C (-R) -" may be substituted with "-N (-R) -", "-O-", or "-S-", and R of any "-C (-R) =" is R ^a Or R ^b R of said arbitrary "-C (-R) = C (-R) -" is R ^a Or R ^b Wherein R of the "-N (-R) -" is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,

Y ¹ and Y ² Is more than B-,

in addition, as the X ¹ Or said X ³ R of "> N-R" may be bonded to the b ring by a single bond or-CR = CR-, as the X ² Or said X ⁴ Wherein R of "> N-R" is bonded to the a ring by a single bond or-CR = CR-, wherein R of "-CR = CR-" is independently hydrogen, an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an alkynyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one hydrogen in R is substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and two adjacent R may be bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

7. The polycyclic aromatic compound according to claim 1, represented by any one of the following structural formulae,

the benzene rings in the structural formula may be independently substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboron group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, at least one hydrogen in the substituent may be substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, the aryl group of the diarylamino group is an aryl group having 6 to 10 carbon atoms, the aryl group of the diarylboron group is an aryl group having 6 to 10 carbon atoms, two aryl groups of the diarylboron group may be bonded via a single bond or a linking group,

8. The polycyclic aromatic compound according to claim 1, represented by any one of the following structural formulae,

9. a reactive compound obtained by substituting a reactive substituent in the polycyclic aromatic compound of any one of claims 1 to 8.

10. A polymer compound obtained by polymerizing the reactive compound according to claim 9 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

11. A pendant polymer compound obtained by substituting the reactive compound according to claim 9 in a main chain polymer or a pendant polymer cross-linked product obtained by further cross-linking the pendant polymer compound.

12. A material for organic devices, comprising the polycyclic aromatic compound according to any one of claims 1 to 8.

13. A material for organic devices, comprising the reactive compound according to claim 9.

14. A material for organic devices, which comprises the polymer compound or the crosslinked polymer according to claim 10.

15. A material for organic devices, which comprises the pendant high molecular compound or the pendant crosslinked high molecular compound according to claim 11.

16. The material for organic devices according to any one of claims 12 to 15, wherein the material for organic devices is a material for organic electroluminescent elements, a material for organic field effect transistors, a material for organic thin-film solar cells, or a material for wavelength conversion filters.

17. The material for an organic device according to claim 16, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

18. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8, and an organic solvent.

19. An ink composition comprising the reactive compound of claim 9 and an organic vehicle.

20. An ink composition comprising a main chain polymer, the reactive compound according to claim 9, and an organic solvent.

21. An ink composition comprising the polymer compound or polymer crosslinked material according to claim 10 and an organic solvent.

22. An ink composition comprising the pendant polymer or the crosslinked pendant polymer according to claim 11 and an organic solvent.

23. An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode; and an organic layer which is disposed between the pair of electrodes and contains the polycyclic aromatic compound according to any one of claims 1 to 8, the reactive compound according to claim 9, the polymer compound or the crosslinked polymer according to claim 10, or the pendant-type polymer compound or the crosslinked polymer according to claim 11.

24. The organic electroluminescent element according to claim 23, wherein the organic layer is a light-emitting layer.

25. The organic electroluminescent element according to claim 24, wherein the light-emitting layer comprises a host, and the polycyclic aromatic compound, the reactive compound, the polymer compound, the crosslinked polymer, the pendant polymer compound, or the crosslinked pendant polymer as a dopant.

26. The organic electroluminescent element according to claim 25, wherein the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a thermally activated delayed fluorescence material,

in the general formula (H3), MU is a divalent group represented by removing any two hydrogen atoms from an aromatic compound, EC is a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogens in MU are replaced by EC or MU, k is an integer of 2 to 50000,

In the general formula (H4), G is = C (-H) -or = N-independently, H in the = C (-H) -can be substituted by substituent or other structure represented by the formula (H4),

in the general formula (H5), the compound (A) is,

R ¹ ～R ¹¹ each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and R is ¹ ～R ¹¹ At least one hydrogen of (a) may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

any of the rings a, b, and C may be substituted with "-N =" where R is R ¹ ～R ¹¹ ，

In the general formula (H6) described above,

27. The organic electroluminescent element according to any one of claims 23 to 26, comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein the 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, hydroxyquinoline-based metal complexes, thiazole derivatives, benzothiazole derivatives, thiaole derivatives and oxazoline derivatives.

28. The organic electroluminescent element according to claim 27, 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.

29. The organic electroluminescent element according to any one of claims 23 to 28, wherein at least one of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer comprises: the polymer compound is formed by polymerizing a low-molecular compound capable of forming each layer as a monomer, or a crosslinked polymer formed by further crosslinking the polymer compound, or a pendant-type polymer compound formed by further crosslinking the pendant-type polymer compound and a main chain-type polymer.

30. A display device or a lighting device comprising the organic electroluminescent element according to any one of claims 23 to 29.

31. A wavelength conversion filter comprising the material for a wavelength conversion filter according to claim 16.