CN114437121A

CN114437121A - Polycyclic aromatic compound, reactive compound, material for organic device, ink composition, and organic electroluminescent element

Info

Publication number: CN114437121A
Application number: CN202111244426.8A
Authority: CN
Inventors: 畠山琢次; 川角亮介; 諌山康平; 近藤靖宏
Original assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Current assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Priority date: 2020-10-30
Filing date: 2021-10-25
Publication date: 2022-05-06
Also published as: KR20220058824A; JP2022074041A

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 polymer, a material for an organic device, an ink composition, an organic electroluminescent element, a display device or a lighting device. An organic EL element having a narrow half-value width of an emission spectrum and excellent color purity, and an organic EL element having excellent quantum efficiency and element life are provided by fabricating an organic EL element using a novel polycyclic aromatic compound as a dopant material, for example.

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 using the polycyclic aromatic compound. In the present specification, the term "organic electroluminescent element" may be referred to as "organic el (electroluminescence) element" or simply "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 studies have been made on the development of organic materials having light-emitting characteristics such as blue or green, which are 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) of holes, electrons, and the like, both of high molecular compounds and low molecular compounds.

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

As the material for the light-emitting layer, three kinds of fluorescent materials, phosphorescent materials, and Thermally Activated Delayed Fluorescence (TADF) materials have been conventionally used. For example, a benzofluorene compound and the like have been developed as a fluorescent material (international publication No. 2004/061047), and a noble metal complex having a multidentate ligand and the like have been developed as a phosphorescent material (japanese patent laid-open No. 2014-239225).

In recent years, a material obtained by improving an azaborine derivative has also been reported (international publication No. 2015/102118). Has a single peak and a narrow emission half-value width, and contains singlet energy (S)¹) And triplet energy (T)¹) Energy difference (Δ S)¹T¹) The compound having a small conjugated structure is useful as a material for a blue or green light-emitting layer because it can achieve high color purity and high efficiency due to Thermally Activated Delayed Fluorescence (TADF). Further, an electron-transporting material or a hole-transporting material which sandwiches the light-emitting layer is also required to have triplet energy (T)¹) Large novel conjugated structures.

However, the fluorescent material has a problem of low emission efficiency, and the phosphorescent material and the TADF material have a problem of low emission color purity due to a wide half-value width of an emission spectrum although they have high emission efficiency, and further, the phosphorescent material has a problem of high price due to the inclusion of a noble metal (Nature vol. 49213 December 2012 and Applied Physics Letters 75,4 (1999)).

[ Prior art documents ]

[ patent document ]

[ patent document 1] International publication No. 2004/061047

[ patent document 2] Japanese patent laid-open No. 2014-239225

[ patent document 3] International publication No. 2015/102118

[ non-patent document ]

[ non-patent document 1] vol.49213Decumber 2012, Nature (Nature)

[ non-patent document 2] Applied physical Letters 75,4(1999)

Disclosure of Invention

[ problems to be solved by the invention ]

As described above, 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 a material containing a compound different from conventional compounds. Further, patent document 3 reports a polycyclic aromatic compound containing boron and an organic EL element using the same, but in order to further improve element characteristics, a material for a light-emitting layer, particularly a dopant material, which can improve color purity, light-emitting efficiency, and element lifetime is required. As shown in non-patent document 1 or non-patent document 2, a thermally activated delayed fluorescent material or a phosphorescent material that effectively utilizes the heavy atom effect has a problem in that the half-value width of the emission spectrum is wide and the color purity is improved.

Further, as a method for forming an organic layer constituting an organic EL element, a wet film formation method is currently used in addition to a vacuum deposition method, and therefore, ink materials for wet film formation for forming a hole injection layer, a hole transport layer, and a light emitting layer are actively developed in particular, and it is also advantageous to search for such ink materials.

[ means for solving the problems ]

The present inventors have made extensive studies to solve the above problems, and as a result, have succeeded in producing a novel polycyclic aromatic compound, and have found that the compound is effective as a material having a small difference between singlet energy and triplet energy required for thermally activating delayed fluorescence. Further, the present inventors have found that an excellent thermally activated delayed fluorescence type organic EL element can be obtained by configuring an organic EL element by disposing a light-emitting layer, which uses such a polycyclic aromatic compound as a dopant material and a compound having a triplet energy larger than that as a host material, between a pair of electrodes, and have completed the present invention.

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 with the substituent a having a carbon number X" means that the "substituent a having a carbon number X" 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. For example, the "substituent B having a carbon number Y substituted by the substituent a" means that the substituent a "(not limited to a carbon number) 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.

Item 1.

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

[ solution 8]

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

R^ais hydrogen or a substituent, -C (-R) in the a ring^a) "may be substituted with" -N ═ f,

ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl or heteroaryl ring, at least one hydrogen in these rings may be substituted,

Y¹、Y²and Y³Each independently is > B-, > P (═ O) -, > P (═ S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of > C (-R) -, > R of Si (-R) -, and R of > Ge (-R) -are each independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl,

X¹and X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, > C (-R)₂And > Si (-R)₂At least one of the two R's to each other may be bonded by a single bond or a linking group,

as X¹R of > N-R, > C (-R) ₂R or > Si (-R)₂R of (A) may be bonded to at least one of the a ring and the B ring via a single bond or a linking group,

as X²R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be bonded to at least one of the a ring and the E ring via a single bond or a linking group,

the C and D rings, the G and B rings, and the F and E rings may be independently bonded by a single bond or a linking group,

wherein in the formula (1A), a CD bond of a C ring and a D ring is present as X¹R of > N-R (said R is limited to said aryl which may be substituted, said heteroaryl which may be substituted, or said cycloalkyl which may be substituted) and X of the B ring¹B bond as X²R of > N-R (said R is limited to said aryl which may be substituted, said heteroaryl which may be substituted, or said cycloalkyl which may be substituted) and X of the E ring²E-key any one or two of the three keys,

in the formula (1B), any one or two bonds among the CD bond of the C-ring and the D-ring, the GB bond of the G-ring and the B-ring, and the FE bond of the F-ring and the E-ring are present,

at least one of the ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by the formula (1A) or formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH in the cycloalkane 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),

R^ais 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 by 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 the a-ring^a) May be substituted with "-N ═ N",

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

Y¹、Y²And Y³Each independently > B-, > P (═ O) -, > P (═ S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of > C (-R) -, > R of Si (-R) -, and R of > Ge (-R) -are each independently aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen of said R being substituted with alkyl or cycloalkyl,

X¹and X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, said > C (-R)₂And > Si (-R)₂Two of RAt least one of which may be bound to each other by a single bond, -CH-, -CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-in a bond, said-CR ═ CR-R, -N (-R) -R, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

As X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring B as X²R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -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 E ring, wherein R, -N (-R) -of-CR, -CR-, - (R) -, of-CR-₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

the C and D rings, the G and B rings, and the F and E rings may be independently bonded to each other by a single bond, -CH ═ CH-, -CR ═ CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

Wherein in the formula (1A), there are a C ring and a D ringCD bond of as X¹R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of the B ring¹B bond as X²R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of the E ring²E-key any one or two of the three keys,

at least one of the ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by the formula (1A) or formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH in the cycloalkane₂-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 the following general formula (2B).

[ solution 9]

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

R^aIs hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl, R^aAt least one hydrogen in (a) may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group,

-C (-R) in the a-ring^a)＝"may be substituted with" -N ═ N ",

R^b、R^c、R^d、R^e、R^fand R^gEach independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl^b、R^c、R^d、R^e、R^fAnd R^gAt least one hydrogen of (a) may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and further R^b、R^c、R^d、R^e、R^fAnd R^gWherein adjoining groups in (a) may be bonded to each other and form, together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, respectively, an aryl ring or a heteroaryl ring, at least one hydrogen in the formed ring may be substituted with an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded by 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, at least one of these substituents may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group,

Any of the "C (-R) ═ rings in ring b, ring C, ring d, ring e, ring f, and ring g (where R is R)^b、R^c、R^d、R^e、R^fOr R^g) May be substituted with "-N ═ and optionally" -C (-R) ═ C (-R) - "(where R is R)^b、R^c、R^d、R^e、R^fOr R^g) 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, and" -Si (-R)₂R of- "is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, orAt least one hydrogen in the above R may be substituted with an alkyl group or a cycloalkyl group, the "-C (-R)₂- "two R of each other and" -Si (-R)₂At least one of the two R groups of- "may be bonded to each other via a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

X¹And X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, said > C (-R)₂And > Si (-R)₂At least one of the two R' S to each other may be replaced by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

as X¹R of said > N-R、＞C(-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring b as X²R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -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 e ring, wherein R of-CR, -N (-R) -, R of-CR, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

the C-and d-rings, g-and b-rings, and f-and e-rings may be independently bonded to each other by a single bond, -CH ═ CH-, -CR ═ CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of ring b ¹b bond as X²R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of the e ring²e-key any one or two of the three keys,

in the formula (2B), any one or two of three bonds, i.e., a cd bond in the c-ring and d-ring, a gb bond in the g-ring and B-ring, and a fe bond in the f-ring and e-ring, are present,

at least one of the B-ring, the c-ring, the d-ring, the e-ring, the f-ring, the g-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 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and wherein at least one-CH in the cycloalkane may be a-CH group₂-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^ahydrogen, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 12 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 12 carbon atoms, and both aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 24 carbon atoms, or cycloalkyl group having 3 to 24 carbon atoms, wherein R is ^aWherein at least one hydrogen atom 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,

-C (-R) in the a-ring^a) "may be substituted with" -N ═ f,

R^b、R^c、R^d、R^e、R^fand R^gIndependently 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, wherein R represents a group^b、R^c、R^d、R^e、R^fAnd R^gAt least one hydrogen in the group (a) 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 atomsSubstituted, in addition, R^b、R^c、R^d、R^e、R^fAnd R^gWherein 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 b, c, d, e, f, and g rings, respectively, at least one hydrogen in the formed ring is 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), 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 at least one hydrogen in these substituents 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,

Any of the rings "C (-R) — (where R is R) among ring b, C, d, e, f, and g^b、R^c、R^d、R^e、R^fOr R^g) May be substituted by "-N ═ or", optionally "-C (-R) ═ C (-R) -" (where R is R^b、R^c、R^d、R^e、R^fOr R^g) 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, and" -Si (-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, or" -C (-R)₂- "two R of each other and" -Si (-R)₂At least one of the two R groups of- "may be bonded to each other via a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂R 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 cycloalkane having 3 to 14 carbon atomsWherein at least one hydrogen in R is 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 form a ring to form a cycloalkylene group having 3 to 14 carbon atoms, an arylene group having 6 to 12 carbon atoms, or a heteroarylene group having 2 to 15 carbon atoms,

Y¹、Y²And Y³Each independently represents > B-, > P (═ O) -, > P (═ S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, wherein R, > C (-R) -, R, > Si (-R) -, and R, > Ge (-R) -are each independently 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 hydrogen in R is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms,

X¹and X²Are each independently > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Wherein 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, or cycloalkyl having 3 to 14 carbon atoms, at least one hydrogen in R is substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

as X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring b as X²R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -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 e ring, wherein R of-CR, -N (-R) -, R of-CR, -C (-R)₂R 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, wherein at least one hydrogen in R is selected from the group consisting of C1 to C6 alkyl or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms,

the C-and d-rings, g-and b-rings, and f-and e-rings may be independently bonded to each other by a single bond, -CH ═ CH-, -CR ═ CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂R 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 hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms,

Wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R (R is limited to the aryl group having 6 to 12 carbon atoms, the heteroaryl group having 2 to 15 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms which may be substituted with the alkyl group having 1 to 6 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms) having a structure of & gtN-R and X in the b ring¹b bond as X²R (R is limited to the aryl group having 6 to 12 carbon atoms, the heteroaryl group having 2 to 15 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms which may be substituted with the alkyl group having 1 to 6 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms) and X in the e-ring²e-key any one or two of the three keys,

at least one of the B-ring, the c-ring, the d-ring, the e-ring, the f-ring, the g-ring, the formed ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or the formula (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^ahydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 20 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 10 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 10 carbon atoms, and two aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 12 carbon atoms, or cycloalkyl group having 3 to 16 carbon atoms, wherein R is^aWherein at least one hydrogen in the group 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,

-C (-R) in the a-ring^a) May be substituted with "-N ═ N",

R^b、R^c、R^d、R^e、R^fand R^gIndependently 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, wherein R represents^b、R^c、R^d、R^e、R^fAnd R^gWherein at least one hydrogen in the group (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 ^b、R^c、R^d、R^e、R^fAnd R^gWherein 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 ring b, ring c, ring d, ring e, ring f and ring g, respectively, and at least one hydrogen in the formed rings may be substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms or a diarylamino group (wherein the aryl group is a groupAryl group having 6 to 10 carbon atoms), diarylboron group (wherein the aryl group is aryl group having 6 to 10 carbon atoms, and both aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 12 carbon atoms, or cycloalkyl group having 3 to 16 carbon atoms, and at least one hydrogen of these substituents may be substituted by aryl group having 6 to 10 carbon atoms, heteroaryl group having 2 to 10 carbon atoms, alkyl group having 1 to 5 carbon atoms, or cycloalkyl group having 5 to 10 carbon atoms,

any of the rings "C (-R) — (where R is R) among ring b, C, d, e, f, and g^b、R^c、R^d、R^e、R^fOr R^g) May be substituted by "-N ═ N",

Y¹、Y²and Y³Each independently > B-, > P (═ O) -, or > P (═ S) -,

X¹and X²Each independently > N-R, > O, > S, or > C (-R)₂R and > C (-R) of said > N-R₂R in the formula (I) is independently hydrogen, 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, at least one hydrogen in R is substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,

As X¹R of > N-R or > C (-R)₂R of (A) may be represented by a single bond, -N (-R) -, -O-, -S-, or-C (-R)₂And is bonded to ring b as X²R of > N-R or > C (-R)₂R of (A) may be represented by a single bond, -N (-R) -, -O-, -S-, or-C (-R)₂-and bonded to the e-ring, R and-C (-R) of said-N (-R) -)₂R is independently hydrogen, 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, at least one hydrogen in R may be substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,

the C-and d-rings, the g-and b-rings, and the f-and e-rings may each independently be bonded by a single bond, -N (-R) -, -O-, -S-, or-C (-R)₂-and bonded, R and-C (-R) of said-N (-R) -)₂R is independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or alkyl having 5 to 1 carbon atom0, 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,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R > N-R (the R is limited to the aryl group having 6 to 10 carbon atoms which may be substituted with the alkyl group having 1 to 5 carbon atoms or the cycloalkyl group having 5 to 10 carbon atoms) and X of the b ring ¹b bond as X²R > N-R (the R is limited to the aryl group having 6 to 10 carbon atoms which may be substituted with the alkyl group having 1 to 5 carbon atoms or the cycloalkyl group having 5 to 10 carbon atoms) and X of the e ring²e-key any one or two of the three keys,

at least one of the B-ring, the c-ring, the d-ring, the e-ring, the f-ring, the g-ring, the formed ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or the formula (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^ahydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 20 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 10 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 10 carbon atoms, and two aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 12 carbon atoms, or cycloalkyl group having 3 to 16 carbon atoms, wherein R is ^aWherein 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,

R^b、R^c、R^d、R^e、R^fand, andR^gindependently 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, wherein R represents^b、R^c、R^d、R^e、R^fAnd R^gWherein 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,

Y¹、Y²and Y³Is more than B-,

X¹and X²Is & gt N-R, wherein R & gt N-R is hydrogen, 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, at least one hydrogen in R can be substituted by alkyl with 1-5 carbon atoms,

as X¹R > N-R may be bonded to the b ring as X through a single bond²R of said > N-R may be bonded to the e-ring by a single bond,

the c-ring and the d-ring, the g-ring and the b-ring, and the f-ring and the e-ring may be independently bonded by a single bond,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R > N-R (R is limited to an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 5 carbon atoms) and X in the b ring ¹b bond as X²R > N-R (R is limited to an aryl group having 6 to 10 carbon atoms which may be substituted with the alkyl group having 1 to 5 carbon atoms) and X of the e ring²e-key any one or two of the three keys,

at least one of the B-ring, the c-ring, the d-ring, the e-ring, the f-ring, the g-ring, the aryl group, and the heteroaryl group in the compound represented by the formula (2A) or the formula (2B) may be condensed with at least one cycloalkane having 3 to 14 carbon atoms, wherein at least one hydrogen in the cycloalkane may be substituted with an alkyl group having 1 to 5 carbon atoms,

Item 7.

The polycyclic aromatic compound according to claim 3, which is represented by any one of the following structural formulae.

[ solution 10]

In the following formulas, the first and second groups,

r is independently 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, 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,

o is an integer of 1 to 3,

p is an integer of 1 to 4,

q is an integer of 1 to 5,

at least one hydrogen in the compounds of each formula may be substituted with deuterium, cyano, or halogen.

Item 8.

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

[ solution 11]

[ solution 12]

[ solution 13]

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 which is disposed between the pair of electrodes and contains 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-type 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 TADF material.

[ solution 14]

In the general formula (H1), L¹Is an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms,

in the general formula (H2), L²And L³Each 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 independently ═ C (-H) -or ═ N-, and H in the ═ C (-H) -may be substituted with a substituent or with a structure represented by another formula (H4),

in the general formula (H5), in the formula,

R¹～R¹¹each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and R is¹～R¹¹At least one hydrogen in (a) may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

R¹～R¹¹may 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 a, b, and C rings "— (C (-R) ═ C (where R is R)¹～R¹¹) May be substituted by "-N ═ N",

in the general formula (H6),

R¹～R¹⁶each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and R is¹～R¹⁶At least one hydrogen in (a) may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl,

R¹～R¹⁶may be bonded to each other and together with the a-, b-, c-or d-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, 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 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-weight compound capable of forming each layer as a monomer, or a crosslinked polymer compound 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 claim 16.

[ Effect of the invention ]

According to a preferred embodiment of the present invention, an organic EL device having a narrow half-value width of an emission spectrum and excellent color purity, and further having excellent quantum efficiency and device lifetime can be provided by manufacturing an organic EL device using a novel polycyclic aromatic compound, for example, as a dopant material. In addition, the novel polycyclic aromatic compound of the present invention has a rigid structure, and many of them have a sharper emission spectrum, a narrow half-value width of the emission spectrum, and provide light emission with high color purity.

Specifically, the present inventors have found that a polycyclic aromatic compound in which aromatic rings are linked by heterogeneous elements such as boron, phosphorus, oxygen, nitrogen, and sulfur has a large Highest Occupied Molecular Orbital (HOMO) -Lowest Unoccupied Molecular Orbital (LUMO) gap (band gap Eg in a thin film) and a high triplet energy. The reason for this is considered to be: since the 6-membered ring containing a hetero element has low aromaticity, the decrease of HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed, and single-occupied molecular orbital (SOMO) 1 and SOMO2 in the triplet excited state are localized by electron perturbation of the hetero element.

Further, since the hetero element-containing polycyclic aromatic compound of the present invention reduces the exchange interaction between both orbitals by localization of SOMO1 and SOMO2 in the triplet excited state, the energy difference between the triplet excited state and the singlet excited state is small, and thermally active delayed fluorescence is exhibited, and thus the compound is also effectively used as a fluorescent material for an organic EL device. In addition, a material having high triplet energy is also effective as an electron transport layer or a hole transport layer of a phosphorescent organic EL device or an organic EL device utilizing thermally active delayed fluorescence. Further, since the energy of HOMO and LUMO can be arbitrarily changed by introducing a substituent into these polycyclic aromatic compounds, ionization potential (ionization potential) and electron affinity (electron affinity) can be optimized according to the surrounding materials.

Drawings

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

[ description of symbols ]

100: organic electroluminescent element

101: substrate

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 of the present invention

< 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). In the above formulae, "B" to "G" in the circle are symbols representing ring structures represented by a circle, "a" to "G" in the 6-membered aromatic ring are benzene rings or rings (6-membered or 5-membered heteroaromatic rings or the like) which are changed depending on the case, and other symbols are the same as defined above. Further, the symbols in all structural formulae shown after the paragraph are also defined as described above.

[ solution 15]

[ solution 16]

The compounds of the present invention have one or two carbazole-like structures in the molecule. As described below, in each formula, a carbazole-like structure may be formed at three sites, and a carbazole-like structure may be formed at one site or two sites of the three sites.

With respect to the carbazole analogous structure, details will be given inIn the formula (1A), the bond between the C ring and the D ring includes "N", and X represents¹Or X²R > N-R is bonded to the B ring or the E ring, respectively. In the formula (2A), for example, a bond (R) between the c-ring and the d-ring ^cAnd R^dThe bond of (b)) comprises "N", and, in addition, at X¹Or X²R > N-R is bonded to the b-ring or the e-ring (R and R, respectively)^bOr R^eA bond of (b) is formed. In the formula (1B), too, the bond between the C ring and the D ring includes "N", the bond between the G ring and the B ring includes "N", and the bond between the F ring and the E ring includes "N". In addition, in the same manner as in the formula (2B), for example, a bond (R) between the c-ring and the d-ring^cAnd R^dThe bond of (A) or (B) includes "N", and further, a bond (R) through the g ring and the b ring^gAnd R^bThe bond of (A) or (B) comprises "N", and is additionally formed by a bond (R) of the f-ring and the e-ring^fOr R^eThe bond of (c) comprises "N".

< description of the Ring Structure and substituents therefor >

Ra is hydrogen or a substituent. As the substituent, preferred is 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 (two aryl groups may be bonded by 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. Examples of the substituent in the case where these groups have a substituent include: aryl, heteroaryl, alkyl, or cycloalkyl. Further, details regarding the substituents listed herein will be described together later.

Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl or heteroaryl ring, at least one hydrogen in these rings may be substituted with a substituent. As the substituent, preferred is 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 (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. Examples of the substituent in the case where these groups have a substituent include: aryl, heteroaryl, alkyl, or cycloalkyl. Further, details regarding the rings or substituents listed herein will be described together later.

R^b、R^c、R^d、R^e、R^fAnd R^gEach independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl ^b、R^c、R^d、R^e、R^fAnd R^gAt least one hydrogen in (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 (i.e., ring B to ring G) in formula (1A) and formula (1B) preferably has a 5-or 6-membered ring that is commonly bonded to the condensed bicyclic structure contained in each formula.

Here, the "condensed bicyclic structure" means that Y is contained in the formula (1A)¹、X¹And N (the first condensed bicyclic structure on the left side in the formula) and a compound containing Y²、X²And N (the second condensed bicyclic structure on the right side in the formula). In addition, in the same manner as in the formula (1B), Y is included¹And two saturated hydrocarbon rings of two N (the first condensed bicyclic structure on the left side in the formula), and Y²And two saturated hydrocarbon rings of two N (the second condensed bicyclic structure on the right side in the formula), and a packageContaining Y³And two saturated hydrocarbon rings composed of two N atoms (the lower third condensed bicyclic structure in the formula). Although not shown in formula (2A) and formula (2B), a condensed bicyclic structure is present at the same site.

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

The ring B, ring C, ring D and ring E in the formula (1A) correspond to the ring B in the formula (2A) and the substituent R thereof, respectively^bC ring and its substituent R^cD ring and its substituent R^dAnd ring e and its substituent R^e. That is, the formula (2A) corresponds to a structure in which "B to E rings having 6-membered rings" are selected as the B to E rings of the formula (1A). The "having" 6-membered ring is because, as described later, for example, the following are present: for ring b as a 6-membered ring, four substituents R ^bWherein adjacent groups are bonded to each other to form a ring, and the ring B as a 6-membered ring is further condensed with another ring to form a ring corresponding to the ring B. In this sense, the rings of formula (1A) are represented by capital letters B to E, while the rings of formula (2A) are represented by lowercase letters B to E.

The ring B, ring C, ring D, ring E, ring F and ring G in the formula (1B) correspond to the ring B in the formula (2B) and the substituent R thereof, respectively^bC ring and its substituent R^cD ring and its substituent R^dE ring and substituents R thereof^eF ring and its substituent R^fAnd g ring and its substituent R^g. That is, the formula (2B) corresponds to a structure in which "B ring to G ring having 6-membered ring" are selected as the B ring to G ring of the formula (1B). The "having" 6-membered ring is because, as described later, for example, the following are present: for ring b as a 6-membered ring, four substituents R^bWherein adjacent groups are bonded to each other to form a ring, and the ring B as a 6-membered ring is further condensed with another ring to form a ring corresponding to the ring B. In this sense, the rings of formula (1B) are represented by capital letters B to G, while the rings of formula (2B) are represented by lowercase letters B to G.

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

Substituents R for ring b, ring c, ring d, ring e, ring f and ring g ^b、R^c、R^d、R^e、R^fAnd R^gMay be bonded to each other and form, together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, respectively, an aryl ring or heteroaryl ring, at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded by a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkylbicycloalkylsilyl group, and at least one hydrogen in these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. Further, details regarding the rings or substituents enumerated herein will be described together later.

Therefore, the polycyclic aromatic compound of the formula (2A) or (2B) has a change in the ring structure of the compound depending on the bonding form of the substituents in the B-ring to g-ring, as shown in the following formula (2A-fr) and formula (2B-fr), for example. The B 'ring and the C' ring in the following formulae correspond to the B ring and the C ring in the formulae (1A) and (1B), respectively. In addition, the d-g rings may be changed in the same manner.

[ chemical formula 17]

When the formulae (2A) and (2B) are given, the B 'ring and the C' ring in the formulae (2A-fr) and (2B-fr) represent a plurality of substituents R^bAnd R^cThe adjacent groups in (b) are bonded to each other and form an aryl ring or a heteroaryl ring together with the b-ring and the c-ring, respectively (may also be referred to as a condensed ring formed by condensing another ring structure in the b-ring or the c-ring). Also, according to the formula, R in the b ring is shown as^bR with ring c^cThat is, substituents in different rings do not correspond to "adjacent groups" with each other, and these are not substantially bonded. That is, the term "adjacent groups" refers to groups adjacent to each other on the same ring.

The above-mentioned formulae (2A-fr) and (2B-fr) have a B 'ring or a C' 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 a B ring or a C ring, and the formed condensed ring B 'or condensed ring C' is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring or the like, respectively.

More specific examples of the formulae (2A-fr) and (2B-fr) are shown below.

[ solution 18]

The formulae (2A-fr-ex) and (2B-fr-ex) are specific examples of the formulae (2A-fr) and (2B-fr), respectively, and are two adjacent R's in the B-rings of the formulae (2A) and (2B) ^bBonded to form an aryl ring (naphthalene ring) represented by B' together with the B ring (benzene ring), and two adjacent R in the c ring^cAnd bonded to and together with the C-ring (benzene ring) to form an aryl ring (dibenzofuran ring) represented by C'. The aryl ring formed has a 6-membered ring (benzene ring b or c) bonded in common with the condensed bicyclic structure. Optional substituents on aryl rings B 'and C' (rings B and C of formulae (1A) and (1B)) other than R^bAnd R^cIn addition, the upper limit of n is the maximum number that can be substituted. Note that the description can be similarly applied to all the embodiments other than the specific examplesFor example, the d-ring to g-ring is changed or other aryl or heteroaryl ring is formed.

< center element Y in Compound¹～Y³Description of (1) >

Y¹、Y²And Y³Each independently is > B-, > P (═ O) -, > P (═ S) -, > Al-, > Ga-, > As-, > C (-R) -, > Si (-R) -, or > Ge (-R) -, R of > C (-R) -, > R of Si (-R) -, and R of > Ge (-R) -are each independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. As Y¹、Y²And Y³Preferably > B-, > P (═ O) -, or > P (═ S) -, more preferably > B-. Further, details regarding the substituents listed herein will be described together later.

< description of the Change in Ring Structure caused by the bond between rings >

The C ring and the D ring in the formulas (1A) and (1B) may be bonded by a single bond or a linking group (these are also collectively referred to as a bonding group). In addition, the G ring and the B ring, and the F ring and the E ring in formula (1B) may be independently bonded by a single bond or a linking group (these are also collectively referred to as a bonding group). The bond between ring C and ring D is also referred to as a CD bond, the bond between ring G and ring B is referred to as a GB bond, and the bond between ring F and ring E is referred to as an FE bond.

Examples of the linking group include: -CH₂-CH₂-、-CHR-CHR-、-CR₂-CR₂-、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R)₂-、-Si(-R)₂-, or-Se-. Furthermore, R, -CR of said-CHR-₂-CR₂R of-R, -CR, -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of (A) and (B) is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, two adjacent R groups may form a ring with each other to form a cycloalkylene group, an arylene group, and a heteroarylene group. Further, details regarding the substituents listed herein will be described together later.

The bonding group is preferably a single bond, or a linking group-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) ₂Further, a single bond, or-CR ═ CR-, -N (-R) -, -O-, and-S-, which are linking groups, is preferable, and a single bond is most preferable.

The position at which two rings 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 rings are bonded at the most adjacent positions, and it is preferable that, for example, the two rings are bonded at the positions adjacent to each other (2-position) based on the bonding position (1-position) of "N" in each ring (see the structural formulae of formulae (1A) and (1B)).

The c-ring and d-ring in the formulae (2A) and (2B) of the lower formulae may be bonded by a single bond or a linking group (these are also collectively referred to as a bonding group) as in the above formulae. In the formula (2B) of the lower formula, the g ring and the B ring, and the f ring and the e ring may be independently bonded by a single bond or a linking group (these are also collectively referred to as a bonding group), as in the above formula. The bonds between ring c and ring d are also referred to as the cd bond, the bonds between ring g and ring b are referred to as the gb bond, and the bonds between ring f and ring e are referred to as the fe bond. The type of the linking group or the bonding position can be referred to the description of the upper formula.

< description of carbazole-like Structure (1) >

In the compound of the present invention, as described above, the C ring and the D ring (C ring and D ring), the G ring and the B ring (G ring and B ring), and the F ring and the E ring (F ring and E ring) may be bonded, so that a first carbazole-like structure may be formed in formula (1A) and formula (2A), and a first, second, and third carbazole-like structure may be formed in formula (1B) and formula (2B). The dotted line in the following structural formula means a bonding group (single bond and linking group). Among them, the compound of the present invention is characterized in that one or two of three carbazole-like structures which can be formed intramolecularly are formed.

[ solution 19]

[ solution 20]

The reason why the structure is referred to as "carbazole-like structure" is because, for example, when the c-ring and the d-ring are bonded to each other at the positions adjacent to the N (2-position) by a single bond based on the bonding position (1-position) of "N" in the case of the formula (2A), a carbazole structure which is the most basic structure is formed in the molecule. Further, as described above, there is also a bonding group other than a single bond as a bonding group, and the bonding position between the rings is not limited, and as described otherwise, each ring such as c-ring is changed in ring structure by bonding of adjacent substituents and the like, and therefore, a structure other than carbazole is formed. Thus, in the sense that a carbazole-like structure is also formed, it is referred to as a "carbazole-like structure".

In the case of forming a carbazole-like structure, the bonding group is preferably a single bond or-CH as a linking group₂-CH₂-、-CHR-CHR-、-CR₂-CR₂-、-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)₂Further, a single bond, and-CR ═ CR-, -N (-R) -, -O-, and-S-, which are linking groups, are preferable, and a single bond is most preferable.

In the case of forming a carbazole-like structure, the positions at which two rings are bonded via a bonding group are not particularly limited as long as they are positions capable of bonding, and are preferably bonded at the most adjacent positions, and are preferably bonded to each other at positions adjacent to the position (2 position) with reference to the bonding position (1 position) of "N" in each ring (see the structural formulae of formula (1A), formula (1B), formula (2A), and formula (2B)).

In the case of forming a carbazole-like structure, both of the bonded rings are preferably benzene rings.

< linking element X in Compound¹And X²Description of (1) >

Formula (1A) andx in the formula (2A)¹And X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (a) is independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted. Further, details regarding the substituents listed herein will be described together later.

As X¹And X²Preferably, > N-R, > O, > S, or > C (-R)₂More preferably, > N-R or > O, and still more preferably, > N-R. From the viewpoint of good TADF properties, > N-R, > O and > S are preferable, more specifically, > N-R is preferable from the viewpoint of localization of orbitals by the multiple resonance effect, and > S is preferable from the viewpoint of the heavy atom effect. In addition, from the viewpoint of emission wavelength, emission at a short wavelength is preferably > O, and emission at a long wavelength is preferably > N-R or > S.

＞C(-R)₂And > Si (-R)₂At least one of the two R's may be bonded 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-CH₂-、-CHR-CHR-、-CR₂-CR₂-、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R)₂-、-Si(-R)₂Examples of-Se-or-Se-include the following structures. Furthermore, R, -CR of said-CHR-₂-CR₂R of-R, -CR, -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, two adjacent R groups may form a ring with each other to form a cycloalkylene group, an arylene group, and a heteroarylene group. Further, details regarding the substituents listed herein will be described together later.

[ solution 21]

The bonding group is preferably a single bond, or a linking group-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)₂Further, a single bond, and-CR ═ CR-, -N (-R) -, -O-, and-S-, which are linking groups, are preferable, and a single bond is most preferable.

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).

< by X¹Or X²Description of the Change in Ring Structure caused by bond to Ring

X in the formulae (1A) and (2A)¹R, > N-R, > C (-R)₂R or > Si (-R)₂R (B) may be bonded to at least one of the a ring and the B ring (B ring) via a single bond or a linking group (these are also collectively referred to as a bonding group).

X in the formulae (1A) and (2A)²R, > N-R, > C (-R)₂R or > Si (-R)₂R (a) may be bonded to at least one of the a-ring and the E-ring (E-ring) via a single bond or a linking group (these are also collectively referred to as a bonding group).

Examples of the linking group include: -CH₂-CH₂-、-CHR-CHR-、-CR₂-CR₂-、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R)₂-、-Si(-R)₂-, and-Se-. Furthermore, R, -CR of said-CHR-₂-CR₂R of-R, -CR, -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, two adjacentAnd R may form a ring with each other to form cycloalkylene, arylene, and heteroarylene groups. Further, details regarding the substituents listed herein will be described together later.

X as a participating bond¹Or X²Preferably > N-R and > C (-R)₂More preferably, > N-R.

The bonding group is preferably a single bond, or a linking group-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)₂Further, a single bond, and-CR ═ CR-, -N (-R) -, -O-, and-S-, which are linking groups, are preferable, and a single bond is most preferable.

As the ring to which it is bonded, with respect to X¹Preferably B ring (B ring), with respect to X²Preferably, it is an E ring (E ring).

In the above formula (1A), "said > R of N-R, > C (-R)₂R or > Si (-R)₂The provision that R of (A) is bonded to at least one of the a-ring and the B-ring (or the E-ring) by a single bond or a linking group corresponds to "R of said > N-R, said > C (-R) in the formula (2A) of the following formula₂R or > Si (-R)₂R of (a) is a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with at least one bond of the a ring and the b ring (or the e ring) ".

The specification can be expressed by the following structural formula, for example. In addition, the substituent R in the structural formula^aA substituent R^bA substituent R^cA substituent R^dAnd a substituent R^eThe display is not performed, but actually exists.

[ solution 22]

In the left structural formula, is X¹And X²(iii) a selection of (2) (> N-R, > C (-R)₂And > Si (-R)₂) R in (1)Examples of bonds to the b-ring and the e-ring, respectively, show other rings to introduce X ¹Or X²A compound of ring B 'and ring E' formed by condensation with ring B (benzene ring) and ring E (benzene ring). The condensed rings B 'and E' to be formed are, for example, phenoxazine, phenothiazine, carbazole, or acridine rings.

The structural formula at the center represents a more specific example of the structural formula at the left side, and is X¹And X²And R (phenyl) of > N-R is bonded to the B-ring (benzene ring) and the E-ring (benzene ring) by single bonds, respectively, to form a carbazole ring B 'and a carbazole ring E' surrounded by a dotted line.

The structural formula on the right side represents a more specific example of the structural formula on the left side, and is X¹And X²R (phenyl) of > N-R is bonded to the B ring (benzene ring) through-O-as a linking group to form a phenoxazine ring B 'surrounded by a dotted line and bonded to the E ring (benzene ring) through-S-as a linking group to form a phenothiazine ring E' surrounded by a dotted line.

X¹And X²(iii) a selection of (2) (> N-R, > C (-R)₂And > Si (-R)₂) The position at which R in (a) is bonded to the rings (B ring, E ring, B ring, and E ring) via a bonding group is not particularly limited as long as it is a position capable of bonding, and it is preferable to bond at the most adjacent position, and for example, when R is a phenyl group, it is preferable to bond the ring to be bonded and "X" in the phenyl group ¹"or" X²"are bonded to each other at the positions adjacent to the (2-position) on the basis of the bonding position (1-position) (see the structural formula).

The description of the specific examples can be similarly applied to all the forms other than the specific examples, for example, X¹And X²Any one of them is bonded to a ring, a ring a, or another linking group.

< description of carbazole-like Structure (2) >

In the compound of the present invention, X in the formula (1A) and the formula (2A) is as described above¹And X²R of (A) may be bonded to the adjacent ring, but in these bonding forms, X is used as X¹"> N-R ofA bond formed by R "(the R is limited to the optionally substituted aryl, optionally substituted heteroaryl, or the optionally substituted cycloalkyl) and the" B ring "or" B ring "(also referred to as X)¹B bond or X¹b bond), a second carbazole-like structure may be present, and thus utilized as X²With "> N-R of (said R is limited to said optionally substituted aryl, said optionally substituted heteroaryl, or said optionally substituted cycloalkyl) and an" E ring "or" E ring "(also referred to as X)²E bond or X²e bond), a third carbazole-like structure may be present.

[ solution 23]

R > N-R, which can form a carbazole-like structure, is preferably an aryl group which may be substituted.

The bonding group between R and the ring is preferably a single bond.

< statement on the number of carbazole-like structures >

As described, in the formulas (1A) and (2A), the first carbazole-like structure is formed by a CD bond or a CD bond, and the second structure is derived from X¹B bond or X¹b bond, the third structure is derived from X²E bond or X²e bond. In the formulae (1B) and (2B), the first carbazole-like structure is formed by a CD bond or a CD bond, the second structure is formed by a GB bond or a GB bond, and the third structure is formed by an FE bond or a FE bond. The compounds of the present invention are characterized by the formation of one or two of these three carbazole-like structures that can be formed intramolecularly.

In the formula (1A) and the formula (2A), there are a case where only the first carbazole-like structure is present (1Cz body), a case where only the second carbazole-like structure is present (2Cz body), a case where the first carbazole-like structure and the second carbazole-like structure are present (12Cz body), and a case where the second carbazole-like structure and the third carbazole-like structure are present (23Cz body), and the 1Cz body, the 12Cz body, and the 23Cz body are preferable, and the 1Cz body and the 12Cz body are more preferable, and the 1Cz body is further preferable.

In the formula (1B) and the formula (2B), there are a case where only the first carbazole-like structure is present (1Cz body) and a case where the first and second carbazole-like structures are present (12Cz body), and the 1Cz body is preferable.

< description of structural changes of ring a, ring b to ring g >

In the description so far, the a-ring, b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring have been illustrated and described as benzene rings, but examples of the change of the a-ring, b-ring to g-ring structures 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 a Ring >

-C (-R) in the a-ring of formula (1A) and formula (2A)^a) May be substituted by "-N-or" to form a pyridine ring. The following structural diagram is a diagram in which only a part of the a-ring and its peripheral structure is extracted.

[ solution 24]

Structural change from ring b to ring g

Any of the B-, C-, d-, e-, f-and g-rings of the formulae (2A) and (2B) — (where R is R) — C (-R) ═ in the ring(s) — (where R is R)^b、R^c、R^d、R^e、R^fOr R^g) May be substituted with "-N ═ N".

[ solution 25]

As indicated above, e.g. -C (-R) in the d-ring^d) The "position" may be substituted with "-N ═ so that the d ring represented by a benzene ring in each formula may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. In addition, theWhen adjacent groups are present on the d ring as described (the remaining two adjacent R groups in the formula) ^d) These may be bonded and form a heteroaryl ring (quinoline ring in the formula) together with the d ring, and the formed ring may be further substituted (represented by n R).

Further, there are also the following modifications.

[ solution 26]

Preferably with respect to X¹、X²Or > N-bonded carbon, ortho-or para-C (-R)^d) Substituted with "-N ═ N".

The same applies to the case where the other site is substituted with "-N", or the case where the b-, c-, e-, f-and g-rings other than the d-ring are changed.

Any of the B-, C-, d-, e-, f-and g-rings of the formulae (2A) and (2B) — C (-R) ═ C (-R) - "(where R is R)^b、R^c、R^d、R^e、R^fOr R^g) 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, and" -Si (-R)₂R 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 27]

As indicated above, e.g. -C (-R) in the d-ring^d)＝C(-R^d) The site of- "may be substituted with" -N (-R) - "," -O- "," -S- "," -C (-R) ₂-”、“-Si(-R)₂- ", or" -Se- ", so that the d ring represented as a benzene ring in each formula may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, other nitrogen/oxygen/sulfur-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). In addition, as mentioned above, in the d ring on the adjacent group cases (in the formula, the other two adjacent R^d) These may be bonded and form together with the d 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 the following modifications.

[ solution 28]

Other sites are substituted with "-N (-R) -", "-O-", "-S-", "-C (-R)₂-”、“-Si(-R)₂The same applies to the case of- ", or" -Se- ", or the case where the b-, c-, e-, f-and g-rings other than the d-ring are changed.

The "-C (-R)₂- "two R of each other and" -Si (-R)₂At least one of the two R groups of- "may be bonded via a single bond or a linking group (these are also collectively referred to as a bonding group). Examples of the linking group include: -CH₂-CH₂-、-CHR-CHR-、-CR₂-CR₂-、-CH＝CH-、-CR＝CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R)₂-、-Si(-R)₂Examples of-Se-or-Se-include the following structures. Furthermore, R, -CR of said-CHR- ₂-CR₂R of-R, -CR, -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl. In addition, two adjacent R's may form a ring with each other to form a cycloalkylene, an arylene, and a heteroarylene. In addition, as to those enumerated hereinDetails of the substituents will be described together later.

[ solution 29]

< 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 B to ring G in the formula (1A) and the formula (1B) corresponds to the "R" defined in the formula (2A) and the formula (2B)^b、R^c、R^d、R^e、R^fAnd R^gThe "formed aryl ring" is an aryl ring formed by bonding adjacent groups in (a) to (b) to each other and forming the b, c, d, e, f, and g rings together with each other, wherein the b to g rings already contain a benzene ring having 6 carbon atoms, and therefore the total carbon number 9 of the condensed rings formed by condensing the smallest 5-membered ring on the benzene ring is the lower limit of the carbon number 9。

Among them, the benzene ring, i.e., the b-g ring, may be changed to a nitrogen-containing heteroaryl ring (6-or 5-membered ring) or an oxygen/sulfur-containing heteroaryl ring (5-membered ring) as described above, and therefore, the number of carbons in the lower limit in the above case is changed accordingly.

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, or a heteroaryl ring having 2 to 10 carbon atoms. 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 ring B to ring G in the formula (1A) and the formula (1B) corresponds to the "R" defined in the formula (2A) and the formula (2B)^b、R^c、R^d、R^e、R^fAnd R^gThe heteroaryl ring(s) in (b) may be a heteroaryl ring in which adjacent groups in (b) are bonded to each other and are formed together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, respectively, and the "formed heteroaryl ring" already includes a benzene ring having 6 carbon atoms, so that the total carbon number of 6 carbon atoms of a condensed ring in which a minimum 5-membered ring is condensed onto the benzene ring becomes the lower limit.

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 ring, a phenazasiline (phenazaline) ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a thiophene ring, an isothiazole ring, a benzothiophene ring, a thiophene ring, a triazine ring, a substituted or a substituted triazine ring, a substituted or a substituted derivative, a, 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 benzobenzindoindolocarbazole 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, or an aryl group having 6 to 10 carbon atoms.

Specific "aryl" groups are for example: phenyl as a monocyclic system, biphenyl (2-biphenyl, 3-biphenyl, or 4-biphenyl) as a bicyclic system, naphthyl (1-naphthyl or 2-naphthyl) as a 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, o-terphenyl-1-naphthyl, P-terphenyl-3-yl, or p-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, or 5-) as a condensed tricyclic group, fluorene- (1-, 2-, 3-, 4-, or 9-) group, phenalene- (1-or 2-) group, phenanthrene- (1-, 2-, 3-, 4-, or 9-) group, or anthracene- (1-, 2-, or 9-) group, tetrabiphenyl (5' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl, or m-quaterphenyl) as a tetracyclic group, 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" 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.

Specific "heteroaryl" includes, for example, 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, quinolizinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazinylsilyl (phenazalinyl), indolizinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, naphthobenzofuryl, thienyl, benzothienyl, isobenzothienyl, oxadiazolyl, thianyl, thiadiazolyl, pyrazinyl, thiazinyl, thiazolinyl, and the like, Dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphole oxide ring monovalent radical, dibenzophosphole oxide ring monovalent radical, furazan, thianthryl, indolocarbazole, benzindolocarbazole, benzobenzindoindolocarbazole, imidazolinyl, oxazolinyl, etc.

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 may be one in which at least one hydrogen atom 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 group" 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, or a heteroarylene group having 2 to 10 carbon atoms. The "heteroarylene group" is, for example, a divalent group of a heterocyclic ring or the like 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 is 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 or heteroaryl group, the description of the "aryl" and "heteroaryl" 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-, -CR-, -C ≡ C-, > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se). Herein, R of the-CR ═ CR-, R of the-N-R, > C (-R)₂R, and > Si (-R)₂R of (a) is aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, at least one hydrogen of said R may in turn be substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. In addition, two adjacent R groups may form a ring with each other to form a cycloalkylene group, an arylene group, and a heteroarylene group. 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 a linear or branched one, and is, for example, a linear 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.

Specific examples of the "alkyl group" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1-diethylpropyl, 1, 2-trimethylpropyl, 1,2, 2-tetramethylpropyl, 1-ethyl-1, 2, 2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1-dimethylbutyl, 3-dimethylbutyl, 1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1, 3-trimethylbutyl, 1-ethyl-1, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-amyl), and the like, 1-methylpentyl, 2-propylpentyl, 1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1, 4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1, 5-trimethylhexyl, 3,5, 5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1-dimethylheptyl, 2-dimethylheptyl, 2, 6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3, 3-tetramethylbutyl), 1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, and the like.

The "alkenyl group" may be a group obtained by substituting a C — C single bond in the structure of the "alkyl group" with a C ═ C double bond, and includes not only a group obtained by substituting one or more single bonds with a double bond (also referred to as an alkadienyl group or alkatrienyl group).

As for the "alkynyl group", a group in which a single C — C bond is substituted by a triple C ≡ C bond in the structure of the "alkyl group" may be referred to as "alkyl group", and a group in which not only one but two or more single bonds are substituted by a triple bond (also referred to as an alkadienyl group or an alkatrienyl 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 a 1 to 5 or 1 to 4 carbon alkyl (particularly methyl) substituent thereof, 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.

The "cycloalkylene group" 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, or a cycloalkylene group having 5 carbon atoms.

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 any of a linear or branched chain, 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.

Specific examples of the "alkoxy group" include methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1-diethylpropoxy, 1, 2-trimethylpropoxy, 1,2, 2-tetramethylpropoxy, 1-ethyl-1, 2, 2-trimethylpropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, 2-ethylbutoxy, 1-dimethylbutoxy, 3-dimethylbutoxy, 1-diethylbutoxy, 1-ethyl-1-methylbutyloxy, 1-propyl-1-methylbutyloxy, 1, 3-trimethylbutoxy, 1-ethyl-1, 3-dimethylbutoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1-diethylbutoxy, 1-ethyl-1, 3-dimethylbutoxy, N-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1, 4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1, 5-trimethylhexyloxy, 3,5, 5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1-dimethylheptyloxy, 2, 2-dimethylheptyloxy group, 2, 6-dimethyl-4-heptyloxy group, n-octyloxy group, t-octyloxy group (1,1,3, 3-tetramethylbutoxy), 1-dimethyloctyloxy group, n-nonyloxy group, n-decyloxy group, 1-methyldecyloxy group, n-undecyloxy group, n-dodecyloxy group, n-tridecyloxy group, n-tetradecyloxy group, n-pentadecyloxy group, n-hexadecyloxy group, n-heptadecyloxy group, n-octadecyloxy group, or n-eicosyloxy group, 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 with respect to the details of the aryl groups, reference is 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, a n-propyldimethylsilyl group, an isopropyldimethylsilyl group, a n-butyldimethylsilyl group, an isobutyldimethylsilyl group, a sec-butyldimethylsilyl group, a methyldiethylsilyl group, a n-propyldiethylsilyl group, a n-butyldiethylsilyl group, a tert-butyldiethylsilyl group, a methyldi-n-propylsilyl group, an ethyldi-n-propylsilyl group, a n-butyldi-n-propylsilyl group, a sec-butyldi-n-propylsilyl group, a tert-butyldi-n-propylsilyl group, a, And a methyl diisopropyl silane, an ethyl diisopropyl silane, an n-butyl diisopropyl silane, a sec-butyl diisopropyl silane, a tert-butyl diisopropyl silane, and the like.

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

Specific examples of the "tricycloalkylsilyl group" include tricyclopentylsilyl group, tricyclohexylsilyl group and 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.

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent or the second substituent, but the group represented by the following structural formula is preferable, and methyl group, tert-butyl group, tert-pentyl group, tert-octyl group, neopentyl 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-tert-butyl) phenyl group, carbazolyl group, 3, 6-dimethylcarbazolyl group, 3, 6-di-tert-butylcarbazolyl group, and phenoxy group are more preferable, and methyl group, tert-butyl group, tert-pentyl group, tert-octyl group, neopentyl group, adamantyl group, phenyl group, o-tolyl group, 2, 6-xylyl group, 2,4, 6-mesitylene, diphenylamino, di-p-tolylamino, bis (p- (tert-butyl) phenyl) amino, carbazolyl, 3, 6-dimethylcarbazolyl and 3, 6-di-tert-butylcarbazolyl. From the viewpoint of ease of synthesis, a group having a large steric hindrance is preferable for selective synthesis, and specifically, t-butyl group, t-amyl group, t-octyl group, adamantyl group, o-tolyl group, p-tolyl group, 2, 4-xylyl group, 2, 5-xylyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, di-p-tolylamino group, bis (p- (t-butyl) phenyl) amino group, 3, 6-dimethylcarbazolyl group, and 3, 6-di-t-butylcarbazolyl group are preferable.

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 "-" represents a bonding position.

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[ solution 47]

< description of Cycloalkane condensation >

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

For example, at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B), ring B, ring C, ring D, ring E, ring F, ring G, the "formed ring", aryl, and heteroaryl in the compound represented by formula (2A) or formula (2B) may be condensed with at least one cycloalkane.

Examples of the "cycloalkane" include: a C3-24 cycloalkane, a C3-20 cycloalkane, a C3-16 cycloalkane, a C3-14 cycloalkane, a C5-10 cycloalkane, a C5-8 cycloalkane, a C5-6 cycloalkane, a C5 cycloalkane, 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, deuterium substituents having 1 to 5 carbon atoms of these, and the like.

Among these, a structure in which at least one hydrogen on the carbon at the α -position of cycloalkane (in cycloalkyl condensed in an aromatic ring or a heteroaromatic ring, the carbon at the position adjacent to the carbon at the condensation position) 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 carbons 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 48]

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, examples in which one or more cycloalkanes are condensed in one benzene ring (phenyl group) are 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 formula (Cy-1-4) and the formula (Cy-2-4) may also be condensed with each other. The same applies to the case where the condensed ring (group) is an aromatic ring or a 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 49]

At least one-CH in cycloalkanes₂-may be substituted by-O-. In which a plurality of-CH₂-when substituted by-O-, adjacent-CH₂-is not substituted by-O-. For example, the following shows one or more-CH's of cycloalkanes condensed in one benzene ring (phenyl group)₂Examples of-O-substitution. 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. The same applies to the case where the condensed ring (group) is an aromatic ring or a 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 50]

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 (e.g., alkyl groups having 1 to 6 carbon atoms), cycloalkyl groups (e.g., cycloalkyl groups having 3 to 14 carbon atoms), halogens (e.g., fluorine), and deuterium. 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 51]

Examples of other forms of the cycloalkane condensation include substitution of the polycyclic aromatic compound of the present invention 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. With regard to the "diarylamino group", the description may be cited.

More specific examples thereof include R in the polycyclic aromatic compound represented by the formula (1A) or (2A)^aAre 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 >

For example, a compound represented by any one of the following structural formulae is preferable.

[ solution 52]

[ Hua 53]

[ solution 54]

[ solution 55]

In the following formulas, the first and second groups,

o is an integer of 1 to 3,

p is an integer of 1 to 4,

q is an integer of 1 to 5 independently,

More specific description of R may refer to description of said aryl group and the like. O, p, and q are preferably 1 or 2, more preferably 1, and still more preferably 0.

< utilization as a Thermally Activated Delayed Fluorescence (TADF) material >

The compounds of the present invention may also be used as TADF materials. In particular, the compounds represented by the formulae (1A) and (2A) are preferable to the compounds represented by the formulae (1B) and (2B), and the ring bonded in common to the condensed bicyclic structure in the B ring to the G ring or the B ring to the G ring is preferably a 6-membered ring, and more preferably a 6-membered aryl ring including the a ring.

The bonding group for forming a carbazole-like structure is preferably a single bond (for example, the following structural formula), and is preferably a group (1Cz body) (1A-111, 1A-112, 1Cz structure) in which only the first carbazole-like structure is present,Structural formulae other than 1A-214), among carbazole-like structures, substitution of an aryl ring such as a phenyl group at a para position (in particular, a para position in the c-ring or d-ring) based on the bonding position of "N" in the carbazole structure is particularly preferable (structural formulae other than 1A-214, 1A-331, and 1A-702), and X is preferably used¹And X²The nitrogen-containing group such as diarylamino group or carbazolyl group is substituted at a meta position (particularly, a meta position in the b ring or the e ring) (structural formula of 1A-31, 1A-32, 1A-38, 1A-407).

[ solution 56]

[ solution 57]

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 58]

[ chemical 59]

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[ chemical 72]

[ chemical 73]

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[ 76]

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[ solution 95]

[ solution 96]

The polycyclic aromatic compound of the present invention may be used as a polymer compound obtained by substituting the reactive substituent for the polycyclic aromatic compound of the present invention as a monomer, or a crosslinked polymer compound obtained by substituting a polymerizable substituent for the monomer, or a suspended polymer compound obtained by substituting a reactive substituent for the suspended polymer compound or a suspended polymer compound obtained by substituting a crosslinkable substituent for the suspended polymer compound, for example, 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 wavelength conversion filter And a polymer cross-linked body obtained by further cross-linking the polymer compound, a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, and a pendant polymer cross-linked body obtained by further cross-linking the pendant polymer compound.

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.

[ solution 97]

L is independently a single bond, -O-, -S-, > C ═ O, -O-C (═ O) -, C1-12 alkylene, C1-12 oxyalkylene, or C1-12 polyoxyalkylene. 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 of the present invention, at least one selected from the group of compounds comprising substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and 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. With regard to the details of the "aryl" group of triarylamine or these substituents, the description of the polycyclic aromatic compounds of the present invention 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 of the present invention

The polycyclic aromatic compounds of the present invention basically utilize a bonding group (containing "N", or X¹Or X²A group) to bond the a ring and the B ring to the G ring or the B ring to the G ring, thereby producing an intermediate (first reaction), followed by the utilization of a bonding group (containing Y)¹～Y³The group (B) bonds the a ring to the B ring to the G ring or the B ring to the G ring, whereby the final product can be produced (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 nucleophilic substitution Reaction, a general Reaction such as Ullmann Reaction (Ullmann Reaction), or the like may be used, and in the case of amination, a general Reaction such as a 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 schemes (1) and (2), the second reaction is to introduce Y bonding the a ring and the B to G rings or the B to G rings¹～Y³The reaction of (3). First, N and X are each para-substituted with N-butyllithium, sec-butyllithium, tert-butyllithium or the like¹And X²The hydrogen atoms in between, or the hydrogen atoms of "N" s in relation to each other, are ortho-metalated. Then, Y such as boron trichloride or boron tribromide is added¹～Y³After the lithium-boron metal exchange, a Bronsted base such as N, N-diisopropylethylamine (Bronsted base) is added to the halide(s) to carry out a Tandem boron-doped Friedel-Crafts Reaction (Tandem Bora-Friedel-Crafts Reaction), whereby the target compound can be obtained. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. Furthermore, symbols in each structural formula in the following flow (1) and flow (2), and further in the following flows The definition of a number is the same as that described.

[ solution 98]

[ solution 99]

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 (3). According to the above method, even when the ortho-metalation is not possible due to the influence of the substituent, the target product can be produced and is useful.

[ solution 100]

The above-mentioned schemes (1) to (3) are Y¹～Y³A typical production method of boron (B) or the like.

Secondly, mixing Y¹～Y³The following schemes (4) and (5) show examples of phosphorus sulfide, phosphorus oxide, or phosphorus atoms. As described above, first, N and X are paired with N-butyllithium or the like¹And X²The hydrogen atoms in between, or the hydrogen atoms of "N" s in relation to each other, are ortho-metalated. Then, phosphorus trichloride and sulfur are sequentially added, and finally Lewis acid such as aluminum trichloride and Bronsted base such as N, N-diisopropylethylamine are added to the mixture, thereby allowing a Tandem phosphofriedel-Crafts Reaction (Tandem Phosphas-Friedel-Crafts Reaction) to be carried out, thereby obtaining Y¹～Y³Is a compound of phosphorus sulfide. The obtained phosphorus sulfide compound was treated with m-Chloroperbenzoic acid (m-CPBA), thereby obtaining a phosphorus sulfide Can obtain Y¹～Y³Y is obtained by treating a compound which is a phosphorus oxide with triethylphosphine¹～Y³Is a compound of phosphorus atom.

[ solution 101]

[ solution 102]

In the above-mentioned scheme, Y is mainly described¹～Y³For example, B, P, P ═ O or P ═ S, and other compounds can be produced by appropriately changing the raw materials.

The following example is shown in the flow: adding Y such as boron trichloride or boron tribromide¹～Y³Before the halide of (2), the pair of "N" and X is made of butyllithium or the like¹And X²While the tandem hetero Friedel-crafts reaction is carried out by subjecting hydrogen atoms (or halogen atoms) between them or hydrogen atoms (or halogen atoms) between "N" to ortho-metallation, it is also possible to add Y such as boron trichloride or boron tribromide without subjecting to ortho-metallation using butyllithium or the like¹～Y³To carry out the reaction.

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

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

As the metal- (Y) used in the above-mentioned scheme¹～Y³) The metal exchange reagent of (2) includes: y is¹～Y³Of (b) a trifluoride, Y¹～Y³Trichloride of (a) and Y¹～Y³Tribromide of (5), Y¹～Y³Y being triiodide or the like¹～Y³Halide of (i), CIPN (NEt)₂)₂Equal Y¹～Y³Of an aminated halide of, Y¹～Y³Alkoxylates of, Y¹～Y³Aryloxy compounds of (a) and the like.

Examples of the bransted base used in the above-mentioned scheme include: n, N-diisopropylethylamine, triethylamine, 2,2,6, 6-tetramethylpiperidine, 1,2,2,6, 6-pentamethylpiperidine, N-dimethylaniline, N-dimethyltoluidine, 2, 6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar, N-diisopropylethylamine, N-tetramethylpiperidine, N-dimethyltoluidine, N-dimethylpyridine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, and mixtures thereof₄BNa、Ar₄BK、Ar₃B、Ar₄Si (Ar is an aryl group such as phenyl) and the like.

As lewis acids used in the above-mentioned schemes, there can be mentioned: AlCl₃、AlBr₃、AlF₃、BF₃·OEt₂、BCl₃、BBr₃、GaCl₃、GaBr₃、InCl₃、InBr₃、In(OTf)₃、SnCl₄、SnBr₄、AgOTf、ScCl₃、Sc(OTf)₃、ZnCl₂、ZnBr₂、Zn(OTf)₂、MgCl₂、MgBr₂、Mg(OTf)₂、LiOTf、NaOTf、KOTf、Me₃SiOTf、Cu(OTf)₂、CuCl₂、YCl₃、Y(OTf)₃、TiCl₄、TiBr₄、ZrCl₄、ZrBr₄、FeCl₃、FeBr₃、CoCl₃、CoBr₃And the like.

In the scheme, in order to promote the cascade of hybrid Friedel-crafts reaction, a Bransted base or Lewis acid can also be used. Wherein, Y is used¹～Y³Of (b) a trifluoride, Y¹～Y³Trichloride of (a) and Y¹～Y³Tribromide of (5), Y¹～Y³Y being triiodide or the like¹～Y³In the case of the halide of (2), with an aromatic hydrocarbonSince an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated by the progress of the electrophilic substitution reaction of the aromatic group, it is effective to use a bronsted base which captures the acid. On the other hand, in the use of Y ¹～Y³Of an aminated halide of, Y¹～Y³In the case of the alkoxylate (b), since an amine or 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 releasing ability of an amino group or an alkoxy group is low, it is effective to use a lewis acid for promoting the release.

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 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 present invention is useful as a material for organic devices. Examples of the organic device include: organic electroluminescent elements, organic field effect transistors, organic thin film solar cells, wavelength conversion filters, or the like.

3-1. 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, the layers may each comprise a single layer, or may comprise multiple layers.

The form of the layers constituting the organic EL element may be, in addition to the structural form of "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode "," substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode "), The structural forms of "substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection 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 according to the purposeThe sheet-like, film-like, or sheet-like shape may be formed, and for example, a glass plate, a metal foil, a plastic film, a plastic sheet, or the like may 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 added₂Etc. soda lime glass for barrier coating (barrier coat) is 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 and 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 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 compoundsA biscarbazole derivative such as a carbazole derivative (e.g., N-phenylcarbazole, polyvinylcarbazole, etc.), bis (N-arylcarbazole) or bis (N-alkylcarbazole), a triarylamine derivative (e.g., a polymer having an aromatic tertiary amino group in the main or side chain, 1-bis (4-di-p-tolylaminophenyl) cyclohexane, 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, a salt thereof, a hydrate thereof, a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing the compound, N, N '-dinaphthyl-N, N' -diphenyl-4, 4 '-diphenyl-1, 1' -diamine, N⁴,N⁴' -Diphenyl-N⁴,N⁴'-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]4,4' -diamine, N⁴,N⁴,N⁴',N⁴'-tetrakis ([1,1' -biphenylyl)]-4-yl) - [1,1' -biphenyl]Triphenylamine derivatives such as-4, 4 '-diamine, 4',4 ″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, starburst amine derivatives, and the like), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, and the like), 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-hexacarbonitrile, and the like), heterocyclic compounds such as porphyrin derivatives, polysilanes, and the like. 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-donating substances, strong electron acceptors such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluorotetracyanoquinodimethane (2,3,5, 6-tetrafluorotrifluoromethyltetracyanoethane-1, 4-benzoquinodimethane, F4TCNQ) are known (see, for example, documents "m. faffir, a. bayer, t. friez, k. rio (m. pfeiffer, a. beyer, t.fritz, k.leo)," applied physics promo (appl. phys. lett.), "73 (22), 3202. qui 3204 (1998)" and documents "j. buherervz, m. faffir, t. friez, k. litt.)," applied physics promo (pff. pff.p.p.p.p.p.), "applied physics, p. ho)," applied physics jeff, k. mez, "applied physics. 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, TPD) or a starburst amine derivative (4,4',4 ″ -tris (N, N-diphenylamino) triphenylamine, TDATA) or a specific metal phthalocyanine (particularly zinc phthalocyanine (ZnPc)) 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 a reactive compound obtained by substituting a reactive substituent with the hole injection layer material and the hole transport layer material as a monomer, or as a polymer crosslinked product thereof obtained by reacting a main chain polymer with the reactive compound, or as a pendant-type polymer compound obtained by substituting a reactive substituent with the hole injection layer material and the hole transport layer material, or as a pendant-type polymer crosslinked product 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 multiple layers, and each of the light-emitting 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 plural kinds, respectively. 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 differs depending on the type of the dopant material, and may be determined by matching the characteristics of the dopant material. The amount of the dopant material 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. In the above range, for example, concentration quenching is preferably prevented. 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 electroluminescent 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. Further, in the organic electroluminescent element using the 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 40 to 99.999 wt%, 59 to 1 wt%, and 20 to 0.001 wt%, 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, of the total material for the light-emitting layer. The compound represented by the general formula (1A) or (1B) and a polymer compound thereof can also be used as an auxiliary dopant material.

Examples of the host material include condensed ring derivatives such as anthracene and pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives, which have been known as light emitting bodies.

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, compounds 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. The compound represented by the general formula (H1) is preferred.

[ solution 103]

< Compound represented by the general formula (H1) >

[ solution 104]

In the formula (H1), L¹The arylene group has 6 to 30 carbon atoms or the heteroarylene group has 2 to 30 carbon atoms, preferably the arylene group has 6 to 24 carbon atoms, more preferably the arylene group has 6 to 16 carbon atoms, further preferably the arylene group has 6 to 12 carbon atoms, particularly preferably the arylene group has 6 to 10 carbon atoms, further preferably the heteroarylene group has 2 to 25 carbon atoms, further preferably the heteroarylene group has 2 to 20 carbon atoms, further preferably the heteroarylene group has 2 to 15 carbon atoms, and particularly preferably the heteroarylene group has 2 to 10 carbon atoms. Specific examples of the arylene group include: a divalent group such as a benzene 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: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenoxazine ring, phenazine azsilicon ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, furazan ring, oxathiane ring, indolocarbazole ring, benzenoxazine ring, thiazole ring, benzpyrole ring, indole ring, or indole ring And a divalent group such as a benzindolinocarbazole ring, and a naphthobenzofuran ring.

At least one hydrogen in the compound represented by the formula (H1) 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.

< Compound represented by the general formula (H2) >

[ chemical 105]

In the formula (H2), L²And L³Each 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, further preferably an aryl group having 6 to 12 carbon atoms, particularly preferably an aryl group having 6 to 10 carbon atoms, and specifically, there can be mentioned: a monovalent group such as a benzene 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. The heteroaryl group is 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, particularly preferably a heteroaryl group having 2 to 10 carbon atoms, and specifically, there can be mentioned: 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 phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazinosilane ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxathianthracene ring, an indolocarbazole ring, a benzindolocarbazole ring, a benzindolizine ring. A monovalent group such as an indole carbazole ring and a naphthobenzofuran ring.

At least one hydrogen in the compound represented by the formula (H2) 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.

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

[ chemical 106]

In the formula (H3), the reaction mixture,

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

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 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 group₂May be-O-or-Si (CH)₃)₂-substitution, of the alkyl radical, directly bonded to the-CH of EC in formula (H3)₂Any other than-CH₂-optionally substituted by an arylene group having 6 to 24 carbon atoms, wherein any hydrogen in the alkyl group may be optionally fluorinatedAnd (4) generation.

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

[ solution 107]

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 108]

[ solution 109]

[ solution 110]

[ solution 111]

[ solution 112]

[ solution 113]

[ chemical formula 114]

[ solution 115]

[ solution 116]

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

[ solution 117]

[ chemical formula 118]

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

< Compounds 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 119]

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 with another structure represented by formula (H4).

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

Examples of the substituent in which H in "═ C (-H) -" of G is substituted are 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, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, azabenzofuryl, 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 dibenzofuryl, dibenzothienyl, carbazolyl and the like, Pyridyl, pyrimidyl, triazinyl, azabenzofuranyl, and azabenzothiophenyl, and the like. Further preferred is a dibenzofuranyl group, a dibenzothienyl group, an azabicyclofuranyl group or an azabicyclofuranyl group.

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

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, phenyldimethylsilyl and the like. 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 diphenylphosphinoxide group and ditolyphosphinoxide group.

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

Examples of the linking group to which the plurality of structures represented by the formula (H4) are bonded include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl group.

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

[ chemical formula 120]

[ solution 121]

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

[ chemical formula 122]

In the formula (H5), in the formula,

R¹～R¹¹each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above is the first substituent), and R is¹～R¹¹At least one hydrogen in (a) may further be substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group (above which is a second substituent),

R¹～R¹¹may be bonded to each other and together with the a-ring, b-ring or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the formed ring being optionally substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (the above being the first substitution)Group), at least one hydrogen of which may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl or cycloalkyl groups (the second substituent being mentioned above),

any of the rings a, b, and C "-C (-R) ═ where R is R¹～R¹¹) May be substituted with "-N ═ 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, b-ring, and C-ring in the formula (H5) — C (-R) ═ where R is R¹～R¹¹) Substituted with "-N ═ and can be changed to pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, other nitrogen-containing heteroaryl rings. The details of the description thereof may refer to the descriptions in the general formula (2A) and the formula (2B).

Preferably in the formula (H5),

R¹～R¹¹independently represents hydrogen, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, diarylamino group (wherein the aryl group is aryl group having 6 to 12 carbon atoms), alkyl group having 1 to 12 carbon atoms or cycloalkyl group having 3 to 16 carbon atoms, and R¹～R¹¹At least one hydrogen in the above-mentioned group 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,

R¹～R¹¹wherein adjacent groups in (a) 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 or c 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), 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 further 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.

Still more preferably, in the formula (H5),

R¹～R¹¹independently represents hydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 15 carbon atoms, diarylamino group (wherein 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 is¹～R¹¹At least one hydrogen in the above-mentioned group 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,

R¹～R¹¹wherein adjacent groups in (a) 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 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 aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, further preferably aryl groups having 6 to 16 carbon atoms, particularly preferably aryl groups having 6 to 12 carbon atoms, and most preferably aryl groups having 6 to 10 carbon atoms. Examples thereof 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-1-2-naphthyl as a tricyclic aryl group, terphenyl-4 ' -yl as a tricyclic aryl group, P-terphenyl-4-yl), acenaphthylene- (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-, 2-) yl, pyrene- (1-, perylene- (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, phenazino-yl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, phosphonyl, tetrazolyl, cinnolinyl, thienyl, benzoxazolyl, thienyl, benzothienyl, dibenzothienyl, benzothienyl, dibenzothienyl, etc, Dibenzophosphoryl group, a monovalent group of a dibenzophosphole oxide ring, a furazan group, a thianthryl group, an indolocarbazolyl group, a benzindolocarbazolyl group, and a benzindolocarbazolyl group.

The "alkyl group" in the first substituent and the second substituent may be either a straight chain or branched chain, and examples thereof include 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), more preferably an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms) or an alkyl group having 1 to 4 carbon atoms (a branched chain 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, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3, 3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 2, 6-dimethyl-4-heptyl, 3,5, 5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-tridecyl, N-heptadecyl, n-octadecyl, n-eicosyl, and the like. Further, examples of the method include: 1-ethyl-1-methylpropyl, 1-diethylpropyl, 1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1, 4-trimethylpentyl, 1, 2-trimethylpropyl, 1-dimethyloctyl, 1-dimethylpentyl, 1-dimethylheptyl, 1, 5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1, 3-dimethylbutyl, 1,2, 2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1-diethylbutyl, 1-ethyl-1-methylpentyl, 1, 3-trimethylbutyl, 1-propyl-1-methylpentyl, 1-ethylbutyl, 1-methylpentyl, 1,1, 2-trimethylpropyl, 1-ethyl-1, 2, 2-trimethylpropyl, 1-propyl-1-methylbutyl, 1-dimethylhexyl and the like.

In the first substituent and the second substituent, as the "cycloalkyl group", there may be mentioned: a cycloalkyl group having 3 to 24 carbon atoms, 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 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a cycloalkyl group having 5 carbon atoms, and the like. Examples thereof include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms of these groups, or 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 R¹、R³、R⁴、R⁵、R¹⁰And R¹¹More preferably, for example, to R¹And R³Substituted with respect to R⁵And R¹⁰Substituted with respect to R⁴And R¹¹Aryl is preferably phenyl.

The substitution position when the first substituent is heteroaryl is preferably R¹、R²、R³、R⁴、R⁵、R⁶、R⁹、R¹⁰And R¹¹More preferably, for example, to R¹Substituted with respect to R²Substituted with respect to R³Substituted with respect to R¹And R³Substituted with respect to R ⁴And R¹¹Substituted with respect to R⁵And R¹⁰Substituted with respect to R⁶And R⁹The 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 formula (H5) include compounds represented by the following structural formulae. Further, "Me" in the formula is methyl.

[ solution 123]

[ solution 124]

The compound represented by formula (H5) can be produced by first bonding the a-ring to c-ring via a bonding group (-O-) to produce an intermediate (first reaction), and then bonding the a-ring to c-ring via 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 125]

In the formula (H6), in the formula,

R¹～R¹⁶each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above is the first substituent), and R is ¹～R¹⁶Which in turn may be substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group (the second substituent above),

R¹～R¹⁶wherein adjoining groups in (a) may be bonded to each other and form together with the a-, b-, c-, or d-ring an aryl or heteroaryl ring, at least one hydrogen in the ring formed may be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (above the first substituent), at least one hydrogen of these substituents may in turn be substituted by aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (above the second substituent),

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

Preferably in said formula (H6),

R¹～R¹⁶independently represents hydrogen, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 12 carbon atoms), alkyl group having 1 to 12 carbon atoms orCycloalkyl having 3 to 16 carbon atoms, wherein R is¹～R¹⁶At least one hydrogen in the above-mentioned group 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,

R¹～R¹⁶Wherein 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, 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 (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.

More preferably, in the formula (H6),

R¹～R¹⁶independently represents hydrogen, aryl group having 6-16 carbon atoms, heteroaryl group having 2-15 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6-10 carbon atoms), alkyl group having 1-6 carbon atoms or cycloalkyl group having 3-14 carbon atoms, and R¹～R¹⁶At least one hydrogen in the above-mentioned group 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,

R¹～R¹⁶wherein 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, 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.

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

Specific examples of the "aryl group" 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, still more preferably aryl groups having 6 to 16 carbon atoms, particularly preferably aryl groups having 6 to 12 carbon atoms, and most preferably aryl groups having 6 to 10 carbon atoms. Examples thereof 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-1-2-naphthyl as a tricyclic aryl group, terphenyl-4 ' -yl as a tricyclic aryl group, P-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) based, phenalene- (1-, 2-) based, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetrabiphenyl (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-, 2-) based as condensed tetracyclic aryl, 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.

The "alkyl group" in the first substituent and the second substituent may be either a straight chain or branched chain, and examples thereof include 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), more preferably an alkyl group having 1 to 12 carbon atoms (a branched chain alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (a branched chain alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (a branched chain alkyl group having 3 to 5 carbon atoms) or an alkyl group having 1 to 4 carbon atoms (a branched chain 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, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3, 3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 2, 6-dimethyl-4-heptyl, 3,5, 5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-tridecyl, N-heptadecyl, n-octadecyl, n-eicosyl, and the like. Further, examples thereof include: 1-ethyl-1-methylpropyl, 1-diethylpropyl, 1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1, 4-trimethylpentyl, 1, 2-trimethylpropyl, 1-dimethyloctyl, 1-dimethylpentyl, 1-dimethylheptyl, 1, 5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1, 3-dimethylbutyl, 1,2, 2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1-diethylbutyl, 1-ethyl-1-methylpentyl, 1, 3-trimethylbutyl, 1-propyl-1-methylpentyl, 1-ethylbutyl, 1-methylpentyl, 1,1, 2-trimethylpropyl, 1-ethyl-1, 2, 2-trimethylpropyl, 1-propyl-1-methylbutyl, 1-dimethylhexyl and the like.

The compound represented by the formula (H6) can be produced by referring to the description 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 with high efficiency, 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.

[ solution 126]

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)¹T¹) Is below 0.2eV (Hiroki UOyama, Xinzhijian (Kenichi Goushi), Zhijin Katsuyuki Shizu, wild village Haozi (Hiroko Nomura), Chihaya Adachi, Nature (Nature), 492, 234-shaped 238 (2012)). Energy difference (Δ S)¹T¹) 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 TADF compound of D-a type) designed to localize HOMO and LUMO within molecules using an electron donating substituent called a donor and an electron accepting substituent called an acceptor to produce efficient reverse intercross 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 a donor or acceptor have a large Spin Orbit Coupling (SOC) and a small exchange interaction between HOMO and LUMO due to structural reasons, and a small Δ E (ST), and thus can achieve a 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 a stable structure in the excited state thereafter), and a broad 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. TADF materials function as auxiliary dopants, while the other components function as emissive dopants. The other component may be a compound in which the absorption spectrum of the compound and the emission peak of the auxiliary dopant at least partially overlap.

As the structure of the donor and the acceptor used in the TADF material, for example, the structures described in chemical of Materials (2017, 29, 1946-. The ED may contain sp ³The functional group of nitrogen, more specifically, can be cited: and groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenylindolinocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolyamine, tetraphenylcarbazolylamine, phenoxazine, dihydrophenazine, phenothiazine, dimethylacridine, diphenylamine, (bis (t-butyl) phenyl) amine, ((diphenylamino) phenyl) diphenylphenylenediamine, dimethylatetraphenyldihydroacridine, tetramethyl-dihydro-indenylacridine, and diphenyl-dihydrodibenzoazacillin. Further, EA includes, for example, an sp-containing compound²Nitrogen aromatic ring, CN-substituted aromatic ring, ketone-containing ring, and cyano group, and more specifically, the following are included: from sulfonylbenzophenones, benzophenones, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, parachlorophthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthrone, anthracenedione, pyridine, cycloheptylpyridine, benzenetricarboxylic nitrile, fluorenedinitrile, pyrazinedicarboxylinitrile, pyridinedicarbonitrile, dibenzoquinophthalonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis (phenylsulfonyl) benzene, dimethylthioxanthene And groups derived from dioxides, 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 member selected from the group consisting of 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 formula (H7-1), formula (H7-2) and formula (H7-3).

[ solution 127]

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)₂From 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, a single bond, -O-, or > N-Ar is preferable,

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

Each Q is independently ═ C (-H) -, or ═ N-, and from the viewpoint of the shallowness of the LUMO of the partial structure formed and the height of the excited singlet level and the excited triplet level, it is preferably ═ N-,

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 in terms of the depth of the HOMO of the partial structure formed and the heights of the excited singlet level and excited triplet level, the preferred is 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 preferred is hydrogen, phenyl, tolyl, xylyl, mesitylphenyl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl or phenylbenzimidazolyl, and further preferred is 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 128]

[ solution 129]

[ solution 130]

[ solution 131]

[ solution 132]

[ solution 133]

[ solution 134]

[ solution 135]

[ solution 136]

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

In addition, as the dopant material, in addition to the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B), a known compound may be used, and the dopant material may 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

iso-condensed ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivativesBiological, 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 1-245087), bisstyrylarylene derivatives (Japanese patent laid-open No. Hei 2-247278), diazabenzodiindene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, ditrimethylphenylisobenzofuran, bis (2-methylphenyl) isobenzofuran, bis (2-trifluoromethylphenyl) isobenzofuran, phenylisobenzofuran, etc., dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidylcoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazoleylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolinylcoumarin derivatives and other coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, quinoxalone derivatives, acridine derivatives, oxazine derivatives, phenyl ether derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2, 5-thiadiazolopyridine derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium salt derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives, and the like.

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

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

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, onium salt derivatives, violanthrone derivatives, phenazine derivatives, phenoxazinone derivatives, and thiadiazolopyriene derivatives, etc., and further, the following compounds are also exemplified as preferable examples: examples of the blue-green-yellow 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 the compounds exemplified above.

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

Among the dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferable.

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

[ solution 137]

In the formula, Ar¹Is an m-valent group derived from an aryl group having 6 to 30 carbon atoms, Ar²And Ar³Each independently an aryl group having 6 to 30 carbon atoms, Ar¹～Ar³At least one of (A) has a stilbene structure, Ar¹～Ar³May 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.

[ 138]

In the formula, Ar²And Ar³Each independently an aryl group having 6 to 30 carbon atoms, Ar²And Ar³May be substituted by aryl, heteroarylAlkyl, 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, phenanthryl, anthryl, fluoranthryl, triphenylenyl, pyrenyl, phenanthrenyl, and phenanthrenyl,

Mesitylene, perylene, 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, toluene, xylene, and the like, 2, 7-bis [4' -bis (diphenylamino) styryl ] -9, 9-dimethylfluorene, 4' -bis (9-ethyl-3-carbazolenyl) -biphenyl, 4' -bis (9-phenyl-3-carbazolenyl) -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 Nos. 11-97178, 2000-133457, 2000-26324, 2001-267079, 2001-267078, 2001-267076, 2000-34234, 2001-267075, and 2001-217077 may 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 139]

In the formula, Ar⁴An n-valent group derived from an aryl group having 6 to 30 carbon atoms, Ar⁵And Ar⁶Each independently an aryl group having 6 to 30 carbon atoms, Ar⁴～Ar⁶May 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 n is an integer of 1 to 4.

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

Divalent radicals of fluorene, benzofluorene or pyrene, Ar⁵And Ar⁶Each independently an aryl group having 6 to 30 carbon atoms, Ar⁴～Ar⁶May 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.

Specific examples of the aryl group having 6 to 30 carbon atoms include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, phenanthrenyl, triphenylenyl, phenanthrenyl, pyrenyl, phenanthrenyl, and phenanthrenyl, phenanthr,

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: n, N, N ', N ' -tetraphenylpyrene-1, 6-diamine, N, N, N ', N ' -tetra (p-tolyl) pyrene-1, 6-diamine, N, N, N ', N ' -tetra (m-tolyl) pyrene-1, 6-diamine, N, N, N ', N ' -tetra (4-isopropylphenyl) pyrene-1, 6-diamine, N, N, N ', N ' -tetra (3, 4-dimethylphenyl) pyrene-1, 6-diamine, N, N ' -diphenyl-N, N ' -di (p-tolyl) pyrene-1, 6-diamine, N, N ' -diphenyl-N, N ' -bis (4-ethylphenyl) pyrene-1, 6-diamine, N, N ' -diphenyl-N, n ' -bis (4-isopropylphenyl) pyrene-1, 6-diamine, N, N ' -diphenyl-N, N ' -bis (4-t-butylphenyl) pyrene-1, 6-diamine, N, N ' -bis (4-isopropylphenyl) -N, N ' -di (p-tolyl) pyrene-1, 6-diamine, N, N, N ', N ' -tetrakis (3, 4-dimethylphenyl) -3, 8-diphenylpyrene-1, 6-diamine, N, N-tetraphenylpyrene-1, 8-diamine, N, N ' -bis (biphenyl-4-yl) -N, N ' -diphenylpyrene-1, 8-diamine ¹,N⁶-diphenyl-N¹,N⁶-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-tert-butylphenyl) anthracene-9, 10-diamine, N, N' -bis (4-isopropylphenyl) -N, N '-di (p-tolyl) anthracene-9, 10-diamine, 2, 6-di-tert-butyl-N, N, N', N '-tetra (p-tolyl) anthracene-9, 10-diamine, 2, 6-di-tert-butyl-N, N' -diphenyl-N, N '-bis (4-isopropylphenyl) anthracene-9, 10-diamine, 2, 6-di-tert-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-tert-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, 2, 6-dicyclohexyl-N, N ' -bis (4-isopropylphenyl) -N, N ' -bis (4-tert-butylphenyl) anthracene-9, 10-diamine, 9, 10-bis (4-diphenylamino-phenyl) anthracene, 9, 10-bis (1-naphthylamino) anthracene, 10-diphenylamino-9- (4-diphenylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (6-diphenylamino-2-naphthyl) anthracene, and the like.

Further, 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' -bis [ 6-diphenylaminonaphthalen-2-yl ] biphenyl, 4 '-bis [ 4-diphenylaminonaphthalen-1-yl ] -p-terphenyl, 4' -bis [ 6-diphenylaminonaphthalen-2-yl ] -p-terphenyl, and the like.

Further, the 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.

Further, coumarin derivatives described in Japanese patent laid-open Nos. 2004-43646, 2001-76876, and 6-298758 may be used.

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

[ solution 140]

Further, pyran derivatives described in Japanese patent laid-open Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081081090, 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 as a polymer cross-linked product thereof obtained by reacting a main chain polymer with the reactive compound, or as a pendant polymer compound obtained by substituting a reactive substituent in the material for the light-emitting layer (host material and dopant material) or as a pendant polymer cross-linked product 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.

< 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 a layer that has high electron injection efficiency and efficiently transports the injected electrons. 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 preventing holes from the anode from flowing 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 which 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 and used arbitrarily from 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, phosphorus 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, naphthalimide derivatives, perylene derivatives, and the like, Pyrazine derivatives, benzoquinoline derivatives (e.g., 2 '-bis (benzo [ h ] quinolin-2-yl) -9,9' -spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (e.g., tris (N-phenylbenzimidazol-2-yl) benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (e.g., 1, 3-bis (2,2 ': 6',2 '-terpyridin-4' -yl) benzene), naphthyridine derivatives (e.g., bis (1-naphthyl) -4- (1, 8-naphthyridin-2-yl) phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, and the like, 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

Examples of the borane derivatives are compounds represented by the following general formula (ETM-1), and are disclosed in detail in Japanese patent laid-open No. 2007-27587.

[ solution 141]

In the formula (ETM-1), R¹¹And R¹²Each 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, R¹³～R¹⁶Each 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 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 142]

In the formula (ETM-1-1), R¹¹And R¹²Each 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, R¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, R²¹And R²²Each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X¹Is an optionally substituted arylene group having 20 or less carbon atoms, n is independently an integer of 0 to 3, and m is independently 0 to E4, or a pharmaceutically acceptable salt thereof. 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 143]

In the formula (ETM-1-2), R¹¹And R¹²Each 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～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X¹Is an arylene group having 20 or less carbon atoms which may be substituted, and n is 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 groups, and the like.

As X¹Specific examples of (3) include divalent groups represented by any one of the following formulae (X-1) to (X-9). Each structural formula represents a bonding site.

[ solution 144]

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

Specific examples of the borane derivative include the following compounds.

[ solution 145]

The borane derivatives can be produced using known starting materials and known synthetic methods.

< pyridine derivatives >

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

[ solution 146]

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 1-4.

In the formula (ETM-2-1), R¹¹～R¹⁸Each 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).

In the formula (ETM-2-2), R¹¹And R¹²Each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), R¹¹And R¹²May 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 the phi, anthracene ring or fluorene ring in each formula via phenylene or naphthylene. Each structural formula represents a bonding site.

[ solution 147]

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 148]

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 R¹¹～R¹⁸The "alkyl group" in (1) may be either a straight chain or branched chain, 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 preferred "alkyl group" is 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 preferred "alkyl group" is 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, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3, 3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 2, 6-dimethyl-4-heptyl, 3,5, 5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-decyl, n-dodecyl, N-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

Further, examples thereof include: 1-ethyl-1-methylpropyl, 1-diethylpropyl, 1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1, 4-trimethylpentyl, 1, 2-trimethylpropyl, 1-dimethyloctyl, 1-dimethylpentyl, 1-dimethylheptyl, 1, 5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1, 3-dimethylbutyl, 1,2, 2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1-diethylbutyl, 1-ethyl-1-methylpentyl, 1, 3-trimethylbutyl, 1-propyl-1-methylpentyl, 1-ethylbutyl, 1-methylpentyl, 1,1, 2-trimethylpropyl, 1-ethyl-1, 2, 2-trimethylpropyl, 1-propyl-1-methylbutyl, 1-dimethylhexyl and the like.

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 R¹¹～R¹⁸Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The preferable "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further 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 which is substituted in a pyridine substituent, the description thereof can be cited.

As R¹¹～R¹⁸The "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, further 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" includes: 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-) as non- (1-, 2-) as condensed tricyclic aryl, (1-, 2-, 3-, 4-, 9-) phenanthrene, triphenylene- (1-, 2-) as condensed tetracyclic aryl, pyrene- (1-, 2-, 4-) as condensed tetracyclic aryl, tetracene- (1-, 2-, 5-) as condensed pentacyclic aryl, perylene- (1-, 2-, 3-) as condensed tetracyclic aryl, perylene- (2-, 3-) as condensed tetracyclic aryl, perylene, and the like, Pentacene- (1-, 2-, 5-, 6-) radicals and the like.

Preferred examples of the "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) ¹¹And R¹²The 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.

[ 149]

The pyridine derivatives can be produced using known starting materials and known synthetic methods.

< fluoranthene derivative >

Fluoranthene derivatives are, for example, compounds represented by the following general formula (ETM-3), and are disclosed in detail in international publication No. 2010/134352.

[ solution 150]

In the formula (ETM-3), X¹²～X²¹Represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. 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 151]

< 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).

[ solution 152]

R¹～R¹¹Each independently hydrogen, 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 silyl¹～R¹¹At least one hydrogen of (a) may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

In addition, R¹～R¹¹May 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, aryloxy or substituted silane 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 the form of the substituent or ring in the formula (ETM-4), or the polymer in which a plurality of structures of the formula (ETM-4) are combined, the description of the polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) can be cited.

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

[ solution 153]

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 154]

Ar is each independently divalent benzene or naphthalene, R¹～R⁴Each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or aryl 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 155]

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 R¹～R⁴The alkyl group having 1 to 6 carbon atoms in the group 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 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, 4-methyl-2-pentyl, 3-dimethylbutyl, or 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, or tert-butyl.

As R¹～R⁴Specific 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 R¹～R⁴The aryl group having 6 to 20 carbon atoms in (A) 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 monocyclic aryl, (2-, 3-, 4-) biphenyl, as condensed bicyclic aryl, (1-, 2-) naphthyl, as tricyclic 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, o-terphenyl-4 '-yl, p-terphenyl-2-yl, p-terphenyl-4' -yl, p-terphenyl-4-yl, p-terphenyl-2-yl, p-cumyl, or the like, 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), 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-, 4-, 9-) phenanthryl as condensed tricyclic aryl, triphenylene- (1-, 9-) -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, 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).

[ solution 156]

Ar¹Each independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar²As the aryl group having 6 to 20 carbon atoms, the same description as "aryl group having 6 to 20 carbon atoms" in the 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.

R¹～R⁴Each independently 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, as described in the above formula (ETM-5-1).

Specific examples of the anthracene derivative include the following compounds.

[ chemical formula 157]

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

< benzofluorene derivative >

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

[ solution 158]

Ar¹As the aryl group having 6 to 20 carbon atoms, the same description as "aryl group having 6 to 20 carbon atoms" in the 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.

Ar²Independently represents hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), or two Ar²May be bonded to form a ring.

As Ar²The "alkyl group" in (1) may be either a straight chain or branched chain, 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 preferred "alkyl group" is 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 preferred "alkyl group" is 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, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

As Ar²Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. Preferred "cycloalkyl groups"Is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further 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 Ar²The "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 examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, pentacenyl, and the like.

Two Ar²The 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.

[ chemical 159]

The benzofluorene derivative can be produced using known raw materials and known synthetic methods.

< 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.

[ solution 160]

R⁵Is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,A cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁶CN, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 5 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms or aryloxy group having 6 to 20 carbon atoms,

R⁷and R⁸Independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁹is 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).

[ solution 161]

R¹～R³Which may be the same or different, are 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.

Ar¹May be the same or different and is an arylene or heteroarylene group. Ar (Ar)²May be the same or different and is aryl or heteroaryl. Wherein Ar is¹And Ar²Has 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 present¹。

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 carbons 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 within a 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 cyclopentenyl group, cyclopentadienyl group, or 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 number of carbon atoms 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 an aromatic hydrocarbon group such as a phenoxy group through 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 means 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 represents 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 silyl 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, Ar¹And R²、Ar¹And R³、Ar²And R²、Ar²And R³、R²And R³、Ar¹And Ar²Etc. to form conjugated or non-conjugated condensed rings therebetween. Here, in the case where n is 1, two R' s¹May form conjugated or non-conjugated condensed rings with each other. These condensed rings may beThe ring-inside structure may contain a nitrogen atom, an oxygen atom, a sulfur atom, and may further be condensed with another ring.

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

[ chemical 162]

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

[ pyrimidine derivative ]

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.

[ chemical 163]

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 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-1-2-naphthyl as a tricyclic aryl group, terphenyl-4 ' -yl as a tricyclic aryl group, P-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) based, phenalene- (1-, 2-) based, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetrabiphenyl (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-, 2-) based as condensed tetracyclic aryl, 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 "optionally substituted 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 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, phenazino-yl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzoxazolyl, tetrazolyl, cinnolinyl, quinoxalinyl, naphthyridinyl, naphthofuranyl, thienyl, naphthobenzothienyl, benzoxazolyl, and/or benzoxazolyl, and/or a, A monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, a furazan group, a thianthrenyl group, an indolocarbazole group, a benzindolocarbazole group, 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.

[ 164]

The pyrimidine derivatives can be produced using known starting materials and known synthetic methods.

< carbazole derivative >

The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a polymer in which a plurality of carbazole derivatives are bonded to each other by a single bond or the like. The details are described in U.S. Pat. No. 2014/0197386.

[ solution 165]

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

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, further 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, phenazino-yl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzoxazolyl, tetrazolyl, cinnolinyl, quinoxalinyl, naphthyridinyl, naphthofuranyl, thienyl, naphthobenzothienyl, benzoxazolyl, and/or benzoxazolyl, and/or a, A monovalent group of a benzo-phosphacyclopentadiene oxide ring, a monovalent group of a dibenzophosphacyclopentadiene oxide ring, a furazan group, a thianthrenyl group, an indolocarbazolyl group, a benzindolocarbazolyl group, and the like.

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

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.

[ chemical 166]

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. Pat. No. 2011/0156013.

[ 167]

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 "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-1-2-naphthyl as a tricyclic aryl group, terphenyl-4 ' -yl as a tricyclic aryl group, P-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) based, phenalene- (1-, 2-) based, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetrabiphenyl (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-, 2-) based as condensed tetracyclic aryl, 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 triazine derivative include the following compounds.

[ chemical 168]

The triazine derivatives can be produced using known starting materials and known synthetic methods.

< benzimidazole derivative >

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

[ 169]

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 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 170]

R in said benzimidazolyl group¹¹Is hydrogen, carbon number 1Alkyl group having 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)¹¹And (4) description.

φ is further preferably an anthracycline or fluorene ring, and the structure in that case can be referred to the description in said formula (ETM-2-1) or formula (ETM-2-2), R in each formula¹¹～R¹⁸The description in said formula (ETM-2-1) or formula (ETM-2-2) may be cited. In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with benzimidazole substituents, two pyridine substituents may be substituted with benzimidazole substituents (that is, n ═ 2), and one pyridine substituent may be substituted with benzimidazole substituents and R may be substituted with benzimidazole substituents¹¹～R¹⁸Substituted with another pyridine substituent (i.e., n ═ 1). Further, R in the formula (ETM-2-1) may be substituted with a benzimidazole-based substituent¹¹～R¹⁸And R is¹¹～R¹⁸Substituted "pyridine-based substituents".

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- (naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-imidazole H-benzo [ d ] imidazole, 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole, 1- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -2-phenyl-1H-benzo [ d ] imidazole, 5- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) -1, 2-diphenyl-1H-benzo [ d ] imidazole, and the like.

[ solution 171]

The benzimidazole derivatives can be produced using known starting materials and known synthetic methods.

[ phenanthroline derivative ]

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

[ solution 172]

Of the formulae R¹¹～R¹⁸Each 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). In addition, R in the formula (ETM-12-1)¹¹～R¹⁸Is bonded to phi as the aryl ring.

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

As R¹¹～R¹⁸Alkyl, cycloalkyl and aryl in (1), R in said formula (ETM-2) can be cited¹¹～R¹⁸And (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.

[ chemical formula 173]

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-phenanthrolin-5-yl) benzene, 9' -difluoro-bis (1, 10-phenanthrolin-5-yl), 2, 9-dimethyl-4, 7-biphenyl-1, 10-phenanthroline (bathocuproine), 1, 3-bis (2-phenyl-1, 10-phenanthrolin-9-yl) benzene, a compound represented by the following structural formula, or the like.

[ solution 174]

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).

[ chemical 175]

In the formula, R¹～R⁶Each 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) (phenoxide), 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 tris (4-methyl-8-quinolinolate), Bis (2-methyl-8-quinolinolato) (2-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 3-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 4-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-diphenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-triphenylpheno) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-trimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5, 6-tetramethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, bis (2-methyl-8-quinolinolato) (2-naphthol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-naphthol) aluminum, bis (2-methyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) aluminum, bis (2-phenylphenolate) aluminum, bis (2-8-phenylphenolate) aluminum, bis (2-phenylphenolate) aluminum, and (2-phenylphenolate) aluminum, Bis (2, 4-dimethyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, 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, and 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-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum -hydroxyquinoline) aluminum, bis (10-hydroxybenzo [ h ] quinoline) beryllium, 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 >

Examples of the thiazole derivative include compounds represented by the following formula (ETM-14-1).

[ solution 176]

Phi- (thiazole series substituents)_n (ETM-14-1)

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

[ solution 177]

Phi- (benzothiazole 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 a "thiazole substituent" or a "benzothiazole substituent" is a substituent in which a pyridyl group in the "pyridine substituent" of the formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is substituted with a thiazolyl group or a 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 178]

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 formula¹¹～R¹⁸Reference may be made to the description in said formula (ETM-2-1) or formula (ETM-2-2). In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with a thiazole substituent (or a benzothiazole substituent), two pyridine substituents (that is, n ═ 2) may be substituted with a thiazole substituent (or a benzothiazole substituent), and one of the pyridine substituents may be substituted with a thiazole substituent (or a benzothiazole substituent) and R may be substituted with a thiazole substituent (or a benzothiazole substituent) ¹¹～R¹⁸Substituted with 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 example¹¹～R¹⁸And R is¹¹～R¹⁸Substituted "pyridine-based substituents".

These thiazole derivatives or 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.

[ chemical 179]

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).

R¹～R⁴Each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, mercapto, 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 R¹～R⁴The halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl, and alkynyl in (1) can be mentioned in detail as described in the general formula (1A) and the general formula (1B).

With respect to R¹～R⁴In (1), alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxyThe alkyl group, aryl group and alkoxy group in (1) may be referred to the descriptions in the general formula (1A) and the general formula (1B).

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, R¹And R²、R²And R³、R³And R⁴Etc. 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 inner structure, and may further be condensed with other rings.

Among them, the compound is preferably represented by the formula R¹And R⁴In the case of phenyl, X and Y are not alkyl or phenyl. In addition, it is preferable that R is not satisfied at the same time¹And R⁴In the case of thienyl, X and Y are alkyl and R²And R³Is alkyl, aryl, alkenyl or R²And R³A cycloalkyl group bonded to form a ring. In addition, it is preferable that when R is¹And R⁴When it is a silane group, R²、R³X and Y are each independently not hydrogen or alkyl of 1 to 6 carbon atoms. In addition, it is preferable that R is ¹And R²In 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.

(Azoline derivatives)

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 180]

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 is¹～R⁵Each independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein Ar in the above-mentioned formula > N-Ar and R are¹～R⁵Any one 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 181]

In the formula (L-1), X¹～X⁶Each independently is ═ CR⁶-or ═ N-, X¹～X⁶At least two of which are ═ CR⁶-，X¹～X⁶Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is a hydrogen atom, and is,

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is 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 182]

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), R¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

in the formula (ETM-16-2), R¹～R⁵Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

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

[ solution 183]

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR ⁶R in (a-C)⁶Is 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: phi is selected from the group consisting of monovalent radicals represented by the following formulas (phi 1-1) to (phi 1-18), divalent radicals represented by the following formulas (phi 2-1) to (phi 2-34), trivalent radicals represented by the following formulas (phi 3-1) to (phi 3-3), and tetravalent radicals represented by the following formulas (phi 4-1) to (phi 4-2), wherein at least one hydrogen of phi 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, a symbol indicates a bonding position.

[ solution 184]

[ solution 185]

[ solution 186]

Z in the formula is > CR₂N-Ar, > N-L, -O-or-S-, > CR₂Wherein 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 is¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Same as R³And R⁴Are the same, and R¹～R⁴All 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.

[ chemical formula 187]

[ solution 188]

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

[ chemical 189]

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 is 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, wherein at least one hydrogen of Ar is substituted with 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,

R¹～R⁴each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkylIn, R¹And R²Same as R³And R⁴Are the same, and R¹～R⁴Not 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.

[ 190 of design ]

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

The oxazoline derivatives can be produced using known starting materials and known synthetic methods.

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 2.36eV), K (work function 2.28eV), Rb (work function 2.16eV), and Cs (work function 1.95eV), and alkaline earth metals such as Ca (work function 2.9eV), Sr (work function 2.0 to 2.5eV), and Ba (work function 2.52eV), and particularly preferable substances have a work function of 2.9eV or less. Among these, K, Rb or Cs as an alkali metal is more preferable as the reducing substance, Rb or Cs is more preferable, and Cs is most preferable. 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 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 such a 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 that 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 minute amount of lithium, cesium, or magnesium into an organic layer and using an electrode having high stability is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also 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, 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 of manufacturing 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 the layers >

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 formed as individual layers, 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 as a polymer binder, 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.

< method for manufacturing organic electroluminescent element >

Each layer constituting the organic EL element can be formed by vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular laminationThe material to be used for each layer is formed into a thin film by a method such as a printing method, a spin coating method, a casting method, or a coating method. 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 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 the boat heating temperature and 10 degrees of vacuum^-6Pa～10^-3Pa, 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. Further, 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 cathode, the electron injection layer, the electron transport layer, the light-emitting layer, the hole transport layer, the hole injection layer, and the anode may be produced in this order.

< Wet film Forming method >

A low-molecular-weight compound capable of forming each organic layer of an 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 formation method forms a coating film by a coating step of coating a substrate with an organic layer forming composition and a drying step of removing a solvent from the coated organic layer forming composition. 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 and a different method may be used.

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 the case of the wet film formation method, lamination may be difficult as compared with the vacuum deposition method. In the case of producing a laminated film by a wet film formation method, it is necessary to prevent dissolution of the lower layer by the composition of the upper layer and to use a composition having controlled solubility, a crosslinking of the lower layer, an Orthogonal solvent (mutually insoluble solvent), and the like. However, even with these techniques, it is sometimes difficult to apply the wet film formation method to the coating of all the films.

Thus, in general, the following methods may 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 of light-emitting layer Forming composition comprising host Material and dopant Material by Wet film formation method

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

(program 6) deposition of an 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 organic layer-forming composition may be a composition which is made into a solid state by removing the solvent from the 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 preferable_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 in Boiling Point (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, a fluorine-containing solvent, and the like, 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, tetradecanol, hexane-2-ol, heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α -terpineol, β -terpineol, γ -terpineol, δ -terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol butyl methyl ether, diethylene glycol butyl ether, ethylene glycol butyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol butyl ether, ethylene glycol dimethyl ether, and the like, 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-fluorophenylmethyl ether, anisole, 2, 3-dimethylpyrazine, bromobenzene, 4-fluorophenylmethyl ether, 3-trifluoromethylanisole, mesitylene, 1,2, 4-trimethylbenzene, tert-butylbenzene, 2-methylanisole, phenetole, benzodioxole (benzodioxyle), 4-methylanisole, sec-butylbenzene, 3-methylanisole, tert-butylbenzene, xylene, 4-fluoro-3-methylanisole, isopropyltoluene (cymene), 1,2, 3-trimethylbenzene, 1, 2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoro-o-dimethoxybenzene (4-fluorodimethoxyantrole), 2, 6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2, 5-dimethylanisole, 2, 4-dimethylanisole, benzonitrile, 3, 5-dimethylanisole, diphenylether, 1-fluoro-3, 5-dimethoxybenzene, methyl benzoate, isoamylbenzene, 3, 4-dimethylanisole, o-tolunitrile (o-tolunitrile), n-pentylbenzene, o-dimethoxybenzene (veratrole), 1,2,3, 4-tetrahydronaphthalene, ethyl benzoate, N-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2 '-dimethylbiphenyl (2,2' -bitolyl), dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2, 3-dihydrobenzofuran, 1-methyl-4- (propoxymethyl) benzene, 1-methyl-4- (butoxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) benzene, 1-methyl-4- (heptyloxymethyl) benzene, benzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether, etc., but 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 organic layer-forming composition 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 one kind or a mixture of two or more kinds.

(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: pelizafelo (Polyflow) No.45, Pelizafelo (Polyflow) KL-245, Pelizafelo (Polyflow) No.75, Pelizafelo (Polyflow) No.90, Pelizao (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 BYK-Chemie (Japan) corporation); 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, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene naphthyl ether, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, polyoxyethylene naphthyl ether, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan monolaurate, and the like, Alkyl benzene sulfonates and alkyl diphenyl ether disulfonates.

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

< composition and Property 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 components and stirring, mixing, heating, cooling, dissolving, dispersing, and the like by a known method. After the preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas substitution/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-forming properties 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 viscosity of the organic layer forming composition is preferably 20 to 40mN/m, more preferably 20 to 30mN/m, in surface tension at 25 ℃. In the present invention, the surface tension is a value measured using a pendant drop method.

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

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

[ solution 191]

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% by weight 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 192]

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 193]

[ solution 194]

[ solution 195]

[ solution 196]

< method for producing Polymer Compound and crosslinkable Polymer Compound

The production methods of the polymer compound and the crosslinkable polymer compound are 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 in 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 formula (H3) or the compound of formula (XLP-1) is produced, it 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 conducting 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 an 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 or a dendrimer (dendrimer) can be synthesized.

[ solution 197]

a. MU or MUx

A polymerizable group x and y (each bond of x and y)

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

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

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

The monomer unit usable in the present invention can be synthesized by the methods described in Japanese patent laid-open Nos. 2010-189630, 2012/086671, 2013/191088, 2002/045184, 2011/049241, 2013/146806, 2005/049546, 2015/145871, 2008-106241, 2010-215886, 2016/031639 and 2011-174062.

Further, specific polymer synthesis procedures can be synthesized according to the 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.

< example of application 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. In addition, 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 panel, 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 segment 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 computer applications in which thinning is an issue in liquid crystal display devices, when it is considered that thinning is difficult in the conventional system including a fluorescent lamp or a light guide plate, the backlight using the light emitting element of the present embodiment has features of thinness and lightweight.

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 an 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 with narrow emission half-value widths are used as phosphors for wavelength conversion filters to expand the color gamut of the display. However, the use of quantum dots has the following problems. High cohesiveness due to its oxidative instability and nanoscale fine particles, and the metals used are regulated as contaminants. The polycyclic aromatic compound of the present invention is useful as a phosphor for a wavelength conversion filter. As the matrix for dispersing the polycyclic aromatic compound, a high molecular material having high transparency, low moisture permeability, low oxygen permeability, and high thermal stability, for example, (meth) acrylic acid polymers (such as polymethyl (meth) acrylate) and cycloolefin polymers (such as Zeonex) are preferable.

[ 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-18)

Boron tribromide (1.13ml, 12mmol, 4eq.) was added to a flask containing compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) and o-dichlorobenzene (400ml) under nitrogen at room temperature. After the completion of the dropwise addition, the temperature was raised to 180 ℃ and the mixture was stirred for 20 hours. After that, it was cooled again to room temperature, and N, N-diisopropylethylamine (7.70ml, 45mmol, 15eq.) was added thereto and stirred until the generation of heat was completed. Thereafter, the reaction solution was distilled off at 60 ℃ and reduced pressure to obtain a crude product. The obtained crude product was washed in the order of acetonitrile, methanol, and toluene, purified by a silica gel column (eluent: toluene), and then recrystallized twice from o-dichlorobenzene to obtain compound (1A-18) (0.84 g).

[ chemical 198]

Hydrogen nuclear magnetic resonance (¹H-nuclear magnetic resonance，¹H-NMR)((CDCl₂)₂,500MHz)：δ＝2.51(m,12H),5.21(s,1H),6.73(d,2H),6.89(d,4H),7.23-7.28(m,6H),7.50(t,2H),7.62(t,4H),7.92(d,4H),8.59(s,2H),8.74(s,2H),9.13(s,2H).

The compound (1A-18) as a target was confirmed at m/z 801.35 by Matrix-assisted laser desorption/ionization-Mass Spectrometer (MALDI-MS).

Synthesis example (2): synthesis of Compound (1A-32)

Compound (1A-32) (0.38g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-32) (3.36g, 3.0mmol, 1 eq.).

[ solution 199]

¹H-NMR(CDCl₃,500MHz)：δ＝9.16(s,2H),8.96(d,2H),8.68(s,2H),7.91(d,4H),7.57(t,4H),7.43(t,2H),7.21(t,8H),7.11(d,8H),7.02(t,6H),6.82(s,2H),6.61(s,4H),6.37(d,2H),5.31(s,1H),2.17(s,12H).

The compound (1A-32) as the target was confirmed by MALDI-MS at m/z 1135.50.

Synthesis example (3): synthesis of Compound (1A-111)

Compound (1A-111) (0.21g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-111) (2.64g, 3.0mmol, 1 eq.).

[ solution 200]

The compound (1A-111) as the target was confirmed by MALDI-MS at m/z 895.33.

Synthesis example (4): synthesis of Compound (1A-214)

Compound (1A-214) (0.30g) was obtained by the same procedure as in synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-214) (3.64g, 3.0mmol, 1 eq.).

[ solution 201]

The compound (1A-214) as the target compound was confirmed at m/z 1229.48 by MALDI-MS.

Synthesis example (5): synthesis of Compound (1A-303)

Compound (1A-303) (0.60g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-303) (4.11g, 3.0mmol, 1 eq.).

[ solution 202]

¹H-NMR(CDCl₃,500MHz)：δ＝1.50(s,36H),1.88(s,12H),2.49(s,6H),5.49(s,1H),7.04(s,4H),7.08(d,2H),7.33(t,2H),7.42(t,4H),7.50(dd,4H),7.65(d,4H),7.72(dd,2H),7.81(d,4H),8.21(s,4H),8.77(s,2H),9.20(s,2H),9.47(s,2H).

The compound (1A-303) as the target was confirmed by MALDI-MS at m/z 1383.75.

Synthesis example (6): synthesis of Compound (1A-407)

Compound (1A-407) (0.56g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-407) (3.35g, 3.0mmol, 1 eq.).

[ solution 203]

¹H-NMR((CDCl₂)₂,500MHz)：δ＝1.63(s,12H),2.03(s,6H),5.20(s,1H),6.31(s,2H),6.53(s,4H),7.04-7.10(m,4H),7.15(d,4H),7.22-7.27(m,6H),7.38-7.45(m,6H),7.48(s,2H),7.57-7.60(m,6H),7.66(d,2H),7.76(d,2H),7.95(d,4H),8.75(s,2H),9.00(d,2H),9.21(s,2H).

The compound (1A-407) as the target was confirmed by MALDI-MS at m/z 1263.56.

Synthesis example (7): synthesis of Compound (1A-702)

Compound (1A-702) (0.42g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-702) (1.62g, 3.0mmol, 1 eq.).

[ 204]

The compound (1A-702) as the target compound was confirmed by MALDI-MS at m/z 555.25.

Synthesis example (8): synthesis of Compound (1A-331)

The same procedure as in Synthesis example 1 was used to obtain compound (1A-331) (0.10g) except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-331) (2.05g, 3.0mmol, 1 eq.).

[ formulation 205]

¹H-NMR((CDCl₂)₂,500MHz)：δ＝5.01(s,1H),6.74(d,2H),7.00-7.01(m,4H),7.27-7.29(m,2H),7.42-7.44(m,8H),7.49(t,1H),7.54(t,1H),7.62(t,1H),7.91(d,1H),8.15(d,1H),8.30(d,1H),8.81(d,1H),8.91-8.95(m,2H),9.33(s,1H).

The compound (1A-331) as the target was confirmed by MALDI-MS at m/z 699.21.

Synthesis example (9): synthesis of Compound (1A-902)

Compound (1A-902) (0.50g) was obtained by the same procedure as in Synthesis example 1, except that compound (Int-1A-18) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-902) (2.32g, 3.0mmol, 1 eq.).

[ solution 206]

The compound (1A-902) as the target was confirmed by MALDI-MS at m/z 789.26.

Synthesis example (10): synthesis of Compound (1A-214) (other method 1)

A flask containing compound (Int-1A-214) (2.36g, 3.0mmol, 1eq.) and tert-butyl benzene (400ml) was charged with 1.6mol/L tert-butyl lithium heptane solution (9.3ml, 15mmol, 5eq.) under nitrogen atmosphere while cooling with ice. After the completion of the dropwise addition, the mixture was stirred at room temperature for 4 hours. Then, boron tribromide (2.25g, 9.0mmol, 3eq.) was slowly added while cooling the flask with ice. After the completion of the dropwise addition, the mixture was stirred at room temperature for 24 hours. Then, 1,2,2,6, 6-pentamethylpiperidine (1.86g,12mmol,4eq.) was added while cooling the flask with ice. Then, it was stirred at 170 ℃ for 24 hours. The temperature was returned to room temperature and water was added until the exotherm was complete. Then, extraction was performed with toluene, and the organic solvents were collectively concentrated under reduced pressure to obtain a crude product. The obtained crude product was washed in the order of acetonitrile, methanol, and toluene, purified by a silica gel column (eluent: toluene), and then recrystallized twice from o-dichlorobenzene to obtain compound (1A-214) (1.10 g). [ solution 207]

The compound (1A-214) as the target compound was confirmed at m/z 1229.4801 by MALDI-MS.

Synthesis example (11): synthesis of Compound (1A-702) (other method 1)

Compound (1A-702) (0.97g) was obtained by the same procedure as in Synthesis example 10, except that compound (Int-1A-214) (2.36g, 3.0mmol, 1eq.) was changed to compound (Int-1A-702) (1.62g, 3.0mmol, 1 eq.).

[ chemical 208]

The compound (1A-702) as the target compound was confirmed at m/z 555.2522 by MALDI-MS.

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

Next, the evaluation of the basic properties of the compound of the present invention, and the production and evaluation of an organic EL device using the compound of the present invention will be described. The application of the compound of the present invention is not limited to the examples shown below, and the film thickness and the constituent material of each layer may be appropriately changed depending on the basic properties of the compound of the present invention.

< evaluation of basic Property >

The compound (1A-18), the compound (1A-32), the compound (1A-111), the compound (1A-214), the compound (1A-303), the compound (1A-331), the compound (1A-407), the compound (1A-702), RGD-1, RGD-2, RGD-3, and RBD-1, which are comparative compounds, were dissolved in toluene so as to be 1 wt%, respectively, together with polymethyl methacrylate (PMMA), and then a thin film was formed on a transparent support substrate (10mm × 10mm) made of quartz by a spin coating method, thereby producing a PMMA dispersion film.

The excitation and measurement of photoluminescence were carried out at 280nm at room temperature. The fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring apparatus (manufactured by Hamamatsu Photonics, Inc.; C11367-01). Specifically, a light-emitting component having a fast fluorescence lifetime and a light-emitting component having a slow fluorescence lifetime were observed at a maximum emission wavelength measured at an excitation wavelength of 280 nm. In the measurement of the fluorescence lifetime of a general organic EL material emitting fluorescence at room temperature, the triplet component is deactivated by heat, and thus a slow light emitting component related to the triplet component derived from phosphorescence is hardly observed. In the case where a slow light-emitting component is observed in a compound to be evaluated, it is observed that triplet energy having a long excitation lifetime is transferred to singlet energy by thermal activation and delayed fluorescence is observed. The results are shown in table 1.

[ Table 1]

The chemical structures of RGD-1, RGD-2, RGD-3, and RBD-1 in Table 1 are shown below.

[ solution 209]

< evaluation of vapor deposition type organic EL element >

Organic EL elements of examples 1-1 to 1-4 and comparative examples 1-1 to 1-4 were fabricated, and luminance was measured at 500cd/m²Emission wavelength, half-value width, driving voltage, external quantum efficiency, and LT50 (at initial luminance of 500 cd/m) ²Current density of up to 250cd/m when continuously driven²The time to date).

[ Table 2]

In Table 2, "NPD" is N, N '-diphenyl-N, N' -dinaphthyl-4, 4 '-diaminobiphenyl, "TcTa" is 4,4',4 "-tris (N-carbazolyl) triphenylamine," mCP "is 1, 3-bis (N-carbazolyl) benzene," Ir (ppy)₃"tris (2-phenylpyridinium) iridium (III)," 2CzBN "3, 4-dicarbazolylbenzonitrile," BPy-TP2 "2, 7-bis ([2,2' -bipyridine)]-5-yl) triphenylene. The chemical structure is shown below together with "GH-1".

[ solution 210]

< example 1-1 >)

A glass substrate (manufactured by Opto Science) of 26mm by 28mm by 0.7mm, which was prepared by polishing ITO formed to a thickness of 200nm by sputtering to a thickness of 50nm, was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat were respectively placed therein, the molybdenum vapor deposition boat containing NPD, TcTa, mCP, GH-1, the compound (1A-18), 2CzBN, and BPy-TP2, and the tungsten vapor deposition boat containing LiF and aluminum.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa, NPD was first heated and vapor-deposited to a film thickness of 40nm to form a hole injection layer. Next, TcTa was heated and vapor-deposited so that the film thickness became 15nm, and further, mCP was heated and vapor-deposited so that the film thickness became 15nm, thereby forming a hole transport layer including two layers. Then, GH-1 and the compound (1A-18) were heated at the same time and vapor-deposited so that the thickness thereof became 20nm to form a light-emitting layer. The deposition rate was adjusted so that the weight ratio of GH-1 to the compound (1A-18) became approximately 99 to 1. Next, 2CZBN is heated and The electron transport layer including two layers was formed by performing vapor deposition so that the film thickness became 10nm, and further performing vapor deposition by heating BPy-TP2 so that the film thickness became 20 nm. The deposition rate of each layer is 0.01nm/sec to 1 nm/sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1nm/sec so that the film thickness became 1nm, and aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. At this time, the deposition rate of aluminum is adjusted so as to be 1nm/sec to 10 nm/sec.

< example 1-2 to example 1-4 >

Each element was produced by changing the compound (1A-18) as the dopant in example 1 to each dopant shown in table 2.

< comparative example 1-1 to comparative example 1-4 >

The evaluation results of the respective elements are shown in table 3.

[ Table 3]

In examples 1-1 to 1-4, the following results were obtained as compared with comparative examples 1-1 to 1-4: has green (500nm to 550nm) emission, and has a balance among the half-value width of the emission spectrum, color purity, external quantum efficiency, and device lifetime at a high level.

Organic EL elements of examples 1-5 to examples 1-8, comparative examples 1-5, examples 1-9 to examples 1-12, and comparative examples 1-6 were prepared, and luminance was measured at 500cd/m²Emission wavelength, half-value width, driving voltage, external quantum efficiency, and LT50 (at initial luminance of 500 cd/m)²Current density of up to 250cd/m when continuously driven²The time until).

[ Table 4]

In Table 4, the chemical structures of "HATCN", "TBB", "CBP", "GH-2" and "TPBi" are shown below.

[ solution 211]

< example 1-5 >

A glass substrate (manufactured by Opto Science) of 26mm by 28mm by 0.7mm, which was prepared by polishing ITO formed to a thickness of 200nm by sputtering to a thickness of 50nm, was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat, in which HATCN, TBB, TcTa, CBP, the compound (1A-32), and TPBi were placed, respectively, were placed, respectively.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa, HATCN was heated and vapor-deposited to a film thickness of 5nm to form a hole injection layer. Next, TBB was heated to form a film thickness of 65nm by vapor deposition, and TcTa was heated to form a film thickness of 10nm by vapor deposition, thereby forming a hole transport layer including two layers. Next, CBP and the compound (1A-32) were simultaneously heated and vapor-deposited so that the film thickness became 30nm, thereby forming a light-emitting layer. The deposition rate was adjusted so that the weight ratio of CBP to the compound (1A-32) became approximately 99 to 1. Next, TPBi was heated and vapor-deposited so that the thickness thereof became 50nm, thereby forming an electron transport layer. The deposition rate of each layer is 0.01nm/sec to 1 nm/sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness became 1nm, and aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. At this time, the evaporation of aluminum The plating rate is adjusted to 1nm/sec to 10 nm/sec.

< examples 1-6 to 1-8, comparative examples 1-5, 1-9 to 1-12 and comparative examples 1-6 >)

Each element was produced by changing the host CBP, the dopant compound (1A-32) and the mixing ratio of examples 1 to 5 to the respective host, the respective dopant and the respective mixing ratio described in table 4.

The evaluation results of the respective elements are shown in table 5.

[ Table 5]

In examples 1 to 5 to 1 to 8 and examples 1 to 9 to 1 to 12, the half width of the emission spectrum was narrower than in comparative examples 1 to 5 and 1 to 6, and high efficiency and long device life were obtained.

Organic EL elements of examples 1 to 13, comparative examples 1 to 7, examples 1 to 14, examples 1 to 15, examples 1 to 16 and comparative examples 1 to 8 were produced, and luminance was measured at 500cd/m²Emission wavelength, half-value width, driving voltage, external quantum efficiency, and LT50 (at initial luminance of 500 cd/m)²Current density of up to 250cd/m when continuously driven²The time until).

[ Table 6]

In Table 6, the chemical structures of "4 CzIPN", "BCC-TPTA", "T2T", and "Liq" are shown below.

[ solution 212]

< examples 1 to 13 >

A glass substrate (manufactured by Opto Science) of 26mm by 28mm by 0.7mm, which was prepared by polishing ITO formed to a thickness of 200nm by sputtering to a thickness of 50nm, was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat were respectively placed therein, the molybdenum vapor deposition boat containing HATCN, TBB, TcTa, 4CzIPN, compound (1A-32), T2T, TPBi, and Liq, and the tungsten vapor deposition boat containing LiF and aluminum.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa, HATCN was heated and vapor-deposited to a film thickness of 5nm to form a hole injection layer. Next, TBB was heated to form a film thickness of 65nm by vapor deposition, and TcTa was heated to form a film thickness of 10nm by vapor deposition, thereby forming a hole transport layer including two layers. Then, TcTa, 4CzIPN and the compound (1A-32) were simultaneously heated and vapor-deposited so that the film thickness became 30nm, thereby forming a light-emitting layer. The deposition rate was adjusted so that the weight ratio of TcTa to 4CzIPN and the compound (1A-32) was approximately 85 to 14 to 1. Next, T2T was heated and vapor-deposited so that the film thickness became 10nm, and then TPBi and Liq were heated and vapor-deposited so that the film thickness became 40nm, thereby forming an electron transport layer including two layers. The deposition rate was adjusted so that the weight ratio of TPBi to Liq became approximately 70 to 30. The deposition rate of each layer is 0.01nm/sec to 1 nm/sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness became 1nm, and aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate of aluminum is adjusted to 1nm/sec to 10 nm/sec.

< comparative examples 1 to 7, examples 1 to 14, examples 1 to 15, examples 1 to 16 and comparative examples 1 to 8 >

Each element was produced by changing the TcTa as the host, 4CzIPN as the auxiliary dopant, and the compound (1A-32) as the dopant and the mixing ratio of examples 1 to 13 to the respective auxiliary dopants and the respective mixing ratios described in table 6.

The evaluation results of the respective elements are shown in table 7.

[ Table 7]

In examples 1 to 13, the half width of the emission spectrum was narrower than that in comparative examples 1 to 7, and high efficiency and long element life were obtained.

Further, by changing the dopants in examples 1 to 13, blue light-emitting elements can be realized as in examples 1 to 14.

Similarly, by changing the element structures of examples 1 to 13, elements using an excited complex and an auxiliary dopant can be realized as in examples 1 to 15.

Examples 1 to 16 showed blue emission, and the half-value width of the emission spectrum was narrow, as compared with comparative examples 1 to 8, and high efficiency and long element life were obtained.

< evaluation of coated organic EL element >

Next, an organic EL device obtained by coating and forming an organic layer 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 having M2 or M3 bonded to the adjacent site of M1 was obtained, and each unit was estimated to be 50: 26: 24 (molar ratio). In the following structural formula, Me is methyl, Bpin is pinacolboronic group, and a is a linking part of each unit.

[ solution 213]

< high molecular hole transporting 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 was bonded to the adjacent site of M4 was obtained, and each unit was estimated to be 40: 10: 50 (molar ratio). In the following structural formula, Me is methyl, Bpin is pinacolboronic group, and a is a linking part of each unit.

[ solution 214]

< example 2-1 to example 2-9 >

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

< production of organic EL elements in examples 2-1 to 2-3 >

The material composition of each layer in the organic EL element is shown in table 8.

[ Table 8]

The structure of "ET 1" in table 8 is shown below.

[ solution 215]

< 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 composition for forming a light-emitting layer was spin-coated on a glass substrate and dried by heating under reduced pressure, whereby a coating film having no film defects and excellent smoothness was obtained.

The compound (a) is a polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) (for example, the compound (1A-32)), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (that is, the monomer has a reactive substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound. The polymer compound used for obtaining the polymer crosslinked body 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 (Clevios (TM) P VP AI4083, PEDOT: aqueous dispersion of PSS, manufactured by Heraeus Holdings).

[ 216]

< preparation of OTPD solution >

OTPD (LT-N159, manufactured by luminescense Technology Corp) and IK-2 (photo cation polymerization initiator, manufactured by sandipro) 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 217]

< preparation of XLP-101 solution >

A 0.6 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 218]

< example 2-1 >)

Spin-coating PEDOT: PSS solution, calcined on a hot plate at 200 ℃ for 1 hour, thus producing PEDOT: PSS film (hole injection layer). Subsequently, 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 ²Exposure was performed, and the film was calcined on a hot plate at 100 ℃ for 1 hour, thereby forming an OTPD film (hole transport layer) having a film thickness of 30nm, which was insoluble in the solution. 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 multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat containing ET1, 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^-4Pa, ET1 was heated and vapor-deposited so that the film thickness became 30nm, thereby forming an electron transport layer. The deposition rate in forming the electron transport layer was set to 1 nm/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 2-2 >

An organic EL element was obtained in the same manner as in example 2-1. 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 2-3 >

An organic EL element was obtained in the same manner as in example 2-1. The hole-transporting layer was formed into a film having a thickness of 30nm by spin-coating PCz solution and calcining the solution on a hot plate at 120 ℃ for 1 hour.

< evaluation of organic EL elements of examples 2-1 to 2-3 >

It is expected that the coating-type organic EL element obtained in the above-described manner also has excellent driving voltage and external quantum efficiency as in the vapor deposition-type organic EL element.

< production of organic EL elements in examples 2-4 to 2-6 >

The material composition of each layer in the organic EL device is shown in table 9.

[ Table 9]

< 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.

0.02% by weight of Compound (A)

mCBP 1.98 wt.%

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.

0.02% by weight of Compound (A)

SPH-1011.98 wt.%

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.

Compound (A) 0.02% by weight

DOBNA 1.98% by weight

98.00% by weight of toluene

In Table 9, "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, "TSPO 1" is diphenyl [4- (triphenylsilyl) phenyl ] phosphine oxide. The chemical structure is shown below.

[ solution 219]

< example 2-4 >

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. Subsequently, an XLP-101 solution 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) having 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, thereby forming a light-emitting layer of 20 nm.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were mounted thereon. The vacuum vessel was depressurized to 5X 10 ^-4Pa, TSPO1 was heated and vapor-deposited to a film thickness of 30nm to form an electron transport layer. The deposition rate in forming the electron transport layer was set to 1 nm/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.

< examples 2 to 5 and 2 to 6 >

An organic EL device was obtained in the same manner as in example 2-4 using the composition (3) for forming a light-emitting layer or the composition (4) for forming a light-emitting layer.

< evaluation of organic EL elements of examples 2-4 to 2-6 >

< production of organic EL elements in examples 2-7 to 2-9 >

The material composition of each layer in the organic EL device is shown in table 10.

[ Table 10]

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

[ solution 220]

< example 2-7 >

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. Subsequently, an XLP-101 solution 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) having 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, thereby forming a light-emitting layer of 20 nm.

< examples 2 to 8 and 2 to 9 >

An organic EL device was obtained in the same manner as in examples 2 to 7, using the composition (6) for forming a light-emitting layer or the composition (7) for forming a light-emitting layer.

< evaluation of organic EL elements of examples 2-7 to 2-9 >

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 ]

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^ais hydrogen or a substituent, -C (-R) in the a ring^a) May be substituted with "-N ═ N",

X¹And X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted, or alkyl which may be substitutedSubstituted cycloalkyl, said > C (-R)₂And > Si (-R)₂At least one of the two R's to each other may be bonded by a single bond or a linking group,

as X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be bonded to at least one of the a ring and the B ring via a single bond or a linking group,

wherein in the formula (1A), a CD bond of a C ring and a D ring is present as X¹R of > N-R (said R is limited to said aryl which may be substituted, said heteroaryl which may be substituted, or said cycloalkyl which may be substituted) and X of the B ring¹B bond as X²R of > N-R (said R is limited to said aryl which may be substituted, said heteroaryl which may be substituted, or said cycloalkyl which may be substituted) and X of the E ring ²E key any one or two of the three keys,

in the formula (1B), any one or two of three bonds, i.e., CD bond of ring C and ring D, GB bond of ring G and ring B, and FE bond of ring F and ring E, are present,

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

R^ais hydrogen, optionally substituted arylOptionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (two aryl radicals may be bonded by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl,

-C (-R) in the a-ring^a) "may be substituted with" -N ═ f,

X¹and X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, said > C (-R) ₂Two R of (A) are each other and > Si (-R)₂At least one of the two R' S to each other may be replaced by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-in a bond, said-CR ═ CR-R, -N (-R) -R, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

as X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring B as X²R of > N-R, > C (-R)₂R of (A), or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -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 E ring, wherein R, -N (-R) -of-CR, -CR-, - (R) -, of-CR-₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

wherein in the formula (1A), a CD bond of a C ring and a D ring is present as X¹R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of the B ring¹B bond as X²R of > N-R (said R being limited to the alkaneAryl, heteroaryl, or cycloalkyl) and ring E²E-key any one or two of the three keys,

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

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

-C (-R) in the a-ring^a) May be substituted with "-N ═ N",

R^b、R^c、R^d、R^e、R^fand R^gEach independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylAn alkylamino group, a diarylboron group (two aryl groups may be bonded by 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 ^b、R^c、R^d、R^e、R^fAnd R^gAt least one hydrogen of (a) may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and further R^b、R^c、R^d、R^e、R^fAnd R^gWherein adjoining groups in (a) may be bonded to each other and form, together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, respectively, an aryl ring or a heteroaryl ring, at least one hydrogen in the formed ring may be substituted with an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboryl group (two aryl groups may be bonded by 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, at least one of these substituents may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group,

any of the "C (-R) ═ rings in ring b, ring C, ring d, ring e, ring f, and ring g (where R is R)^b、R^c、R^d、R^e、R^fOr R^g) May be substituted with "-N ═ and optionally" -C (-R) ═ C (-R) - "(where R is R)^b、R^c、R^d、R^e、R^fOr R^g) 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, 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) ₂Two R of- "are each other and" -Si (-R)₂At least one of the two R groups of- "may be bonded to each other via a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

X¹and X²Independently from each other > N-R, > O, > S, > C (-R)₂、＞Si(-R)₂Or > Se, R, > C (-R) of > N-R₂R, and > Si (-R)₂Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, said > C (-R) ₂And > Si (-R)₂At least one of the two R' S to each other may be replaced by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, or heteroarylene,

as X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring b as X²R, > of said > N-RC(-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -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 e ring, wherein R of-CR, -N (-R) -, R of-CR, -C (-R)₂R of-and-Si (-R)₂Each R of (A) and (B) is 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 form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

The C-and d-rings, g-and b-rings, and f-and e-rings may be independently bonded to each other by a single bond, -CH ═ CH-, -CR ═ CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-in a bond, said-CR ═ CR-R, -N (-R) -R, -C (-R)₂R of-and-Si (-R)₂Each R of-is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one of which may be substituted with alkyl or cycloalkyl, and further, two adjacent R's may form a ring with each other to form cycloalkylene, arylene, and heteroarylene,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of ring b¹b bond as X²R of > N-R (said R is limited to said aryl, said heteroaryl, or said cycloalkyl which may be substituted with said alkyl or cycloalkyl) and X of the e ring²e-key any one or two of the three keys,

at least one of the B-ring, the c-ring, the d-ring, the e-ring, the f-ring, the g-ring, the formed ring, the aryl group and the heteroaryl group in the compound represented by the formula (2A) or the formula (2B) may be at least one cycloalkane having 3 to 24 carbon atoms Condensing, wherein at least one hydrogen in the cycloalkane is substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and at least one-CH in the cycloalkane₂-may be substituted by-O-,

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

R^ahydrogen, aryl group having 6 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 12 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 12 carbon atoms, and both aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 24 carbon atoms, or cycloalkyl group having 3 to 24 carbon atoms, wherein R is^aWherein at least one hydrogen in the above-mentioned group 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,

-C (-R) in the a-ring^a) May be substituted with "-N ═ N",

R^b、R^c、R^d、R^e、R^fand R^gIndependently 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, wherein R represents a group ^b、R^c、R^d、R^e、R^fAnd R^gWherein at least one hydrogen in the group (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^b、R^c、R^d、R^e、R^fAnd R^gWherein adjacent groups 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 ring b, ring c, ring d, ring e, ring f and ring g, respectivelyAt least one hydrogen in the ring is 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, and both aryl groups may be bonded by a single bond or a linking group), a diaryl boron 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 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,

any of the "C (-R) ═ rings in ring b, ring C, ring d, ring e, ring f, and ring g (where R is R)^b、R^c、R^d、R^e、R^fOr R^g) May be substituted with "-N ═ and optionally" -C (-R) ═ C (-R) - "(where R is R)^b、R^c、R^d、R^e、R^fOr R^g) 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 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, or" -C (-R)₂- "two R of each other and" -Si (-R)₂At least one of the two R groups of- "may be bonded to each other via a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-with a bond, R of-CR- (-CR-) -R of-N (-R) -, -C (-R)₂R of-and-Si (-R)₂R 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 hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms,

as X¹R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-is bonded to at least one of the ring a and the ring b as X²R of > N-R, > C (-R)₂R or > Si (-R)₂R of (A) may be represented by a single bond, -CH-, -CR-, -C.ident.C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂or-Se-bonded to at least one of the a ring and the e ring, wherein R, -N (-R) -of-CR, -C (-R)₂R of-and-Si (-R)₂R 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 hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms,

c-and d-rings, g-and b-rings, and f-and e-ringsCan be respectively and independently separated by a single bond, -CH ═ CH-, -CR ═ CR-, -C ≡ C-, -N (-R) -, -O-, -S-, -C (-R)₂-、-Si(-R)₂-, or-Se-in a bond, said-CR ═ CR-R, -N (-R) -R, -C (-R)₂R of-and-Si (-R)₂R 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 hydrogen in R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R (R is limited to the aryl group having 6 to 12 carbon atoms, the heteroaryl group having 2 to 15 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms which may be substituted with the alkyl group having 1 to 6 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms) having a structure of & gtN-R and X in the b ring¹b bond as X²R (R is limited to the aryl group having 6 to 12 carbon atoms, the heteroaryl group having 2 to 15 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms which may be substituted with the alkyl group having 1 to 6 carbon atoms or the cycloalkyl group having 3 to 14 carbon atoms) and X in the e-ring ²e-key any one or two of the three keys,

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

R^ahydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 20 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 10 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 10 carbon atoms, and two aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 12 carbon atoms, or cycloalkyl group having 3 to 16 carbon atoms, wherein R is ^aWherein at least one hydrogen in the group 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,

-C (-R) in the a-ring^a) May be substituted with "-N ═ N",

R^b、R^c、R^d、R^e、R^fand R^gIndependently 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, wherein R represents^b、R^c、R^d、R^e、R^fAnd R^gWherein at least one hydrogen in the group (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^b、R^c、R^d、R^e、R^fAnd R^gWherein 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 b, c, d, e, f and g rings, respectively, at least one hydrogen in the formed ring is substituted by 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 at least one hydrogen in these substituents is substituted by an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 6 to 15 carbon atoms, or a heteroaryl group having 3 to 16 carbon atoms, A C2-10 heteroaryl group, a C1-5 alkyl group, or a C5-10 cycloalkyl group,

Y¹、Y²and Y³Each independently > B-, > P (═ O) -, or > P (═ S) -,

The C-and d-rings, g-and b-rings, and f-and e-rings may each independently be bonded via a single bond, -N (-R) -, -O-, -S-, or-C (-R)₂-and a bond, R and-C (-R) of said-N (-R) -)₂R is independently hydrogen, 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, at least one hydrogen in R may be substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R > N-R (the R is limited to those having 1 to 5 carbon atomsAn aryl group having 6 to 10 carbon atoms substituted with an alkyl group or a cycloalkyl group having 5 to 10 carbon atoms) and X of the b ring¹b bond as X²R > N-R (the R is limited to the aryl group having 6 to 10 carbon atoms which may be substituted with the alkyl group having 1 to 5 carbon atoms or the cycloalkyl group having 5 to 10 carbon atoms) and X of the e ring²e-key any one or two of the three keys,

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

R^ahydrogen, aryl group having 6 to 16 carbon atoms, heteroaryl group having 2 to 20 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 10 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 10 carbon atoms, and two aryl groups may be bonded by a single bond or a linking group), alkyl group having 1 to 12 carbon atoms, or cycloalkyl group having 3 to 16 carbon atoms, wherein R is^aAt least one hydrogen in the group (a) may be substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms,

R^b、R^c、R^d、R^e、R^fand R^gIndependently 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), or a group having 1 to 1 carbon atom2 or cycloalkyl group having 3 to 16 carbon atoms, wherein R is^b、R^c、R^d、R^e、R^fAnd R^gWherein 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,

Y¹、Y²and Y³Is more than B-,

As X¹R > N-R may be bonded to the b ring as X through a single bond²R of said > N-R may be bonded to the e-ring through a single bond,

wherein in the formula (2A), a cd bond of a c-ring and a d-ring is present as X¹R > N-R (R is limited to an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 5 carbon atoms) and X in the b ring¹b bond as X²R > N-R (R is limited to an aryl group having 6 to 10 carbon atoms which may be substituted with the alkyl group having 1 to 5 carbon atoms) and X of the e ring²e-key any one or two of the three keys,

7. The polycyclic aromatic compound according to claim 3, which is represented by any one of the following structural formulae,

in the formula (I), the first and second groups of,

o is an integer of 1 to 3,

p is an integer of 1 to 4,

q is an integer of 1 to 5,

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 the polycyclic aromatic compound according to any one of claims 1 to 8 with a reactive substituent.

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 crosslinked polymer obtained by further crosslinking 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 polymer crosslinked material according to claim 10.

15. A material for organic devices, which comprises the pendant polymeric compound or the crosslinked pendant polymeric 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 organic devices according to claim 16, wherein the material for organic electroluminescent elements is a material for light-emitting layers.

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 compound or the pendant crosslinked 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 (H4), G is each independently ═ C (-H) -or ═ N-, wherein H in the ═ C (-H) -may be substituted with a substituent or another structure represented by formula (H4),

in the general formula (H5),

R¹～R¹¹may be bonded to each other and together with the a-ring, b-ring or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the ring formed being substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkylAt 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 R¹～R¹¹) May be substituted with "-N ═ N",

in the general formula (H6), in the formula,

at least one hydrogen in the compound or structure represented by each formula can be substituted by alkyl with 1-6 carbon atoms, cycloalkyl with 3-14 carbon atoms, cyano, halogen or deuterium.

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 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.

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.