KR20220157312A - Polycyclic aromatic compound - Google Patents

Abstract

The present invention is to provide a novel polycyclic aromatic compound, and an organic EL element based thereon. A polycyclic aromatic compound represented by general formula (1A) or general formula (1B) increases the choice of materials for organic devices. In addition, an excellent element is provided by manufacturing, for example, an organic EL element using the novel material. An A ring and a B ring are each an aryl ring or the like; R^c is H or a substituent; Y^1 and Y^2 are each >B- or the like; X^1, X^2, X^3 and X^4 are each >N-R or the like; at least one of X^1 to X^4 is bonded to the A ring, the B ring or a c ring by "-CR=CR-" as a linking group; two adjacent Rs in "-CR=CR-" are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; and the compound may be condensed with a cycloalkane, and may be substituted with deuterium or the like.

Description

Polycyclic aromatic compound {POLYCYCLIC AROMATIC COMPOUND}

The present invention relates to a polycyclic aromatic compound, an organic electroluminescent element using the same, an organic field effect transistor, an organic thin film solar cell, and an organic device such as a wavelength conversion filter, and a display device and a lighting device. In addition, in this specification, "organic electroluminescence element" may be expressed as "organic EL element" or simply "element".

Conventionally, display devices using electroluminescent light-emitting elements have been variously researched because power reduction and thinning are possible, and furthermore, organic electroluminescent elements made of organic materials have been actively studied because they are easy to reduce in weight and increase in size. . In particular, for the development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities (possibly becoming semiconductors or superconductors) such as holes and electrons, polymer compounds , regardless of low molecular weight compounds, have been actively studied so far.

An organic EL element has a structure consisting of a pair of electrodes composed of an anode and a cathode, and one layer or a plurality of layers disposed between the pair of electrodes and containing an organic compound. Layers containing organic compounds include a light emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons. Various organic materials suitable for these layers have been developed.

For example, as a material used for an organic EL device or an organic thin-film solar cell, a material obtained by improving a triphenylamine derivative has also been reported (International Publication No. 2012/118164). This material refers to N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which is already in practical use, It is a material characterized by improving its planarity while arranging nitrogen at the center of the ring structure by linking aromatic rings constituting phenylamine with each other. In this document, for example, the charge transport properties of NO-linked compounds (Compound 1 on page 63) are evaluated, but no method for producing materials other than NO-linked compounds is described. Furthermore, if the elements to be linked are different, Since the electronic state of the entire compound is different, properties obtained with materials other than NO-linked compounds have not been known.

A host material of an organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene or carbazole are connected by single bonds or phosphorus atoms or silicon atoms. This is because a large HOMO-LUMO gap (band gap Eg in the thin film) required for the host material is ensured by linking a large number of relatively small aromatic rings in a conjugated system. Furthermore, although a high triplet excitation energy (E _T ) is also required for a host material of an organic EL device using a phosphorescent material or a thermally activated delayed fluorescent material, by linking a donor or acceptor aromatic ring or substituent to a molecule, the triplet The triplet excitation energy (E _T ) can be improved by localizing SOMO1 and SOMO2 in the term excited state (T1) and reducing the exchange interaction between both orbits. However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules with existing aromatic rings connected as host materials do not have sufficient life. On the other hand, polycyclic aromatic compounds having an extended π-conjugated system generally have excellent redox stability, but have low HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation energy (E _T ), so host materials has been considered unsuitable for

Under such circumstances, recently, a compound in which a plurality of aromatic rings are condensed with boron or the like as a central atom has also been reported (International Publication No. 2015/102118). In this document, evaluation of an organic EL device using a compound obtained by condensing a plurality of aromatic rings as a dopant material for a light emitting layer is performed. In addition, an example in which such a compound is further multiplied (International Publication No. 2018/212169) or an example in which a conjugated system is expanded by a linking group in a molecule has been reported (Korean Patent Publication No. 10-2020-0121228, International Publication No. 2020/217229).

Patent Document 1: International Publication No. 2012/118164 Patent Document 2: International Publication No. 2015/102118 Patent Document 3: International Publication No. 2018/212169 Patent Document 4: Korean Patent Publication No. 10-2020-0121228 Patent Document 5: International Publication No. 2020/217229

As reported in Patent Literatures 1 to 5, various materials have been developed as materials used for organic EL devices, but in order to increase the choice of materials for organic EL devices, development of materials composed of compounds different from those of the prior art is desired. have. In particular, it is useful to search for organic EL properties obtained with materials other than NO-linked compounds in which nitrogen is arranged at the center of the ring structure and a method for producing the same.

Further, in Patent Literatures 2 to 5, boron-containing polycyclic aromatic compounds and organic EL devices using the same are reported, but a large number of compounds are disclosed in these documents, and in order to further improve device characteristics, luminous efficiency and device It is beneficial to search for materials for light emitting layers, particularly dopant materials, etc., which can improve organic EL characteristics such as lifetime.

In addition, as a method of forming an organic layer constituting an organic EL device, a wet film forming method is currently used in addition to a vacuum deposition method. , it is also beneficial to search for such an ink material.

As a result of intensive studies to solve the above problems, the inventors of the present invention have found that, for example, an organic EL element is constituted by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes, thereby providing an excellent organic EL element. was obtained, and the present invention was completed. That is, the present invention provides materials for organic devices, such as materials for organic EL devices, containing the following polycyclic aromatic compounds and furthermore, the following polycyclic aromatic compounds.

In addition, in the present specification, chemical structures and substituents are sometimes expressed as carbon atoms. In the case where a substituent is substituted in a chemical structure or a substituent is further substituted in a substituent, the number of carbon atoms in the chemical structure or substituent means the number of carbon atoms in each of the substituents. , It does not mean the total number of carbon atoms of the chemical structure and substituents, or the total number of carbon atoms of substituents and substituents. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and substituent It is not the carbon number of the sum of B. Further, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent A (with no carbon number limitation)" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and It is not the carbon number of the sum of the substituents B.

Section 1.

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

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

Ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,

R ^c is each independently hydrogen or a substituent;

"-C(-R ^c )=" in the c ring may be substituted with "-N=";

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

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently hydrogen, optionally substituted aryl, and optionally substituted heteroaryl. , alkyl which may be substituted, or cycloalkyl which may be substituted,

In addition, the two Rs of “>C(-R) ₂ ” and the two Rs of “>Si(-R) ₂ ” as X ¹ to X ⁴ are each independently bonded by a single bond or a linking group you can do it,

In addition, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ¹ or X ³ are each independently and at least one of the B rings, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ² or X ⁴ , Each independently may be bonded to at least one of the A ring and the c ring by a single bond or a linking group;

However, at least one of X ¹ to X ⁴ is bonded to the A ring, B ring, or c ring by "-CR=CR-" as a linking group, and R of the "-CR=CR-" , are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Two R's combine to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

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

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

clause 2.

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

Ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, Optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, substituted optionally substituted with cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;

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

"-C(-R ^c )=" in the c ring may be substituted with "-N=";

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

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl; At least one hydrogen in R may be substituted with alkyl or cycloalkyl,

In addition, the two Rs of “>C(-R) ₂ ” and the two Rs of “>Si(-R) ₂ ” as X ¹ to X ⁴ are each independently a single bond, -CH=CH -, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or - may be bonded by Se-, R of "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si( -R) R in _2- ” is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is substituted with alkyl or cycloalkyl may be, or two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

In addition, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ¹ or X ³ are each independently and at least one of the B rings, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ² or X ⁴ , Each independently, with at least one ring of the A ring and the c ring, a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - They may be bonded by S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and R in "-CR=CR-" or "-N(-R) R of -”, R of “-C(-R) ₂ -”, and R of “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, or alky Nyl or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs bond to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring you can do it,

However, at least one of the above X ¹ to X ⁴ is bonded to the above-mentioned ring A, ring B, or c ring by the above-mentioned “-CR=CR-” as a linking group, and also the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

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

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

The polycyclic aromatic compound according to claim 1.

clause 3.

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

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

R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single bonds or through a linking group may be bonded), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, corresponding R ^a , R ^b , And at least one hydrogen in R ^c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent groups of R ^a and R ^b bond together, together with ring a and ring b , You may form an aryl ring or heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl may be bonded through a single bond or a linking group), substituted with alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl may be, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl,

"-C(-R ^c )=" in the c ring may be substituted with "-N=";

Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", "-C(- R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C(-R) ₂ -" R of -” and R of “-Si(-R) ₂ -” are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R is alkyl or cycloalkyl may be substituted, and the two Rs of "-C(-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" are each independently a single bond, -CH=CH- , -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se may be bonded by -, R of the above "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si(- R) R of _2- ” is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is substituted with alkyl or cycloalkyl, may be present, and two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

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

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, or >C(-R) ₂ , and R of “>NR” and “>C(- R) R of ₂ ” is each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl,

In addition, the two Rs of “>C(-R) ₂ ” as X ¹ to X ⁴ are single bonds, -CH=CH-, -CR=CR-, -C≡C-, -N(-R )-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R in the above "-CR=CR-" , R in “-N(-R)-”, R in “-C(-R) ₂ -”, and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, or hetero aryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs are bonded to form a cycloalkylene ring, aryl A rene ring or a heteroarylene ring may be formed,

In addition, R of ">NR" and R of ">C(-R) ₂ " as X ¹ or X ³ are each independently a combination of at least one of the a ring and the b ring, and the X ² or R of ">NR" and R of ">C(-R) ₂ " as X ⁴ are each independently a member of at least one of the a ring and the c ring, and a single bond, -CH=CH-, - CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded together by, R of "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and R of "-Si(-R) _2- ” R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl , Two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

However, at least one of the above X ¹ to X ⁴ is bonded to the a ring, b ring, or c ring by the above “-CR=CR-” as a linking group, and the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,

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

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

clause 4.

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

R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 24 carbon atoms, or a cycloalkyl of 3 to 24 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and R ^c may be substituted with aryl of 6 to 12 carbon atoms, heteroaryl of 2 to 15 carbon atoms, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, In addition, adjacent groups of R ^a and R ^b may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring and the b ring, and in the ring formed At least one hydrogen is aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, diarylamino (provided that aryl is an aryl of 6 to 12 carbon atoms), diarylboryl (provided that aryl is an aryl of 6 to 12 carbon atoms, and , The two aryls may be bonded through a single bond or a linking group), may be substituted with C1-24 alkyl or C3-24 cycloalkyl, and at least one hydrogen in these substituents is may be substituted with aryl of 6 to 12, heteroaryl of 2 to 15 carbon atoms, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms,

"-C(-R ^c )=" in the c ring may be substituted with "-N=";

Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", "-C(- R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C(-R) ₂ -" R in -” and R in “-Si(-R) ₂ -” are hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or carbon atoms 3 to 14 cycloalkyl, and at least one hydrogen in R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two R of "-C(-R) ₂ -" Each other and the two Rs of "-Si(-R) ₂ -" are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)- , -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R in the above "-CR=CR-", " R of -N(-R)-", R of "-C(-R) ₂ -", and R of "-Si(-R) ₂ -" are independently hydrogen or 6 to 10 carbon atoms. aryl, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, alkenyl of 1 to 5 carbon atoms, alkynyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, at least one of The hydrogen of may be substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, and two adjacent R's bond to form a cycloalkylene ring of 3 to 14 carbon atoms, an arylene ring of 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms may be formed;

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

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, or >S, and R in “>NR” is hydrogen, aryl having 6 to 12 carbon atoms, or 2 to 12 carbon atoms Heteroaryl of 15, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in R is substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, may be,

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

However, at least one of the above X ¹ to X ⁴ is bonded to the a ring, b ring, or c ring by the above “-CR=CR-” as a linking group, and the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms,

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

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

The polycyclic aromatic compound according to claim 3.

Section 5.

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

R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 10 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 12 carbon atoms, or a cycloalkyl of 3 to 16 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and ^Rc may be substituted with aryl of 6 to 10 carbon atoms, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, In addition, adjacent groups of R ^a and R ^b may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring and the b ring, and in the ring formed At least one hydrogen is aryl of 6 to 16 carbon atoms, heteroaryl of 2 to 20 carbon atoms, diarylamino (provided that aryl is an aryl of 6 to 10 carbon atoms), diarylboryl (provided that aryl is an aryl of 6 to 10 carbon atoms, and , The two aryls may be bonded through a single bond or a linking group), may be substituted with C1-C12 alkyl or C3-C16 cycloalkyl, and at least one hydrogen in these substituents is may be substituted with aryl of 6 to 10, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms,

"-C(-R ^c )=" in the c ring may be substituted with "-N=";

Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", or "-C( may be substituted with -R) ₂ -”, and R in “-N(-R)-” and R in “-C(-R) ₂ -” are hydrogen, aryl having 6 to 12 carbon atoms, or 2 carbon atoms -15 heteroaryl, C1-6 alkyl, or C3-14 cycloalkyl, and at least one hydrogen in R is substituted with C1-6 alkyl or C3-14 cycloalkyl may be,

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

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, or >S, and R in “>NR” is hydrogen, aryl having 6 to 12 carbon atoms, or 2 to 12 carbon atoms Heteroaryl of 15, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in R is substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, may be,

In addition, R of ">NR" as X ¹ or X ³ is with the b ring, and R of ">NR" as X ² or X ⁴ is with the a ring, a single bond, -CH=CH-, - CR=CR-, -N(-R)-, -O-, -S-, or -C(-R) ₂ - may be bonded, and the R of "-CR=CR-", "- R in "N(-R)-" and R in "-C(-R) ₂ -" are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or 1 to 5 carbon atoms. is alkyl, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in R is an alkyl having 1 to 5 carbon atoms or 5 to 10 carbon atoms may be substituted with cycloalkyl of , and two adjacent Rs may be bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

However, at least one of the above X ¹ and X ³ is bonded to the b ring by the above "-CR=CR-" as a linking group, and furthermore, two adjacent in the "-CR=CR-" R is bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

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

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

The polycyclic aromatic compound according to claim 3.

clause 6.

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

R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 10 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 12 carbon atoms, or a cycloalkyl of 3 to 16 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and ^Rc may be substituted with C1-C5 alkyl or C5-C10 cycloalkyl,

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

Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", or any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) may be substituted with "-N(-R)-", "-O-", or "-S-" , R in "-N(-R)-" is an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms,

Y ¹ and Y ² are >B-;

X ¹ , X ² , X ³ , and X ⁴ are each independently >NR or >O, and R in “>NR” is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or Alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms, and at least one hydrogen in R may be substituted with alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms,

In addition, R of ">NR" as X ¹ or X ³ is with the b ring, and R of ">NR" as X ² or X ⁴ is with the a ring by a single bond or -CR=CR- may be bonded together, and R in "-CR=CR-" is each independently hydrogen, aryl of 6 to 10 carbon atoms, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, alkyl of 1 to 5 carbon atoms alkenyl, alkynyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, and at least one hydrogen in R may be substituted with alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms , Two adjacent Rs may be bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

However, at least one of the above X ¹ and X ³ is bonded to the b ring by the above "-CR=CR-" as a linking group, and furthermore, two adjacent in the "-CR=CR-" R is bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,

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

The polycyclic aromatic compound according to claim 3.

clause 7.

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

The benzene rings in the above structural formula are independently selected from aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), and diarylboryl (wherein aryl is 6 to 10 carbon atoms). 10 aryl, two aryls may be bonded by a single bond or a linking group), may be substituted with C1-12 alkyl or C3-16 cycloalkyl, and at least one of the substituents Hydrogen may be substituted with C1-5 alkyl or C5-10 cycloalkyl,

At least one hydrogen in the compound represented by the above structural formula may be substituted with heavy hydrogen, cyano or halogen.

Section 8.

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

clause 9.

A reactive compound wherein a reactive substituent is substituted for the polycyclic aromatic compound according to any one of claims 1 to 8.

Section 10.

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

Section 11.

A pendant type polymer compound in which the reactive compound according to item 9 is substituted for a main chain type polymer, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.

Section 12.

A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 8.

Section 13.

A material for organic devices containing the reactive compound according to claim 9.

Section 14.

A material for organic devices containing the polymer compound or polymer crosslinked product according to claim 10.

Section 15.

A material for an organic device comprising the pendant type polymer compound or pendant type polymer crosslinked product according to claim 11.

Section 16.

The material for an organic device according to any one of items 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.

Section 17.

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

Section 18.

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

Section 19.

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

Section 20.

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

Article 21.

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

Article 22.

An ink composition comprising the pendant-type polymer compound or pendant-type polymer crosslinked product according to claim 11, and an organic solvent.

Article 23.

It is disposed between a pair of electrodes composed of an anode and a cathode, and the pair of electrodes, wherein the polycyclic aromatic compound according to any one of items 1 to 8, the reactive compound according to item 9, the polymer compound according to item 10, or the polymer crosslinking agent An organic electroluminescent device comprising a sieve or an organic layer containing the pendant polymer compound or pendant polymer crosslinked product according to claim 11.

Article 24.

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

Article 25.

The organic electroluminescent device according to item 24, wherein the light emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinked product, pendant type polymer compound or pendant type polymer crosslinked product as a dopant.

Article 26.

The light emitting layer includes 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), and a structure represented by the following general formula (H4) The organic electroluminescent device according to item 25, further comprising at least one selected from the group consisting of a compound, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material.

In Formula (H1), L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms;

In Formula (H2), L ² and L ³ are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms;

In the above general formula (H3), MU is a divalent group each independently represented by removing any two hydrogen atoms from an aromatic compound, EC is a divalent group each independently represented by removing any one hydrogen atom from an aromatic compound It is a monovalent group, two hydrogens in MU are substituted with EC or MU, k is an integer from 2 to 50000,

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

In the above general formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹¹ hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;

Adjacent groups among R ¹ to R ¹¹ may be bonded together to form an aryl ring or heteroaryl ring together with ring a, b or c, and at least one hydrogen in the formed ring is aryl, heteroaryl, may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be,

Arbitrary “-C(-R)=” (where R is R ¹ to R ¹¹ ) in ring a, ring b, and ring c may be substituted with “-N=”;

In the above general formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹⁶ hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;

Adjacent groups among R ¹ to R ¹⁶ may be bonded together to form an aryl ring or heteroaryl ring together with the a ring, b ring, c ring, or d ring, and at least one hydrogen in the formed ring is aryl; It may be substituted with heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be further substituted with , and

At least one hydrogen in the compound or structure represented by the above formulas may be substituted with C1-C6 alkyl, C3-C14 cycloalkyl, cyano, halogen or deuterium.

Article 27.

At least one of an electron transport layer and an electron injection layer is disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, or a BO-based Derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole An organic electroluminescent device according to any one of items 23 to 26, containing at least one selected from the group consisting of derivatives, silole derivatives and azoline derivatives.

Article 28.

At least one layer of the electron transport layer and the electron injection layer is an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, or a rare earth metal. The organic electroluminescent device according to item 27, which further contains at least one selected from the group consisting of oxides of, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

Article 29.

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 is a high molecular compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or further crosslinking the high molecular compound. Item 23 comprising a polymer crosslinked product, a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant type polymer crosslinked product obtained by further crosslinking the pendant type polymer compound. The organic electroluminescent device according to any one of to 28.

Section 30.

A display device or lighting device provided with the organic electroluminescent element according to any one of claims 23 to 29.

Article 31.

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

According to a preferred aspect of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as, for example, a material for organic devices such as a material for organic EL devices. Organic devices such as EL elements can be provided.

Specifically, the present inventors found that a polycyclic aromatic compound in which an aromatic ring is connected with a hetero element such as boron, phosphorus, oxygen, nitrogen, or sulfur has a large HOMO-LUMO gap or a small HOMO depending on the connection method of the hetero element. - Found something with a LUMO gap (band gap Eg in a thin film). This is considered to be because the 6-membered ring containing a hetero element has low aromaticity, so that expansion of the conjugated system and reduction of the HOMO-LUMO gap due to localization or delocalization of each orbital are suppressed or promoted. Since these polycyclic aromatic compounds have a rigid skeleton in which 5- or 6-membered rings are condensed or connected, the half width of the fluorescence emission peak is narrow, and emission of high color purity is obtained when used as an emitter of an organic EL device. Furthermore, by selecting a method of linking hetero elements, thermally activated delayed fluorescence can be exhibited, and high efficiency can be obtained when used as an emitter of an organic EL device. In addition, since the energies of HOMO and LUMO can be moved arbitrarily by introducing a substituent, it is possible to optimize the ionization potential or electron affinity according to the surrounding material. However, the present invention is not particularly limited to these principles.

1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.
Fig. 2 shows the result of fluorescence lifetime measurement of compound (1A-1).

1. Polycyclic aromatic compounds

<Description of the overall structure of the compound>

The present invention is a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B), preferably a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). In addition, the definition of the symbol in each structural formula is the same as the above-mentioned definition, and furthermore, the definition of the symbol in all the structural formulas shown after this paragraph is also the same as the above-mentioned definition.

Both compounds contain two unit structures formed by condensation of ring A, ring B, and ring c in a condensed bicyclic structure, and these two unit structures share c ring to form a condensed ring-type condensed structure have The condensed ^bicyclic structure is ^a structure in which ^{two 6} -membered saturated hydrocarbon rings are condensed. It is a decahydronaphthalene-type structure on the right side composed of X ³ and X ⁴ .

There are meta-type and para-type compounds. The meta-type compound has a structure in which two unit structures are condensed so that Y ¹ and Y ² are located at the meta position of c ring, and the para-type compound has Y ¹ and Y 2 . It has a structure in which two unit structures are condensed so that ² is located at the para position of ring c.

<Description of the ring structure and substituents in the compound>

Ring A and ring B in each formula are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. These substituents include optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino (amino groups having aryl and heteroaryl) ), optionally substituted diarylboryl (two aryls may be bonded through a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryl Oxy or substituted silyl is preferred. When these substituents further have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (even if two aryls are bonded through a single bond or a linking group) ), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. In addition, details of the rings and substituents enumerated here will be summarized and described later.

R ^a , R ^b , and R ^c in each formula are hydrogen or a substituent, specifically, hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted Diheteroarylamino, optionally substituted arylheteroarylamino (amino group having aryl and heteroaryl), optionally substituted diarylboryl (two aryls may be bonded via a single bond or a linking group), even if substituted preferably substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl. When these substituents further have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (even if two aryls are bonded through a single bond or a linking group) ), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. In addition, the details of the rings and substituents enumerated here will be summarized and described later.

Specific examples of R ^a , R ^b , and R ^c in each formula are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, At least one hydrogen in R ^a , R ^b , and R ^c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the details of the substituents enumerated here will be summarized and described later.

The aryl ring or heteroaryl ring as the A ring and the B ring preferably has a 5-membered ring or a 6-membered ring that shares a bond with the condensed bicyclic structure described above.

Here, "a 6-membered ring sharing a bond with a condensed bicyclic structure" means a ring and b ring (benzene ring ( 6-membered ring)). In addition, "the aryl ring or heteroaryl ring (which is the A ring and the B ring) has this 6-membered ring" means that the A ring and the B ring are formed only with this 6-membered ring, or by further condensing this 6-membered ring with another ring, etc. It means that A ring and B ring are formed so that this 6-membered ring may be included. In other words, "an aryl ring or heteroaryl ring having a 6-membered ring (which is an A ring and a B ring)" as used herein means that the 6-membered rings constituting all or part of the A ring and the B ring are condensed into a condensed bicyclic structure. it means. In addition, the same explanation is applied also to "5-membered ring."

Ring A and ring B in formulas (1A) and (1B) correspond to ring a and its substituent R ^a and ring b and its substituent R ^b in formulas (2A) and (2B), respectively. That is, formulas (2A) and (2B) are in the structure in which "ring A and ring B having a 6-membered ring (which is a benzene ring)" are selected as the A ring and the B ring in the formulas (1A) and (1B), respectively. respond In that sense, each ring in formulas (2A) and (2B) is represented by lowercase letters "a" and "b".

<Description of change in ring structure due to bonding of substituents>

Adjacent groups of the substituents R ^a and R ^b of the a ring and the b ring are bonded to each other and may form an aryl ring or a heteroaryl ring together with the a ring or b ring, and at least one hydrogen in the formed ring is Aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, tri It may be substituted with arylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents is aryl, heteroaryl, alkyl, or cyclo It may be substituted by alkyl. In addition, the details of the rings and substituents enumerated here will be summarized and described later.

Therefore, the polycyclic aromatic compound of formula (2A) or formula (2B) is represented by the following formulas (2AB-fr1) to (2AB-fr3) depending on the mutual bonding form of the substituents in the a ring and the b ring. As such, the ring structure constituting the compound is changed. Ring A' and ring B' in each formula correspond to ring A and ring B in formulas (1A) and (1B), respectively. In addition, each formula briefly shows only a part of a unit structure, and a compound is constituted by condensing two unit structures in a meta- or para-type.

When the A' ring and the B' ring in the formulas (2AB-fr1) to (2AB-fr3) are explained by formulas (2A) and (2B), adjacent groups among a plurality of substituents R ^a and R ^b are Represents an aryl ring or heteroaryl ring formed by bonding together with ring a and ring b, respectively (it can also be said to be a condensed ring formed by condensation of ring structure a or b with another ring structure). In addition, as can be seen from the above formula, for example, the substituent R a of ring ^a and the substituent R b of ring ^b do not correspond to "adjacent groups", and they do not bond. That is, "adjacent groups" mean adjacent groups on the same ring.

Specific examples of the formulas (2AB-fr1) to (2AB-fr3) include, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring with respect to a benzene ring which is ring a or b. A structure having an A' ring or a B' ring formed by condensation of the like, and the condensed ring A' or condensed ring B' formed is, respectively, a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or Dibenzothiophene ring etc.

For example, more specific examples of formulas (2AB-fr1) to (2AB-fr3) are shown below.

The above formula (2AB-fr1-ex) is a specific example of formula (2AB-fr1), and two adjacent R ^a in the a ring of formula (2A) or formula (2B) are bonded to form a ring ( This is an example in which an aryl ring (naphthalene ring) represented by A' is formed together with a benzene ring). The formed aryl ring has a 6-membered ring (benzene ring a) sharing a bond with the condensed bicyclic structure described above. In addition, the arbitrary substituents on the aryl ring A' (ring A of formula (1A) or formula (1B)) are represented by n pieces of R other than R ^a , and the upper limit of n is the maximum number that can be substituted.

The formula (2AB-fr2-ex) is a specific example of the formula (2AB-fr2), and two adjacent R bs in the ^b ring of the formula (2A) or formula (2B) are bonded together to form the b ring ( This is an example in which a heteroaryl ring (carbazole ring) represented by B' is formed together with a benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring b) sharing a bond with the condensed bicyclic structure described above. Arbitrary substituents on the aryl ring B' (ring B in formula (1A) or formula (1B)) are represented by n pieces of R in addition to R ^b , and the upper limit of n is the maximum number that can be substituted.

The formula (2AB-fr3-ex) is a specific example of the formula (2AB-fr3), and two adjacent R ^a in the a ring of formula (2A) or formula (2B) are bonded to form a ring ( benzene ring), a heteroaryl ring (dibenzofuran ring) represented by A' is formed, two adjacent R ^bs in b ring are bonded together with b ring (benzene ring) to form B' This is an example in which an aryl ring (naphthalene ring) is formed. The formed heteroaryl ring and aryl ring have a 6-membered ring (benzene ring a and benzene ring b) sharing a bond with the condensed bicyclic structure described above. In addition, any substituents on heteroaryl ring A' (ring A of formula (1A) or formula (1B)) and aryl ring B' (ring B of formula (1A) or formula (1B)) are selected from R ^a and R ^b In addition to , it is represented by n number of Rs, and the upper limit of n is the maximum number of substitutions possible.

The above description can similarly be applied to all forms other than the specific example mentioned above.

<Description of central elements Y ¹ and Y ² in the compound>

Y ¹ and Y ² in each formula are >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(- R)-, >Si(-R)-, or >Ge(-R)-, wherein R of ">C(-R)-", R of ">Si(-R)-", and "> R in "Ge(-R)-" is each independently an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. In the case of >P(=O)-, >P(=S)-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, ring A (ring a) , the atoms bonded to the B ring (b ring) and the c ring are P, C, Si, or Ge. Y is preferably >B-, >P-, >P(=O)-, >P(=S)-, >C(-R)-, or >Si(-R)-, and >B- , >P-, >P(=O)-, or >P(=S)- are more preferable, and >B- is particularly preferable. In addition, the details of the substituents enumerated here will be summarized and described later.

<Description of connecting elements X ¹ , X ² , X ³ , and X ⁴ in the compound>

X ¹ , X ² , X ³ , and X ⁴ in each formula are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se , R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently hydrogen, optionally substituted aryl, or substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

As X ¹ , X ² , X ³ , and X ⁴ , from the viewpoint of stability, >NR, >O, >S, or >C(-R) ₂ is preferable, and >NR or >O is more preferable. Further, from the viewpoint of light emission with a short wavelength, >NR, >O, or >C(-R) ₂ is preferable, and >O or >C(-R) ₂ is more preferable.

In addition, the details of the substituents enumerated here will be summarized and described later.

In addition, the two Rs of “>C(-R) ₂ ” and the two Rs of “>Si(-R) ₂ ” as X ¹ to X ⁴ are each independently a single bond or a linking group (these are summarized Also referred to as a coupling group) may be bonded. As this linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples thereof include the following structures. In addition, R in “-CHR-CHR-”, R in “-CR ₂ -CR ₂ -”, R in “-CR=CR-”, R in “-N(-R)-”, and “-C R in (-R) ₂ -” and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and At least one hydrogen in R may be substituted with alkyl or cycloalkyl. Further, “-CHR-CHR-”, “-CR ₂ -CR ₂ -”, “-CR=CR-”, “-C(-R) ₂ -”, and “-Si(-R) ₂ -” Two adjacent Rs in may be bonded to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (refer to the rightmost structural formula in the following structural formulas). In addition, the details of the substituents enumerated here will be summarized and described later.

As a bonding group, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a single bond or a linking group. Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond or linking group are more preferable, and a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are more preferred, and -CR=CR- as a single bond and linking group are most preferred.

The position at which two R are bonded by a bonding group is not particularly limited as long as it can be bonded to, but it is preferable to bond at the most adjacent position, for example, when the two R's are a phenyl group, "C" in the phenyl group Or, it is preferable to bond to each other at ortho (second position) positions based on the bonding position (first position) of "Si" (see the structural formula above).

<Description of changes in ring structure due to the combination of X ¹ to X ⁴ with the ring>

As X ¹ or X ³ , R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently formed by a single bond or a linking group , may be bonded to at least one of ring A (ring a) and ring B (ring b), and as X ² or X ⁴ , R of “>NR”, R of “>C(-R) ₂ ”, and R in ">Si(-R) ₂ " may be each independently bonded to at least one of the A ring (a ring) and the c ring through a single bond or a linking group.

As X ¹ that may be involved in bonding, >NR and >C(-R) ₂ are preferable, and >NR is more preferable.

As the ring to be bonded, a B ring (b ring) is preferable for X ¹ or X ³ , and an A ring (a ring) is preferable for X ² or X ⁴ .

Examples of the linking group bonding R and the ring are -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, - N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se-, -CH=CH-, -CR =CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are preferred, -CH=CH-, -CR=CR-, -N(-R )-, -O-, and -S- are more preferred, -CR=CR-, -N(-R)-, -O-, and -S- are even more preferred, and -CR=CR- particularly preferred. In addition, R in “-CHR-CHR-”, R in “-CR ₂ -CR ₂ -”, R in “-CR=CR-”, R in “-N(-R)-”, and “-C R in (-R) ₂ -” and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and At least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs may be bonded to each other to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. At least one hydrogen in these rings may also be substituted with alkyl or cycloalkyl.

In addition, the details of the substituents enumerated here will be summarized and described later.

In formulas (1A) and (1B), “R of “>NR” as “X ¹ or X ³ , R of “>C(-R) ₂ ”, and “>Si(-R) ₂ ” R of is each independently selected from at least one of the A ring and the B ring, and R of ">NR", R of ">C(-R) ₂ ", and "> as X ² or X ⁴ . R of Si(-R) ₂ ” is each independently bonded to at least one of the A ring and the c ring by a single bond or a linking group”, formulas (2A) and (2B) In “X ¹ or X ³ , R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently and at least one of the b rings, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ² or X ⁴ , Each independently, at least one of the a-ring and c-ring, and a single bond, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR= bonded by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- It responds to the rule of “doing”.

This regulation can be expressed in the meta form, for example, by the following structural formula. In addition, substituents R ^a , R ^b and R ^c in the structural formula are not shown, but actually exist. In addition, the same explanation can be made for paraforms.

The structural formula on the left is in formula (2A),

When R in the X ¹ options (>NR, >C(-R) ₂ , and >Si(-R) ₂ ) binds to the b ring (benzene ring) via a single bond or a linking group, X ¹ is accepted. while condensing other rings with respect to the b ring (benzene ring) to form the B' ring,

When R in the X ² options (>NR, >C(-R) ₂ , and >Si(-R) ₂ ) is bonded to the left a ring (benzene ring) by a single bond or a linking group, X ² While accepting, another ring is condensed to the left a ring (benzene ring) to form the left A' ring,

When R in the X ³ options (>NR, >C(-R) ₂ , and >Si(-R) ₂ ) is bonded to the a ring (benzene ring) on the right by a single bond or a linking group, X ³ While accepting , another ring is condensed with the right a ring (benzene ring) to form the right A' ring.

The formed condensed ring B', left condensed ring A', and right condensed ring A' are, for example, a ring having an azepine structure, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring. to be. In addition, although not included in the above structural formula, there are examples in which X ⁴ bonds with a ring, examples in which ring c bonds, and the like.

The structural formula on the right shows a more specific example of the structural formula on the left,

R (phenyl group) of >NR, which is X ¹ , is bonded to b ring (benzene ring) by linking group "-CR=CR-" (two adjacent Rs are bonded to form an aryl ring, which is a phenylene ring) and ring B' having an azepine structure surrounded by a broken line is formed,

R (phenyl group) of >NR, which is X ² , is bonded to the a ring (benzene ring) on the left by "-O-" as a linking group, forming a phenoxazine ring A' (left) surrounded by a broken line,

A compound in which R (phenyl group) of >NR, which is X ³ , is bonded to the a ring (benzene ring) on the right side through a single bond to form a carbazole ring A' (right side) surrounded by a broken line.

However, at least one of X ¹ to X ⁴ in each formula is bonded to ring A (ring a), ring B (ring b), or ring c by "-CR=CR-" as a linking group. Preferably, at least one of X ¹ and X ³ is bonded to ring B (ring b) by the above “-CR=CR-”. In addition, two adjacent Rs in "-CR=CR-" are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring, and at least one hydrogen in these rings is alkyl Or it may be substituted with cycloalkyl.

In addition, the description of the specific example mentioned above is similarly applicable to all forms other than these specific examples.

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

In the description so far, basically, ring c in formulas (1A) and formulas (1B), ring a, ring b, and ring c in formulas (2A) and formulas (2B) are described as benzene rings. However, examples in which these rings change to a 5-membered or 6-membered aryl ring or heteroaryl ring instead of a benzene ring will be described below. In addition, the description so far is similarly understood also when these rings undergo the following structural changes.

<Structure change of ring c>

"-C(-Rc)=" in the ^c ring is substituted with "-N=", and may be a pyridine ring or a pyrazine ring. In addition, the following structural formula is an expression which extracted only part of c-ring and its peripheral structure.

<Structure change of ring a and b (1)>

Arbitrary "-C(-R)=" (where R is R ^a or R ^b ) in ring a and b may be substituted with "-N=". In addition, the following structural formula is an expression which extracted only a part of a ring or b ring and its peripheral structure.

As described above, the a ring or b ring represented as a benzene ring in formulas (2A) and (2B) is changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, and other nitrogen-containing heteroaryl rings. You can do it. In addition, when adjacent groups exist on the a ring or the b ring (two R ^a and two R ^bs in the above structural formula), they bond together to form a heteroaryl ring (in the above structural formula, forms a quinoline ring), and the formed ring may be further substituted (represented by n R's) as described above.

The same applies to cases where other positions are substituted with "-N=" or when adjacent substituents bond to each other to form another heteroaryl ring.

<aStructure change of ring (2)>

Arbitrary "-C(-R ^a )=C(-R ^a )-" in the a ring is "-N(-R)-", "-O-", "-S-", " -C(-R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C( R in -R) ₂ - and R in "-Si(-R) ₂ -" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is an alkyl or It may be substituted by cycloalkyl. In addition, the details of the substituents enumerated here will be summarized and described later.

The structural formulas above are formulas extracting only a part of the ring a and its surrounding structures, and the broken lines representing the partial structures are omitted in order to avoid cumbersomeness.

As described above, the a ring represented as a benzene ring in formulas (2A) and (2B) is an R-substituted pyrrole ring, a furan ring, a thiophene ring, and other nitrogen/oxygen/sulfur/silicon/selenium rings. You may change to a heteroaryl ring (5-membered ring) or an aryl ring (5-membered ring).

Other positions are "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -", or " The same applies to the case where it is substituted with -Se-”.

The two Rs of "-C(-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" are each independently formed by a single bond or a linking group (collectively, they are also referred to as bonding groups). may be combined. As this linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples thereof include the following structures. In addition, R in “-CHR-CHR-”, R in “-CR ₂ -CR ₂ -”, R in “-CR=CR-”, R in “-N(-R)-”, and “-C R in (-R) ₂ -” and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and At least one hydrogen in R may be substituted with alkyl or cycloalkyl. Further, “-CHR-CHR-”, “-CR ₂ -CR ₂ -”, “-CR=CR-”, “-C(-R) ₂ -”, and “-Si(-R) ₂ -” Two adjacent Rs in may be bonded to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (refer to the rightmost structural formula in the following structural formulas). Incidentally, the details of the substituents enumerated here will be summarized and described later.

As a bonding group, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and- as a single bond or a linking group. Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond or linking group are more preferable, and a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are more preferred, and -CR=CR- as a single bond and linking group are most preferred.

The position at which two R are bonded by a bonding group is not particularly limited as long as it can be bonded to, but it is preferable to bond at the most adjacent position, for example, when the two R's are a phenyl group, "C" in the phenyl group Or, it is preferable to bond to each other at ortho (second position) positions based on the bonding position (first position) of "Si" (see the structural formula above).

<Changes in the structure of ring b (2)>

Arbitrary "-C(-R ^b )=C(-R ^b )-" in the b ring is "-N(-R)-", "-O-", "-S-", " -C(-R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C( R in -R) ₂ - and R in "-Si(-R) ₂ -" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is an alkyl or It may be substituted by cycloalkyl. In addition, the details of the substituents enumerated here will be summarized and described later.

The above structural formula is an expression obtained by extracting only part of the b ring and its peripheral structure.

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

In addition, there are also the following modified examples.

Other positions are "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -", or " The same applies to the case where it is substituted with -Se-”.

The two Rs of "-C(-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" are each independently formed by a single bond or a linking group (collectively, they are also referred to as bonding groups). may be combined. As this linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples thereof include the following structures. In addition, R in “-CHR-CHR-”, R in “-CR ₂ -CR ₂ -”, R in “-CR=CR-”, R in “-N(-R)-”, and “-C R in (-R) ₂ -” and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and At least one hydrogen in R may be substituted with alkyl or cycloalkyl. Further, “-CHR-CHR-”, “-CR ₂ -CR ₂ -”, “-CR=CR-”, “-C(-R) ₂ -”, and “-Si(-R) ₂ -” Two adjacent Rs in may be bonded to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (refer to the rightmost structural formula in the following structural formulas). In addition, the details of the substituents enumerated here will be summarized and described later.

As a bonding group, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a single bond or a linking group. Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond or linking group are more preferable, and a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are more preferred, and -CR=CR- as a single bond and linking group are most preferred.

The position at which two R are bonded by a bonding group is not particularly limited as long as it can be bonded to, but it is preferable to bond at the most adjacent position, for example, when the two R's are a phenyl group, "C" in the phenyl group Or, it is preferable to bond to each other at ortho (second position) positions based on the bonding position (first position) of "Si" (see the structural formula above).

<Specific explanation of ring or substituent>

Next, the details of the rings and substituents (including the second substituent further substituted for the first substituent) listed in the above description will be summarized and described.

"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, or a carbon number 6 to 12 ring. an aryl ring of 10; and the like.

In addition, the “aryl ring” as the A ring and the B ring in formulas (1A) and (1B) is defined as “adjacent groups among R ^a and R ^b defined in formulas (2A) and (2B) Combined, it corresponds to the "formed aryl ring", but since the a ring or the b ring is already composed of a benzene ring having 6 carbon atoms, this benzene ring contains at least 5 The total carbon number of the condensed ring in which the circular rings are condensed is 9, which is the lower limit of the number of carbon atoms.

Specific "aryl rings" include, for example, a monocyclic benzene ring, a condensed bicyclic naphthalene ring, a condensed tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, or a phenanthrene ring, an anthracene ring, or a condensed tricyclic ring. A ring system, such as a triphenylene ring, a pyrene ring, or a naphthacene ring, or a condensed five-ring system, such as a perylene ring or a pentacene ring.

The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, and preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, and a heteroaryl ring having 2 to 15 carbon atoms. , or a heteroaryl ring having 2 to 10 carbon atoms. In addition, a "heteroaryl ring" is, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

In addition, the "heteroaryl ring" as the A ring and the B ring in formulas (1A) and (1B) is defined as "adjacent groups among R ^a and R ^b " defined in formulas (2A) and (2B). is bonded to correspond to the "heteroaryl ring formed together with the a ring and the b ring", but for this "formed aryl ring", since the a ring or the b ring is already composed of a benzene ring having 6 carbon atoms, this benzene ring has at least The total number of carbon atoms of the condensed ring in which the 5-membered rings of is 6 is the lower limit of the number of carbon atoms. However, since this benzene ring, ring a and ring b, may be changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing heteroaryl ring (5-membered ring) as described above, in this case, Accordingly, the number of carbon atoms in the lower limit changes.

Specific "heteroaryl rings" include, 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, and a pyrazole ring. , Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, Phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole oxide ring, dibenzophosphole oxide ring, furazan ring, thianthrene ring, They are an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, or an oxazoline ring.

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

Specific "aryl" includes, for example, monocyclic phenyl, bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), condensed bicyclic naphthyl (1- naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl -3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4 -yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p -terphenyl-4-yl), condensed tricyclic, acenaphthylene-(1-, 3-, 4-, or 5-)yl, fluorene-(1-, 2-, 3-, 4-, Or 9-)yl, phenalen-(1- or 2-)yl, or phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, tetracyclic quaterphenylyl (5' -phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-terphenyl), condensed tetracyclic ring phosphorus, triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacen-(1-, 2-, or 5-)yl, or condensation perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl, etc., which are pentacyclic.

In addition, in the aryl as the second substituent, that is, the aryl as the substituent (second substituent) further substituted by the substituent (first substituent), at least one hydrogen in the aryl is aryl such as phenyl (specific examples are group), a structure substituted with an alkyl such as methyl (specific examples are described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are described later) is also included in the aryl as the second substituent.

As an example thereof, when the second substituent is a fluorenyl group, at least one hydrogen at the ninth position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. fluorenyl group and the like, and such groups are also included in the aryl as the second substituent.

"Arylene (ring)" is, for example, arylene having 6 to 30 carbon atoms, preferably arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or and arylene having 6 to 10 carbon atoms.

Examples of specific "arylene" include a structure made into a divalent group by removing one hydrogen from the aforementioned "aryl" (monovalent group).

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms. heteroaryl of 10; and the like. Further, "heteroaryl" is a monovalent group such as a heterocyclic ring containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyrid denyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl , isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, Phenoxazinil, phenothiazinil, phenazinyl, phenazacillinyl, indolizinil, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, Isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl , indolocarbazolyl, benzoindolocarbazolyl, benzobenzoindolocarbazolyl, imidazolinyl, oxazolinyl, or dibenzosilacyclopentadienyl.

In addition, in the heteroaryl as the second substituent, that is, the heteroaryl as the substituent (second substituent) further substituted by the substituent (first substituent), at least one hydrogen in the heteroaryl is aryl such as phenyl (specific examples is the group described above), alkyl such as methyl (specific examples are groups described later), or structures substituted with cycloalkyls such as cyclohexyl or adamantyl (specific examples are groups described later), and heteroaryl as the second substituent included in

As an example thereof, when the second substituent is a carbazolyl group, at least one hydrogen at the ninth position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. carbazolyl group, and the like, and such groups are also included in the heteroaryl group as the second substituent.

"Heteroarylene (ring)" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms. heteroarylene or heteroarylene having 2 to 10 carbon atoms. In addition, "heteroarylene" is a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

A specific "heteroarylene" is, for example, a structure made into a divalent group by removing one hydrogen from the above-mentioned "heteroaryl" (monovalent group).

"Diarylamino" is an amino group in which two aryls are substituted, and the description of "aryl" described above can be cited for details of this aryl.

"Diheteroarylamino" is an amino group in which two heteroaryls are substituted, and the description of "heteroaryl" described above can be cited for details of this heteroaryl.

"Arylheteroarylamino" is an amino group in which aryl and heteroaryl are substituted, and the description of "aryl" and "heteroaryl" described above can be cited for details of the aryl and heteroaryl.

"Diarylboryl" is a boryl group in which two aryls are substituted, and the description of "aryl" described above can be cited for details of this aryl. In addition, these two aryls are a single bond or a linking group (for example, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR- , -C≡C-, >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se). Here, R in “-CHR-CHR-”, R in “-CR ₂ -CR ₂ -”, R in “-CR=CR-”, R in “>NR”, R in “>C(-R) ₂ R of ", and R of ">Si(-R)" are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least in R One hydrogen may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Moreover, two adjacent Rs may form a ring, and may form cycloalkylene, arylene, and heteroarylene. For the details of the substituents listed here, the description of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" described above, and "alkyl" and "alkyl" described later Descriptions of "kenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" can be cited.

"Alkyl" may be either straight chain or branched chain, and is, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, preferably, alkyl having 1 to 18 carbon atoms (C 3 to 24 carbon atoms). branched chain alkyl of 18), alkyl of 1 to 12 carbon atoms (branched chain alkyl of 3 to 12 carbon atoms), alkyl of 1 to 6 carbon atoms (branched chain alkyl of 3 to 6 carbon atoms), alkyl of 1 to 5 carbon atoms (3 carbon atoms) to 5 branched chain alkyl), C1-4 alkyl (C3-4 branched chain alkyl), and the like.

Specific "alkyl" includes, for example, methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1 ,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3 ,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethyl Butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethyl pentyl, 1-ethyl-1-methylpentyl, 1-propyl -1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1 -Methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-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.

Regarding "alkenyl", the description of "alkyl" described above can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is substituted with a C=C double bond, and not only one but two or more groups Also included are groups in which a bond is replaced by a double bond (also called alkadien-yl or alkanetrien-yl).

Regarding "alkynyl", the description of "alkyl" described above can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is substituted with a C≡C triple bond, and not only one but two or more bonds are substituted. Groups in which a single bond is replaced by a triple bond (also called alkadiyn-yl or alkanetriin-yl) are also included.

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

Specific "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyls having 1 to 5 carbon atoms or 1 to 4 carbon atoms (especially methyl) substituent, 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, diamantyl, decahydronaphtharenyl, or decahydroazulenyl, and the like.

"Cycloalkylene (ring)" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, or a cycloalkylene having 3 to 14 carbon atoms. Cycloalkylene, C3-C12 cycloalkylene, C5-C10 cycloalkylene, C5-8 cycloalkylene, C5-C6 cycloalkylene, or C5 cycloalkylene.

Specific examples of "cycloalkylene" include a structure made into a divalent group by removing one hydrogen from the aforementioned "cycloalkyl" (monovalent group).

"Alkoxy" may be either straight-chain or branched, and is, for example, straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms, and preferably alkoxy having 1 to 18 carbon atoms (carbon atoms 3 to 24). 18 branched alkoxy), C1-12 alkoxy (C3-12 branched alkoxy), C1-6 alkoxy (C3-6 branched alkoxy), C1-5 alkoxy (C3 to 5 branched alkoxy), C1-C4 alkoxy (C3-C4 branched alkoxy), and the like.

Specific "alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2- Trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2 -Ethyl butoxy, 1,1-dimethyl butoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyl Oxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1, 4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1, 5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy , 2,6-dimethyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n -decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy cy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy, and the like.

"Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)", and the description of "aryl" described above can be cited for details of this aryl.

"Substituted silyl" is, for example, silyl substituted with at least one of aryl, alkyl, and cycloalkyl, preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl dicycloalkylsilyl.

"Triarylsilyl" is a silyl group substituted with three aryls, and the description of "aryl" described above can be cited for details of this aryl.

Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

"Trialkylsilyl" is a silyl group substituted with three alkyls, and the description of "alkyl" described above can be cited for details of this alkyl.

Specific "trialkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, trin-propylsilyl, triisopropylsilyl, trin-butylsilyl, triisobutylsilyl, tris-butylsilyl, trit- Butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldi Ethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldin- propylsilyl, s-butyldin-propylsilyl, t-butyldin-propylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t -Butyldiisopropylsilyl, etc.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyls, and the description of "cycloalkyl" described above can be cited for details of this cycloalkyl.

Specific "tricycloalkylsilyl" is, for example, tricyclopentylsilyl or tricyclohexylsilyl.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the descriptions of "alkyl" and "cycloalkyl" described above can be cited for details of these alkyls and cycloalkyls. .

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyls, and for details of these alkyls and cycloalkyls, the descriptions of "alkyl" and "cycloalkyl" described above can be cited. .

Since substituents (including the first substituent and the second substituent) affect the emission wavelength of the polycyclic aromatic compound due to the steric hindrance, electron donating, and electron withdrawing properties of the structure, the selection of the substituent causes emission of light. Wavelength can be adjusted. It is preferably a group represented by the following structural formula, more preferably methyl, t-butyl, bicyclooctyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl , 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, diphenyl boryl, dimethylboryl, dibenzooxaboryl, phenyldibenzodivorinyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy; Even more preferably, methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-( t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of the ease of synthesis, a larger steric hindrance is preferred for selective synthesis, specifically, t-butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di -t-butylcarbazolyl is preferred.

In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents a bonding position.

<Description of cycloalkane condensation>

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

For example, an aryl ring and a heteroaryl ring which are ring A and ring B, an aryl group as the first and second substituents on these rings (aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy or triaryl aryl group part in silyl) and heteroaryl group (heteroaryl part in heteroaryl, diheteroarylamino or arylheteroarylamino), aryl ring and heteroaryl ring, ring a and b, ring a and b An aryl ring or heteroaryl ring formed by bonding adjacent substituents in , an aryl group (same as above) and a heteroaryl group (same as above) as the first and second substituents on ring a and b, X ¹ to X ⁴ , at least one of an aryl group or a heteroaryl group as R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ”, It may be condensed with one cycloalkane.

Preferably, an aryl ring and a heteroaryl ring, which are the A ring and the B ring, an aryl group (the aryl group moiety in aryl, diarylamino, diarylboryl or aryloxy) as the first substituent on these rings, and a heteroaryl group. (Heteroaryl moiety in heteroaryl or diheteroarylamino), an aryl ring and a heteroaryl ring of ring a and b, an aryl ring or heteroaryl ring formed by bonding adjacent substituents in ring a and b , an aryl group (same as above) and a heteroaryl group (same as above) as the first substituents on ring a and b, X ¹ to X ⁴ , R of ">NR", ">C(-R) At least one of the aryl group or heteroaryl group as R of ₂ ” and R of “>Si(-R) ₂ ” may be condensed with at least one cycloalkane.

More preferably, an aryl ring which is ring A and ring B, an aryl group (aryl group part in aryl or diarylamino) and heteroaryl group (heteroaryl part in heteroaryl) as the first substituent on these rings. , an aryl ring which is a ring and b ring, an aryl ring formed by bonding adjacent substituents in a ring and b ring, an aryl group as the first substituent for ring a and b, and a heteroaryl group (similar to the above) (Similar to the above), at least one of the aryl groups as R of ">NR" of X ¹ to X ⁴ may be condensed with at least one cycloalkane.

Even more preferably, an aryl ring which is ring A and ring B, an aryl group as a first substituent for these rings (the aryl group part in aryl or diarylamino), an aryl ring which is ring a and b, ring a and b At least one of the aryl group as the first substituent on the ring (similar to the above) and the aryl group as R of ">NR" of X ¹ to X ⁴ may be condensed with at least one cycloalkane.

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

Specific examples of cycloalkanes 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, dia mantane, decahydronaphthalene and decahydroazulene, and alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, halogen (particularly fluorine) substituents, and deuterium substituents, and the like.

Among these, as shown in the following structural formula, for example, at least one of the carbons at the α-position of cycloalkanes (the carbons adjacent to the carbons at condensed sites in cycloalkyls condensed to aromatic rings or heteroaromatic rings) A structure in which hydrogen of is substituted is preferable, a structure in which two hydrogens in the α-position carbon are substituted is more preferable, and a structure in which a total of 4 hydrogens in the two α-position carbons are substituted is even more preferable. do. As this substituent, a C1-C5 alkyl (particularly methyl) substituent, a halogen (particularly fluorine) substituent, a heavy hydrogen substituent, etc. are mentioned.

The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, still more preferably 1. For example, examples in which one or a plurality of cycloalkanes are condensed to one benzene ring (phenyl group) are shown below. * in each structural formula means a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and means the bond substituted in the skeleton structure of a compound in the case of a phenyl group. Condensed cycloalkanes may condense as shown in formulas (Cy-1-4) and (Cy-2-4). The same applies even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and even if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

At least one -CH ₂ - in the cycloalkane may be substituted with -O-. However, when a plurality of -CH ₂ - is substituted with -O-, adjacent -CH ₂ - is not substituted with -O-. For example, an example in which one or a plurality of -CH ₂ - in a cycloalkane condensed to one benzene ring (phenyl group) is substituted with -O- is shown below. * in each structural formula means a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and means the bond substituted in the skeleton structure of a compound in the case of a phenyl group. The same applies even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and even if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

At least one hydrogen in the cycloalkane may be substituted, and as this substituent, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano or halogen, details of which refer to the description of the first substituent described above. can do. Among these substituents, alkyl (eg, alkyl having 1 to 6 carbon atoms), cycloalkyl (eg, cycloalkyl having 3 to 14 carbon atoms), halogen (eg, fluorine), deuterium, and the like are preferable. In addition, when cycloalkyl is substituted, the substitution form which forms a spiro structure may be sufficient, For example, the example in which the spiro structure was formed in the cycloalkane condensed to one benzene ring (phenyl group) is shown below. * in each structural formula means a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and means the bond substituted in the skeleton structure of a compound in the case of a phenyl group.

As another form of cycloalkane condensation, a polycyclic aromatic compound represented by formula (1A), formula (1B), formula (2A), or formula (2B) is, for example, a diarylamino group condensed with cycloalkane (this aryl group), a carbazolyl group condensed with a cycloalkane (condensed with this benzene ring part), or a benzocarbazolyl group condensed with cycloalkane (condensed with this benzene ring part). have. As for the "diarylamino group", the groups described above as the "first substituent" are exemplified.

Further, as a more specific example, R ^{a in the polycyclic aromatic compound represented by Formula (2A) or Formula (2B) (particularly, R a at} the para position with respect to Y ¹ and Y ² ) is condensed with cycloalkane. Examples include a lylamino group (condensed to this aryl group part) or a carbazolyl group condensed with a cycloalkane (condensed to this benzene ring part).

<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 heavy hydrogen, cyano or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

<Description of specific examples of polycyclic aromatic compounds of the present invention>

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

The benzene rings in the above structural formula are independently selected from aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), and diarylboryl (wherein aryl is 6 to 10 carbon atoms). 10 aryl, two aryls may be bonded by a single bond or a linking group), may be substituted with C1-12 alkyl or C3-16 cycloalkyl, and at least one of the substituents Hydrogen may be substituted with C1-C5 alkyl or C5-C10 cycloalkyl. For specific examples of these substituents, the above description can be referred to. The number of substituents in the case of being substituted is from 1 to the maximum number that can be substituted in each benzene ring, 1 or 2 are preferable, and 1 is more preferable.

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

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

<Description of High Molecularization of Polycyclic Aromatic Compounds>

The polycyclic aromatic compound represented by the general formula (1A) or (1B) is a polymeric compound obtained by polymerizing a reactive compound having a reactive substituent substituted thereon as a monomer (the monomer for obtaining this polymeric compound is a polymerizable substituent) ), or a polymer crosslinked product obtained by further crosslinking the corresponding polymer compound (the polymer compound for obtaining the polymer crosslinked product has a crosslinkable substituent), or a pendant polymer obtained by reacting a main chain polymer with the reactive compound compound (the reactive compound for obtaining the pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked product obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining the pendant polymer crosslinked product) has a crosslinkable substituent), it can also be used for materials for organic devices, such as materials for organic electroluminescent devices, materials for organic field effect transistors, materials for organic thin-film solar cells, or wavelength conversion filters.

As the above-mentioned reactive substituent (including the polymerizable substituent, the crosslinkable substituent, and a reactive substituent for obtaining a pendant-type polymer, hereinafter also simply referred to as a "reactive substituent"), the polycyclic aromatic compound can be made high in molecular weight. It is not particularly limited as long as it has a substituent, a substituent capable of further crosslinking the polymer compound thus obtained, and a substituent capable of pendant reaction with the main chain polymer, but a substituent having the following structure is preferable. * in each structural formula represents a bonding position.

L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, C1-C12 alkylene, C1-C12 oxyalkylene, and C1 -12 polyoxyalkylene. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferable. and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

Such high molecular compounds, crosslinked polymers, pendant type high molecular compounds, and crosslinked pendant type polymers include substituted or unsubstituted triarylamines in addition to repeating units of polycyclic aromatic compounds represented by formula (1A) or formula (1B). , 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 repeating at least one selected from the group consisting of unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran. may be included as a unit.

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

Details of the use of such a polymer compound, polymer crosslinked product, pendant type polymer compound, and pendant type polymer crosslinked product (hereinafter, simply referred to as "polymer compound and polymer crosslinked product") will be described later.

2. Method for producing polycyclic aromatic compounds

The polycyclic aromatic compound of the present invention is basically prepared by first bonding A ring (a ring), B ring (b ring), and c ring with a bonding group (a group containing X ¹ to X ⁴ ) to produce an intermediate (first reaction), and then, ring A (ring a), ring B (ring b), and ring c are combined with a bonding group (a group containing central elements Y ¹ and Y ² , hereinafter “Y ¹ and Y ² ”). is abbreviated as "Y") to produce a final product (second reaction). The manufacturing method described in International Publication No. 2015/102118 can be referred to.

In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Birchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic electron transfer reaction, hereinafter the same) can be used.

As shown in the following scheme (1), the second reaction is a reaction of introducing the central element Y that binds ring A (ring a), ring B (ring b), and ring c. First, a hydrogen atom between X ¹ and X ² and a hydrogen atom between X ³ and X ⁴ are ortho-metalized with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Then, a halide of Y such as boron trichloride or boron tribromide is added to perform metal exchange of lithium-boron, and then a Bronsted base such as N,N-diisopropylethylamine is added to obtain tandem purple A target product can be obtained by a Friedel Crafts reaction. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. In addition, the definition of the code|symbol in each structural formula in the following scheme (1) and also in the subsequent scheme is the same as the definition mentioned above.

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

In the above schemes (1) and (2), Y is boron (>B-), etc. are typical production methods.

Next, as an example, the case where Y is a phosphine sulfide, phosphine oxide or phosphorus atom is shown in the following schemes (3) and (4). As before, first, the hydrogen atom between X ¹ and X ² and the hydrogen atom between X ³ and X ⁴ are ortho-metalized with n-butyllithium or the like. Then, phosphorus trichloride and sulfur are added in this order, and finally a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to cause a tandem phosphor Friedel Crafts reaction, A compound in which Y is phosphine sulfide can be obtained. In addition, a compound in which Y is phosphine oxide can be obtained by treating the obtained phosphine sulfide compound with m-chloro perbenzoic acid (m-CPBA), and a compound in which Y is a phosphorus atom can be obtained by treating with triethylphosphine. .

In the above scheme, examples such as Y being >B-, >P-, >P(=O)- or >P(=S)- have been described, but other compounds can also be produced by appropriately changing the raw material. can

In the above scheme, before adding a halide of Y such as boron trichloride or boron tribromide, a hydrogen atom (or halogen atom) between X ¹ and X ² and a hydrogen atom (or halogen atom) between X ³ and X ⁴ are added. An example of a tandem hetero-Fridel Crafts reaction by ortho-metalation with butyllithium or the like has been presented, but the reaction by addition of a Y halide such as boron trichloride or boron tribromide without performing ortho-metalation using butyllithium or the like may proceed.

Examples of the solvent used in the above scheme include t-butylbenzene and xylene.

As the ortho-metalation reagent used in the above scheme, alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldi and organic alkali compounds such as silazide and potassium hexamethyldisilazide, and dispersed alkali metals such as Na dispersed in organic solvents.

Examples of the metal-Y metal exchange reagent used in the above scheme include Y halides such as Y trifluoride, Y trichloride, Y tribromide, and Y triiodide, CIPN(NEt ₂ ) ₂ , etc. An aminated halide of Y, an alkoxide of Y, an aryloxide of Y, and the like.

As the Bronsted base used in the above scheme, N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-penta Methylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Si (Ar is aryl such as phenyl), and the like.

As Lewis acids used in the above scheme, AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In(OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaOTf, KOTf, Me ₃ SiOTf, Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , CoBr ₃ and the like.

In the above scheme, a Bronsted base or a Lewis acid may be used to promote the tandem hetero Friedel Crafts reaction. However, when Y halides such as Y trifluoride, Y trichloride, Y tribromide, Y triiodide, etc. are used, the aromatic electron transfer reaction progresses along with hydrogen fluoride, hydrogen chloride, and bromination. Since acids such as hydrogen and hydrogen iodide are produced, the use of a Bronsted base to capture the acid is effective. On the other hand, when an aminated halide of Y or an alkoxide of Y is used, amines and alcohols are formed as the aromatic electron transfer reaction progresses, so in many cases it is not necessary to use a Bronsted base, but amino groups Since the elimination ability of the alkoxy group is low, the use of a Lewis acid that promotes the elimination is effective.

The polycyclic aromatic compounds of the present invention also include compounds in which at least a part of hydrogen is substituted with deuterium, cyano or halogen. By using a halogenated raw material, it can manufacture similarly to the above.

3. Organic Device

In the chemical structural formulas illustrated below, "Me" represents a methyl group, and "tBu" represents a t-butyl group.

The polycyclic aromatic compound according to the present invention can be used as a material for organic devices. As an organic device, an organic electroluminescent element, an organic field effect transistor, an organic thin-film solar cell, or a wavelength conversion filter etc. are mentioned, for example.

3-1. Organic electroluminescence device

The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. Hereinafter, the organic EL element according to the present embodiment will be described in detail based on the drawings. 1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.

<Structure of organic electroluminescent device>

An organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer. The hole transport layer 104 provided on 103, the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electrons provided on the electron transport layer 106 It has an injection layer 107 and a cathode 108 provided on the electron injection layer 107.

In addition, the organic EL element 100 is manufactured by reversing the manufacturing order, for example, the substrate 101, the cathode 108 provided on the substrate 101, and the electron injection layer provided on the cathode 108 ( 107), an electron transport layer 106 provided on the electron injection layer 107, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer It is good also as a structure which has the hole injection layer 103 provided on 104, and the anode 102 provided on the hole injection layer 103.

Not all of the above layers are indispensable, and the minimum structural unit is composed of an anode 102, a light emitting layer 105, and a cathode 108, and a hole injection layer 103, a hole transport layer 104, and an electron transport layer 106 ), the electron injection layer 107 is an arbitrarily provided layer. In addition, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

As an aspect of the layer constituting the organic EL element, in addition to the constitutional aspect of the above-described "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/ Emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/emission layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/emission layer/electron injection layer" / cathode", "substrate/anode/hole injection layer/hole transport layer/emission layer/electron transport layer/cathode", "substrate/anode/emission layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/emission 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 transport layer/cathode”, or “substrate/anode/light emitting layer/electron injection layer/cathode” may be used.

<Substrate in organic electroluminescence device>

The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic or the like is used. The substrate 101 is formed in the shape of a plate, film, or sheet depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. In the case of a glass substrate, soda-lime glass, non-alkali glass, etc. are used, and thickness should just be sufficient thickness to maintain mechanical strength, so what is necessary is just 0.2 mm or more, for example. As an upper limit of thickness, it is 2 mm or less, for example, Preferably it is 1 mm or less. Regarding the material of the glass, an alkali-free glass is preferable since it is preferable to have fewer ions eluted from the glass, but soda lime glass coated with a barrier coat of SiO ₂ or the like is also commercially available and can be used. In addition, a gas barrier film such as a dense silicon oxide film may be formed on at least one side of the substrate 101 to improve gas barrier properties, and in particular, a plate, film or sheet made of synthetic resin having low gas barrier properties is used as the substrate. When using in (101), it is preferable to form a gas barrier film.

<Anode in Organic Electroluminescence Device>

The anode 102 serves to inject holes into the light emitting layer 105 . In addition, 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 them. do.

Materials 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 (such as copper iodide), copper sulfide, carbon black, ITO glass and Nessa glass. As an organic compound, conductive polymers, such as polythiophene, such as poly(3-methylthiophene), polypyrrole, and polyaniline, etc. are mentioned, for example. In addition, it can be used suitably selected from materials used as anodes of organic EL elements.

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 it is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω/□ or less functions as an element electrode, but at present it is possible to supply a substrate of about 10 Ω/□, so for example, 100 to 5 Ω/□, preferably 50 to 5 Ω/□. It is particularly preferable to use a low-resistance product of The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm in many cases.

<Hole Injection Layer, Hole Transport Layer in Organic Electroluminescent Device>

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or into the hole transport layer 104 . The hole transport layer 104 serves 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 or mixing one or more hole injection/transport materials, or a mixture of a hole injection/transport material and a polymeric binder, respectively. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection/transport material.

As the hole injection/transport material, 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 preferable to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable that the material has a small ionization potential, a high hole mobility, and excellent stability, and is difficult to generate trap impurities during production and use. In the present invention, a polycyclic aromatic compound represented by the general formula (1A) or (1B) can be used as a material for the hole injection layer and the hole transport layer.

As the material forming the hole injection layer 103 and the hole transport layer 104, in the photoconductive material, a compound conventionally used as a hole charge transport material, a p-type semiconductor, a hole injection layer of an organic EL device, and a hole Any compound may be selected and used from known compounds used in the transport layer.

Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine Derivatives (polymer having aromatic tertiary amino in main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3 -Methylphenyl) -4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N ,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl -1,1'-diamine, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4 '-diamine, N4,N4,N4',N4'-tetra[1,1-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4' Triphenylamine derivatives such as , 4″-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, Hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7 , 10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonates having the above monomers in their side chains, styrene derivatives, polyvinylcarbazole, polysilanes, etc. are preferred. , It is not particularly limited as long as it is a compound capable of forming a thin film necessary for manufacturing a light emitting device, injecting holes from an anode, and transporting holes.

It is also known that the conductivity of an organic semiconductor is strongly influenced by its doping. Such an organic semiconductor matrix material is composed of a compound having good electron donating property or a compound having good electron accepting property. For doping of electron donor materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are used. known (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz , M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. As matrix materials having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburstamine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly, zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Laid-Open 2005 -167175).

The material for the hole injection layer and the material for the hole transport layer described above are a polymer compound obtained by polymerizing a reactive compound having a reactive substituent substituted thereto as a monomer, or a crosslinked polymer thereof, or a main chain polymer and the reactive compound reacted A pendant-type polymer compound or a pendant-type polymer crosslinked product thereof can also be used for the hole layer material. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

The details of the use of such a high molecular compound and high molecular crosslinked product will be described later.

<Light-emitting layer in organic electroluminescent device>

The light-emitting layer 105 is a layer that 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. As the material forming the light-emitting layer 105, any compound (luminescent compound) that is excited by recombination of holes and electrons and emits light (luminescent compound) can form a stable thin film shape, and has strong light emission (fluorescence) efficiency in a solid state. It is preferable that it is a compound which represents. 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 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 consist of a plurality of layers, and is formed of materials for the light emitting layer (host material, dopant material), respectively. The host material and the dopant material may be one type or a combination of a plurality of materials, or may be any. In addition, the material for the hole transport layer or the material for the electron transport layer may be mixed with the host material, or a combination thereof may be used. The dopant material may be entirely contained in the host material, may be partially contained, or may be any. As the doping method, it can be formed by co-evaporation with the host material, but it may be deposited simultaneously after mixing with the host material in advance, or formed into a film by wet film forming after mixing with the host material in advance with an organic solvent.

The amount of host material used varies depending on the type of host material, and may be determined according to the characteristics of the host material. The standard for the amount of host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, still more preferably 90 to 99.9% by weight of the total amount of materials for the light emitting layer.

The usage amount of the dopant material varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, still more preferably 0.1 to 10% by weight of the total light emitting layer material. The above range is preferable in that, for example, the concentration quenching phenomenon can be prevented. From the standpoint of durability, it is also preferable that part or all of the hydrogen atoms of the dopant material are deuterated.

On the other hand, in an organic EL device using a thermally activated delayed fluorescent dopant material, a low concentration of the dopant material is preferable in that concentration quenching can be prevented, but a high concentration of the dopant material is thermally activated delayed. This is preferable from the viewpoint of the efficiency of the fluorescent instrument. Further, in an organic EL device using a thermally activated delayed fluorescence assist dopant material, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material, the amount of the dopant material used is preferably lower than the amount of the assist dopant material.

In the case where the assist dopant material is used, the host material, the assist dopant material, and the amount of the dopant material used are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight of the total light emitting layer material, respectively. is preferably 60 to 99.99 weight, 39 to 5 weight% and 10 to 0.01 weight%, more preferably 70 to 99.95 weight, 29 to 10 weight% and 5 to 0.05 weight%, respectively. The polycyclic aromatic compound and its high molecular compound represented by the general formula (1A) or (1B) can also be used as an assist dopant material.

As the host material, condensed ring derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclo A pentadiene derivative etc. are mentioned. In particular, an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound is preferred. Moreover, it is also preferable that some or all of the hydrogen atoms of the host material are deuterated from the viewpoint of durability. It is also preferable to configure the light emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated and a dopant compound in which some or all of the hydrogen atoms are deuterated.

The triplet energy of the host material is preferably higher than the triplet energy of the dopant or assist dopant having the highest triplet energy in the light emitting layer, from the viewpoint of promoting the generation of TADF in the light emitting layer without hindering it. In this case, the triplet energy of the host material is preferably 0.01 eV or more, more preferably 0.03 eV or more, and still more preferably 0.1 eV or more. Further, a compound having TADF activity may be used for the host material.

As a host material, for example, 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 represented by the following general formula (H4) A compound containing a structure, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. Preferably it is a compound represented by general formula (H1).

<Compound represented by general formula (H1)>

In the formula (H1), L ¹ represents arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms, preferably arylene having 6 to 24 carbon atoms, and more preferably arylene having 6 to 16 carbon atoms, , arylene having 6 to 12 carbon atoms is more preferred, arylene having 6 to 10 carbon atoms is particularly preferred, heteroarylene having 2 to 25 carbon atoms is more preferred, and heteroarylene having 2 to 20 carbon atoms is more preferred. Preferably, heteroarylene having 2 to 15 carbon atoms is more preferable, and heteroarylene having 2 to 10 carbon atoms is particularly preferable. Specific examples of the arylene include a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and Divalent groups, such as a pentacene ring, are mentioned. In addition, as heteroarylene, specifically, 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, and a pyridine ring. , Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, iso Quinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring , phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadia Divalent groups, such as a sol ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring, are mentioned.

At least one hydrogen in the compound represented by formula (H1) may be substituted with C1-C6 alkyl, C3-C14 cycloalkyl, cyano, halogen or deuterium.

<Compound represented by general formula (H2)>

In the formula (H2), L ² and L ³ each independently represent an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. The aryl is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, even more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. , benzene ring, biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perylene ring and pentacene ring, etc. monovalent can lift As the heteroaryl, a heteroaryl having 2 to 25 carbon atoms is preferable, a heteroaryl having 2 to 20 carbon atoms is more preferable, a heteroaryl having 2 to 15 carbon atoms is still more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. And, specifically, 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. , pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, new Nolin ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, tiant and monovalent groups such as a rene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.

At least one hydrogen in the compound represented by formula (H2) may be substituted with C1-C6 alkyl, C3-C14 cycloalkyl, cyano, halogen or deuterium.

<Compound represented by general formula (H3) (an example of polymer host material)>

In formula (H3),

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

More specifically,

MU is each independently arylene, heteroarylene, diarylene arylamino, diarylene arylboryl, oxaborine-diyl, azaborin-diyl,

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

At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl;

k is an integer of 2 to 50000;

It is preferable that k is an integer of 20-50000, and it is more preferable that it is an integer of 100-50000.

At least one hydrogen in MU and EC in formula (H3) may be substituted with C1-C24 alkyl, C3-C24 cycloalkyl, halogen, or deuterium, and further, any -CH ₂ - may be substituted with -O- or -Si(CH ₃ ) ₂ -, and any -CH ₂ - except for -CH ₂ - directly connected to EC in formula (H3) in the above alkyl. may be substituted with arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

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

More specifically, a divalent group represented by any one of the following structures is exemplified. In these, the MU binds to another MU or EC in *.

Moreover, as EC, the monovalent group represented by the structure of any one of the following is mentioned, for example. In these, EC binds to MU in *.

The compound represented by formula (H3) preferably has 10 to 100% of MU of the total number of MUs (k) in the molecule having alkyl having 1 to 24 carbon atoms, from the viewpoint of solubility and coating film forming property, and the total number of MUs in the molecule ( It is more preferable that 30 to 100% of MU of k) has an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and 50 to 100% of MU of the total number of MUs in the molecule (k) has 1 carbon atom. It is even more preferable to have ~12 alkyl (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the MUs of the total number of MUs (k) in the molecule have alkyls having 7 to 24 carbon atoms, and 30 to 100% of the total number of MUs (k) in the molecule It is more preferable that MU of has C7-C24 alkyl (C7-C24 branched chain alkyl).

<Compound containing structure represented by general formula (H4)>

The compound is a compound containing a structure represented by the following formula (H4), and includes a plurality of structures, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2. , Most preferably, one is included, and when a plurality is included, the structures are directly bonded to each other by a single bond or bonded to a specific linking group.

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

As the compound containing the structure represented by the general formula (H4), for example, compounds described in International Publication No. 2012/153780 and International Publication No. 2013/038650 can be used, and prepared according to the method described in the above literature. can do.

Examples of substituents in the case where H in "=C(-H)-" which is G is substituted are as follows, but are not limited thereto.

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

Specific examples of the "heteroaryl group" as a substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, Indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, aza Dibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothia zinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanil, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl and the like, preferably di benzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl and azadibenzothienyl; and the like. Even more preferred are dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl.

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

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

It is also preferable that the "substituted phosphine oxide group" which is a substituent is a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

As a "substituted carboxyl group" which is a substituent, benzoyloxy etc. are mentioned, for example.

Examples of the linking group for bonding a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl and heteroaryl.

The specific example of the compound containing the structure represented by general formula (H4) is shown below.

<Compound represented by general formula (H5)>

In the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (above, first substituent), and corresponding R ¹ to R At least one hydrogen in ¹¹ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent);

Adjacent groups among R ¹ to R ¹¹ may be bonded together to form an aryl ring or heteroaryl ring together with ring a, b or c, and at least one hydrogen in the formed ring is aryl, heteroaryl, It may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, first substituent), and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, may be further substituted with alkyl or cycloalkyl (above, second substituent);

Arbitrary “-C(-R)=” (where R is R ¹ to R ¹¹ ) in ring a, ring b, and ring c may be substituted with “-N=”;

At least one hydrogen in the compound represented by formula (H5) may each independently be substituted with a halogen or heavy hydrogen.

Arbitrary “-C(-R)=” (where R is R ¹ to R ¹¹ ) in ring a, ring b, and c in formula (H5) is substituted with “-N=”, and pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, and other nitrogen-containing heteroaryl rings. For details of this description, the descriptions in the general formulas (2A) and (2B) can be cited.

Preferably, in the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 12 carbon atoms, or Cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ¹ to R ¹¹ is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, or diarylamino (wherein aryl is 6 to 12 carbon atoms) aryl), may be further substituted with C1-C12 alkyl or C3-C16 cycloalkyl,

Adjacent groups of R ¹ to R ¹¹ may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring, and at least One hydrogen is aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl of 6 to 12 carbon atoms), alkyl of 1 to 12 carbon atoms, or cycloalkyl of 3 to 16 carbon atoms. It may be substituted, and at least one hydrogen in these substituents is aryl having 6 to 30 prime atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), and 1 to 12 carbon atoms. It may be further substituted with alkyl or C3-C16 cycloalkyl.

Even more preferably, in the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or Cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in R ¹ to R ¹¹ is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (wherein aryl is 6 to 10 carbon atoms) aryl), may be further substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

Adjacent groups of R ¹ to R ¹¹ may be bonded together 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 ring, b ring, or c ring, and at least One hydrogen is aryl of 6 to 16 carbon atoms, heteroaryl of 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl of 6 to 10 carbon atoms), alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms. It may be substituted, and at least one hydrogen in these substituents is aryl of 6 to 16 carbon atoms, heteroaryl of 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl of 6 to 10 carbon atoms), carbon atoms of 1 to 6 It may be further substituted with alkyl or C3-C14 cycloalkyl.

In the first substituent and the second substituent, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following examples.

Specific examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and more preferably aryl having 6 to 16 carbon atoms. More preferably, an aryl having 6 to 12 carbon atoms is particularly preferable, and an aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, and terphenylyl which is a 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, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-ter phenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, acene Naphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl , (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-ter Phenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1- , 2-, 4-) day, naphthacene- (1-, 2-, 5-) day, condensed pentacyclic aryl perylene- (1-, 2-, 3-) day, pentacene- (1- , 2-, 5-, 6-) days and the like.

Specific examples of the "heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, and having 2 to 15 carbon atoms. The heteroaryl of is more preferred, and the heteroaryl having 2 to 10 carbon atoms is particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridine Dazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cin Nolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathynyl, phenoxazinyl, phenothiazinyl, phenazinyl, Fenazasilinil, Indolizinil, Furanil, Benzofuranil, Isobenzofuranil, Dibenzofuranil, Naphthobenzofuranil, Thiophenyl, Benzothiophenyl, Isobenzothiophenyl, Dibenzothiophenyl, Naf Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar bazolyl and benzobenzoindolocarbazolyl; and the like.

In the first substituent and the second substituent, "alkyl" may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. , C1-C18 alkyl (C3-C18 branched chain alkyl) is preferable, C1-C12 alkyl (C3-C12 branched chain alkyl) is more preferable, C1-C6 alkyl (C1-C6 alkyl) Branched chain alkyl of 3 to 6 carbon atoms) is more preferred, and alkyl of 1 to 5 carbon atoms (branched chain alkyl of 3 to 5 carbon atoms) and alkyl of 1 to 4 carbon atoms (branched chain alkyl of 3 to 4 carbon atoms) is particularly preferred. and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n -Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n -Undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n - Eikosil etc. can be mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

In the first substituent and the second substituent, "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. Cycloalkyl of 5 to 10 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, cycloalkyl of 5 carbon atoms, and the like. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms 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, diamantyl, decahydronaphtharenyl, decahydroazulenyl and the like.

When the first substituent is aryl, the substitution position is preferably R ¹ , R ³ , R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ , for example, substitution with R ¹ and R ³ , R ⁵ and R Substitution with ¹⁰ and substitution with R ⁴ and R ¹¹ are more preferable, and aryl is preferably a phenyl group.

When the first substituent is heteroaryl, the substitution position is preferably R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ and R ¹¹ , for example, as R ¹ substitution with R ² , substitution with R ³ , substitution with R ¹ and R ₃ , substitution with R ⁴ and R ¹¹ , substitution with R ⁵ and R ¹⁰ , substitution with R ⁶ and R ⁹ are more preferred; , Heteroaryl is preferably a carbazolyl group. This heteroaryl (for example, carbazolyl) may be substituted at the said position via a phenylene group.

As a specific example of the compound represented by formula (H5), the compound represented by the following structural formula is mentioned, for example. In addition, "Me" in formula is a methyl group.

The compound represented by formula (H5) first produces an intermediate by bonding rings a to c with a bonding group (-O-) (first reaction), and then bonding rings a to c with B (boron). The final product can be prepared (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or a Ullman reaction can be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic electron transfer reaction) can be used. For details of the first and second reactions, the description described in International Publication No. 2015/102118 can be referred to.

<Compound represented by general formula (H6)>

In the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (above, first substituent), and corresponding R ¹ to R At least one hydrogen in ¹⁶ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent);

Adjacent groups among R ¹ to R ¹⁶ may be bonded together to form an aryl ring or heteroaryl ring together with the a ring, b ring, c ring, or d ring, and at least one hydrogen in the formed ring is aryl , heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, first substituent) may be substituted, and at least one hydrogen in these substituents is aryl, heteroaryl, may be further substituted with diarylamino, alkyl or cycloalkyl (above, second substituent);

At least one hydrogen in the compound represented by formula (H6) may each independently be substituted with a halogen or heavy hydrogen.

Preferably, in the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 12 carbon atoms, or Cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ¹ to R ¹⁶ is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, or diarylamino (wherein aryl is 6 to 12 carbon atoms) aryl), may be further substituted with C1-C12 alkyl or C3-C16 cycloalkyl,

Adjacent groups among R ¹ to R ¹⁶ may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring, c ring, or d ring, and the formed ring At least one hydrogen in is aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl of 6 to 12 carbon atoms), alkyl of 1 to 12 carbon atoms or 3 to 16 carbon atoms may be substituted with cycloalkyl, and at least one hydrogen in these substituents is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), carbon atoms It may be further substituted with an alkyl of 1 to 12 or a cycloalkyl of 3 to 16 carbon atoms.

Even more preferably, in the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or Cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in R ¹ to R ¹⁶ is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or diarylamino (provided that aryl has 6 to 10 carbon atoms). aryl), may be further substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

Adjacent groups among R ¹ to R ¹⁶ may be bonded together 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 ring, b ring, c ring, or d ring, and the ring formed At least one hydrogen in is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or carbon atoms 3 to 14 may be substituted with cycloalkyl, and at least one hydrogen in these substituents is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), carbon atoms It may be further substituted with an alkyl of 1 to 6 or a cycloalkyl of 3 to 14 carbon atoms.

In the first substituent and the second substituent, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following examples.

Specific examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and more preferably aryl having 6 to 16 carbon atoms. More preferably, an aryl having 6 to 12 carbon atoms is particularly preferable, and an aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, and terphenylyl which is a 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, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-ter phenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, acene Naphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl , (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-ter Phenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1- , 2-, 4-) day, naphthacene- (1-, 2-, 5-) day, condensed pentacyclic aryl perylene- (1-, 2-, 3-) day, pentacene- (1- , 2-, 5-, 6-) days and the like.

Specific examples of the "heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, and having 2 to 15 carbon atoms. The heteroaryl of is more preferred, and the heteroaryl having 2 to 10 carbon atoms is particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridine Dazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cin Nolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathynyl, phenoxazinyl, phenothiazinyl, phenazinyl, Fenazasilinil, Indolizinil, Furanil, Benzofuranil, Isobenzofuranil, Dibenzofuranil, Naphthobenzofuranil, Thiophenyl, Benzothiophenyl, Isobenzothiophenyl, Dibenzothiophenyl, Naf Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar bazolyl and benzobenzoindolocarbazolyl; and the like.

In the first substituent and the second substituent, "alkyl" may be either straight-chain or branched chain, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. , C1-C18 alkyl (C3-C18 branched chain alkyl) is preferable, C1-C12 alkyl (C3-C12 branched chain alkyl) is more preferable, C1-C6 alkyl (C1-C6 alkyl) Branched chain alkyl of 3 to 6 carbon atoms) is more preferred, and alkyl of 1 to 5 carbon atoms (branched chain alkyl of 3 to 5 carbon atoms) and alkyl of 1 to 4 carbon atoms (branched chain alkyl of 3 to 4 carbon atoms) is particularly preferred. and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n -Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n -Undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Ecosil etc. can be mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

In the first substituent and the second substituent, "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. Cycloalkyl of 5 to 10 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, cycloalkyl of 5 carbon atoms, and the like. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms 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, diamantyl, decahydronaphtharenyl, decahydroazulenyl and the like.

The compound represented by formula (H6) can be manufactured with reference to the description described in International Publication No. 2014/042197.

<TADF material>

By reducing the energy difference between the singlet excited state and the triplet excited state, the reverse energy transfer from the triplet excited state to the excited singlet state, which usually has a low transition probability, is generated with high efficiency, thereby emitting light from the singlet (thermal activation). delayed fluorescence, TADF) is expressed. In normal fluorescence emission, since 75% of triplet excitons generated by current excitation pass through the thermal deactivation pathway, they cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence, and a highly efficient organic EL device is realized.

Examples of TADF materials that can be used for such purposes include compounds represented by the following general formula (H7) or compounds having the following general formula (H7) as a partial structure.

In Formula (H7), ED is an electron-donating group, Ln is a bonding group, EA is an electron-accepting group, and the singlet energy (S ¹ ) and triplet energy (T ¹ ) of the compound represented by Formula (H7) The energy difference (ΔS ¹ T ¹ ) of is 0.2 eV or less (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS ¹ T ¹ ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, still more preferably 0.08 eV or less.

TADF materials are designed to localize HOMO and LUMO in a molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, so that efficient reverse intersystem crossing occurs. It is preferable that it is an acceptor type TADF compound (D-A type TADF compound).

Here, in the present specification, "electron-donating substituent" (donor) means a substituent and partial structure in which the LUMO orbital is localized in a TADF compound molecule, and "electron-accepting substituent" (acceptor) means a TADF compound molecule Among them, substituents and partial structures in which the HOMO orbital is localized are meant.

In general, a TADF compound using a donor or acceptor has a large spin-orbit coupling (SOC) due to its structure, and also has a small exchange interaction between HOMO and LUMO and a small ΔE(ST), so it is very Fast inverse interterm crossing velocities are obtained. On the other hand, a TADF compound using a donor or acceptor exhibits greater structural relaxation in the excited state (in some molecules, since the stable structures are different between the ground state and the excited state, conversion from the ground state to the excited state by external stimuli) If this occurs, the structure is then changed to a stable structure in an excited state), giving a wide luminescence spectrum, so when used as a luminescent material, color purity may be reduced.

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

As a structure of donor property and acceptor property used for TADF material, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used, for example. Examples of ED include functional groups containing sp ³ nitrogen, and more specifically, carbazole, dimethylcarbazole, di-tbutylcarbazole, dimethoxycarbazole, tetramethylcarbazole, and benzofluorocarbons. Locarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydro Phenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4 -groups derived from diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazacillin; and the like. Examples of EA include sp ² nitrogen-containing aromatic rings, CN-substituted aromatic rings, ketone-containing rings and cyano groups, more specifically, sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), Benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzooxazole, benzobis(oxa sol), quinoline, benzoimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, pyridine, 5H-cyclopenta[1,2-b:5,4-b' ]Dipyridine, benzenetricarbonitrile, fluorenedicarbonitrile, pyrazinedicarbonitrile, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltrile and groups derived from azine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylene, and more specifically, phenylene, biphenylene, naphthylene and the like. In any structure, hydrogen may be substituted with alkyl, cycloalkyl or aryl. Particularly, as partial structures, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thia It is preferably a compound having at least one selected from diazole and benzophenone.

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

Among the formulas (H7-1), (H7-2) and (H7-3),

M is, each independently, a single bond, -O-, >N-Ar, or >C(-AR) ₂ , and the depth of the HOMO and the height of the excitation singlet energy level and the excitation triplet energy level of the partial structure to be formed From the point of view, it is preferably a single bond, -O- or >N-Ar,

J is a spacer structure that divides the donor substructure and the acceptor substructure, and each independently is an arylene having 6 to 18 carbon atoms, from the viewpoint of the size of the conjugate exuded from the donor substructure and the acceptor substructure, Arylene having 6 to 12 carbon atoms is preferable, and more specifically, phenylene, methylphenylene and dimethylphenylene are exemplified,

Q is each independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the substructure to be formed and the height of the excitation singlet energy level and the excitation triplet energy level, preferably = is N-,

Ar is each independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 18 carbon atoms, and the depth and excitation of the HOMO of the partial structure to be formed From the viewpoint of the height of the singlet energy level and the triplet excitation energy level, preferably hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or cycloalkyl having 6 to 10 carbon atoms. and, more preferably, hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tbutylcarbazolyl, benzo imidazole or phenylbenzoimidazole, even more preferably hydrogen, phenyl or carbazolyl;

m is 1 or 2;

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

At least one hydrogen in the compound represented by each of the above formulas may be further substituted with a halogen or heavy hydrogen.

As a compound represented by Formula (H7), the compound represented by the following structure is mentioned, for example. In the structural formula, * indicates a bonding position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

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

In addition, as the dopant material, other than the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B), known compounds can be used, and can be selected from various materials according to the desired emission color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, and benzothiazole derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, Tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Laid-Open No. 1-245087), bisstyrylarylene derivatives (Japanese Patent Laid-Open No. 2 -247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenyl isobenzofuran, dimethyl isobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)iso Isobenzofuran derivatives such as benzofuran and phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7 -Coumarin derivatives such as acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzoimidazolylcoumarin derivatives, and 3-benzooxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine Derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrillium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives , quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrimethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, bioranthrone derivatives, phena gin derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives; and the like.

When exemplified by color emission, examples of blue to blue-green dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, derivatives thereof, furan, pyrrole, and thi Ophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyl Aromatic heterocyclic compounds such as ridine, quinoxaline, pyrrolopyridine, and thioxanthen or their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazoles, thiazoles, thiadia azole derivatives such as sol, carbazole, oxazole, oxadiazole, and triazole, metal complexes thereof, and N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl Aromatic amine derivatives typified by -1,1'-diamine; and the like.

Further, as the green to yellow dopant material, coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, rubrene, etc. naphthacene derivatives of , and compounds exemplified as the blue to blue-green dopant materials are introduced with substituents such as aryl, heteroaryl, arylvinyl, amino, and cyano that enable long wavelengths are also preferred. can be cited as an example.

Further, examples of the orange to red dopant material include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, and Eu using acetylacetone, benzoylacetone, phenanthroline, and the like as ligands. Rare earth complexes such as complexes, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and analogs thereof, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhoda Mineral compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, bioanthrone derivatives, phenazine derivatives, fenoxa Zoned derivatives and thiadiazolopyrene derivatives, etc., and substituents that enable long wavelengths such as aryl, heteroaryl, arylvinyl, amino, cyano, etc. in the compounds exemplified as the blue to cyan and green to yellow dopant materials Compounds introduced with are also exemplified as preferred examples.

In addition, as the dopant, it can be appropriately selected and used from among compounds described in Chemical Industries, June 2004, page 13, and reference literature published therein.

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

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

In the formula, Ar ¹ is an m-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, and at least one of Ar ¹ to Ar ³ is stilbene structure, Ar ¹ to Ar ³ may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and m is an integer from 1 to 4.

As for the amine having a stilbene structure, diaminostilbene represented by the following formula is more preferable.

In the formula, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (among aryl, alkyl and cycloalkyl). at least one tri-substituted silyl) or cyano may be substituted.

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl , perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, distyrylfluorenyl and the like.

Specific examples of amines having a stilbene structure are N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'- Tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N', N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N' -di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diphenyl-4, 4'-diaminostilbene, 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]- Benzene, 2,7-bis [4'-bis (diphenylamino) styryl] -9,9-dimethylfluorene, 4,4'-bis (9-ethyl-3-carbazovinylene) -biphenyl , 4,4'-bis(9-phenyl-3-carbazobinylene)-biphenyl, and the like.

Moreover, you may use the amine which has a stilbene structure described in Unexamined-Japanese-Patent No. 2003-347056, Unexamined-Japanese-Patent No. 2001-307884, etc.

Examples of the perylene derivative include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, and 3,10-diphenylphenyl. Rylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)- 8,11-di (t-butyl) perylene, 3- (9'-anthryl) -8,11-di (t-butyl) perylene, 3,3'-bis (8,11-di (t -butyl) perylenyl) and the like.

Further, Japanese Unexamined Patent Publication No. 11-97178, Japanese Unexamined Patent Publication No. 2000-133457, Japanese Unexamined Patent Publication No. 2000-26324, Japanese Unexamined Patent Publication No. 2001-267079, Japanese Unexamined Patent Publication No. 2001-267078, Japanese Patent You may use the perylene derivative described in Unexamined-Japanese-Patent No. 2001-267076, Unexamined-Japanese-Patent No. 2000-34234, Unexamined-Japanese-Patent No. 2001-267075, Unexamined-Japanese-Patent No. 2001-217077, etc.

Examples of the borane derivative include 1,8-diphenyl-10-(dimesityl boryl) anthracene, 9-phenyl-10-(dimethyl boryl) anthracene, and 4-(9'-anthryl)dimes. Tylborylnaphthalene, 4- (10'-phenyl-9'-antryl) dimethyl boryl naphthalene, 9- (dimethyl boryl) anthracene, 9- (4'-biphenylyl) -10- (dimes) tilboryl) anthracene, 9-(4'-(N-carbazolyl)phenyl)-10-(dimethyl boryl) anthracene, and the like.

In addition, you may use the borane derivative described in the pamphlet of International Publication No. 2000/40586, etc.

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

In the formula, Ar ⁴ is an n-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are aryl, heteroaryl, It may be substituted with alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl and cycloalkyl), or cyano, and n is an integer of 1 to 4.

In particular, Ar ⁴ is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are, Aromatic amine derivatives which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 2 are more preferred. .

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl , perylenyl, pentacenyl, and the like.

Examples of the aromatic amine derivative include N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl) as the chrysene type. Chrysene-6,12-diamine, N, N, N', N'-tetra (m-tolyl) chrysene-6,12-diamine, N, N, N', N'-tetrakis (4-iso Propylphenyl) chrysene-6,12-diamine, N,N,N',N'-tetra (naphthalen-2-yl)chrysene-6,12-diamine, N,N'-diphenyl-N,N '-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N' -Diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene -6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine, etc. are mentioned.

Examples of the pyrene type include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1, 6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1 ,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p- Tolyl) pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N' -bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N '-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl) -3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N, N'-diphenylpyrene-1,8-diamine, N ¹ ,N ⁶ -diphenyl-N ¹ ,N ⁶ -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6- Diamine etc. are mentioned.

Examples of the anthracene type include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10- Diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene -9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis( 4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis (4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra (p -Tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl -N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4 -Isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis( 4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di- p-Tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6-diphenylamino-2 -naphthyl) anthracene; and the like.

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

Moreover, you may use the aromatic amine derivative described in Unexamined-Japanese-Patent No. 2006-156888 etc.

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

In addition, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, Unexamined-Japanese-Patent No. 6-298758, etc.

As a pyran derivative, the following DCM, DCJTB, etc. are mentioned.

Further, Japanese Unexamined Patent Publication No. 2005-126399, Japanese Unexamined Patent Publication No. 2005-097283, Japanese Unexamined Patent Publication No. 2002-234892, Japanese Unexamined Patent Publication No. 2001-220577, Japanese Unexamined Patent Publication No. 2001-081090, and Japanese Patent You may use the pyran derivative described in Unexamined-Japanese-Patent No. 2001-052869 etc.

The above-mentioned materials for the light emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound having a reactive substituent substituted thereto as a monomer, or a cross-linked polymer thereof, or a main chain polymer and the reactive compound. The reacted pendant type polymer compound or its pendant type polymer crosslinked product can also be used for the material for the light emitting layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

The details of the use of such a high molecular compound and high molecular crosslinked product will be described later.

<Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Device>

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or into the electron transport layer 106 . The electron transport layer 106 serves 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 transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport/injection materials, or a mixture of an electron transport/injection material and a polymeric binder.

The electron injection/transport layer is a layer responsible for injecting electrons into the cathode and transporting electrons, and preferably has high electron injection efficiency and efficiently transports the injected electrons. For this purpose, it is preferable to use a material that has high electron affinity, high electron mobility, excellent stability, and is difficult to generate trap impurities during production and use. However, in the case of considering the transport balance of holes and electrons, when the role of efficiently preventing the flow of holes from the anode to the cathode side without recombination is mainly performed, even if the electron transport capacity is not so high, the luminous efficiency is improved. The effect is equivalent to that of a material having a high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer capable of effectively blocking the movement of holes.

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in photoconductive materials, an electron injection layer and an electron transport layer of an organic EL device. It can be used by selecting it arbitrarily from known compounds in use. In the present invention, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used as the electron transport material.

As the material used for the electron transport layer or the electron injection layer, compounds comprising an aromatic ring or heteroaromatic ring composed of at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives, and condensates thereof It is preferable to contain at least one selected from ring derivatives and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, and quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, carbazole derivatives and indole derivatives. Examples of the electron-accepting nitrogen-containing metal complex include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Although these materials are used alone, you may mix and use them with other materials.

In addition, as specific examples of other electron transfer compounds, 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-t-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 auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -spirofluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, Oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene, etc.), naphthyridine derivatives ( bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc. can be heard

In addition, metal complexes having electron-accepting nitrogen can also be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. and benzoquinoline metal complexes.

The above materials are used alone, but may be used in combination with other materials.

Among the above materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, Phenanthroline derivatives and quinolinol-based metal complexes are preferred.

<Boranic derivative>

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

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

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

In formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyanocyclic group. at least one of N, R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and R ²¹ and R ²² are each independently hydrogen; At least one of alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X ¹ is optionally substituted arylene having 20 or less carbon atoms, and n are each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. Moreover, as a substituent in the case of "may be substituted" or "is substituted", aryl, heteroaryl, alkyl, or cycloalkyl etc. are mentioned.

In formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyanocyclic group. at least one of N, R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and X ¹ is optionally substituted aryl having 20 or less carbon atoms; Ren, and n is an integer of 0 to 3 each independently. Moreover, as a substituent in the case of "may be substituted" or "is substituted", aryl, heteroaryl, alkyl, or cycloalkyl etc. are mentioned.

Specific examples of X ¹ include divalent groups represented by any of the following formulas (X-1) to (X-9). * in each structural formula represents a bonding position.

(In each formula, R ^a is each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

As a specific example of this borane derivative, the following compounds are mentioned, for example.

This borane derivative can be produced using known raw materials and known synthetic methods.

<Pyridine derivative>

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

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 is an integer

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

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

In each formula, the "pyridine-based substituent" is any one of the following formulas (Py-1) to (Py-15), and the pyridine-based substituents are each independently an alkyl having 1 to 4 carbon atoms or an alkyl having 5 to 10 carbon atoms. It may be substituted by cycloalkyl. In addition, the pyridine substituent may be bonded to φ in each formula, the anthracene ring or the fluorene ring via a phenylene group or a naphthylene group. * in each structural formula represents a bonding position.

The pyridine-based substituent is any one of the formulas (Py-1) to (Py-15), and among these, any one of the following formulas (Py-21) to (Py-44) is preferable. * in each structural formula represents a bonding position.

At least one hydrogen in each pyridine derivative may be substituted with a deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and formulas (ETM-2-2) One may be substituted by aryl.

"Alkyl" in R ¹¹ to R ¹⁸ may be straight-chain or branched, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Preferable "alkyl" is C1-C18 alkyl (C3-C18 branched chain alkyl). More preferable "alkyl" is C1-C12 alkyl (C3-C12 branched chain alkyl). More preferable "alkyl" is C1-C6 alkyl (C3-C6 branched chain alkyl). Especially preferable "alkyl" is C1-C4 alkyl (C3-C4 branched chain alkyl).

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

Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

As C1-C4 alkyl substituted by the pyridine-type substituent, the description of the said alkyl can be cited.

As "cycloalkyl" in ^R11 - ^R18 , C3-C12 cycloalkyl is mentioned, for example. Preferable "cycloalkyl" is a C3-C10 cycloalkyl. More preferable "cycloalkyl" is a C3-C8 cycloalkyl. Even more preferable "cycloalkyl" is a C3-C6 cycloalkyl.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

As the cycloalkyl having 5 to 10 carbon atoms substituted with a pyridine-based substituent, the description of the cycloalkyl described above can be cited.

As the "aryl" for R ¹¹ to R ¹⁸ , a preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, and even more preferably an aryl having 6 to 14 carbon atoms. Preferably, it is an aryl of 6 to 12 carbon atoms.

Specific "aryls having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl, (1-, 2-) naphthyl, which is a fused bicyclic aryl, and acenaphthylene- (1-, 3-, 4 -, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-) phenanthryl, condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2- , 5-)yl, perylene-(1-,2-,3-)yl which is a condensed pentacyclic aryl, pentacene-(1-,2-,5-,6-)yl and the like.

Preferable examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, or triphenylenyl, and more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl. , and particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

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

As a specific example of this pyridine derivative, the following compounds are mentioned, for example.

This pyridine derivative can be produced using known raw materials and known synthetic methods.

<Fluoranthene derivatives>

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

In the formula (ETM-3), X ¹² to X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. indicates Here, as a substituent in the case of being substituted, an aryl, heteroaryl, alkyl, or cycloalkyl etc. are mentioned.

As a specific example of this fluoranthene derivative, the following compounds are mentioned, for example.

<BO derivative>

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

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

In addition, adjacent groups among R ¹ to R ¹¹ may be bonded together to form an aryl ring or heteroaryl ring together with ring a, b or c, and at least one hydrogen in the formed ring is aryl or heteroaryl. may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, At least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

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

Regarding the description of the substituent and ring formation in formula (ETM-4) and the multimer formed by combining a plurality of structures of formula (ETM-4), the description described in International Publication No. 2015/102118 or the above formula The description of the polycyclic aromatic compound represented by (1A) or Formula (1B) can be cited.

As a specific example of this BO type derivative, the following compounds are mentioned, for example.

This BO derivative can be produced using known raw materials and known synthetic methods.

<Anthracene derivatives>

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

Ar is each independently divalent benzene or naphthalene, and R ¹ to R ⁴ are each independently hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or aryl of 6 to 20 carbon atoms.

Ar can each independently be appropriately selected from divalent benzene or naphthalene, and the two Ars may be different or the same, but from the viewpoint of the ease of synthesis of the anthracene derivative, they are preferably the same. Ar is bonded to pyridine to form "a moiety composed of Ar and pyridine", and this moiety is, for example, a group represented by any of the following formulas (Py-1) to (Py-12), and is bonded to anthracene are doing * in each structural formula represents a bonding position.

Among these groups, a group represented by any of the formulas (Py-1) to (Py-9) is preferable, and a group represented by any of the formulas (Py-1) to (Py-6) is more preferable. . The two "sites composed of Ar and pyridine" bonded to anthracene may have the same or different structures, but from the viewpoint of the ease of synthesis of the anthracene derivative, they are preferably the same structure. However, from the viewpoint of element characteristics, it is preferable that the structures of the two "sites composed of Ar and pyridine" be the same or different.

Alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either straight-chain or branched-chain. That is, it is C1-C6 straight-chain alkyl or C3-C6 branched chain alkyl. More preferably, it is C1-C4 alkyl (C3-C4 branched chain alkyl). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- hexyl, 1-methylpentyl, 3,3-dimethylbutyl, or 2-ethylbutyl; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t- Butyl is preferred, and methyl, ethyl, or t-butyl is more preferred.

Specific examples of cycloalkyl having 3 to 6 carbon atoms in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl. can

Regarding the aryl having 6 to 20 carbon atoms in R ¹ to R ⁴ , an aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl having 6 to 20 carbon atoms" include phenyl which is a monocyclic aryl, (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, bicyclic aryl (2-, 3- , 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl , m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl- 2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, anthracene-(1-, 2-, 9-)yl, acenaphthylene-(1- , 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2 -, 3-, 4-, 9-) phenanthryl, condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, tetracene-( 1-, 2-, 5-)yl, perylene-(1-,2-,3-)yl which is a condensed pentacyclic aryl, etc. are mentioned.

Preferred "aryl having 6 to 20 carbon atoms" is phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl. -5'-yl, more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, most preferably phenyl.

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

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

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

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

Specific examples of these anthracene derivatives include the following compounds.

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

<Benzofluorene derivative>

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

Ar ¹ is each independently an aryl having 6 to 20 carbon atoms, and the same description as “aryl having 6 to 20 carbon atoms” in the formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl and the like. can

Ar ² is each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). , and two Ar ² may be bonded to form a ring.

As "alkyl" for Ar ² , either straight-chain or branched chain may be used, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Preferable "alkyl" is C1-C18 alkyl (C3-C18 branched chain alkyl). More preferable "alkyl" is C1-C12 alkyl (C3-C12 branched chain alkyl). More preferable "alkyl" is C1-C6 alkyl (C3-C6 branched chain alkyl). Especially preferable "alkyl" is C1-C4 alkyl (C3-C4 branched chain alkyl). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl) , n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

^As "cycloalkyl" in Ar2, C3-C12 cycloalkyl is mentioned, for example. Preferable "cycloalkyl" is a C3-C10 cycloalkyl. More preferable "cycloalkyl" is a C3-C8 cycloalkyl. Even more preferable "cycloalkyl" is a C3-C6 cycloalkyl. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

As the "aryl" in Ar ² , a preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, still more preferably an aryl having 6 to 14 carbon atoms, and particularly preferably Aryl of 6 to 12 carbon atoms.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, and the like. can

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

As a specific example of this benzofluorene derivative, the following compounds are mentioned, for example.

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

<Phosphine oxide derivative>

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

R ⁵ is substituted or unsubstituted alkyl of 1 to 20 carbon atoms, cycloalkyl of 3 to 20 carbon atoms, aryl of 6 to 20 carbon atoms or heteroaryl of 5 to 20 carbon atoms;

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

R ⁷ and R ⁸ are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms;

R ⁹ is oxygen or sulfur;

j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.

Here, as a substituent in the case of being substituted, an aryl, heteroaryl, alkyl, or cycloalkyl etc. are mentioned.

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

R ¹ to R ³ , which may be the same or different, are hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an arylether group, and an arylthio group. It is selected from an ether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a condensed ring formed between adjacent substituents.

Ar ¹ may be the same or different, and is an arylene group or a heteroarylene group. Ar ² may be the same or different, and is an aryl group or a heteroaryl group. However, at least one of Ar ¹ and Ar ² has a substituent or forms a condensed ring between adjacent substituents. n is an integer of 0 to 3. When n is 0, no unsaturated structure moiety exists, and when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group represents a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, and a butyl group, for example, and this may be unsubstituted or substituted. The substituent in the case of being substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, and these points are also common to the description below. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 in view of availability and cost.

In addition, a cycloalkyl group represents a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, for example, and may be unsubstituted or substituted. The number of carbon atoms in the alkyl group portion is not particularly limited, but is usually in the range of 3 to 20.

In addition, an aralkyl group represents an aromatic hydrocarbon group through an aliphatic hydrocarbon, such as a benzyl group and a phenylethyl group, for example, and both aliphatic hydrocarbons and aromatic hydrocarbons may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

In addition, an alkenyl group represents an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, and a butadienyl group, for example, and this may be unsubstituted or substituted. Although the number of carbon atoms in the alkenyl group is not particularly limited, it is usually in the range of 2 to 20.

In addition, the cycloalkenyl group represents an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, and a cyclohexene group, for example, and this may be unsubstituted or substituted.

In addition, an alkynyl group represents an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an acetylenyl group, for example, and this may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

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

In addition, an alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

In addition, a cycloalkylthio group is a group in which the oxygen atom of the ether bond of the cycloalkoxy group is substituted with a sulfur atom.

In addition, an aryl ether group represents an aromatic hydrocarbon group through an ether bond such as a phenoxy group, for example, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

In addition, an arylthio ether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

In addition, an aryl group represents aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group, for example. An aryl group may be unsubstituted or substituted. Although the number of carbon atoms in the aryl group is not particularly limited, it is usually in the range of 6 to 40.

In addition, the heterocyclic group represents, for example, a cyclic structural group having atoms other than carbon such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group, which is unsubstituted or substituted. It doesn't matter if there is Although the number of carbon atoms in the heterocyclic group is not particularly limited, it is usually in the range of 2 to 30.

Halogen represents fluorine, chlorine, bromine, and iodine.

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

In addition, an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, and a heterocyclic ring may be unsubstituted or substituted.

A silyl group represents a silicon compound group, such as a trimethylsilyl group, for example, and this may be unsubstituted or substituted. Although the number of carbon atoms in the silyl group is not particularly limited, it is usually in the range of 3 to 20. Moreover, the number of silicon is 1-6 normally.

Condensed rings formed between adjacent substituents are, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , Ar ¹ and Ar It is a conjugated or non-conjugated condensed ring formed between ^two etc. Here, when n is 1, two R ^1s may form a conjugated or non-conjugated condensed ring. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the intra-ring structure, or may further condense with other rings.

As a specific example of this phosphine oxide derivative, the following compounds are mentioned, for example.

This phosphine oxide derivative can be produced using known raw materials and known synthetic methods.

<Pyrimidine derivatives>

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

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

Examples of the “aryl” of the “aryls which may be substituted” include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and more More preferably, it is an aryl of 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a fused bicyclic aryl, and tertiary aryl which is a tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2- ) day, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacen-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days, etc. are mentioned.

Examples of the "heteroaryl" of the "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, a heteroaryl having 2 to 15 carbon atoms is still more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Moreover, as a heteroaryl, the heterocyclic etc. which contain 1-5 hetero atoms selected from oxygen, sulfur, and nitrogen other than carbon as a ring constituting atom are mentioned, for example.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazacillinyl, indolizinil, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar bazolyl and benzobenzoindolocarbazolyl; and the like.

In addition, at least one hydrogen in the said aryl and heteroaryl may be substituted, and may be substituted with the said aryl or heteroaryl, respectively, for example.

As a specific example of this pyrimidine derivative, the following compounds are mentioned, for example.

This pyrimidine derivative can be produced using known raw materials and known synthetic methods.

<Carbazole derivatives>

A carbazole derivative is, for example, a compound represented by the following formula (ETM-9) or a multimer in which a plurality of them are bonded with a single bond or the like. Details are described in US Publication No. 2014/0197386.

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

Examples of the “aryl” of the “aryls which may be substituted” include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and more More preferably, it is an aryl of 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a fused bicyclic aryl, and tertiary aryl which is a tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2- ) day, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacen-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days, etc. are mentioned.

Examples of the "heteroaryl" of the "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, a heteroaryl having 2 to 15 carbon atoms is still more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Moreover, as a heteroaryl, the heterocyclic etc. which contain 1-5 hetero atoms selected from oxygen, sulfur, and nitrogen other than carbon as a ring constituting atom are mentioned, for example.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazacillinyl, indolizinil, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar bazolyl and benzobenzoindolocarbazolyl; and the like.

In addition, at least one hydrogen in the said aryl and heteroaryl may be substituted, and may be substituted with the said aryl or heteroaryl, respectively, for example.

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

As a specific example of this carbazole derivative, the following compounds are mentioned, for example.

This carbazole derivative can be produced using known raw materials and known synthetic methods.

<Triazine derivatives>

The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/0156013.

Ar is each independently an optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1 to 3, preferably 2 or 3.

Examples of the “aryl” of the “aryls which may be substituted” include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and more More preferably, it is an aryl of 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a fused bicyclic aryl, and tertiary aryl which is a tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2- ) day, (1-, 2-, 3-, 4-, 9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacen-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days, etc. are mentioned.

Examples of the "heteroaryl" of the "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, a heteroaryl having 2 to 15 carbon atoms is still more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Moreover, as a heteroaryl, the heterocyclic etc. which contain 1-5 hetero atoms selected from oxygen, sulfur, and nitrogen other than carbon as a ring constituting atom are mentioned, for example.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazacillinyl, indolizinil, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar bazolyl and benzobenzoindolocarbazolyl; and the like.

In addition, at least one hydrogen in the said aryl and heteroaryl may be substituted, and may be substituted with the said aryl or heteroaryl, respectively, for example.

As a specific example of this triazine derivative, the following compounds are mentioned, for example.

This triazine derivative can be produced using known raw materials and known synthetic methods.

<Benzimidazole derivatives>

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

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 It is an integer, and the "benzoimidazole-based substituent" means that the pyridyl group in the "pyridine-based substituent" in the above formulas (ETM-2), (ETM-2-1) and (ETM-2-2) is benzo. It is a substituent substituted with an imidazole group, and at least one hydrogen in the benzoimidazole derivative may be substituted with heavy hydrogen. * in the following structural formula represents a bonding position.

R ¹¹ in the benzoimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and is represented by the formulas (ETM-2-1) and (ETM The description of R ¹¹ in -2-2) can be cited.

φ is also preferably an anthracene ring or a fluorene ring, and the structure in this case can refer to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2), and in each formula For R ¹¹ to R ¹⁸ , the description in the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described in a bonded form. When these are substituted with benzoimidazole-based substituents, both pyridine-based substituents may be substituted with a benzoimidazole-based substituent (ie, n=2), or one pyridine-based substituent may be substituted with a benzoimidazole-based substituent and the other pyridine-based substituent may be substituted with R ¹¹ to R ¹⁸ (ie, n =1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) may be substituted with a benzoimidazole substituent, and the “pyridine substituent” may be substituted with R ¹¹ to R ¹⁸ .

Specific examples of this benzoimidazole derivative include, for example, 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10) -(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl )phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole Dazole, 1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-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 etc. are mentioned.

This benzoimidazole derivative can be produced using known raw materials and known synthetic methods.

<Phenanthroline derivatives>

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

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 is an integer

R ¹¹ to R ¹⁸ in each formula are independently selected from hydrogen, alkyl (preferably having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably having 1 to 12 carbon atoms). 6 to 30 aryl). In the formula (ETM-12-1), any one of R ¹¹ to R ¹⁸ is bonded to φ which is an aryl ring.

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

As the alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ , the descriptions of R ¹¹ to R ¹⁸ in the formula (ETM-2) can be cited. In addition, phi includes the following structural formulas, for example, in addition to the above examples. On the other hand, R in the following structural formula is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl. In addition, * in each structural formula represents a bonding position.

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

This phenanthroline derivative can be produced using known raw materials and known synthetic methods.

<Quinolinol-based metal complexes>

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

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

Specific examples of the quinolinol-based metal complex include 8-quinolinollithium, tris(8-quinolinolato) aluminum, tris(4-methyl-8-quinolinolato) aluminum, tris(5-methyl-8- Quinolinolato) Aluminum, Tris(3,4-dimethyl-8-quinolinolato) Aluminum, Tris(4,5-dimethyl-8-quinolinolato) Aluminum, Tris(4,6-dimethyl-8 -Quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum, bis (2-methyl-8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8 -Quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato) (4-phenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6 -Dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethyl phenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6 -Diphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2 ,4,6-trimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,5,6-tetramethylphenolato)aluminum, bis(2-methyl-8-quinolinato) Norato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinolato) (2-naphtholato) aluminum, bis (2,4-dimethyl-8-quinolinolato) ( 2-phenylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3-phenylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(4- Phenylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3, 5-di-t-butylphenolato) 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, 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-que nolinolato) 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, bis( 10-hydroxybenzo [h] quinoline) beryllium; and the like.

This quinolinol-based metal complex can be produced using known raw materials and known synthetic methods.

<Thiazole derivatives and benzothiazole derivatives>

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

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

φ in each formula 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 1 It is an integer of to 4, and "thiazole-based substituent" or "benzothiazole-based substituent" is "pyridine The pyridyl group in "substituent group" is a substituent substituted with the following thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with a deuterium. * in the following structural formula represents a bonding position.

φ is also preferably an anthracene ring or a fluorene ring, and the structure in this case can refer to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2), and in each formula For R ¹¹ to R ¹⁸ , the description in the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, but when they are substituted with a thiazole-based substituent (or benzothiazole-based substituent), Both pyridine-based substituents may be substituted with thiazole-based substituents (or benzothiazole-based substituents) (that is, n = 2), either pyridine-based substituent is substituted with a thiazole-based substituent (or benzothiazole-based substituent), and the other The pyridine-based substituent of R ¹¹ to R ¹⁸ may be substituted (that is, n=1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) is substituted with a thiazole-based substituent (or benzothiazole-based substituent), and “pyridine-based substituent” is replaced with R ¹¹ to R ¹⁸ may be replaced with

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

<Silole derivatives>

A silole derivative is a compound represented by the following formula (ETM-15), for example. Details are described in Japanese Unexamined Patent Publication No. 9-194487.

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

Further, X and Y may be bonded to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated), and the details of this cycloalkyl ring are cycloalkyl in the above general formulas (1A) and (1B) You can refer to the description of

R ¹ to R ⁴ are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy , arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso , formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano group, which may be substituted with alkyl, cycloalkyl, aryl or halogen, adjacent substituents A condensed ring may be formed between and.

For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in R ¹ to R ⁴ , the formulas (1A) and (1B) The explanation in can be cited.

Alkyl among alkyl carbonyl, aryl carbonyl, alkoxy carbonyl, aryloxy carbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in R ¹ to R ⁴ , aryl and alkoxy can also be cited in the explanations in the general formulas (1A) and (1B) above.

Examples of the silyl include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with aryl, alkyl or cycloalkyl, preferably trisubstituted silyl, triarylsilyl, trialkyl silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl; and the like. For the details of aryl, alkyl and cycloalkyl in these, the explanations in the general formula (1A) and general formula (1B) can be cited.

The condensed ring formed between adjacent substituents is, for example, a conjugated or non-conjugated condensed ring formed between R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and the like. These condensed rings may contain nitrogen, oxygen, and sulfur atoms in the intra-ring structure, or may further condense with another ring.

However, preferably, when R ¹ and R ⁴ are phenyl groups, X and Y are not alkyl or phenyl. Also, preferably, when R ¹ and R ⁴ are thienyl groups, X and Y are alkyl, R ² and R ³ are alkyl, aryl, alkenyl, or R ² and R ³ are bonded to form a ring. It is a structure that does not simultaneously satisfy the cycloalkyl Also preferably, when R ¹ and R ⁴ are silyl groups, R ² , R ³ , X and Y are each independently not hydrogen or an alkyl having 1 to 6 carbon atoms. Further, preferably, in the case of a structure in which benzene rings are condensed in R ¹ and R ² , X and Y are not alkyl and phenyl.

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

<Azoline derivatives>

An azoline derivative is a compound represented by the following formula (ETM-16), for example. Details are described in International Publication No. 2017/014226.

In formula (ETM-16),

φ 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 heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen in φ is an alkyl having 1 to 6 carbon atoms, or an alkyl having 3 to 14 carbon atoms. may be substituted with cycloalkyl, aryl of 6 to 18 carbon atoms or heteroaryl of 2 to 18 carbon atoms,

Y is each independently -O-, -S- or >N-Ar, Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is 1 to 4 carbon atoms may be substituted with alkyl, cycloalkyl of 5 to 10 carbon atoms, aryl of 6 to 12 carbon atoms or heteroaryl of 2 to 12 carbon atoms, R ¹ to R ⁵ are each independently hydrogen, alkyl of 1 to 4 carbon atoms or carbon atoms Cycloalkyl of 5 to 10, provided that Ar in the above >N-Ar and any one of R ¹ to R ⁵ is a site bonded to L;

L is each 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),

In formula (L-1), X ¹ to X ⁶ are each independently =CR ⁶ - or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, and 2 of X ¹ to X ⁶ R ⁶ in =CR ⁶ - of dog is a site that binds to φ or an azoline ring, and R ⁶ in =CR ⁶ - other than that is hydrogen;

In formula (L-2), X ⁷ to X ¹⁴ are each independently =CR ⁶ - or =N-, at least two of X ⁷ to X ¹⁴ are =CR ⁶ -, and 2 of X ⁷ to X ¹⁴ R ⁶ in =CR ⁶ - of dog is a site that binds to φ or an azoline ring, and R ⁶ in =CR ⁶ - other than that is hydrogen;

At least one hydrogen of L may be substituted with C1-C4 alkyl, C5-C10 cycloalkyl, C6-C10 aryl or C2-C10 heteroaryl,

m is an integer of 1 to 4, and when m is 2 to 4, the group formed by the azoline 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 heavy hydrogen.

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

Among formulas (ETM-16-1) and formulas (ETM-16-2),

φ 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 heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen in φ is an alkyl having 1 to 6 carbon atoms, or an alkyl having 3 to 14 carbon atoms. may be substituted with cycloalkyl, aryl of 6 to 18 carbon atoms or heteroaryl of 2 to 18 carbon atoms,

In formula (ETM-16-1), Y is each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and Ar At least one hydrogen may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms,

In formula (ETM-16-1), R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same;

In formula (ETM-16-2), R ¹ to R ⁵ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same,

Among formulas (ETM-16-1) and formulas (ETM-16-2),

L is each 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),

In formula (L-1), X ¹ to X ⁶ are each independently =CR ⁶ - or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, and 2 of X ¹ to X ⁶ R ⁶ in =CR ⁶ - of dog is a site that binds to φ or an azoline ring, and R ⁶ in =CR ⁶ - other than that is hydrogen;

In formula (L-2), X ⁷ to X ¹⁴ are each independently =CR ⁶ - or =N-, at least two of X ⁷ to X ¹⁴ are =CR ⁶ -, and 2 of X ⁷ to X ¹⁴ R ⁶ in =CR ⁶ - of dog is a site that binds to φ or an azoline ring, and R ⁶ in =CR ⁶ - other than that is hydrogen;

At least one hydrogen of L may be substituted with C1-C4 alkyl, C5-C10 cycloalkyl, C6-C10 aryl or C2-C10 heteroaryl,

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

At least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with heavy hydrogen.

Preferably, φ is a monovalent group represented by the following formulas (φ1-1) to (φ1-18), a divalent group represented by the following formulas (φ2-1) to (φ2-34), and the following It is selected from the group consisting of trivalent groups represented by formulas (φ3-1) to (φ3-3) and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), wherein at least One hydrogen may be substituted by C1-C6 alkyl, C3-C14 cycloalkyl, C6-C18 aryl, or C2-C18 heteroaryl. * in the following structural formula represents a bonding position.

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

Preferably, L is benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine. It is a divalent group of a ring selected from the group consisting of, and at least one hydrogen of L is substituted with C1-C4 alkyl, C5-C10 cycloalkyl, C6-C10 aryl or C2-C10 heteroaryl, There may be.

Preferably, Ar in >N-Ar as Y or Z is phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyl It is selected from the group consisting of ridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one of Ar in >N-Ar as Y has 1 to 4 carbon atoms may be substituted with an alkyl of , a cycloalkyl of 5 to 10 carbon atoms, or an aryl of 6 to 10 carbon atoms.

Preferably, R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same; Further, not all of R ¹ to R ⁴ become hydrogen at the same time, m is 1 or 2, and when m is 2, the group formed from the azoline ring and L is the same.

Specific examples of the azoline derivative include the following compounds. In addition, "Me" in structural formula represents a methyl group.

More preferably, φ consists of a divalent group represented by the following formulas (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33) and formula (φ2-34). It is selected from the group, and at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms, * in each structural formula represents a bonding position,

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

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

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, R ³ and R ⁴ are the same, and R ¹ Not all of -R ⁴ become hydrogen at the same time, and

m is 2, and the group formed from the azoline ring and L is the same.

Other specific examples of the azoline derivative include, for example, the following compounds. In addition, "Me" in structural formula represents a methyl group.

For details of alkyl, cycloalkyl, aryl or heteroaryl in each of the above formulas defining this azoline derivative, the explanations in the above general formulas (1A) and (1B) can be cited.

This azoline derivative can be produced using known raw materials and known synthetic methods.

The electron transport layer or electron injection layer may further contain a substance capable of reducing a material forming the electron transport layer or electron injection layer. As the reducing substance, as long as it is a substance having a certain reducing property, various substances are used. For example, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, At least one selected from the group consisting of alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes can be preferably used. .

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV copper), Rb (2.16 eV copper) or Cs (1.95 eV copper), Ca (2.9 eV copper), and Sr (2.0 eV copper). to 2.5 eV) or Ba (copper 2.52 eV), etc., and materials with a work function of 2.9 eV or less are particularly preferred. Among these, a more preferable reducing substance is an alkali metal of K, Rb or Cs, even more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and the addition of a relatively small amount to the material forming the electron transport layer or the electron injection layer can improve the light emission luminance and lengthen the lifetime of the organic EL device. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and a combination of Na and K is preferred. By including Cs, the reducing ability can be exhibited efficiently, and the addition to the material forming the electron transport layer or the electron injection layer can improve the light emission luminance and lengthen the lifetime of the organic EL device.

The material for the electron injection layer and the material for the electron transport layer described above are a polymer compound obtained by polymerizing a reactive compound having a reactive substituent substituted thereon as a monomer, or a polymer crosslinked product thereof, or a main chain polymer and the reactive compound reacted A pendant-type polymer compound or a pendant-type polymer crosslinked product thereof can also be used for the electronic layer material. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be cited.

The details of the use of such a high molecular compound and high molecular crosslinked product will be described later.

<Cathode in organic electroluminescence device>

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

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, but the same material as the material forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium -Indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.), etc. are preferable. In order to improve device characteristics by increasing electron injection efficiency, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in air in many cases. In order to improve this point, a method is known in which, for example, an organic layer is doped with a small amount of lithium, cesium or magnesium to use an electrode having high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

In addition, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbons for electrode protection Preferred examples include laminating a polymeric compound or the like. Methods for producing these electrodes are not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating and coating.

<Binder that can be used for each layer>

The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinyl carbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, Used by dispersing with solvent-soluble resins such as ABS resins and polyurethane resins, or curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins. It is also possible to do

<Method of manufacturing organic electroluminescence device>

For each layer constituting the organic EL device, the material constituting each layer is formed into a thin film by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating, casting, or coating. By doing so, it can be formed. The film thickness of each layer formed in this way is not particularly limited and can be appropriately set depending on the nature of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. In the case of forming a thin film using a vapor deposition method, the deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. Deposition conditions are generally boat heating temperature +50 to +400 ° C, vacuum degree 10 ^-6 to 10 ^-3 Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300 ° C, film thickness 2 nm to 5 μm. It is desirable to set appropriately within the range.

In the case of applying a direct current voltage to the organic EL element obtained in this way, the anode may be applied with + and the cathode as the polarity, and when a voltage of about 2 to 40 V is applied, the transparent or translucent electrode side (anode or cathode) , and both) can observe luminescence. In addition, this organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the alternating current to apply may be arbitrary.

Next, as an example of a method for manufacturing an organic EL device, a method for manufacturing an organic EL device composed of an anode/a hole injection layer/a hole transport layer/a light emitting layer composed of a host material and a dopant material/an electron transport layer/an electron injection layer/cathode Explain.

<Deposition method>

After fabricating an anode by forming a thin film of anode material on a suitable substrate by vapor deposition or the like, thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-evaporated on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for the cathode is formed by a vapor deposition method or the like to form a cathode. An organic EL element is obtained. In addition, in fabricating the organic EL device described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer and anode in this order.

<Wet film forming method>

The wet film forming method is performed by preparing a low-molecular compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using the same. When there is no suitable organic solvent that dissolves the low molecular weight compound, a composition for forming an organic layer is made of a reactive compound obtained by substituting a reactive substituent in the low molecular weight compound and polymerized together with other monomers or main chain polymers having a soluble function. you can prepare

In the wet film forming method, generally, a coating film is formed by passing through an application step of applying a composition for forming an organic layer to a substrate and a drying step of removing a solvent from the applied composition for forming an organic layer. When the above polymeric compound has a crosslinkable substituent (this is also referred to as a crosslinkable polymer compound), it is further crosslinked in this drying step to form a polymeric crosslinked body. Depending on the difference in the coating process, the method using a spin coater is spin coating, the method using a slit coater is a slit coating method, and the method using a plate is gravure, offset, reverse offset, flexo printing, and inkjet printers. The method of using is called the inkjet method, and the method of spraying in the form of mist is called the spray method. The drying process includes methods such as air drying, heating, and drying under reduced pressure. The drying step may be performed only once, or may be performed a plurality of times using different methods and conditions. In addition, you may use other methods together, such as baking under reduced pressure, for example.

The wet film forming method is a film forming method using a solution, and includes, for example, some printing methods (inkjet method), a spin coat method, a cast method, a coating method, and the like. Unlike the vacuum deposition method, the wet film formation method does not require the use of an expensive vacuum deposition apparatus and can form a film under atmospheric pressure. In addition, the wet film forming method enables large-area and continuous production, leading to reduction in manufacturing cost.

On the other hand, when compared with the vacuum deposition method, the wet film formation method sometimes makes lamination difficult. When a multilayer film is produced using a wet film forming method, it is necessary to prevent dissolution of the lower layer by the composition of the upper layer, so a composition with controlled solubility, cross-linking of the lower layer and orthogonal solvent (solvent that does not dissolve in each other), etc. this is spoken However, even if these techniques are used, there are cases where it is difficult to use the wet film formation method for coating all films.

Therefore, generally, a method of fabricating an organic EL device by using a wet film forming method for only a few layers and vacuum evaporation is employed for the rest.

For example, a procedure for fabricating an organic EL device by partially applying a wet film forming method is shown below.

(Procedure 1) Film formation by vacuum evaporation of the anode

(Procedure 2) Formation of a composition for forming a hole injection layer containing a material for a hole injection layer by a wet film forming method

(Procedure 3) Formation of a composition for forming a hole transport layer containing a material for a hole transport layer by a wet film forming method

(Procedure 4) Formation of a composition for forming a light emitting layer containing a host material and a dopant material by a wet film forming method

(Procedure 5) Film formation of the electron transport layer by vacuum evaporation

(Procedure 6) Formation of electron injection layer by vacuum deposition method

(Procedure 7) Film formation by vacuum evaporation of the cathode

By passing through this procedure, an organic EL device composed of an anode/a hole injection layer/a hole transport layer/a light emitting layer composed of a host material and a dopant material/an electron transport layer/an electron injection layer/cathode is obtained.

Of course, there is a means for preventing the dissolution of the lower light emitting layer, or a means for forming a film from the cathode side contrary to the above procedure is used to prepare a composition for forming a layer containing a material for an electron transport layer or a material for an electron injection layer, , these can be formed into a film by a wet film forming method.

<Other Tabernacling Methods>

A laser heating drawing method (LITI) can be used for film formation of the composition for forming an organic layer. LITI is a method of heating and depositing a compound attached to a substrate with a laser, and a composition for forming an organic layer can be used for a material applied to the substrate.

<Random process>

Appropriate treatment steps, washing steps, and drying steps may be suitably incorporated before and after each step of film formation. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, washing treatment using an appropriate solvent, heat treatment, and the like. In addition, a series of steps for producing a bank are also mentioned.

A photolithography technique can be used for fabrication of the bank. As a usable bank material for photolithography, a positive resist material and a negative resist material can be used. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, a permanent resist material may be used.

Materials used for the bank include polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biomolecular compounds, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, and polyethers. Mead, polysulfide, polysulfone, polyphenylene, polyphenylether, polyurethane, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (ABS ), silicone resin, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene, fluoropolymers Copolymers of olefin-hydrocarbon olefins and fluorocarbon polymers are exemplified, but are not limited thereto.

<Composition for Forming Organic Layer Used in Wet Film Formation>

The composition for forming an organic layer is obtained by dissolving in an organic solvent a low-molecular compound capable of forming each organic layer of an organic EL device or a high-molecular compound obtained by polymerizing the low-molecular compound. For example, a composition for forming a light emitting layer includes at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one as a third component. Contains a species of organic solvent. 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 that dissolves the first and second components in the composition, and upon application, imparts a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

<Organic Solvent>

The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent at the time of film formation, it is possible to control and improve the film formability and the presence or absence of defects, surface roughness, and smoothness of the coating film. Further, in the case of film formation using the inkjet method, the meniscus stability in the pinhole of the inkjet head can be controlled to control and improve ejection properties. Furthermore, by controlling the drying speed of the film and the orientation of the derivative molecules, it is possible to improve the electrical characteristics, light-emitting characteristics, efficiency, and lifetime of the organic EL device having the organic layer obtained from the composition for forming the organic layer.

(1) physical properties of organic solvents

The boiling point of the at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, still more preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet ejection properties. In addition, when the boiling point is lower than 300 ° C., it is preferable from the viewpoint of defectivity, surface roughness, residual solvent and smoothness of the coating film. The organic solvent is more preferably composed of two or more kinds of organic solvents from the viewpoint of good inkjet ejection properties, film formability, smoothness, and low residual solvent. On the other hand, depending on the case, a composition made into a solid state by removing the solvent from the composition for forming an organic layer may be used in consideration of transportability and the like.

Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point of the good solvent (GS) (BP _GS ) is the boiling point of the poor solvent (PS) (BP _PS ) A configuration lower than that is particularly preferred.

By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first at the time of film formation, and the concentration of the content and the concentration of the poor solvent in the composition increase, thereby promoting rapid film formation. As a result, a coating film having few defects, small surface roughness, and high smoothness is obtained.

The difference in solubility (S _GS -S _PS ) is preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. The difference in boiling point (BP _PS -BP _GS ) is preferably 10°C or higher, more preferably 30°C or higher, and still more preferably 50°C or higher.

After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to perform heating at a glass transition temperature (Tg) of at least one of the solutes +30°C or less from the viewpoint of improving coating film formability. Further, from the viewpoint of reducing the residual solvent, it is preferable to heat to at least one glass transition point (Tg) of -30°C or higher of the solute. Since the film is thin even when the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed. Moreover, 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 organic solvents used in the composition for forming an organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-based solvents and the like, and specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptan-2- Ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, ter Pineol (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 isopropylmethyl ether, dipropylene Glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether , triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutein Deine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole , 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butyl Benzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3 -Trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene ), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzoni Tril, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolnitrile, n-amyl Benzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxy Toluene, 2,2'-bitril, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxy Methyl)benzene, 1-methyl-4-(butyloxymethyl)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 and the like, but is not limited thereto. In addition, a solvent may be used singly or may be mixed.

<Optional ingredients>

The composition for forming an organic layer may contain arbitrary components within a range that does not impair its properties. As an arbitrary component, a binder, surfactant, etc. are mentioned.

(1) Binder

The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the obtained film to the substrate. In addition, it serves to dissolve, disperse, and bind other components in the composition for forming the organic layer.

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, and Ionomer, chlorinated polyether, diarylphthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers, but are not limited thereto. don't

The binder used in the composition for forming an organic layer may be used alone or in combination of multiple types.

(2) Surfactants

The composition for forming an organic layer may contain, for example, a surfactant for controlling the uniformity of the film surface and the solvent affinity and liquid repellency of the film surface of the composition for forming an organic layer. Surfactants are classified into ionic and nonionic according to the structure of the hydrophilic group, and also classified into alkyl, silicone and fluorine based according to the structure of the hydrophobic group. In addition, according to the structure of the molecule, it is classified into a monomolecular system having a relatively small molecular weight and a simple structure, and a macromolecular system having a large molecular weight and side chains or branches. In addition, according to the composition, it is classified into a single system and a mixed system in which two or more types of surfactants and a substrate are mixed. As the surfactant that can be used for the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include Polyflow No.45, Polyflow KL-245, Polyflow No.75, Polyflow No.90, and Polyflow No.95 (trade name, manufactured by Kyoeisha Chemical Industry Co., Ltd.) , Disperbyk 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK300 , BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (Brand name, manufactured by Shin-Etsu Chemical Co., Ltd.), Supreon SC-101, Supreon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Phtagent 222F, Phtagent 251, FTX-218 (trade name, ( Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi Materials Co., Ltd.), Megapack F-470, Megapack F -471, Megapack F-475, Megapack R-08, Megapack F-477, Megapack F-479, Megapack F-553, Megapack F-554 (trade name, manufactured by DIC Co., Ltd.), Fluoro Alkylbenzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis (fluoroalkyl polyoxy ethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, poly Oxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan Palmitate, Polyoxyethylene Sorby and tanstearate, polyoxyethylene sorbitanolate, polyoxyethylene naphthyl ether, alkylbenzenesulfonic acid salts and alkyldiphenyl ether disulfonic acid salts.

In addition, surfactant may be used by 1 type, and may use 2 or more types together.

<Composition and physical properties of composition for forming organic layer>

The content of each component in the composition for forming an organic layer is such that each component in the composition for forming an organic layer has good solubility, storage stability, and film formability, and the quality of a coating film obtained from the composition for forming an organic layer is of good quality. It is determined in consideration of the good ejection properties of the case, good electrical characteristics, light emitting characteristics, efficiency, and lifetime of an organic EL element having an organic layer produced using the composition. For example, in the case of the composition for forming a light emitting layer, the first component is 0.0001% to 2.0% by weight based on the total weight of the composition for forming a light emitting layer, and the second component is 0.0999% by weight based on the total weight of the composition for forming a light emitting layer. % to 8.0% by weight, and the third component is preferably 90.0% to 99.9% by weight with respect to the total weight of the composition for forming a light emitting layer.

More preferably, the first component is 0.005% to 1.0% by weight based on the total weight of the composition for forming a light emitting layer, and the second component is 0.095% to 4.0% by weight based on the total weight of the composition for forming a light emitting layer. The three components are 95.0% by weight to 99.9% by weight with respect to the total weight of the composition for forming a light emitting layer. Even more preferably, the first component is 0.05% to 0.5% by weight based on the total weight of the composition for forming a light emitting layer, the second component is 0.25% to 2.5% by weight based on the total weight of the composition for forming a light emitting layer, The third component is 97.0% to 99.7% by weight based on the total weight of the composition for forming a light emitting layer.

The composition for forming an organic layer can be prepared by appropriately selecting and performing stirring, mixing, heating, cooling, dissolution, dispersion, etc. of the above-mentioned components by a known method. After preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, and inert gas replacement/encapsulation treatment may be appropriately selected and performed.

As for the viscosity of the composition for forming an organic layer, a higher viscosity results in better film formability and better ejection properties in the case of using the inkjet method. On the other hand, it is easier to form a thin film when the viscosity is low. From these points, it is preferable that the viscosity in 25 degreeC is 0.3-3 mPa*s, and, as for the viscosity of the said composition for organic layer formation, it is more preferable that it is 1-3 mPa*s. In the present invention, the viscosity is a value measured using a cone-plate rotational viscometer (conical plate type).

As for the surface tension of the composition for forming an organic layer, the lower the surface tension, the better film formability and defect-free coating can be obtained. On the other hand, the higher the better, the better inkjet ejection properties can be obtained. From these points, it is preferable that the surface tension in 25 degreeC of the viscosity of this composition for organic layer formation is 20-40 mN/m, and it is more preferable that it is 20-30 mN/m. In the present invention, the surface tension is a value measured using the hanging drop method.

<Crosslinkable High Polymer Compound: Compound Represented by Formula (XLP-1)>

Next, the case where the above-mentioned high molecular compound has a crosslinkable substituent is demonstrated. Such a crosslinkable high molecular compound is, for example, a compound represented by the following general formula (XLP-1).

In formula (XLP-1),

MUx, ECx, and k have the same definitions as MU, EC, and k in the formula (H3), provided that the compound represented by the formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably Preferably, the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight in the molecule.

0.5 to 50 weight% is preferable, and, as for content of the monovalent or divalent aromatic compound which has a crosslinkable substituent, 1 to 20 weight% is more preferable.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the polymer compound described above, but the following structural substituents are preferable. * in each structural formula represents a bonding position.

L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, C1-C12 alkylene, C1-C12 oxyalkylene, and C1 -12 polyoxyalkylene. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferable. and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

As a divalent aromatic compound which has a crosslinkable substituent, the compound which has the following partial structure is mentioned, for example. * in the following structural formula represents a bonding position.

<Method for producing high molecular compound and crosslinkable high molecular compound>

The method for producing the high molecular compound and the crosslinkable high molecular compound will be described by taking the compound represented by the formula (H3) and the compound represented by the 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 aromatic solvents, saturated/unsaturated hydrocarbon solvents, alcohol solvents, and ether solvents, and examples thereof include dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2- (2-ethoxyethoxy) ethane etc. are mentioned.

Also, the reaction may be performed in a two-phase system. When making it react in a two-phase system, you may add a phase transfer catalyst, such as a quaternary ammonium salt, as needed.

When the compound of formula (H3) and the compound of formula (XLP-1) are produced, they may be produced in one step or may be produced through multiple steps. Alternatively, it may be carried out by a batch polymerization method in which the reaction is started after all the raw materials are put into a reaction vessel, or may be carried out by a dropping polymerization method in which the raw materials are added dropwise into a reaction vessel, or the product precipitates as the reaction proceeds. Precipitation polymerization may be carried out, and these can be synthesized by appropriately combining them. For example, when synthesizing the compound represented by formula (H3) in one step, the target product is obtained by reacting with the monomer unit (MU) and the end cap unit (EC) added to the reaction vessel. Further, when synthesizing the compound represented by the general formula (H3) in multiple stages, the monomer unit (MU) is polymerized to a desired molecular weight, and then the end cap unit (EC) is added and reacted to obtain the desired product. When the reaction is performed by adding different types of monomer units (MU) in multiple steps, a polymer having a concentration gradient with respect to the structure of the monomer units can be produced. In addition, after preparing the precursor polymer, the target polymer can be obtained by post-reaction.

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

As the monomer unit usable in the present invention, Japanese Patent Laid-Open No. 2010-189630, International Publication No. 2012/086671, International Publication No. 2013/191088, International Publication No. 2002/045184, International Publication No. 2011/049241 . , It is compoundable according to the method described in Unexamined-Japanese-Patent No. 2011-174062.

In addition, regarding the specific polymer synthesis procedure, Japanese Patent Laid-Open No. 2012-036388, International Publication No. 2015/008851, Japanese Patent Laid-Open No. 2012-36381, Japanese Patent Laid-Open No. 2012-144722, International Publication No. 2015/194448 International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, and International Publication No. 2011/049241. .

<Application example of organic electroluminescence device>

Further, the present invention can also be applied to a display device including an organic EL element or a lighting device including an organic EL element.

A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment to a known drive device, and known methods such as direct current drive, pulse drive, and alternating current drive. It can be driven by appropriately using a driving method.

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 electroluminescent (EL) display, and the like (eg, Japanese Patent Laid-Open No. 10-335066, Japanese Unexamined Patent Publication No. 2003-321546, Japanese Unexamined Patent Publication No. 2004-281086, etc.). In addition, as a display method of a display, a matrix method, a segment method, etc. are mentioned, for example. Also, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally in a lattice or mosaic pattern, and characters or images are displayed by a set of pixels. The shape or size of the pixel is determined according to the purpose. For example, for displaying images and characters on computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, and in the case of large displays such as display panels, pixels on the order of mm are used. will do In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are arranged and displayed. In this case, there are typically a delta type and a stripe type. Incidentally, as a driving method for this matrix, either a line-sequential driving method or an active matrix may be used. Line-sequential driving has the advantage of having a simple structure, but when operating characteristics are taken into consideration, the active matrix method may be superior, so it is necessary to use this also according to the purpose.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is illuminated. For example, time or temperature display in a digital watch or thermometer, operation status display of an audio device or electric cooker, and panel display of an automobile may be cited.

Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, and the like (for example, Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, Japanese Patent). Publication No. 2004-119211, etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light themselves, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display panels, and signs. In particular, considering that it is difficult to reduce the thickness of a liquid crystal display device, especially a backlight for a computer where thinning is a problem, because the conventional method consists of a fluorescent lamp or a light guide plate, the backlight using the light emitting element according to the present embodiment is thin. and is characterized by being lightweight.

3-2. Other organic devices

The polycyclic aromatic compound according to the present invention can be used for fabrication 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 device described above.

An organic field effect transistor is a transistor that controls a current by an electric field generated by inputting a voltage, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode is arbitrarily blocked, and the current can be controlled. Field effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

The structure of the organic field effect transistor is usually provided with a source electrode and a drain electrode in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and furthermore, an insulating layer (dielectric layer) in contact with the organic semiconductor active layer is interposed therebetween. and the gate electrode is installed. As the element structure, the following structures are mentioned, for example.

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

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

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

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

The organic field effect transistor constructed as described above can be applied as a pixel driving switching element of an active matrix driving liquid crystal monitor or an organic light emitting element display.

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 according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. The organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like other than the above. For organic thin-film solar cells, well-known materials used for organic thin-film solar cells can be appropriately selected and combined.

For the purpose of wide color gamut of a display, quantum dots having a narrow emission half-width are used as phosphors of a wavelength conversion filter. On the other hand, there are problems such as instability to oxidation, high aggregation due to nano-sized fine particles, and the metal used is regulated as a contaminant. The polycyclic aromatic compound according to the present invention can be used as a phosphor of a wavelength conversion filter. As the matrix for dispersing the polycyclic aromatic compound, a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability is preferable, and examples thereof include (meth)acrylic acid such as polymethyl (meth)acrylate. Cycloolefin polymers, such as a polymer and Zeonex, etc. are mentioned.

[Example]

Hereinafter, the present invention will be described more specifically by means of examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds are described below.

Synthesis Example (1): Synthesis of Compound (1A-1)

Compound (Int-1A-1) (1.39g, 1.0mmol, 1.0eq.), 2,6-di-tert-butylpyridine (0.57g, 3.0mmol, 3.0eq.) and 1,2,4-trichloro To a flask containing benzene (50 ml), iodine tribromide (2.35 g, 6.0 mmol, 6.0 eq.) was added at room temperature under a nitrogen atmosphere. Then, the mixture was heated and stirred at 60°C for 4 hours. The reaction solution was cooled to room temperature. Phosphate buffer (30 ml) was added to the reaction solution, and the organic layer was collected by liquid separation and concentrated under reduced pressure. The obtained crude product was purified by a silica gel column (eluent: hexane/dichloromethane = 1/1 (volume ratio)) and washed with methanol to obtain compound (1A-1) as a yellow solid (10.1 mg).

The target compound (1A-1) was confirmed at m/z = 1413.6820 by MALDI-TOF/MS.

Synthesis Example (2): Synthesis of Compound (1A-2)

In the synthesis method described in Synthesis Example (1), compound (Int-1A-1) (1.39g, 1.0mmol, 1.0eq.) was mixed with compound (1nt-1A-2) (1.45g, 1.0mmol, 1.0eq. ), but compound (1A-2) was obtained (0.18 g) by synthesizing in the same manner.

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

Synthesis Example (3): Synthesis of Compound (1A-19)

In the synthesis method described in Synthesis Example (1), compound (Int-1A-1) (1.39g, 1.0mmol, 1.0eq.) was mixed with compound (1nt-1A-19) (1.35g, 1.0mmol, 1.0eq. ), compound (1A-19) was obtained (0.18 g) by synthesizing in the same procedure except for changing to.

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

Synthesis Example (4): Synthesis of Compound (1A-33)

In the synthesis method described in Synthesis Example (1), compound (Int-1A-1) (1.39g, 1.0mmol, 1.0eq.) was mixed with compound (1nt-1A-33) (1.32g, 1.0mmol, 1.0eq. ), compound (1A-33) was obtained (0.11 g) by synthesizing in the same manner except for changing to ).

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

Synthesis Example (5): Synthesis of Compound (1A-88)

Compound (Int-1A-88) (138 mg, 0.10 mmol), 2,6-di-tert-butylpyridine (64.9 μL, 0.30 mmol), 1, 2,4-trichlorobenzene (1.0 mL) was added, and the mixture was heated and stirred at 60°C for 4 hours. After cooling the reaction solution to room temperature, a phosphate buffer solution (pH = 7) was added, extracted three times with dichloromethane, and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was washed with hexane to obtain compound (1A-88) as a yellow solid (12.4 mg, yield 8.9%).

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

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

¹¹ B-NMR (128 MHz, CDCl3): δ = 36.9

MALDI-TOF/MS:m/z=1394.73

Other polycyclic aromatic compounds of the present invention can be synthesized by a method according to the synthesis example described above by appropriately changing the compound of the raw material.

Next, examples of organic EL devices using the compounds of the present invention are shown in order to explain the present invention in more detail, but the present invention is not limited thereto.

<A. Evaluation of basic physical properties>

preparation of samples

When evaluating the absorption characteristics and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, there are cases in which the compound to be evaluated is dissolved in a solvent and evaluated in a solvent or in a thin film state. In the case of evaluation in a thin film state, depending on the mode of use of the compound to be evaluated in an organic EL device, when only the compound to be evaluated is thinned and evaluated, and the compound to be evaluated is dispersed in an appropriate matrix material to form a thin film. Sometimes it is evaluated.

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

In addition, the thin film sample in case the matrix material was a host compound was produced as follows. A quartz transparent support substrate (10 mm × 10 mm × 1.0 mm) is fixed to a substrate holder of a commercially available evaporation device (manufactured by Choshu Sangyo Co., Ltd.), a molybdenum evaporation boat containing a host compound, and a molybdenum evaporation boat containing a dopant compound. After mounting the boat for deposition, the vacuum chamber was reduced to 5×10 ^-4 Pa. Next, the two deposition boats were simultaneously heated, and both compounds were deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and the dopant compound. Here, the deposition rate was controlled according to the set mass ratio of the host compound and the dopant compound.

Evaluation of absorption and emission characteristics

The absorption spectrum of the sample was measured using a spectrophotometer (UV-2600, manufactured by Shimadzu Co., Ltd.). In addition, the fluorescence spectrum or phosphorescence spectrum of the sample was measured using a spectrophotometer (F-7000 manufactured by Hitachi High-Tech Co., Ltd.).

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

Further, the fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring device (C9920-02G manufactured by Hamamatsu Photonics Co., Ltd.).

Assessment of fluorescence lifetime (delayed fluorescence)

The fluorescence lifetime was measured at 300 K using a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, fast emission components and slow emission components of the fluorescence lifetime were observed at the maximum emission wavelength measured at an appropriate excitation wavelength. In the measurement of the fluorescence lifetime of a general organic EL material that emits fluorescence at room temperature, a slow light emission component involving a triplet component derived from phosphorescence is rarely observed due to deactivation of the triplet component by heat. When a slow emission component is observed in the compound to be evaluated, triplet energy with a long excitation lifetime is transferred to singlet energy by thermal activation and observed as delayed fluorescence.

Calculation of energy gap (Eg)

Eg = 1240/A was calculated from the long-wavelength end A (nm) of the absorption spectrum obtained by the method described above.

Calculation of E(S, Sh), E(T, Sh) and ΔE(ST)

The singlet excitation energy level E(S, Sh) is E(S, Sh) = 1240/B from the wavelength B _Sh (nm) at the intersection of the tangent line passing through the inflection point on the peak short wavelength side of the fluorescence spectrum and the base line Calculated as _Sh . Further, the triplet excitation energy level E(T, Sh) is E(T, _Sh ) = Calculated as 1240/C _Sh .

ΔE(ST) is defined as ΔE(ST)=E(S, Sh)-E(T, Sh), which is the energy difference between E(S, Sh) and E(T, Sh). Further, ΔE(ST) is, for example, "Purely organic electroluminescent material realizing 100% conversion from electricity to light", H.Kaji, H.Suzuki, T.Fukushima, K.Shizu, K.Katsuaki, S.Kubo , T.Komino, H.Oiwa, F.Suzuki, A.Wakamiya, Y.Murata, C.Adachi, Nat.Commun.2015, 6, 8476.

<Example A1>

Evaluation of basic physical properties of compound (1A-1)

[Absorption characteristics]

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

[Light emission characteristics]

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

In addition, a thin film forming substrate (quartz material) in which compound (1A-1) was dispersed in PMMA at a concentration of 1% by mass was prepared, excited at an excitation wavelength of 340 nm, and fluorescence quantum yield PLQY was measured. As a result, it was very high as 85%. it was worth

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

When ΔE(ST) was calculated, it became 0.01 eV.

As a result of measuring the lifetime of the delayed fluorescence component using a thin film forming substrate (quartz material) in which compound (1A-1) was dispersed in PMMA at a concentration of 1% by mass and using a fluorescence lifetime measuring device, it was 3.0 μsec (Fig. 2). In fluorescence lifetime measurement, fluorescence with an emission lifetime of 100 ns or less is determined as immediate fluorescence, and fluorescence with an emission lifetime of 0.1 μsec or more is determined as delayed fluorescence. of data was used.

<Examples A2 to A4 and A5>

In the evaluation of Example A1, the same conditions were used except that compound (1A-1) was changed to compound (1A-2), compound (1A-19), compound (1A-33) or compound (1A-88). evaluated. The results are summarized in Table A1.

<Comparative Examples RA1 and RA2>

In the evaluation of Example A1, evaluation was performed under the same conditions except that the compound (1A-1) was changed to R-BD1 or R-BD2. The results are summarized in Table A1.

[Table A1]

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

<B. Evaluation of vapor deposition type organic EL device>

<Example B1>

On a glass substrate (26 mm x 28 mm x 0.7 mm) formed with an anode made of ITO (indium tin oxide) with a thickness of 50 nm, each thin film was laminated by vacuum evaporation at a vacuum degree of 5 x 10 ^-4 Pa.

First, on ITO, NPD was deposited to a film thickness of 40 nm, and thereon, TcTa was deposited to a film thickness of 15 nm to form a two-layered hole layer. Subsequently, mCP was deposited to a film thickness of 15 nm to form an electron blocking layer. Next, compound DOBNA1 as a host and compound (1A-1) as a dopant were co-evaporated from another evaporation source to form a light emitting layer having a film thickness of 20 nm. At this time, the mass ratio of the host and the emitting dopant was 99:1. Next, 2CzBN was deposited to a film thickness of 10 nm, followed by BPy-TP2 to a film thickness of 20 nm to form a two-layer electron transport layer. Subsequently, LiF was deposited to a film thickness of 1 nm, and aluminum was deposited thereon to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device (Table B1).

<Examples B2 to B4, and B8>

In the device fabrication step of Example B1, the same is true except that compound (1A-1) is changed to compound (1A-2), compound (1A-19), compound (1A-33) or compound (1A-88). Devices were fabricated under the conditions of (Table B1).

<Comparative Examples RB1 and RB2>

In the device fabrication step of Example B1, devices were fabricated under the same conditions except for changing the compound (1A-1) to R-BD1 or R-BD2 (Table B1).

[Table B1]

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

Next, for each device manufactured, voltage (V), current density (mA/cm ² ), external quantum efficiency (EQE,%), and emission wavelength (nm), which are characteristics at the time of 1000 cd/m ² emission, were measured. Then, the time to maintain the luminance of 50% or more of the initial luminance when driven with constant current at a current density of 10 mA/cm ² was measured.

[Table B2]

<Example B5>

On a glass substrate (26 mm x 28 mm x 0.7 mm) formed with an anode made of ITO (indium tin oxide) with a thickness of 50 nm, each thin film was laminated by vacuum evaporation at a vacuum degree of 5 x 10 ^-4 Pa.

First, on ITO, NPD was deposited to a film thickness of 40 nm, and thereon, TcTa was deposited to a film thickness of 15 nm to form a two-layered hole layer. Subsequently, mCP was deposited to a film thickness of 15 nm to form an electron blocking layer. Next, mCBP as a host, 4CzIPN as an assisting dopant (AD), and compound (1A-1) as a dopant were co-evaporated from different evaporation sources to form a light emitting layer having a film thickness of 20 nm. At this time, the mass ratio of the host, the assisting dopant, and the dopant was 82:17:1. Next, 2CzBN was deposited to a film thickness of 10 nm, followed by BPy-TP2 to a film thickness of 20 nm to form a two-layer electron transport layer. Subsequently, LiF was deposited to a film thickness of 1 nm, and aluminum was deposited thereon to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device (Table B3).

<Examples B6 and B7>

In the device fabrication process of Example B5, devices were fabricated under the same conditions except that the constituent materials of the light emitting layer were changed to the materials listed in Table B3 (Table B3).

<Comparative Example RB3>

In the device fabrication process of Example B5, devices were fabricated under the same conditions except that the constituent materials of the light emitting layer were changed to the materials listed in Table B3 (Table B3).

[Table B3]

※ The host material of Example B7 is a mixture of Tris-PCz:3Cz-TRZ = 1:1 (mass ratio).

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

Next, for each device manufactured, voltage (V), current density (mA/cm ² ), external quantum efficiency (EQE,%), and emission wavelength (nm), which are characteristics at the time of 1000 cd/m ² emission, were measured. Then, the time to maintain the luminance of 50% or more of the initial luminance when driven with constant current at a current density of 10 mA/cm ² was measured.

[Table B4]

<C. Evaluation of coating type organic EL device>

Next, an organic EL element obtained by application and formation of an organic layer will be described.

<Polymer Host Compound: Synthesis of SPH-101>

According to the method described in International Publication No. 2015/008851, SPH-101 was synthesized. A copolymer in which M2 or M3 is bonded next to M1 is obtained, and it is estimated that each unit is 50:26:24 (molar ratio) from the input ratio.

<Polymer Hole Transport Compound: Synthesis of XLP-101>

According to the method described in Japanese Unexamined Patent Publication No. 2018-61028, XLP-101 was synthesized. A copolymer in which M5 or M6 is bonded next to M4 is obtained, and from the input ratio, it is estimated that each unit is 40:10:50 (molar ratio).

<Examples C1 to C9>

A coating solution for the material forming each layer is prepared to fabricate a coating type organic EL device.

<Production of Organic EL Devices of Examples C1 to C3>

Table C1 shows the material composition of each layer in the organic EL device.

[Table C1]

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

<Preparation of Composition for Forming Light-Emitting Layer (1)>

The composition for forming a light emitting layer (1) is prepared by stirring the following components until they become a uniform solution. The prepared composition for forming a light emitting layer is spin-coated on a glass substrate and heat-dried under reduced pressure to obtain a coated film free from film defects and excellent in smoothness.

SPH-101 1.96% by weight

Compound (X) 0.04% by weight

Xylene 69.00% by weight

Decalin 29.00% by weight

Further, compound (X) is a polycyclic aromatic compound represented by the general formula (1A) or (1B), or a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (ie, the monomer has a reactive substituent). , A crosslinked polymer obtained by further crosslinking the polymer compound, a pendant polymer compound obtained by substituting the above monomer in a main chain polymer, or a pendant polymer compound obtained by further crosslinking the pendant polymer compound. A polymer compound or a pendant-type polymer compound for obtaining a cross-linked polymer or a pendant-type polymer has a cross-linkable substituent.

<PEDOT:PSS solution>

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

<Preparation of OTPD solution>

OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, manufactured by San-Apro) were dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight. .

<Preparation of XLP-101 solution>

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

<Preparation of PCz solution>

PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7% by weight PCz solution.

<Example C1>

A PEDOT:PSS solution is spin-coated on a glass substrate on which ITO is deposited to a thickness of 150 nm, and fired on a hot plate at 200° C. for 1 hour to form a PEDOT:PSS film with a thickness of 40 nm (hole injection layer). Then, the OTPD solution was spin-coated, dried on a hot plate at 80° C. for 10 minutes, exposed with an exposure machine at an exposure intensity of 100 mJ/cm ² , and baked on a hot plate at 100° C. for 1 hour to obtain a solution-insoluble film An OTPD film having a thickness of 30 nm is formed (hole transport layer). Next, the composition for forming a light-emitting layer (1) is spin-coated and baked on a hot plate at 120° C. for 1 hour to form a light-emitting layer having a thickness of 20 nm.

The produced multilayer film is fixed to a substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum evaporation boat containing ET1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum Equip After depressurizing the vacuum chamber to 5×10 ^-4 Pa, ET1 is heated and deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transporting layer is 1 nm/sec. After that, LiF is heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example C2>

An organic EL element was obtained in the same manner as in Example C1. Further, the hole transport layer is formed by spin-coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film having a thickness of 30 nm.

<Example C3>

An organic EL element was obtained in the same manner as in Example C1. Further, the hole transport layer is formed by spin-coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film having a thickness of 30 nm.

<Production of Organic EL Devices of Examples C4 to C6>

Table C2 shows the material composition of each layer in the organic EL device.

[Table C2]

<Preparation of Compositions (2) to (4) for Forming Light-Emitting Layer>

A composition for forming a light emitting layer (2) is prepared by stirring the following components until they become a uniform solution.

mCBP 1.98% by weight

Compound (X) 0.02% by weight

Toluene 98.00% by weight

The composition for forming a light emitting layer (3) is prepared by stirring the following components until they become a uniform solution.

SPH-101 1.98wt%

Compound (X) 0.02% by weight

Xylene 98.00% by weight

The composition for forming a light emitting layer (4) is prepared by stirring the following components until they become a uniform solution.

DOBNA 1.98% by weight

Compound (X) 0.02% by weight

Toluene 98.00% by weight

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

<Example C4>

After spin-coating a solution of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) on a glass substrate on which ITO was formed to a thickness of 45 nm, heating at 50 ° C. for 3 minutes in an air atmosphere, and further heating at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Next, the XLP-101 solution is spin-coated and heated on a hot plate at 200 DEG C for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the composition 2 for forming a light emitting layer is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm light emitting layer.

The produced multilayer film is fixed to a substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum Equip After depressurizing the vacuum chamber to 5×10 ^-4 Pa, TSPO1 is heated and evaporated to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transporting layer is 1 nm/sec. After that, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness is 1 nm. Next, aluminum is heated and deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples C5 and C6>

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

<Production of Organic EL Devices of Examples C7 to C9>

Table C3 shows the material composition of each layer in the organic EL device.

[Table C3]

<Preparation of Compositions (5) to (7) for Forming Light-Emitting Layer>

The composition for forming a light emitting layer (5) is prepared by stirring the following components until they become a uniform solution.

mCBP 1.80% by weight

2PXZ-TAZ 0.18% by weight

Compound (X) 0.02% by weight

Toluene 98.00% by weight

A composition for forming a light emitting layer (6) is prepared by stirring the following components until they become a uniform solution.

SPH-101 1.80% by weight

2PXZ-TAZ 0.18% by weight

Compound (X) 0.02% by weight

Xylene 98.00% by weight

A composition for forming a light emitting layer (7) is prepared by stirring the following components until they become a uniform solution.

DOBNA 1.80% by weight

2PXZ-TAZ 0.18% by weight

Compound (X) 0.02% by weight

Toluene 98.00% by weight

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

<Example C7>

After spin-coating a solution of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) on a glass substrate on which ITO was formed to a thickness of 45 nm, heating at 50 ° C. for 3 minutes in an air atmosphere, and further heating at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Next, the XLP-101 solution is spin-coated and heated on a hot plate at 200 DEG C for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, a 20 nm light emitting layer is formed by spin-coating the composition 5 for forming a light emitting layer and heating it at 130° C. for 10 minutes in a nitrogen gas atmosphere.

The produced multilayer film is fixed to a substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum Equip After depressurizing the vacuum chamber to 5×10 ^-4 Pa, TSPO1 is heated and evaporated to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transporting layer is 1 nm/sec. After that, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness is 1 nm. Next, aluminum is heated and deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples C8 and C9>

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

As described above, some of the compounds according to the present invention were evaluated as materials for organic EL devices, and it was shown that they were excellent materials. Since it is a compound having, those skilled in the art can understand that it is similarly an excellent material for organic EL devices.

According to a preferred aspect of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as, for example, a material for organic devices such as a material for organic EL devices. Organic devices such as EL elements can be provided.

100 organic electroluminescent device
101 substrate
102 anode
103 hole injection layer
104 hole transport layer
105 light emitting layer
106 electron transport layer
107 electron injection layer
108 Cathode

Claims (31)

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

In the above formula (1A) or formula (1B),
Ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,
R ^c is each independently hydrogen or a substituent;
"-C(-R ^c )=" in the c ring may be substituted with "-N=";
Y ¹ and Y ² are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C( -R)-, >Si(-R)-, or >Ge(-R)-, wherein R of ">C(-R)-", R of ">Si(-R)-", and " R of >Ge(-R)-” is each independently an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl,
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently hydrogen, optionally substituted aryl, and optionally substituted heteroaryl. , alkyl which may be substituted, or cycloalkyl which may be substituted,
In addition, the two Rs of “>C(-R) ₂ ” and the two Rs of “>Si(-R) ₂ ” as X ¹ to X ⁴ are each independently bonded by a single bond or a linking group you can do it,
In addition, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ¹ or X ³ are each independently and at least one of the B rings, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ² or X ⁴ , Each independently may be bonded to at least one of the A ring and the c ring by a single bond or a linking group;
However, at least one of X ¹ to X ⁴ is bonded to the A ring, B ring, or c ring by "-CR=CR-" as a linking group, and R of the "-CR=CR-" , are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Two R's combine to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
In the compound represented by the formula (1A) or formula (1B), at least one of ring A, ring B, ring c, the aryl, and the heteroaryl may be condensed with at least one cycloalkane, At least one hydrogen in the cycloalkane may be substituted, and at least one "-CH ₂ -" in the cycloalkane may be substituted with "-O-";
At least one hydrogen in the compound represented by the formula (1A) or formula (1B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 1,
In the above formula (1A) or formula (1B),
Ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, Optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, substituted optionally substituted with cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;
R ^c is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, substituted optionally substituted diarylboryl (two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;
"-C(-R ^c )=" in the c ring may be substituted with "-N=";
Y ¹ and Y ² are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C( -R)-, >Si(-R)-, or >Ge(-R)-, wherein R of ">C(-R)-", R of ">Si(-R)-", and " R of >Ge(-R)-” is each independently aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl,
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl; At least one hydrogen in R may be substituted with alkyl or cycloalkyl,
In addition, the two Rs of “>C(-R) ₂ ” and the two Rs of “>Si(-R) ₂ ” as X ¹ to X ⁴ are each independently a single bond, -CH=CH -, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or - may be bonded by Se-, R of "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si( -R) R in _2- ” is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is substituted with alkyl or cycloalkyl may be, or two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
In addition, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ¹ or X ³ are each independently and at least one of the B rings, R of “>NR”, R of “>C(-R) ₂ ”, and R of “>Si(-R) ₂ ” as X ² or X ⁴ , Each independently, with at least one ring of the A ring and the c ring, a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - They may be bonded by S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and R in "-CR=CR-" or "-N(-R) R of -”, R of “-C(-R) ₂ -”, and R of “-Si(-R) ₂ -” are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, or alky Nyl or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs bond to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring you can do it,
However, at least one of the above X ¹ to X ⁴ is bonded to the above-mentioned ring A, ring B, or c ring by the above-mentioned “-CR=CR-” as a linking group, and also the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
In the compound represented by the formula (1A) or formula (1B), at least one of ring A, ring B, ring c, the aryl, and the heteroaryl may be condensed with at least one cycloalkane, At least one hydrogen in the cycloalkane may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and at least one "-CH ₂ -" in the cycloalkane is "-O-" may be substituted,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (1A) or formula (1B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 1,
A polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B).

In the above formula (2A) or formula (2B),
R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single bonds or through a linking group may be bonded), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, corresponding R ^a , R ^b , And at least one hydrogen in R ^c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent groups of R ^a and R ^b bond together, together with ring a and ring b , You may form an aryl ring or heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl may be bonded through a single bond or a linking group), substituted with alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl may be, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl,
"-C(-R ^c )=" in the c ring may be substituted with "-N=";
Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", "-C(- R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C(-R) ₂ -" R of -” and R of “-Si(-R) ₂ -” are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R is alkyl or cycloalkyl may be substituted, and the two Rs of "-C(-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" are each independently a single bond, -CH=CH- , -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se may be bonded by -, R of the above "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si(- R) R of _2- ” is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is substituted with alkyl or cycloalkyl, may be present, and two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
Y ¹ and Y ² are each independently >B-, >P-, >P(=O)-, or >P(=S)-;
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, >S, or >C(-R) ₂ , and R of “>NR” and “>C(- R) R of ₂ ” is each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl,
In addition, the two Rs of “>C(-R) ₂ ” as X ¹ to X ⁴ are single bonds, -CH=CH-, -CR=CR-, -C≡C-, -N(-R )-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R in the above "-CR=CR-" , R in “-N(-R)-”, R in “-C(-R) ₂ -”, and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl, or hetero aryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs are bonded to form a cycloalkylene ring, aryl A rene ring or a heteroarylene ring may be formed,
In addition, R of ">NR" and R of ">C(-R) ₂ " as X ¹ or X ³ are each independently a combination of at least one of the a ring and the b ring, and the X ² or R of ">NR" and R of ">C(-R) ₂ " as X ⁴ are each independently a member of at least one of the a ring and the c ring, and a single bond, -CH=CH-, - CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded together by, R of "-CR=CR-", R of "-N(-R)-", R of "-C(-R) ₂ -", and R of "-Si(-R) _2- ” R is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl , Two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
However, at least one of the above X ¹ to X ⁴ is bonded to the a ring, b ring, or c ring by the above “-CR=CR-” as a linking group, and the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring,
In the compound represented by the formula (2A) or formula (2B), at least one of ring a, ring b, ring c, the formed ring, the aryl, and the heteroaryl is condensed with at least one cycloalkane. , and at least one hydrogen in the cycloalkane may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and at least one "-CH ₂ -" in the cycloalkane is "- O-" may be substituted,
At least one hydrogen in the compound represented by the formula (2A) or formula (2B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 3,
In the above formula (2A) or formula (2B),
R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 24 carbon atoms, or a cycloalkyl of 3 to 24 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and R ^c may be substituted with aryl of 6 to 12 carbon atoms, heteroaryl of 2 to 15 carbon atoms, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, In addition, adjacent groups of R ^a and R ^b may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring and the b ring, and in the ring formed At least one hydrogen is aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, diarylamino (provided that aryl is an aryl of 6 to 12 carbon atoms), diarylboryl (provided that aryl is an aryl of 6 to 12 carbon atoms, and , The two aryls may be bonded through a single bond or a linking group), may be substituted with C1-24 alkyl or C3-24 cycloalkyl, and at least one hydrogen in these substituents is may be substituted with aryl of 6 to 12, heteroaryl of 2 to 15 carbon atoms, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms,
"-C(-R ^c )=" in the c ring may be substituted with "-N=";
Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", "-C(- R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R of the above "-N(-R)-", "-C(-R) ₂ -" R in -” and R in “-Si(-R) ₂ -” are hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or carbon atoms 3 to 14 cycloalkyl, and at least one hydrogen in R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two R of "-C(-R) ₂ -" Each other and the two Rs of "-Si(-R) ₂ -" are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)- , -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R in the above "-CR=CR-", " R of -N(-R)-", R of "-C(-R) ₂ -", and R of "-Si(-R) ₂ -" are independently hydrogen or 6 to 10 carbon atoms. aryl, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, alkenyl of 1 to 5 carbon atoms, alkynyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, at least one of The hydrogen of may be substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, and two adjacent R's bond to form a cycloalkylene ring of 3 to 14 carbon atoms, an arylene ring of 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms may be formed;
Y ¹ and Y ² are each independently >B-, >P-, >P(=O)-, or >P(=S)-;
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, or >S, and R in “>NR” is hydrogen, aryl having 6 to 12 carbon atoms, or 2 to 12 carbon atoms Heteroaryl of 15, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in R is substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, may be,
In addition, R of ">NR" as X ¹ or X ³ is at least one ring of the a ring and b ring, and R of ">NR" as X ² or X ⁴ is the a ring and At least one of the c rings, a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R ) ₂ -, -Si(-R) ₂ -, or may be bonded by -Se-, wherein R in "-CR=CR-", R in "-N(-R)-", or "-C R in (-R) ₂ -” and R in “-Si(-R) ₂ -” are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or 1 to 6 carbon atoms. is alkyl, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in R is an alkyl having 1 to 6 carbon atoms or 3 to 14 carbon atoms may be substituted with cycloalkyl of , and two adjacent Rs may be bonded to form a cycloalkylene ring of 3 to 14 carbon atoms, an arylene ring of 6 to 12 carbon atoms, or a heteroarylene ring of 2 to 15 carbon atoms. ,
However, at least one of the above X ¹ to X ⁴ is bonded to the a ring, b ring, or c ring by the above “-CR=CR-” as a linking group, and the “-CR=CR-” Two adjacent Rs in are bonded to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms,
In the compound represented by the formula (2A) or formula (2B), at least one of the a ring, b ring, c ring, the formed ring, the aryl, and the heteroaryl is at least one of 3 to 24 carbon atoms may be condensed with a cycloalkane, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkane having 3 to 16 carbon atoms. may be substituted with alkyl,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or formula (2B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 3,
In the above formula (2A) or formula (2B),
R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 10 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 12 carbon atoms, or a cycloalkyl of 3 to 16 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and ^Rc may be substituted with aryl of 6 to 10 carbon atoms, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, In addition, adjacent groups of R ^a and R ^b may be bonded together to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring and the b ring, and in the ring formed At least one hydrogen is aryl of 6 to 16 carbon atoms, heteroaryl of 2 to 20 carbon atoms, diarylamino (provided that aryl is an aryl of 6 to 10 carbon atoms), diarylboryl (provided that aryl is an aryl of 6 to 10 carbon atoms, and , The two aryls may be bonded through a single bond or a linking group), may be substituted with C1-C12 alkyl or C3-C16 cycloalkyl, and at least one hydrogen in these substituents is may be substituted with aryl of 6 to 10, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms,
"-C(-R ^c )=" in the c ring may be substituted with "-N=";
Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", and any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) is "-N(-R)-", "-O-", "-S-", or "-C( may be substituted with -R) ₂ -”, and R in “-N(-R)-” and R in “-C(-R) ₂ -” are hydrogen, aryl having 6 to 12 carbon atoms, or 2 carbon atoms -15 heteroaryl, C1-6 alkyl, or C3-14 cycloalkyl, and at least one hydrogen in R is substituted with C1-6 alkyl or C3-14 cycloalkyl may be,
Y ¹ and Y ² are each independently >B-, >P-, >P(=O)-, or >P(=S)-;
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR, >O, or >S, and R in “>NR” is hydrogen, aryl having 6 to 12 carbon atoms, or 2 to 12 carbon atoms Heteroaryl of 15, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in R is substituted with alkyl of 1 to 6 carbon atoms or cycloalkyl of 3 to 14 carbon atoms, may be,
In addition, R of ">NR" as X ¹ or X ³ is with the b ring, and R of ">NR" as X ² or X ⁴ is with the a ring, a single bond, -CH=CH-, - CR=CR-, -N(-R)-, -O-, -S-, or -C(-R) ₂ - may be bonded, and the R of "-CR=CR-", "- R in "N(-R)-" and R in "-C(-R) ₂ -" are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or 1 to 5 carbon atoms. is alkyl, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in R is an alkyl having 1 to 5 carbon atoms or 5 to 10 carbon atoms may be substituted with cycloalkyl of , and two adjacent Rs may be bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,
However, at least one of the above X ¹ and X ³ is bonded to the b ring by the above "-CR=CR-" as a linking group, and furthermore, two adjacent in the "-CR=CR-" R is bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,
In the compound represented by the formula (2A) or formula (2B), at least one of the a ring, b ring, c ring, the formed ring, the aryl, and the heteroaryl is at least one of 3 to 16 carbon atoms may be condensed with a cycloalkane, and at least one hydrogen in the cycloalkane is an aryl of 6 to 10 carbon atoms, a heteroaryl of 2 to 10 carbon atoms, an alkyl of 1 to 5 carbon atoms, or a cycloalkane of 5 to 10 carbon atoms. may be substituted with alkyl,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or formula (2B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 3,
In the above formula (2A) or formula (2B),
R ^a , R ^b , and R ^c are, each independently, hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), diarylboryl (However, aryl is an aryl of 6 to 10 carbon atoms, and two aryls may be bonded through a single bond or a linking group), an alkyl of 1 to 12 carbon atoms, or a cycloalkyl of 3 to 16 carbon atoms, corresponding R ^a , R At least one hydrogen in ^b and ^Rc may be substituted with C1-C5 alkyl or C5-C10 cycloalkyl,
"-C(-R ^c )=" in the c ring may be substituted with "-N=",
Any "-C(-R)=" (where R is R ^a or R ^b ) in the a ring and the b ring may be substituted with "-N=", or any "-C(- R)=C(-R)-" (where R is R ^a or R ^b ) may be substituted with "-N(-R)-", "-O-", or "-S-" , R in "-N(-R)-" is an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms,
Y ¹ and Y ² are >B-;
X ¹ , X ² , X ³ , and X ⁴ are each independently >NR or >O, and R in “>NR” is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, or Alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms, and at least one hydrogen in R may be substituted with alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms,
In addition, R of ">NR" as X ¹ or X ³ is with the b ring, and R of ">NR" as X ² or X ⁴ is with the a ring by a single bond or -CR=CR- may be bonded together, and R in "-CR=CR-" is each independently hydrogen, aryl of 6 to 10 carbon atoms, heteroaryl of 2 to 10 carbon atoms, alkyl of 1 to 5 carbon atoms, alkyl of 1 to 5 carbon atoms alkenyl, alkynyl of 1 to 5 carbon atoms, or cycloalkyl of 5 to 10 carbon atoms, and at least one hydrogen in R may be substituted with alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 10 carbon atoms , Two adjacent Rs may be bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,
However, at least one of the above X ¹ and X ³ is bonded to the b ring by the above "-CR=CR-" as a linking group, and furthermore, two adjacent in the "-CR=CR-" R is bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or formula (2B) may be substituted with heavy hydrogen, cyano or halogen. According to claim 1,
A polycyclic aromatic compound represented by any one of the following structural formulas.

The benzene rings in the above structural formula are independently selected from aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), and diarylboryl (wherein aryl is 6 to 10 carbon atoms). 10 aryl, two aryls may be bonded by a single bond or a linking group), may be substituted with C1-12 alkyl or C3-16 cycloalkyl, and at least one of the substituents Hydrogen may be substituted with C1-5 alkyl or C5-10 cycloalkyl,
At least one hydrogen in the compound represented by the above structural formula may be substituted with heavy hydrogen, cyano or halogen. According to claim 1,
A polycyclic aromatic compound represented by any one of the following structural formulas.

A reactive compound in which a reactive substituent is substituted for the polycyclic aromatic compound according to any one of claims 1 to 8. A polymer compound obtained by polymerizing the reactive compound according to claim 9 as a monomer, or a polymer crosslinked product obtained by further crosslinking the polymer compound. A pendant-type polymer compound in which the reactive compound according to claim 9 is substituted for a main chain-type polymer, or a pendant-type polymer crosslinked product in which the pendant-type polymer compound is further crosslinked. A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 8. A material for organic devices containing the reactive compound according to claim 9. A material for organic devices containing the polymer compound or polymer crosslinked product according to claim 10. A material for organic devices containing the pendant type polymer compound or the pendant type polymer crosslinked product according to claim 11. According to any one of claims 12 to 15,
The material for an organic device, 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. According to claim 16,
The material for an organic device, wherein the material for an organic electroluminescent element is a material for a light emitting layer. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent. An ink composition comprising the reactive compound according to claim 9 and an organic solvent. An ink composition comprising a principal chain polymer, the reactive compound according to claim 9, and an organic solvent. An ink composition comprising the polymer compound or polymer crosslinked product according to claim 10 and an organic solvent. An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to claim 11 and an organic solvent. A pair of electrodes composed of an anode and a cathode, disposed between the pair of electrodes, and the polycyclic aromatic compound according to any one of claims 1 to 8, the reactive compound according to claim 9, and the reactive compound according to claim 10 An organic electroluminescent device having an organic layer containing the polymer compound or cross-linked polymer described above or the pendant polymer compound or cross-linked polymer according to claim 11. According to claim 23,
An organic electroluminescent device in which the organic layer is a light emitting layer. According to claim 24,
The organic electroluminescent device, wherein the light emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinked product, pendant type polymer compound or pendant type polymer crosslinked material as a dopant. According to claim 25,
The light emitting layer includes 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), and a structure represented by the following general formula (H4) An organic electroluminescent device further comprising at least one selected from the group consisting of a compound, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material.

In Formula (H1), L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms;
In Formula (H2), L ² and L ³ are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms;
In the above general formula (H3), MU is a divalent group each independently represented by removing any two hydrogen atoms from an aromatic compound, EC is a divalent group each independently represented by removing any one hydrogen atom from an aromatic compound It is a monovalent group, two hydrogens in MU are substituted with EC or MU, k is an integer from 2 to 50000,
In the formula (H4), G is each independently =C(-H)- or =N-, and H in the =C(-H)- is substituted with a substituent or another structure represented by formula (H4). may be,
In the above general formula (H5),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹¹ hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;
Adjacent groups among R ¹ to R ¹¹ may be bonded together to form an aryl ring or heteroaryl ring together with ring a, b or c, and at least one hydrogen in the formed ring is aryl, heteroaryl, may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be,
Arbitrary “-C(-R)=” (where R is R ¹ to R ¹¹ ) in ring a, ring b, and ring c may be substituted with “-N=”;
In the above general formula (H6),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹⁶ hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;
Adjacent groups among R ¹ to R ¹⁶ may be bonded together to form an aryl ring or heteroaryl ring together with the a ring, b ring, c ring, or d ring, and at least one hydrogen in the formed ring is aryl; It may be substituted with heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be further substituted with , and
At least one hydrogen in the compound or structure represented by the above formulas may be substituted with C1-C6 alkyl, C3-C14 cycloalkyl, cyano, halogen or deuterium. The method of any one of claims 23 to 26,
At least one of an electron transport layer and an electron injection layer is disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, or a BO-based Derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole An organic electroluminescent device containing at least one selected from the group consisting of derivatives, silole derivatives and azoline derivatives. The method of claim 27,
At least one layer of the electron transport layer and the electron injection layer is an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal halide, or a rare earth metal. An organic electroluminescent device further comprising at least one selected from the group consisting of oxides of, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. The method of any one of claims 23 to 28,
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 is a high molecular compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or further crosslinking the high molecular compound. An organic electric field comprising a crosslinked polymer, a pendant polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a crosslinked pendant polymer obtained by further crosslinking the pendant polymer compound. light emitting element. A display device or lighting device provided with the organic electroluminescent element according to any one of claims 23 to 29. A wavelength conversion filter comprising the material for a wavelength conversion filter according to claim 16.

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