KR20200132733A - Organic electroluminescent element - Google Patents

Abstract

The present invention relates to an organic electroluminescent device. According to the present invention, the organic electroluminescent device comprises: a pair of electrodes consisting of a positive electrode and a negative electrode; a light-emitting layer arranged between the pair of electrodes; and at least one of an electron transport layer and an electron injection layer arranged between the negative electrode and the light-emitting layer. According to the present invention, at least one of the quantum efficiency, the driving voltage, and the lifespan of the device can be improved.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT ELEMENT}

In the present invention, at least one of a material for an electron transport layer and a material for an electron injection layer (hereinafter, collectively referred to as ``material for an electron layer''), a polycyclic aromatic compound and its multimer (hereinafter, collectively referred to as a ``polycyclic aromatic compound'') It relates to an organic electroluminescent device manufactured by combining a) and a specific compound, and a display device and a lighting device using the same. In addition, in this specification, the "organic electroluminescent element" may be referred to as "organic EL element" or simply "element".

BACKGROUND ART Conventionally, a display device using an electroluminescent light emitting element has been studied in various ways in that power saving or thinning is possible, and an organic electroluminescent element made of an organic material is actively studied in that it is easy to reduce weight or increase in size. Has been. In particular, for the development of organic materials having luminescence properties such as blue, which is one of the three primary colors of light, and development of organic materials having the ability to transport charges such as holes and electrons (having the possibility of becoming a semiconductor or superconductor), polymer compounds , Regardless of the low molecular weight compound, it has been actively studied so far.

The organic EL device has a structure comprising a pair of electrodes consisting of an anode and a cathode, and one layer or a plurality of layers which are disposed between the pair of electrodes and contain an organic compound. The layer containing the organic compound includes a light emitting layer, a charge transport/injection layer for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As the material for the light emitting layer, for example, a benzofluorene-based compound has been developed (International Publication No. 2004/061047). In addition, as a hole transport material, for example, triphenylamine compounds have been developed (Japanese Patent Laid-Open No. 2001-172232). In addition, as a material for an electron layer, for example, anthracene-based compounds have been developed (Japanese Patent Laid-Open No. 2005-170911).

In addition, in recent years, as a material for use in an organic EL device, 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 was already in practical use, It is a material characterized in that the planarity is improved by connecting aromatic rings constituting phenylamine. In this document, for example, the charge transport properties of the NO-linked compound (compound 1 on page 63) are evaluated, but the method for producing materials other than the NO-linked compound is not described, and the element to be linked is If they are different, since the electronic state of the whole compound is different, the properties obtained from materials other than the NO-linked compound are not yet known. Examples of such compounds can be found elsewhere (International Publication No. 2011/107186). For example, a compound having a conjugated structure having a large triplet exciton energy (T1) is advantageous as a material for a blue light-emitting layer because it can emit phosphorescence of a shorter wavelength. Further, a compound having a conjugated structure having a large T1 is advantageous also as a material for an electron layer and a hole layer sandwiching the light emitting layer therebetween.

[Patent Document 1] International Publication No. 2004/061047 [Patent Document 2] Japanese Patent Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2012/118164 [Patent Document 5] International Publication No. 2011/107186 [Patent Document 6] International Publication No. 2015/102118

As described above, various materials have been developed as materials used in organic EL devices, and in International Publication No. 2015/102118, a polycyclic aromatic compound containing boron and an organic EL device using the same are reported. However, in order to further improve the device characteristics, a material for an electronic layer capable of improving any one or more of quantum efficiency, driving voltage, and device life, in particular, a composite material for an electronic layer capable of appropriately adjusting the characteristics by combining a plurality of compounds is required. Has become.

The present inventors, as a result of earnest study in order to solve the above problems, constitute an organic EL device by disposing at least one of an electron transport layer and an electron injection layer formed by combining a polycyclic aromatic compound and a specific compound between a pair of electrodes. By doing so, it was discovered that an excellent organic EL device was obtained, and the present invention was completed. That is, the present invention provides an organic EL device produced by using the following composite material for an electron layer.

In addition, in the present specification, a chemical structure or a substituent may be represented by carbon number, but the number of carbon atoms in a case where a substituent is substituted in a chemical structure or a substituent is further substituted on a substituent is the number of carbon atoms of each chemical structure or substituent. It means, and does not mean the total carbon number of a chemical structure and a substituent, or the total carbon number of a substituent and a substituent. For example, ``the substituent B of the carbon number Y substituted with the substituent A of the carbon number X'' means that the ``the substituent A of the carbon number X'' is substituted with the ``the substituent B of the carbon number Y'', and the carbon number Y is the substituent A and It is not the number of carbon atoms in the sum of B. In addition, for example, ``substituent B of carbon number Y substituted with substituent A'' means that ``substituent A'' is substituted with ``substituent B of carbon number Y'', and the number of carbons Y represents substituent A and It is not the total number of carbon atoms of the substituent B.

Clause 1.

An organic electroluminescent device having at least one of a pair of electrodes consisting of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, and an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, At least one of the electron transport layer and the electron injection layer is a polycyclic aromatic compound represented by the following general formula (1) as a first component or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1), and a second As a component, borane derivative, pyridine derivative, fluoranthene derivative, BO derivative, anthracene derivative, benzofluorene derivative, phosphine oxide derivative, pyrimidine derivative, carbazole derivative, triazine derivative, benzoimidazole derivative, phenanthroline An organic electroluminescent device containing at least one compound selected from the group consisting of derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives.

(In the above formula (1),

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

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is aryl, alkyl or cycloalkyl. ,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S, or >Se, and R of >NR is an optionally substituted aryl or optionally substituted heteroaryl , Optionally substituted alkyl or optionally substituted cycloalkyl, wherein R in >C(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or substituted Cycloalkyl which may be present, and at least one R of the >NR and the >C(-R) ₂ is bonded to at least one of the A ring, the B ring and the C ring by a linking group or a single bond, May be,

At least one of ring A, ring B, ring C, aryl, and heteroaryl in the compound or structure represented by formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane Hydrogen of the dog may be substituted, at least one of -CH ₂ -in the cycloalkane may be substituted with -O-, and,

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

Item 2.

In the above formula (1),

Ring A, Ring B, and Ring C are each independently an aryl ring or heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Of diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded through a single bond or a linking group), Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy or substituted silyl may be substituted, and these rings are Y ¹ , X ¹ and X ^It has a 5-membered ring or a 6-membered ring that shares a bond with the condensed bicyclic structure of the above formula consisting of 2,

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is aryl, alkyl or cycloalkyl. ,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of >NR is an aryl or alkyl which may be substituted with alkyl or cycloalkyl. Or heteroaryl, alkyl or cycloalkyl which may be substituted with cycloalkyl, and R of >C(-R) ₂ may be substituted with aryl, alkyl or cycloalkyl which may be substituted with hydrogen, alkyl or cycloalkyl. Is heteroaryl, alkyl, or cycloalkyl, and at least one of R of the >NR and >C(-R) ₂ is -O-, -S-, -C(-R) ₂ -or a single bond May be bonded to at least one of the ring A, ring B, and ring C, and R of -C(-R) ₂ -is hydrogen, alkyl or cycloalkyl,

At least one of ring A, ring B, ring C, aryl, and heteroaryl in the compound or structure represented by formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane Hydrogen may be substituted, at least one -CH ₂ -in the cycloalkane may be substituted with -0-,

In the case of a multimer, it is a dimer or trimer having two or three structures represented by general formula (1), and,

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

The organic electroluminescent device according to item 1.

Clause 3.

The polycyclic aromatic compound represented by the formula (1) is a polycyclic aromatic compound represented by the following general formula (2), and a multimer of a polycyclic aromatic compound having a plurality of structures represented by the formula (1) is represented by the following general formula (2). The organic electroluminescent device according to item 1, which is a multimer of a polycyclic aromatic compound having a plurality of.

(In the above formula (2),

Arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) may be substituted with "-N=" , Arbitrary ``-C(-R)=C(-R)-'' (where R is R <sup>1</sup> to R <sup>11</sup> in formula (2)), ``-N(-R)-'', ``-O -" or "-S-" may be substituted, and R of "-N(-R)-" is an aryl, alkyl or cycloalkyl,

R ¹ to R ¹¹ are each independently hydrogen, 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, and at least one hydrogen in these is aryl, hetero Aryl, alkyl or cycloalkyl may be substituted, and adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring, and the formed ring At least one hydrogen in is 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 may be substituted, and at least one hydrogen in them is aryl, May be substituted with heteroaryl, alkyl or cycloalkyl,

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, C1-C6 alkyl or C3-C14 cycloalkyl,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of >NR is an aryl having 6 to 12 carbon atoms, and having 2 to 15 carbon atoms. Heteroaryl, C1-C6 alkyl or C3-C14 cycloalkyl, and R of >C(-R) ₂ is hydrogen, C6-C12 aryl, C2-C15 heteroaryl, C1 -6 alkyl or C3-C14 cycloalkyl, and at least one R of >NR and >C(-R) ₂ is -O-, -S-, -C(-R) ₂ -Or by a single bond, it may be bonded to at least one of the ring a, ring b, and ring c, and R of -C(-R) ₂ -is an alkyl having 1 to 6 carbon atoms or 3 to 14 carbon atoms. Cycloalkyl,

At least one of the a ring, the b ring, the c ring, the formed ring, aryl, and heteroaryl in the compound or structure represented by formula (2) is at least one cycloalkane having 3 to 24 carbon atoms. Condensation may be sufficient, and at least one hydrogen in the cycloalkane may be substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a C1-C24 alkyl, or a C3-C24 cycloalkyl And at least one of -CH ₂ -in the cycloalkane may be substituted with -O-,

In the case of a multimer, it is a dimer or trimer having two or three structures represented by formula (2), and,

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

Item 4.

In the above formula (2),

Arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) may be substituted with "-N=" , Arbitrary ``-C(-R)=C(-R)-'' (where R is R <sup>1</sup> to R <sup>11</sup> in formula (2)), ``-N(-R)-'', ``-O -" or "-S-" may be substituted, and R of "-N(-R)-" is a C6-C12 aryl, a C1-C6 alkyl, or a C3-C14 cycloalkyl, ,

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 12 carbon atoms), diaryl boryl (however, aryl Is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (however, aryl is 6 carbon atoms -12 aryl) or trialkylsilyl (however, alkyl is an alkyl having 1 to 6 carbon atoms), and adjacent groups among R ¹ to R ¹¹ are bonded to each other to form a ring a, a ring b, or a ring c together with 9 to carbon atoms. A 16 aryl ring or a C6-C15 heteroaryl ring may be formed, and at least one hydrogen in the formed ring is a C6-C30 aryl, a C2-C30 heteroaryl, or a diarylamino (provided , Aryl is an aryl having 6 to 12 carbon atoms), diaryl boryl (however, aryl is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), alkyl having 1 to 24 carbon atoms, C3-C24 cycloalkyl, triarylsilyl (however, aryl is a C6-C12 aryl) or trialkylsilyl (however, alkyl is a C1-C6 alkyl) may be substituted,

Y ¹ is B, P, P=O, P=S or Si-R, and R of Si-R is a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl Is,

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , or >S, and R of >NR is aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or It is a C5-C10 cycloalkyl, wherein R of >C(-R) ₂ is hydrogen, a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl,

At least one of the a ring, the b ring, the c ring, the formed ring, aryl, and heteroaryl in the compound or structure represented by formula (2) is at least one cycloalkane having 3 to 20 carbon atoms. Condensation may be performed, and at least one hydrogen in the cycloalkane may be substituted with a C6-C16 aryl, a C2-C22 heteroaryl, a C1-C12 alkyl, or a C3-C16 cycloalkyl. Become,

In the case of a multimer, it is a dimer having two structures represented by formula (2), and,

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

The organic electroluminescent device according to item 3.

Item 5.

In the above formula (2),

Even if arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) is substituted with "-N=" And arbitrary "-C(-R)=C(-R)-" (where R is R ¹ to R ¹¹ in Formula (2)) is "-N(-R)-", "- O-" or "-S-" may be substituted, and R of "-N(-R)-" is a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl Is,

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 10 carbon atoms), diaryl boryl (however, aryl Is a C6-C10 aryl, the two aryl may be bonded through a single bond or a linking group), C1-C12 alkyl or C3-C16 cycloalkyl,

Y ¹ is B, P, P=O or P=S,

X ¹ and X ² are each independently >O or >NR, and R of >NR is an aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,

At least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R in the compound or structure represented by formula (2) is at least 1 having 3 to 16 carbon atoms. May be condensed with two cycloalkanes, and at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

In the case of a multimer, it is a dimer having two structures represented by formula (2), and,

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

The organic electroluminescent device according to item 3.

Clause 6.

In the above formula (2),

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 10 carbon atoms), diaryl boryl (however, aryl is an aryl having 6 to 10 carbon atoms, , Two aryl may be bonded through a single bond or a linking group), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,

Y ¹ is B,

X ¹ and X ² are each independently >O or >NR, and R of >NR is an aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,

At least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R in the compound or structure represented by formula (2) is a cycloalkane having 3 to 14 carbon atoms. May be condensed with, at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 5 carbon atoms,

In the case of a multimer, it is a dimer having two structures represented by formula (2), and,

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

The organic electroluminescent device according to item 3.

Item 7.

The organic electroluminescent device according to item 1, wherein the polycyclic aromatic compound as the first component is a compound represented by any one of the following formulas.

"Me" in the above structural formula represents a methyl group.

Item 8.

The organic electroluminescent device according to any one of items 1 to 7, wherein the borane derivative as the second component is a compound represented by the following general formula (ETM-1-1).

In formula (ETM-1-1),

R ¹¹ and R ¹² are each independently aryl, heteroaryl, alkyl, cycloalkyl, triarylsilyl, trialkylsilyl, or cyano, and n is each independently an integer of 0 to 3,

R ¹³ to R ¹⁶ are each independently aryl, alkyl, or cycloalkyl,

R ²¹ and R ²² are each independently aryl, heteroaryl, alkyl, cycloalkyl, triarylsilyl, trialkylsilyl, or cyano, and m is each independently an integer of 0-4,

X ¹ is a divalent group represented by any one of the following formulas (X-1) to (X-9), and * in each structural formula represents a bonding position,

In the formulas (X-1) to (X-9), each of R is independently alkyl, cycloalkyl, or aryl which may be substituted with alkyl,

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

Item 9.

In formula (ETM-1-1),

R ¹¹ and R ¹² are each independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (however, aryl is Aryl of ~ 10), trialkylsilyl (however, alkyl is an alkyl having 1 to 5 carbon atoms), or cyano, and n is each independently an integer of 0 to 2,

R ¹³ to R ¹⁶ are each independently aryl having 6 to 16 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,

R ²¹ and R ²² are each independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (however, aryl is Aryl of ~ 10), trialkylsilyl (however, alkyl is an alkyl having 1 to 5 carbon atoms), or cyano, m is each independently an integer of 0-2,

X ¹ is a divalent group represented by any one of formulas (X-1) to (X-9), and * in each structural formula represents a bonding position,

In the above formulas (X-1) to (X-9), R is each independently a number of carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or alkyl having 1 to 5 carbon atoms. 6-10 aryl,

At least one hydrogen in the compound represented by the formula (ETM-1-1) may be substituted with deuterium,

The organic electroluminescent device according to item 8.

Item 10.

The organic electroluminescent device according to item 8, wherein the borane derivative as the second component is a compound represented by any one of the following formulas.

"Me" in the above structural formula represents a methyl group.

Clause 11.

The organic electroluminescent device according to any one of items 1 to 7, wherein the pyridine derivative as the second component is a compound represented by the following general formula (ETM-2-1).

In the above formula (ETM-2-1),

R ¹¹ to R ¹⁸ are each independently hydrogen, aryl, alkyl, or cycloalkyl,

Py is each independently a group represented by any one of the following formulas (Py-1) to (Py to 15), and at least one hydrogen in this group may be substituted with alkyl or cycloalkyl, and * in each structural formula Represents the bonding position,

Py may be bonded to the anthracene ring in the formula (ETM-2-1) via a phenylene group or a naphthylene group,

At least one of two Py in the formula (ETM-2-1) is a group represented by any one of the formulas (Py-1) to (Py-15), the other may be aryl, and the aryl is alkyl or May be substituted with cycloalkyl,

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

Item 12.

In formula (ETM-2-1),

R ¹¹ to R ¹⁸ are each independently hydrogen, aryl having 6 to 16 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,

Py is each independently a group represented by any one of the following formulas (Py-21) to (Py-44), and at least one hydrogen in this group is an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. May be substituted with, and * in each structural formula represents a bonding position,

Py may be bonded to the anthracene ring in the formula (ETM-2-1) via a 1,4-phenylene group or a 1,4-naphthylene group,

At least one of two Py in the formula (ETM-2-1) is a group represented by any one of the formulas (Py-21) to (Py-44), and the other may be aryl having 6 to 16 carbon atoms, The said aryl may be substituted with C1-C12 alkyl or C3-C16 cycloalkyl,

At least one hydrogen in the compound represented by the formula (ETM-2-1) may be substituted with deuterium,

The organic electroluminescent device according to item 11.

Item 13.

The organic electroluminescent device according to item 11, wherein the pyridine derivative as the second component is a compound represented by any one of the following formulas.

Item 14.

The organic electroluminescent device according to any one of items 1 to 7, wherein the pyrimidine derivative as the second component is a compound represented by the following general formula (ETM-8-1).

In the above formula (ETM-8-1),

Ar is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these may be substituted with alkyl, cycloalkyl, or halogen,

At least one hydrogen in the compound represented by the formula (ETM-8-1) may be substituted with deuterium.

Item 15.

In formula (ETM-8-1),

Ar is each independently a C6-C16 aryl, a C2-C15 heteroaryl, a C1-C12 alkyl, or a C3-C16 cycloalkyl, and at least one hydrogen in these is C1 It may be substituted with ~12 alkyl, C3-C16 cycloalkyl, or halogen,

At least one hydrogen in the compound represented by the formula (ETM-8-1) may be substituted with deuterium,

The organic electroluminescent device according to item 14.

Clause 16.

The organic electroluminescent device according to item 14, wherein the pyrimidine derivative as the second component is a compound represented by any one of the following formulas.

Clause 17.

The organic electroluminescent device according to any one of items 1 to 7, wherein the azoline derivative as the second component is a compound represented by the following general formula (ETM-16-1) or (ETM-16-2).

In formula (ETM-16-1) and formula (ETM-16-2),

Φ is a divalent group represented by the following formula (Φ2-1), formula (Φ2-31), formula (Φ2-32), formula (Φ2-33), or formula (Φ2-34), in Φ At least one hydrogen may be substituted with C1-C6 alkyl, C6-C18 aryl, or C2-C18 heteroaryl, and * in each structural formula represents a bonding position,

m is 2,

Y is each independently -O-, -S-, or >N-Ar, Ar is a C6-C12 aryl or a C2-C12 heteroaryl, and at least one hydrogen in Ar is a C1 It may be substituted with an alkyl of ~4, aryl of 6 to 12 carbons, or heteroaryl of 2 to 12 carbons,

R ¹ to R ⁵ are each independently hydrogen or alkyl having 1 to 4 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same,

L is selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline and pteridine. It is a divalent group of the ring, and at least one hydrogen in L may be substituted with an alkyl having 1 to 4 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms,

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

Clause 18.

In formula (ETM-16-1) and formula (ETM-16-2),

Φ is a divalent group represented by the above formula (Φ2-31), formula (Φ2-32), formula (Φ2-33), or formula (Φ2-34), and at least one hydrogen in Φ has 6 carbon atoms May be substituted with aryl of ~18,

m is 2,

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 in Ar has 1 carbon number. It may be substituted with an alkyl of ~4 or aryl of 6 to 10 carbon atoms,

R ¹ to R ⁴ are each independently hydrogen or alkyl having 1 to 4 carbon atoms, provided that R ¹ and R ² are the same, R ³ and R ⁴ are the same, and all of R ¹ to R ⁴ are simultaneously hydrogen There is no case,

L is a divalent group of a ring 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, and 6 to carbon atoms. It may be substituted with 10 aryl or C2-C10 heteroaryl,

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

The organic electroluminescent device according to item 17.

Clause 19.

The organic electroluminescent device according to item 17, wherein the azoline derivative as the second component is a compound represented by any one of the following formulas.

Item 20.

At least one of the electron transport layer and electron injection layer is an alkali metal, alkaline earth metal, rare earth metal, oxide of alkali metal, halide of alkali metal, oxide of alkaline earth metal, halide of alkaline earth metal, oxide of rare earth metal The organic electric field according to any one of items 1 to 19, further containing at least one selected from the group consisting of a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. Light-emitting element.

Clause 21.

A display device or a lighting device including the organic electroluminescent element according to any one of items 1 to 20.

According to a preferred embodiment of the present invention, by producing an organic EL device using at least one of an electron transport layer and an electron injection layer formed by combining a polycyclic aromatic compound represented by formula (1) and a specific compound, quantum efficiency and driving voltage And an organic EL device excellent in any one or more of the device life.

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

1. Organic electroluminescent device

The present invention provides an organic electric field having at least one of a pair of electrodes consisting of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, and an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer. A light-emitting device, wherein at least one of the electron transport layer and the electron injection layer is a polycyclic aromatic compound represented by the general formula (1) as a first component or a polycyclic aromatic compound having a plurality of structures represented by the general formula (1) And, an organic electroluminescent device containing a specific compound as a second component.

2. Polycyclic aromatic compounds as the first component and their multimers

The first component constituting at least one of the electron transport layer and the electron injection layer is a polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1). , Preferably, it is a polycyclic aromatic compound represented by the following general formula (2), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2). The definition of each sign in the following structural formula is the same as the definition of each sign in General Formula (1) or (2).

Ring A, ring B, and ring C in the general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. This substituent is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (aryl and Amino group having heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded through a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted Substituted alkoxy, substituted or unsubstituted aryloxy or substituted silyl are preferred. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the aryl ring or heteroaryl ring preferably has a 5-membered ring or a 6-membered ring that shares a bond with the central condensed bicyclic structure of General Formula (1) consisting of Y ¹ , X ¹ and X ² .

Here, the "condensed bicyclic structure" means a structure in which two saturated hydrocarbon rings containing Y ¹ , X ¹ and X ² are condensed as shown in the center of General Formula (1). In addition, "a 6-membered ring which shares a condensed bicyclic structure and a bond" means, for example, a ring condensed into the condensed bicyclic structure (benzene ring (6-membered ring)), as represented by the general formula (2). Means. In addition, "the (ring A) aryl ring or heteroaryl ring has this 6-membered ring" means that ring A is formed only with this 6-membered ring, or other rings are further condensed with this 6-membered ring so as to contain this 6-membered ring, and A It means that a ring is formed. In other words, "the aryl ring (which is a ring A) or a heteroaryl ring having a 6-membered ring" herein means that the 6-membered ring constituting all or part of the ring A is condensed into the condensed bicyclic structure. The same description applies to "B ring (b ring)", "C ring (c ring)", and also "5-membered ring".

A ring (or B ring, C ring) in general formula (1) is a ring and its substituents R ¹ to R ^{3 in} general formula (2) (or b ring and its substituents R ⁸ to R ¹¹ , c It corresponds to a ring and its substituents R ⁴ to R ⁷ ). That is, the general formula (2) corresponds to a structure in which "the A to C ring having a six-membered ring" is selected as the A to C ring in the general formula (1). In that sense, each ring of General Formula (2) is represented by lowercase letters a to c.

In general formula (2), adjacent groups in the substituents R ¹ to R ¹¹ of the a ring, b ring and c ring may be bonded to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring, 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, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl may be substituted, and at least one hydrogen in these may be aryl, It may be substituted with heteroaryl, alkyl or cycloalkyl. Therefore, the polycyclic aromatic compound represented by the general formula (2) is represented by the following formulas (2-1) and (2-2), depending on the mutual bonding form of the substituents in the a ring, b ring and c ring. Likewise, the ring structure constituting the compound changes. The A'ring, B'ring, and C'ring in each formula correspond to the A ring, B ring, and C ring respectively in General formula (1). The definition of each sign in the following structural formula is the same as the definition of each sign in General Formula (2).

The A'ring, B'ring, and C'ring in the above formulas (2-1) and (2-2), when explained by general formula (2), adjacent groups in the substituents R ¹ to R ¹¹ are bonded to each other, , Represents an aryl ring or heteroaryl ring formed together with ring a, ring b, and ring c, respectively (it may also be referred to as a condensed ring formed by condensation of another ring structure with ring a, ring b, or ring c). In addition, although not shown in the formula, there are also compounds in which all of the a ring, b ring, and c ring are changed to the A'ring, B'ring, and C'ring. In addition, as can be seen from the above formulas (2-1) and (2-2), for example, R ⁸ of the b ring and R ⁷ of the c ring, R ¹¹ of the b ring and R ¹ of the a ring, R ^{4 of the} c ring, and R ³ and the like of the a ring do not correspond to "adjacent groups", and they are not bound. That is, "adjacent group" means a group adjacent to the same ring.

The compound represented by the above formula (2-1) or formula (2-2) is, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzene ring that is a ring a (or ring b or c). It is a compound having an A'ring (or B'ring or C'ring) formed by condensation of a benzothiophene ring, and the condensed ring A'(or condensed ring B'or condensed ring C') formed by being formed is a naphthalene ring, It is a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

Y ¹ in the general formula (1) is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is Aryl, alkyl or cycloalkyl. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the A ring, B ring, or C ring is P, Si or Ge. Y ¹ is preferably B, P, P=O, P=S, or Si-R, and B is particularly preferred. This explanation is also the same for Y ¹ in General Formula (2).

X ¹ and X ² in General Formula (1) are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of >NR may be substituted. Aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, wherein R of >C(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, Alkyl which may be substituted or cycloalkyl which may be substituted, and at least one R of the >NR and >C(-R) ₂ is a linking group or a single bond, wherein the ring A, ring B, and C It may be bonded to at least one of the rings, and as a linking group, -O-, -S-, or -C(-R) ₂ -is preferable. In addition, R in said "-C(-R) ₂ -" is hydrogen, alkyl, or cycloalkyl. It is preferable that each of X ¹ and X ² is independently >O or >NR, more preferably >O. In addition, when both X ¹ and X ² are >O, it is preferable that Y ¹ is B. This description is also the same for X ¹ and X ² in General Formula (2).

Here, in the general formula (1), "at least one R of the above >NR and the >C(-R) ₂ is at least one of the A ring, the B ring, and the C ring by a linking group or a single bond. The rule that it is bonded with the ring of dogs" is, in the general formula (2), "at least one R of the above >NR and >C(-R) ₂ is -O-, -S-, -C(-R) ₂ -or by a single bond, it is bonded to at least one of ring a, ring b, and ring c."

This regulation can be expressed by a compound having a ring structure in which X ¹ or X ² is introduced into the condensed ring B'and the condensed ring C', represented by the following formula (2-3-1). That is, for example, the B'ring (or C'formed by condensing other rings by introducing X ¹ (or X ² ) to the benzene ring that is the b ring (or c ring) in the general formula (2)) Ring). The formed condensed ring B'(or condensed ring C') is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

In addition, the above regulation is also a compound having a ring structure in which at least one of X ¹ and X ² is introduced into the condensed ring A′, represented by the following formula (2-3-2) or formula (2-3-3). I can express it. That is, for example, a compound having an A'ring formed by condensation of other rings by introducing X ¹ (or X ² , or X ¹ and X ² ) to the benzene ring, which is the a ring in the general formula (2). to be. The formed condensed ring A'is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

The definition of each sign in the following structural formula is the same as the definition of each sign in General Formula (2).

In formula (2), arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) is "-N It may be substituted with "=".

As shown above, for example, the position of "-C(-R ⁵ )=" in the c ring may be substituted with "-N=", and thus c represented as a benzene ring in formula (2) The ring may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. In addition, when there are adjacent groups on the c ring (R ⁶ and R ^{7 in the} above formula), they are bonded to form a heteroaryl ring (quinoline ring in the above formula) together with the c ring, and the formed ring is further substituted What may be (represented by n Rs) is as described above.

In addition, there are also the following modifications.

The same applies to the case where the other positions are substituted with "-N=" or the case where the a ring or b ring is changed.

In formula (2), arbitrary "-C(-R)=C(-R)-" in a ring, b ring, and c ring (wherein R is R ¹ to R ¹¹ in formula (2) Im) may be substituted with "-N(-R)-", "-O-" or "-S-", and R of "-N(-R)-" is aryl, alkyl, or It is cycloalkyl. In addition, details of the substituents enumerated here are collectively described later.

As shown above, for example, the position of "-C(-R ⁷ ) = C(-R ⁶ )-" in the c ring is "-N(-R)-" and "-O-" Alternatively, it may be substituted with "-S-", and in this way, the c ring represented as a benzene ring in formula (2) is an R-substituted pyrrole ring, a furan ring, a thiophene ring, and other nitrogen-containing, oxygen, sulfur heteroaryl It may change into a ring. In addition, when a group adjacent to the c ring is present (R ⁴ and R ^{5 in the} above formula), they are bonded to the c ring together with a heteroaryl ring (in the formula, R-substituted indole ring, benzofuran ring, or benzo Thiophene ring) may be formed and the formed ring may be further substituted (represented by n Rs) as described above.

In addition, there are also variations as follows.

The same applies to the case where the other positions are substituted with "-N(-R)-", "-O-" or "-S-", or the case where the a ring or the b ring is changed.

In addition, in the description of the above formulas (2-1), (2-2), (2-3-1), (2-3-2), and (2-3-3), a ring, Although the b ring and the c ring were described as a benzene ring, the same applies to the case where the a ring to the c ring is changed to a nitrogen-containing heteroaryl ring (6- or 5-membered ring) or an oxygen-containing/sulfur heteroaryl ring (5-membered ring).

Examples of the "aryl ring" which is the A ring, the B ring and the C ring in the general formula (1) include, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, and An aryl ring of is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable. In addition, this "aryl ring" corresponds to "an aryl ring formed with a ring a, a ring b, or a ring c by bonding of adjacent groups in R ¹ to R ¹¹ " as defined in General Formula (2), and Since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring condensed with the 5-membered ring becomes the lower limit carbon number.

As a specific "aryl ring", a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), condensation Tricyclic phosphorus, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, condensed 5 ring perylene ring, pentacene ring, etc. have.

Examples of the "heteroaryl ring" which is the A ring, the B ring and the C ring in the general formula (1) include, for example, a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable, and A 2-20 heteroaryl ring is more preferable, a C2-C15 heteroaryl ring is still more preferable, and a C2-C10 heteroaryl ring is especially preferable. In addition, examples of the "heteroaryl ring" include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituent atom. In addition, this "heteroaryl ring" corresponds to "a heteroaryl ring formed with a ring a, a ring b, or a ring c by bonding of adjacent groups in R ¹ to R ¹¹ " as defined in General Formula (2), Further, since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring condensed with the 5-membered ring is 6 carbon atoms at the lower limit.

As a specific "heteroaryl ring", for example, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring , Isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, ph Noxazine 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, benzophospol ring, dibenzophosphole ring, benzophospol oxide ring, dibenzophosphole oxide ring, furazane ring, thianthrene ring, indole A locarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, an oxazoline ring, etc. are mentioned.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" is a first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", or a substituted or unsubstituted "aryl" Diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls are bonded through a single bond or a linking group) May be)”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “cycloalkyl”, substituted or unsubstituted “alkoxy”, substituted or unsubstituted “aryloxy”, or substituted “silyl” Although it may be substituted with, "aryl" or "heteroaryl" as this first substituent, aryl of "diarylamino", heteroaryl of "diheteroarylamino", aryl and heteroaryl of "arylheteroarylamino", Examples of the aryl of "diaryl boryl" and the aryl of "aryloxy" include monovalent groups such as "aryl ring" or "heteroaryl ring" described above.

Moreover, as "alkyl" as a 1st substituent, either a linear chain or a branched chain may be sufficient, For example, a C1-C24 linear-chain alkyl or a C3-C24 branched alkyl is mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, and alkyl having 1 to 6 carbon atoms (3 carbon atoms -6 branched alkyl) is more preferable, C1-C5 alkyl (C3-C5 branched chain alkyl) is particularly preferable, and C1-C4 alkyl (C3-C4 branched alkyl) is more preferable. Most preferred.

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 -Eikosil, etc. are mentioned.

Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl And the like.

In addition, as "cycloalkyl" as a 1st substituent, a C3-C24 cycloalkyl, a C3-C20 cycloalkyl, a C3-C16 cycloalkyl, a C3-C14 cycloalkyl, a C3-C12 cyclo Alkyl, a C5-C10 cycloalkyl, a C5-C8 cycloalkyl, a C5-C6 cycloalkyl, a C5 cycloalkyl, etc. are mentioned.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents having 1 to 5 carbon atoms or 1 to 4 carbon atoms, Norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[1.1.1]pentyl Cyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

Moreover, as "alkoxy" as a 1st substituent, a C1-C24 linear or C3-C24 branched alkoxy is mentioned, for example. C1-C18 alkoxy (C3-C18 branched chain alkoxy) is preferable, C1-C12 alkoxy (C3-C12 branched chain alkoxy) is more preferable, and C1-C6 alkoxy ( Branched chain alkoxy having 3 to 6 carbon atoms) is more preferable, alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferable, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) Chain alkoxy) is most preferred.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neo Pentyloxy, t-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1- Methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6 -Dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy , 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-eicosyloxy, etc. I can.

In addition, as the "substituted silyl" as the first substituent, for example, a silyl substituted with at least one of aryl, alkyl and cycloalkyl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or Alkyldicycloalkylsilyl is mentioned.

As the "triarylsilyl", a group in which three hydrogens in the silyl group are each independently substituted with an aryl, and this aryl can be cited as the group described as "aryl" in the above-described first substituent.

A specific "triarylsilyl" is, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl.

As the "trialkylsilyl", a group in which three hydrogens in the silyl group are each independently substituted with alkyl, and the alkyl can be a group described as "alkyl" in the above-described first substituent. Preferred alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specifically, methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, t-amyl, and the like are mentioned.

Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyl Dimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldi Ethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldi Propylsilyl, t-amyldipropylsilyl, methyldii-propylsilyl, ethyldii-propylsilyl, butyldii-propylsilyl, sec-butyldii-propylsilyl, t-butyldii-propylsilyl, t -Amyldi i-propylsilyl, etc. are mentioned.

As ``tricycloalkylsilyl'', a group in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl refers to the group described as ``cycloalkyl'' in the above-described first substituent. I can. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo [2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaph Thalenyl, decahydroazulenyl, and the like.

As a specific tricycloalkylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, etc. are mentioned.

As a specific example of a dialkylcycloalkylsilyl substituted with two alkyl and one cycloalkyl, and an alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyl, a group selected from the specific alkyl and cycloalkyl described above is substituted. It can be cited the silyl.

In addition, as the "aryl" in "diaryl boryl" as the first substituent, the above description of aryl can be cited. In addition, these two aryls may be bonded via a single bond or a linking group (for example, >C(-R) ₂ , >O, >S, or >NR). Here, R of >C(-R) ₂ and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and the first substituent includes aryl , Heteroaryl, alkyl, or cycloalkyl (above, second substituent) may be further substituted, and specific examples of these groups include aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or Aryloxy's explanation can be cited.

Specifically, the light emission wavelength can be adjusted by steric hindrance, electron donating, and electron attracting properties of the structure of the first substituent, preferably the following structural formulas (S-1) to (S-94) and structural formulas (S- 101) to (S-130) is a group represented by any one, more preferably, formula (S-1), formula (S-2), formula (S-5), formula (S-9) to formula ( S-19), a group represented by any one of formulas (S-24) to (S-50), and formulas (S-51) to (S-94), more preferably formula (S-1) , Formula (S-2), Formula (S-5), Formula (S-9), Formula (S-10), Formula (S-15), Formula (S-16), Formula (S-24), Formula (S-30), Formula (S-46), Formula (S-48), Formula (S-50), Formula (S-51), Formula (S-56) to Formula (S-58), Formula (S-70), Formula (S-71), Formula (S-73), Formula (S-74), Formula (S-76), Formula (S-79), Formula (S-80), Formula ( S-83) and a group represented by any one of formula (S-84).

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

In general formula (2), arbitrary "-C(-R)=C(-R)-" (wherein R is R ¹ to R ¹¹ in formula (2)) can be substituted with "-N ( R of -R)-" is aryl, alkyl, or cycloalkyl, but examples of this aryl, alkyl or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably Cyclohexyl or adamantyl) is preferred.

The first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted Substituted “arylheteroarylamino”, substituted or unsubstituted “diarylboryl (two aryls may be bonded through a single bond or a linking group)”, substituted or unsubstituted “alkyl”, substituted or unsubstituted "Cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy", as described as "substituted or unsubstituted", at least one hydrogen in these is the second You may be substituted with a substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific groups thereof are monovalent groups of the above-described "aryl ring" or "heteroaryl ring", and also the first substituent. The description of "alkyl" or "cycloalkyl" as can be referred to. In addition, in the aryl or heteroaryl as the second substituent, at least one hydrogen in these groups is an aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described above), cyclohexyl, etc. Groups substituted with cycloalkyl (specific examples are the groups described above) are included in aryl or heteroaryl as the second substituent. As an example, when the second substituent is a carbazolyl group, the carbazolyl group in which at least one hydrogen at the 9 position is substituted with an aryl such as phenyl or an alkyl such as methyl or a cycloalkyl such as cyclohexyl is the second It is included in heteroaryl as a substituent.

Aryl of R ¹ to R ¹¹ of the general formula (2), heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, or As the aryl of aryloxy, a monovalent group of the "aryl ring" or "heteroaryl ring" described in the general formula (1) can be mentioned. In addition, as the alkyl, cycloalkyl or alkoxy in R ¹ to R ¹¹ , refer to the description of “alkyl”, “cycloalkyl” or “alkoxy” as the first substituent in the description of the above-described general formula (1). can do. In addition, as the triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl for R ¹ to R ¹¹ , the first in the description of the above general formula (1) The description of "substituted silyl" as a substituent can be referred to. In addition, aryl, heteroaryl, alkyl, or cycloalkyl as a substituent for these groups is also the same. In addition, when adjacent groups in R ¹ to R ¹¹ are bonded to each other to form an aryl ring or heteroaryl ring together with a ring, b ring or c ring, heteroaryl, diarylamino, di Heteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl and better The same applies to the substituents aryl, heteroaryl, alkyl or cycloalkyl.

R of Si-R and Ge-R in Y ¹ of the general formula (1) is aryl, alkyl or cycloalkyl, but examples of this aryl, alkyl or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably Cyclohexyl or adamantyl) is preferred. This explanation is also the same for Y ¹ in General Formula (2).

R in >NR and >C(-R) ₂ in X ¹ and X ² in the general formula (1) is aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the second substituent described above, and aryl, At least one hydrogen in heteroaryl, alkyl, or cycloalkyl may be substituted with, for example, alkyl or cycloalkyl. The groups mentioned above are mentioned as this aryl, heteroaryl, alkyl, and cycloalkyl. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g. carbazolyl, etc.), alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms ( For example, methyl, ethyl, etc.), and C3-C16 cycloalkyl (for example, bicyclooctyl, adamantyl, etc.) are preferable. This description is also the same for X ¹ and X ² in General Formula (2).

R of "-C(-R) ₂ -" which is a linking group in the general formula (1) is hydrogen, alkyl or cycloalkyl, but examples of this alkyl or cycloalkyl include the groups described above. In particular, C1-C5 or C1-C4 alkyl (for example, methyl, ethyl, etc.) or C5-C10 cycloalkyl (preferably cyclohexyl or adamantyl) is preferable. This explanation is also the same in "-C(-R) ₂ -" which is a linking group in General Formula (2).

Further, the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), and preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (2). As for the multimer, a 2-6-mer is preferable, a 2-trimer is more preferable, and a dimer is especially preferable. The multimer may be a form having a plurality of the unit structures in one compound, for example, a form in which the unit structure is multiple bonded with a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. In addition to (linked multimer), any ring (ring A, ring B or C, ring a, ring b, or ring c) contained in the unit structure is bonded to share in a plurality of unit structures (ring A covalent multimer) may be used, and any ring (ring A, ring B or C, ring a, ring b, or ring c) contained in the unit structure may be condensed and bonded to each other (ring condensation type multimer Sieve) may be used, but a ring covalent multimer and a ring condensed multimer are preferable, and a ring covalent multimer is more preferable.

As such a multimer, for example, the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5- 4) or a multimeric compound represented by formula (2-6) can be mentioned. The multimeric compound represented by the following formula (2-4), when explained by the general formula (2), has a large amount of unit structures represented by a plurality of general formulas (2) in one compound by sharing a benzene ring as a ring a It is a sieve compound (cyclic covalent multimer). In addition, the multimeric compound represented by the following formula (2-4-1), when explained by the general formula (2), is made to share a benzene ring which is a ring, so that one unit structure represented by two general formulas (2) is It is a multimer compound (cyclic covalent multimer) contained in a compound. In addition, the multimeric compound represented by the following formula (2-4-2), when explained by the general formula (2), is made to share a benzene ring, which is a ring, so that one unit structure represented by the three general formulas (2) is It is a multimer compound (cyclic covalent multimer) contained in a compound. In addition, the multimeric compound represented by any one of the following formulas (2-5-1) to (2-5-4) shares a benzene ring which is a b ring (or c ring) when explained by general formula (2). Thus, it is a multimer compound (cyclic covalent multimer) having a unit structure represented by a plurality of general formulas (2) in one compound. In addition, the multimeric compound represented by the following formula (2-6) is explained by the general formula (2), for example, a benzene ring which is a b ring (or a ring, c ring) of a certain unit structure and a certain unit structure It is a multimer compound (ring condensation type multimer) which has a unit structure represented by a plurality of general formulas (2) in one compound by condensing the benzene ring as ring b (or ring a, ring c). The definition of each sign in the following structural formula is the same as the definition of each sign in General Formula (2).

The multimeric compound is a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), and formula (2-5-1) to formula (2- Any one of 5-4) or a multimer in which a multimerization form represented by Formula (2-6) may be combined, and represented by any of Formulas (2-5-1) to (2-5-4) It may be a multimer in which a multimerization form and a multimerization form represented by formula (2-6) are combined, and can be expressed by formula (2-4), formula (2-4-1), or formula (2-4-2). Even if it is a multimer in which the multimerization form expressed and the multimerization form expressed by any one of formulas (2-5-1) to (2-5-4) and the multimerization form expressed by formula (2-6) are combined do.

In addition, all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and its multimer may be cyano, halogen, or deuterium. For example, in formula (1), A ring, B ring, C ring (A to C ring is an aryl ring or heteroaryl ring), a substituent to A to C ring, Y ¹ is Si-R or Ge-R To R (=alkyl, cycloalkyl, aryl) when X ¹ and X ² are >NR or >C(-R) ₂ (= hydrogen, aryl, heteroaryl, alkyl, cycloalkyl) The hydrogen in may be substituted with cyano, halogen or deuterium, but among these, all or part of the hydrogen in aryl or heteroaryl may be substituted with cyano, halogen or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine or chlorine.

As another form, the polycyclic aromatic compound represented by general formula (1) or (2) and its multimer are, for example, a diarylamino group, a diarylboryl group (two aryls may be bonded through a single bond or a linking group). And examples substituted with a carbazolyl group or a benzocarbazolyl group. As for the "diarylamino group" and the "diaryl boryl group", the groups described above as the "first substituent" can be mentioned. As a substitution form of cyano, halogen or deuterium on a diarylamino group, a diaryl boryl group, a carbazolyl group, and a benzocarbazolyl group, some or all hydrogens of the aryl ring or benzene ring in these groups are cyano, halogen or deuterium. Examples substituted with.

In addition, as a more specific example, R ² in the polycyclic aromatic compound represented by the general formula (2) and its multimer is a diarylamino group, a fluorine-substituted diaryl boryl group (two aryls are bonded through a single bond or a linking group, May be present) or a carbazolyl group.

As an example, a polycyclic aromatic compound represented by the following general formula (2-A), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2-A) can be mentioned. The definition of each sign in the following structural formula is the same as the definition of each sign in General Formula (2).

Further, specific examples of the deuterium-substituted polycyclic aromatic compound and its multimer of the present invention include compounds in which at least one hydrogen in one or more aromatic rings among the compounds is substituted with one or more deuterium, , For example, compounds substituted with 1 to 2 deuterium are mentioned.

In addition, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or (2) and the multimer thereof may be condensed with at least one cycloalkane.

For example, aryl groups (aryl, diarylamino) as the first and second substituents on the A ring, B ring, C ring, a ring, b ring and c ring aryl ring and heteroaryl ring, and A ring to C ring , Aryl group moiety in arylheteroarylamino, diarylboryl, aryloxy or triarylsilyl) and heteroaryl group (heteroaryl moiety in heteroaryl, diheteroarylamino or arylheteroarylamino), ring a an aryl group (same as above) and a heteroaryl group (same as above) as the first and second substituents in the ~c ring, an aryl group as R of Si-R and Ge-R in Y ¹ (same as above), and , At least one of an aryl group (same as above) and a heteroaryl group (same as above) as R of >NR, >Si(-R) ₂ and >C(-R) _{2 which} are X ¹ and X ² It may be condensed with one cycloalkane.

Preferably, an aryl group (aryl, diarylamino, diaryl) as the first substituent on the A ring, B ring, C ring, a ring, b ring and c ring aryl ring and heteroaryl ring, and ring A to C ring An aryl group moiety in boryl or aryloxy) and a heteroaryl group (heteroaryl moiety in heteroaryl or diheteroarylamino), an aryl group as the first substituent in ring a to ring c (same as above), and A heteroaryl group (same as above) and an aryl group (same as above) and a heteroaryl group as R of >NR, >Si(-R) ₂ and >C(-R) ₂ wherein X ¹ and X ² In the same way), at least one may be condensed with at least one cycloalkane.

More preferably, an aryl group (an aryl group in aryl or diarylamino) as the first substituent on the A ring, B ring, C ring, a ring, b ring and c ring aryl ring, and ring A to ring C ) And heteroaryl group (heteroaryl moiety in heteroaryl), aryl group (same as above) and heteroaryl group (same as above) as the first substituent in ring a to ring c, and X ¹ and X ² At least one of the aryl groups (same as the above) as R of phosphorus >NR, >Si(-R) ₂ and >C(-R) ₂ may be condensed with at least one cycloalkane.

More preferably, an aryl group (an aryl or aryl group in the diarylamino) as the first substituent on the A ring, B ring, C ring, a ring, b ring and c ring aryl ring, or ring A to C ring ), an aryl group (same as the above) as the first substituent in the a ring to the c ring, and aryl as R of >NR, >Si(-R) ₂ and >C(-R) _{2 which} are X ¹ and X ² At least one of the groups (same as above) may be condensed with at least one cycloalkane.

As a ``cycloalkane'', a C3-C24 cycloalkane, a C3-C20 cycloalkane, a C3-C16 cycloalkane, a C3-C14 cycloalkane, a C5-C10 cycloalkane, a C5-C8 Cycloalkane, C5-C6 cycloalkane, C5 cycloalkane, etc. are mentioned.

As a specific cycloalkane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane , Bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, Diamantane, decahydronaphthalene and decahydroazulene, and their alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, deuterium substituents, and the like.

Among these, for example, in the carbon at the α-position of a cycloalkane (a carbon at a position adjacent to the carbon of the condensation site in the cycloalkyl condensed to an aromatic ring or a heteroaromatic ring) as shown in the following structural formula A structure in which at least one hydrogen is substituted is preferable, a structure in which two hydrogens in the carbon at the α-position are substituted is more preferable, and a structure in which a total of 4 hydrogens in the carbon at the two α-positions is substituted is even more. desirable. As this substituent, a C1-C5 alkyl (especially methyl) substituent, a halogen (especially fluorine) substituent, a deuterium substituent, etc. are mentioned.

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

At least one of -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 with one benzene ring (phenyl group) is substituted with -O- is shown below. In each structural formula, * in the case of a benzene ring means a benzene ring contained in the skeleton structure of the compound, and in the case of a phenyl group means the number of bonds substituted for the skeleton structure of the compound. The same applies when the condensed ring (group) is an aromatic ring other than a benzene ring (phenyl group) or a heteroaromatic ring, or when the cycloalkane to be condensed is cyclopentane or other cycloalkane other than cyclohexane.

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

As another form of cycloalkane condensation, a polycyclic aromatic compound represented by the general formula (1) or (2) and its multimer are, for example, a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety), a cycloalkane Examples of substituted with a carbazolyl group condensed with (condensed to this benzene ring moiety) or a benzocarbazolyl group condensed with a cycloalkane (condensed to this benzene ring moiety) can be given. As for the "diarylamino group", the group described as the above "first substituent" can be mentioned.

Further, as a more specific example, R ² in the polycyclic aromatic compound represented by the general formula (2) and its multimer is a diarylamino group condensed with a cycloalkane (condensed with this aryl group moiety) or a car condensed with a cycloalkane. Examples of a bazolyl group (condensed to this benzene ring moiety) are exemplified.

As an example, a polycyclic aromatic compound represented by the following general formula (2-Cy), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2-Cy) can be mentioned. In the following structural formula, Cy is a cycloalkane, n is each independently an integer of 1 to 3 (preferably 1), and ``=(Cy)n'' is condensed at any position in the structure in which n cycloalkanes are condensed. It means (in the following structural formula, n cycloalkanes are condensed to a benzene ring (phenyl group)), and the definition of each sign in the structural formula is the same as the definition of each sign in General Formula (2).

Specifically, the compound represented by the following formula is mentioned. In the following formula, "Cy" represents a cycloalkane, and n is each independently 0 to the maximum condensable number (however, all n is not 0), preferably 0 to 2 (however, all n is 0 No case), more preferably 1, and "=(Cy)n" means that n number of cycloalkanes are condensed at an arbitrary position in the structure to be condensed (for example, the following formula "2- In "Cy-(1)", n number of cycloalkanes are condensed at any position of each benzene ring). In the following structural formula, "OPh" represents a phenoxy group, "Me" represents a methyl group, and each compound may be substituted with the above-described first and second substituents.

As a specific example of the polycyclic aromatic compound of this invention, the compound represented by the following structural formula is mentioned. In the following structural formula, "Me" is a methyl group, "Et" is an ethyl group, "tBu" is a t-butyl group, "iPr" is an isopropyl group, "Hep" is a heptyl group, "Ph" is a phenyl group, and "D" Represents deuterium.

In addition, the polycyclic aromatic compound represented by formula (1) is a para with respect to the central atom "B" (boron) in at least one of A ring, B ring, and C ring (a ring, b ring, and c ring). By introducing a phenyloxy group, a carbazolyl group, or a diphenylamino group at the position, an improvement in T1 energy (approximately 0.01 to 0.1 eV improvement) can be expected. In particular, by introducing a phenyloxy group at the para position with respect to B (boron), the HOMO on the benzene ring, which is the A ring, B ring and C ring (a ring, b ring and c ring), is more localized at the meta position for boron. (局在化), and since LUMO is localized in the ortho and para positions for boron, an improvement in T1 energy can be particularly expected.

As such a specific example, the compound represented by following formula (1-4501)-(1-4522) is mentioned, for example.

In addition, R in the formula is alkyl, and may be either a linear 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. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, and alkyl having 1 to 6 carbon atoms (3 carbon atoms -6 branched alkyl) is more preferable, a C1-C5 alkyl (C3-C5 branched alkyl) is particularly preferable, and a C1-C4 alkyl (C3-C4 branched alkyl) is more preferable. Most preferred. In addition, as R, phenyl and the above-described cycloalkyl are mentioned.

In addition, "PhO-" is a phenyloxy group, and this phenyl may be substituted with linear or branched alkyl, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, and 1 carbon atom. -18 alkyl (C3-C18 branched chain alkyl), C1-C12 alkyl (C3-C12 branched chain alkyl), C1-C6 alkyl (C3-C6 branched chain alkyl), carbon number You may be substituted with 1-5 alkyl (C3-C5 branched chain alkyl), C1-C4 alkyl (C3-C4 branched chain alkyl). In addition, this phenyl may be substituted with the above-described cycloalkyl.

In addition, as a specific example of the polycyclic aromatic compound represented by formula (1), in the above-described compound, at least one hydrogen in one or more aromatic rings is one or more alkyl, cycloalkyl, or aryl. A substituted compound is mentioned, More preferably, a compound substituted with a C1-C12 alkyl, a C3-C16 cycloalkyl, or a C6-C10 aryl is mentioned.

Specifically, the following compounds are mentioned. R in the following formulas are each independently alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, or aryl having 6 to 10 carbon atoms, preferably alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or phenyl. and n are each independently 0 to 2, preferably 1. In addition, "Me" in a structural formula represents a methyl group.

In addition, as a specific example of the polycyclic aromatic compound represented by formula (1), at least one hydrogen in one or more phenyl groups or one phenylene group in the compound is one or more C1-C4 alkyl or C5 Cycloalkyl of ~10, preferably a compound substituted with an alkyl having 1 to 3 carbon atoms (preferably one or more methyl groups), more preferably, hydrogen in the ortho position of one phenyl group (All two of the two places, preferably any one place) or a compound in which hydrogen (all four of a maximum of four places, preferably any one place) at the ortho position of one phenylene group is substituted with a methyl group Can be lifted.

By substituting at least one hydrogen in the ortho position of the terminal phenyl group or p-phenylene group in the compound with a methyl group, etc., neighboring aromatic rings tend to be orthogonal and conjugate weakens, resulting in triplet excitation energy (E _T ) It becomes possible to increase.

3. Method for producing polycyclic aromatic compound as first component and its multimer

The polycyclic aromatic compound represented by the general formula (1) or (2) can be produced according to the method described in many known documents including International Publication No. 2015/102118.

Basically, first, an intermediate is prepared by combining A ring (a ring), B ring (b ring), and C ring (c ring) with a linking group (a group containing X ¹ or X ² ) (first reaction) , After that, the final product can be prepared by combining the A ring (a ring), B ring (b ring), and C ring (c ring) with a coupling group (a group containing the central element B (boron)) 2 reactions). In the first reaction, for example, if it is an etherification reaction, a general reaction such as nucleophilic substitution reaction and Ullmann reaction can be used, and if it is an amination reaction, a general reaction such as Buchwald-Hartwig reaction is used. Can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electron substitution reaction, hereinafter the same) can be used. In addition, somewhere in these reaction processes, by using a cyanoated, halogenated or deuterated raw material, or by adding a process of cyanation, halogenation or deuteration, the desired position can be produced a cyanoated, halogenated or deuterated compound. I can.

In the second reaction, as shown in the following schemes (1) or (2), the central element B (boron) which bonds the A ring (a ring), B ring (b ring) and C ring (c ring) is introduced. It is a reaction to do, and the case where X ¹ and X ² are >O is shown below, for example. First, the hydrogen atom between X ¹ and X ² is orthometalized with n-butyllithium, sec-butyllithium or t-butyllithium. Then, boron trichloride, boron tribromide, etc. are added to perform a metal exchange of lithium-boron, and then a Bronsted base such as N,N-diisopropylethylamine is added, thereby causing a tandem Bora Friedel Crafts reaction. , You can get the object. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. In addition, the definition of the code in each structural formula in the following schemes (1) to (9) is the same as the definition described above.

In addition, the above schemes (1) and (2) mainly show a method for producing a polycyclic aromatic compound represented by general formulas (1) or (2), but for the multimer, a plurality of A rings (a ring), It can be produced by using an intermediate having a B ring (b ring) and a C ring (c ring). In detail, it demonstrates with the following schemes (3)-(5). In this case, the target product can be obtained by making the amount of a reagent such as butyl lithium to be used in a double or triple amount.

In addition, when X ¹ and X ² are >NR, or when either one is >NR, it can be produced in the same manner as described above by using an amine compound as an intermediate.

Next, for example, the case where Y ¹ is an insulfide, phosphorus oxide or phosphorus atom, and X ¹ and X ² are oxygen atoms is shown in the following schemes (6) to (9). As until now, first, the hydrogen atom between X ¹ and X ² is orthometalized with n-butyllithium or the like. Subsequently, phosphorus trichloride and sulfur are added in the order, and finally, a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to react by tandem phospha Friedel Crafts, A compound in which Y ¹ is an insulfide can be obtained. In addition, by treating the obtained insulfide compound with m-chloroperbenzoic acid (m-CPBA), a compound in which Y ¹ is phosphorus oxide can be obtained, and by treatment with triethylphosphine, a compound in which Y ¹ is a phosphorus atom can be obtained. .

Here, the example in which Y ¹ is B, P, P=O or P=S, and X ¹ and X ² are >O or >NR is described, but by appropriately changing the raw material, Y ¹ is Al, Ga, As , Si-R or Ge-R, or a compound in which X ¹ and X ² are >C(-R) ₂ , >S or >Se can also be synthesized.

Specific examples of the solvent used in the above reaction are t-butylbenzene, xylene, and the like.

In addition, as the orthometallization reagent, alkyl lithium such as methyl lithium, n-butyl lithium, sec-butyl lithium, and t-butyl lithium, lithium diisopropylamide, lithium tetramethyl piperidide, lithium hexamethyl disilazide, And organic alkali compounds such as potassium hexamethyldisilazide.

As for the metal of the metal exchange reagent -Y ^1, Y ¹ of 3 fluorine, Y ¹ of the third chloride, bromide Y 3, Y ¹ of halide, such as iodide of 3 Y ¹ of ^1, CIPN (NEt ₂₎ and the like _2, and the amination halides, aryloxy product of the alkoxide, Y ¹ Y ¹ of the Y ^1.

In addition, as Bronsted base, N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperi Dean, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar _3B , Ar ₄ Si (In addition, Ar is an aryl such as phenyl), and the like.

In addition, as a Lewis acid, 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 each of the above schemes, a Bronsted base or Lewis acid may be used to accelerate the tandem hetero Friedel Crafts reaction. Stage, Y when on 3 fluorides, 3 chloride, halides of Y ^1, such as 3-bromide, iodide of Y ¹ a Y ¹ of the Y ¹ of Figure ^1, with the progress of the aromatic obtain electrophilic substitution reaction, hydrogen fluoride , Hydrogen chloride, hydrogen bromide, and hydrogen iodide, the use of a Bronsted base to capture the acid is effective. On the other hand, when it halo amination of Y ¹ with the alkoxide of the cargo, Y ¹ is, because with the progress of the aromatic obtain electrophilic substitution reaction, an amine, an alcohol is produced, in most cases, Bronsted necessary to use a base However, since the ability of the amino group or the alkoxy group to leave is low, the use of Lewis acid to promote the separation is effective.

4. Compound as second component

The compound of the second component constituting at least one of the electron transport layer and the electron injection layer is not particularly limited, and a compound conventionally used as an electron transport compound in a photoconductive material, an electron injection layer and an electron of an organic EL device It can be arbitrarily selected and used from known compounds used in the transport layer.

As the second component, in particular, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole It is preferably at least one member selected from the group consisting of derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives.

4-1. Borane derivatives

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

In formula (ETM-1),

R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heteroaryl, or cyano,

R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl,

X is an optionally substituted arylene,

Y is optionally substituted aryl having 6 to 16 carbon atoms, optionally substituted carbazolyl or substituted boryl, and,

n is an integer of 0-3 each independently.

In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

For details of the alkyl, cycloalkyl, aryl and nitrogen-containing heteroaryl described as a group in the formula (ETM-1), the description in the above formulas (1) and (2) can be cited.

Examples of the "substituted silyl" include groups in which at least one of the three hydrogens of the silyl group is each independently substituted with aryl, alkyl, or cycloalkyl, tri-substituted silyl is preferred, and triarylsilyl, trialkylsilyl , Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, and the like. About the details of aryl, alkyl, and cycloalkyl in these, description in said Formula (1) and Formula (2) can be cited.

As "arylene", the divalent group of the aryl ring demonstrated by the said formula (1) and formula (2) is mentioned.

As "carbazolyl which may be substituted" or "substituted boryl", it will be described in formulas (ETM-1-1) and (ETM-1-2) described later.

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

In formula (ETM-1-1),

R ¹¹ to R ¹⁶ and n are the same as the definition in the formula (ETM-1),

R ²¹ and R ²² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heteroaryl, or cyano,

X ¹ is an optionally substituted arylene having 6 to 20 carbon atoms, and,

m is each independently an integer of 0-4.

In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

In formula (ETM-1-2),

R ¹¹ to R ¹⁶ and n are the same as the definition in the above formula (ETM-1), and,

X ¹ is an arylene having 6 to 20 carbon atoms which may be substituted.

In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

For details of the alkyl, cycloalkyl, aryl, heteroaryl, substituted silyl and arylene described as groups in the formulas (ETM-1-1) and (ETM-1-2), the above formula (ETM-1 The explanation in) can be cited.

As a specific example of X ¹ , a divalent group represented by any one of following formula (X-1)-formula (X-9) is mentioned. * In each structural formula represents a bonding position.

(In each formula, R ^a is each independently alkyl, cycloalkyl, or phenyl which may be substituted. The substituent to phenyl is, for example, alkyl or cycloalkyl. For details of these alkyl and cycloalkyl, the above-described The explanation in Equation (1) and Equation (2) can be cited.)

As a specific example of this borane derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

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

4-2. Pyridine derivatives

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

In the above formula (ETM-2-1), R ¹¹ to R ¹⁸ are each independently hydrogen, alkyl, cycloalkyl, or aryl. For the details of these alkyl, cycloalkyl and aryl, the description in the above formulas (1) and (2) can be cited.

In the formula (ETM-2-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl or aryl, and R ¹¹ and R ¹² may be bonded to form a spiro ring. For the details of these alkyl, cycloalkyl and aryl, the description in the above formulas (1) and (2) can be cited.

In each formula, the "pyridine substituent" is a group in any one of the following formulas (Py-1) to (Py-15), and the pyridine substituents may each independently be substituted with alkyl or cycloalkyl. For the details of these alkyl and cycloalkyl, descriptions in the above formulas (1) and (2) can be cited. In addition, the pyridine-based substituent may be bonded to Φ in each formula, an anthracene ring, or a fluorene ring via a phenylene group or a naphthylene group. * In each structural formula represents a bonding position.

The pyridine-based substituent is a group of any one of the above formulas (Py-1) to (Py-15), but among these, it is preferable to be a group of any one of the following formulas (Py-21) to (Py to 44). Do. * In each structural formula represents a bonding position.

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) May be substituted with aryl. For the details of this aryl, the description in the above formulas (1) and (2) can be cited.

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

As a specific example of this pyridine derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

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

4-3. Fluoranthene derivatives

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

In the above formula (ETM-3), R ¹² to R ²¹ each independently represent hydrogen, halogen, alkyl, cycloalkyl, alkoxy, cycloalkyloxy, aryl which may be substituted, or heteroaryl which may be substituted. Here, examples of the substituent in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

For the details of halogen, alkyl, cycloalkyl, alkoxy, aryl and heteroaryl described as a group in the formula (ETM-3), the description in the above formulas (1) and (2) can be cited.

Cycloalkyloxy is a group in which an alkyl group in an alkoxy group is substituted with a cycloalkyl group, and the description in the above formulas (1) and (2) can be cited for details of this cycloalkyl.

As a specific example of this fluoranthene derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

This fluoranthene derivative can be produced using a known raw material and a known synthesis method.

4-4. BO derivative

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

In formula (ETM-4), R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single bonds or It may be bonded through a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

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

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

For the description of a multimer formed by combining a plurality of substituents and ring formations in formula (ETM-4) and structures of formula (ETM-4), the description in formulas (1) and (2) above. Can be cited.

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

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

4-5. Anthracene derivatives

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

In formula (ETM-5-1), Ar is each independently phenylene or naphthylene, and R ¹ to R ⁴ are each independently hydrogen, alkyl, cycloalkyl, or aryl. For the details of these alkyl, cycloalkyl and aryl, the description in the above formulas (1) and (2) can be cited.

Ar can each independently be appropriately selected from phenylene or naphthylene, and may be the same even if the two Ar are different, but the same is preferable from the viewpoint of easy synthesis of an anthracene derivative. Ar is bonded to pyridine to form a "site consisting of Ar and pyridine", and this site is bound to anthracene as a group represented by any of the following formulas (Py-1) to (Py-12). . * 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. Two "sites consisting of Ar and pyridine" bonded to anthracene may have the same or different structures, but are preferably the same structure from the viewpoint of easy synthesis of anthracene derivatives. However, from the viewpoint of device characteristics, it is preferable that the structures of the two "sites consisting of Ar and pyridine" are the same or different.

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

In formula (ETM-5-2), R ¹ to R ⁴ are each independently hydrogen, alkyl, cycloalkyl, or aryl, and Ar ² is each independently aryl. For the details of these alkyl, cycloalkyl and aryl, the description in the above formulas (1) and (2) can be cited.

Each Ar ¹ is independently a single bond or an arylene. As this arylene, the divalent group of the aryl ring demonstrated by said Formula (1) and Formula (2) is mentioned.

As a specific example of these anthracene derivatives, the following compounds are mentioned, for example.

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

4-6. Benzofluorene derivatives

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

In formula (ETM-6),

Each Ar ¹ is independently aryl,

Ar ² is each independently hydrogen, alkyl, cycloalkyl, or aryl, and two Ar ² may be bonded to form a spiro ring.

For the details of these aryl, alkyl and cycloalkyl, the description in the above formulas (1) and (2) can be cited.

Two Ar ² may be bonded to form a spiro ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. may be spiro bonded to the 5-membered ring of the fluorene skeleton. You can do it.

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

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

4-7. Phosphine oxide derivatives

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

In formula (ETM-7-1),

R ⁵ is substituted or unsubstituted alkyl, cycloalkyl, aryl or heteroaryl,

R ⁶ is CN, substituted or unsubstituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, alkoxy or aryloxy,

R ⁷ and R ⁸ are each independently a substituted or unsubstituted aryl or heteroaryl,

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, examples of the substituent in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

For details of the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy and aryloxy described as a group in the formula (ETM-7-1), the description in the above formulas (1) and (2) can be cited. have.

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

R ¹ to R ³ are each independently hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, arylthio, aryl, heteroaryl, It is selected from halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl which may be substituted, and a condensed ring formed between an adjacent substituent.

Ar ¹ is each independently arylene or heteroarylene. Ar ² is each independently aryl or heteroaryl. 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, there is no unsaturated structure part, and when n is 3, R ¹ does not exist.

For details of the alkyl, cycloalkyl, alkoxy, aryl, heteroaryl and halogen described as a group in the formula (ETM-1), the description in the above formulas (1) and (2) can be cited.

In addition, aralkyl represents alkyl substituted with an aryl such as benzyl or phenylethyl, and both alkyl and aryl may be unsubstituted or substituted. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For the details of these aryl, alkyl, cycloalkyl, and halogen, descriptions in the above formulas (1) and (2) can be cited.

In addition, alkenyl represents an alkyl containing a double bond such as vinyl, allyl or butadienyl, which may be unsubstituted or substituted. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For the details of these alkyl, cycloalkyl, and halogen, descriptions in the above formulas (1) and (2) can be cited.

In addition, cycloalkenyl represents a cycloalkyl containing a double bond, such as cyclopentenyl, cyclopentadienyl, or cyclohexene, which may be unsubstituted or substituted. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For the details of these alkyl, cycloalkyl, and halogen, descriptions in the above formulas (1) and (2) can be cited.

In addition, alkynyl represents alkyl containing triple bonds, such as acetylenyl, for example, and may be unsubstituted or substituted. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For the details of these alkyl, cycloalkyl, and halogen, descriptions in the above formulas (1) and (2) can be cited.

In addition, alkylthio is a group in which an oxygen atom of an alkoxy ether bond is substituted with a sulfur atom. For details of the alkyl moiety in this alkylthio, the description in the above formulas (1) and (2) can be cited.

In addition, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is substituted with a sulfur atom. For details of the cycloalkyl moiety in this cycloalkylthio, the description in the above formulas (1) and (2) can be cited.

In addition, an aryl ether represents an aryl through an ether bond such as phenoxy, and aryl may be unsubstituted or substituted. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For the details of these aryl, alkyl, cycloalkyl, and halogen, descriptions in the above formulas (1) and (2) can be cited.

In addition, arylthio is a group in which the oxygen atom of the ether bond of the aryl ether is substituted with a sulfur atom. For details of the aryl moiety in this arylthio, the description in the above formulas (1) and (2) can be cited.

Aldehyde, carbonyl, amino may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl, etc., and the descriptions in the above formulas (1) and (2) can be cited for details of these substituents. .

Examples of the silyl which may be substituted include a silyl group and a group in which at least one of the three hydrogens of the silyl group is each independently substituted with aryl, alkyl, or cycloalkyl, trisubstituted silyl is preferable, and triarylsilyl, trialkyl Silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, and the like. For the details of aryl, alkyl and cycloalkyl in these, explanations in the above formulas (1) and (2) can be cited.

The condensed ring formed between adjacent substituents is, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , Ar ¹ and Ar ^It is a conjugated or non-conjugated condensed ring formed between ² and the like. Here, when n is 1, two R ^1s may form a conjugated or non-conjugated condensed ring. These condensed rings may contain nitrogen, oxygen, and sulfur atoms in the intra-ring structure, or may be further condensed 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 a known raw material and a known synthesis method.

4-8. Pyrimidine derivatives

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

Ar is each independently alkyl, cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For details of these alkyl, cycloalkyl, aryl, heteroaryl and halogen, the descriptions in the above formulas (1) and (2) can be cited. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

As a specific example of this pyrimidine derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

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

4-9. Carbazole derivatives

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

Ar is each independently alkyl, cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For details of these alkyl, cycloalkyl, aryl, heteroaryl and halogen, the descriptions in the above formulas (1) and (2) can be cited. n is each independently an integer of 0 to 4, preferably 0 to 3, and more preferably 0 or 1.

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

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

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

4-10. Triazine derivatives

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

Ar is each independently alkyl, cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl. Examples of the substituent in the case of being substituted include alkyl, cycloalkyl, or halogen. For details of these alkyl, cycloalkyl, aryl, heteroaryl and halogen, the descriptions in the above formulas (1) and (2) can be cited. n is an integer of 1 to 3, preferably 2 or 3.

As a specific example of this triazine derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

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

4-11. Benzoimidazole derivatives

Benzoimidazole derivatives are compounds represented by the following formula (ETM-11), for example.

Φ is an n-valent aryl ring, and examples of this aryl ring include the rings described in the above formulas (1) and (2). n is an integer of 1 to 4, and ``benzoimidazole-based substituent'' is a ``pyridine-based substituent exemplified by the above formulas (ETM-2), (ETM-2-1), and (ETM-2-2) In ", the pyridyl group is a substituent substituted with a benzoimidazole group of the following structure, and at least one hydrogen in the benzoimidazole derivative may be substituted with deuterium. * In the following structural formula represents a bonding position.

R ¹¹ in the benzoimidazole group is hydrogen, alkyl, cycloalkyl or aryl, and the descriptions in the above formulas (1) and (2) can be cited for details of these groups.

Φ is also preferably an anthracene ring or a fluorene ring, and the structure in this case can refer to the description in the above formula (ETM-2-1) or (ETM-2-2), and R in each formula ¹¹ to R ¹⁸ can refer to the description in the above formula (ETM-2-1) or (ETM-2-2). In addition, in the above formula (ETM-2-1) or (ETM-2-2), two pyridine-based substituents are combined, but when these are substituted with a benzoimidazole-based substituent, both pyridine-based substituents May be substituted with a benzoimidazole-based substituent (i.e., n=2), any 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 (I.e., n=1). In addition, for example, even if at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) is substituted with a benzoimidazole-based substituent, and “pyridine-based substituent” is substituted with R ¹¹ to R ¹⁸ do.

Specific examples of this benzoimidazole derivative include, for example, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-( 10-(naphthalen-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo-[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracene-9 -Yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzo[d ]Imidazole, 1-(4-(10-(naphthalen-2-yl)anthracene-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)anthracene -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, a compound represented by the following structural formula, etc. are mentioned. In addition, "Et" in a structural formula represents an ethyl group.

This benzoimidazole derivative can be produced using a known raw material and a known synthesis method.

4-12. Phenanthroline derivatives

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

Φ is an n-valent aryl ring, and examples of this aryl ring include the rings described in the above formulas (1) and (2). n is an integer of 1-4.

R ¹¹ to R ¹⁸ in each formula are each independently hydrogen, alkyl, cycloalkyl, or aryl. For the details of these alkyl, cycloalkyl and aryl, the description in the above formulas (1) and (2) can be cited. Further, in the above 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,

In addition, in addition to the above-described examples, Φ includes, for example, groups of the following structural formulas. In addition, 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 this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, and 9 ,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10 -Phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), vasocuproin, 1,3-bis(2-phenyl- 1,10-phenanthroline-9-yl)benzene, a compound represented by the following structural formula, etc. are mentioned.

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

4-13. Quinolinol-based metal complex

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, and the details of these alkyl, cycloalkyl, alkoxy and aryl are described above. The description in formulas (1) and (2) can be cited, and the description in the above formula (ETM-7-2) can be cited for details of aralkyl and alkenyl. M is Li, Al, Ga, Be, or Zn, and n is an integer of 1 to 3.

Specific examples of the quinolinol-based metal complex include 8-quinolinol lithium, tris(8-quinolinolate) aluminum, tris(4-methyl-8-quinolinolate) aluminum, and tris(5-methyl-8-) Quinolinolate) aluminum, tris (3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8 -Quinolinoleate) aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (4-methylphenolate) aluminum, bis (2-methyl-8 -Quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,6 -Dimethylphenolate) aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethyl Phenolate) aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6 -Diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2 ,4,6-trimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinoli) Nolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (2- Phenylphenolate) aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate(4-phenylphenolate) ) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) Aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo -Bis(2-methyl-8-quinolinolate) aluminum, bis(2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinol) Rate) aluminum, bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2- Methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano -8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-qui Nolinoleate) aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium or represented by the following structural formula Compounds, etc. are mentioned. In addition, "Me" in a structural formula represents a methyl group.

This quinolinol-based metal complex can be produced using a known raw material and a known synthesis method.

4-14. Thiazole derivatives and benzothiazole derivatives

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

The 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, and examples of this aryl ring include the rings described in the formulas (1) and (2). n is an integer of 1 to 4, and "thiazole-based substituent" or "benzothiazole-based substituent" is exemplified in the above formulas (ETM-2), (ETM-2-1), and (ETM-2-2). Among the "pyridine-based substituents", the pyridyl group is a substituent substituted with a thiazole group or a benzothiazole group of the following structure, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with 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 description in the above formula (ETM-2-1) or (ETM-2-2), R ¹¹ to R ¹⁸ may refer to the description in the above formula (ETM-2-1) or (ETM-2-2). Further, in the above formula (ETM-2-1) or (ETM-2-2), two pyridine-based substituents are combined, but when these 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) (i.e., n=2), and any one pyridine-based substituent is substituted with a thiazole-based substituent (or benzothiazole-based substituent), and another You may substitute the other pyridine-based substituent with R ¹¹ to R ¹⁸ (that is, n=1). In addition, 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 ^You may substitute ¹⁸ .

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

4-15. Silol derivatives

The silol derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in Japanese Patent Laid-Open No. Hei 9-194487.

X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, and heteroaryl, and these may be substituted. For the details of these groups, the description in the above formulas (1) and (2) and the description in the above 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 given in the above formula (ETM-7-2). The explanation in can be cited.

Further, X and Y may be bonded to each other to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated), and the details of this cycloalkyl ring are described in the above formulas (1) and (2). You can refer to.

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, isocyanate, cyanate, isocyanate, thiocyanate, isothiocyanate, or cyano, these may be substituted with alkyl, cycloalkyl, aryl or halogen, and condensed ring between adjacent substituents May be formed.

For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in R ¹ to R ⁴ , in the above formulas (1) and (2) You can cite an explanation.

Alkyl and aryl in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy for R ¹ to R ⁴ And also about the detail of alkoxy, the description in said Formula (1) and Formula (2) can be cited.

Examples of silyl include a silyl group and a group in which at least one of the three hydrogens of the silyl group is each independently substituted with aryl, alkyl or cycloalkyl, tri-substituted silyl is preferred, and triarylsilyl, trialkylsilyl, tricyclo Alkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, etc. are mentioned. About the details of aryl, alkyl, and cycloalkyl in these, description in said Formula (1) and Formula (2) 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 be further condensed with other rings.

However, preferably, when R ¹ and R ⁴ are phenyl groups, X and Y are not alkyl or phenyl. Further, preferably, when R ¹ and R ⁴ are thienyl groups, X and Y represent alkyl, and R ² and R ³ represent alkyl, aryl, alkenyl, or a cyclo where R ² and R ³ are bonded to form a ring. It is a structure that does not satisfy alkyl at the same time. Further, preferably, when R ¹ and R ⁴ are silyl groups, R ² , R ³ , X and Y are each independently hydrogen or not alkyl having 1 to 6 carbon atoms. Further, preferably, when a benzene ring is condensed by R ¹ and R ² , X and Y are not alkyl and phenyl.

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

4-16. Azoline derivatives

An azoline derivative is a compound represented by the following formula (ETM-16), for example. Details are set forth 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 heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of Φ is an alkyl having 1 to 6 carbon atoms, and 3 to 14 carbon atoms May be substituted with cycloalkyl, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms,

Y is each independently -O-, -S- or >N-Ar, Ar is a C6-C12 aryl or a C2-C12 heteroaryl, and at least one hydrogen of Ar is a C1-C4 alkyl , being optionally substituted by a heteroaryl group having a carbon number of 5-10 cycloalkyl, C 6 - 12 aryl or a carbon number of 2 to 12 of, R ¹ - R ⁵ are each independently hydrogen, alkyl having a carbon number of 1 to 4 carbon atoms of 5 to It is a cycloalkyl of 10, provided that Ar in the >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), and * in each structural formula is an azoline ring moiety and a Φ moiety Represents the bonding position of,

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 dogs is a site bonded 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 dogs is a site bonded to Φ or an azoline ring, and R ⁶ in =CR ⁶ -other than that is hydrogen,

At least one hydrogen in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms,

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

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

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

In formula (ETM-16-1) and formula (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 heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of Φ is an alkyl having 1 to 6 carbon atoms, and 3 to 14 carbon atoms May be substituted with cycloalkyl, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms,

In the formula (ETM-16-1), Y is each independently -O-, -S-, or >N-Ar, Ar is a C6-C12 aryl or C2-C12 heteroaryl, at least among Ar One hydrogen may be substituted with C1-C4 alkyl, C5-C10 cycloalkyl, C6-C12 aryl, or C2-C12 heteroaryl,

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,

In formula (ETM-16-1) and formula (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), and * in each structural formula is an azoline ring moiety and a Φ moiety Represents the bonding position of,

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 dogs is a site bonded 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 dogs is a site bonded to Φ or an azoline ring, and R ⁶ in =CR ⁶ -other than that is hydrogen,

At least one hydrogen in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms,

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

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

Preferably, Φ is a monovalent group represented by the following formula (Φ1-1) to formula (Φ1-18), a divalent group represented by the following formula (Φ2-1) to formula (Φ2-34), the following formula (Φ3 -1) is selected from the group consisting of a trivalent group represented by the formula (Φ3-3), and a tetravalent group represented by the following formula (Φ4-1) to the formula (Φ4-2), and at least one hydrogen of Φ is a carbon number You may be substituted with 1-6 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 are each independently alkyl having 1 to 4 carbon atoms or 5 to 10 carbon atoms Cycloalkyl, C6-C12 aryl or C2-C12 heteroaryl, R may be bonded to each other to form a ring, and Ar in >N-Ar is a C6-C12 aryl or C2 It is a heteroaryl of -12, and L in >NL is L in the said general formula (ETM-16), a formula (ETM-16-1), or a general formula (ETM-16-2).

Preferably, L is composed of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine. It is a divalent group of the ring selected from the group, and at least one hydrogen of L is substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms do.

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 lidinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y has 1 to 4 carbon atoms. You may be substituted with alkyl, C5-C10 cycloalkyl, or C6-C10 aryl.

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, all of R ¹ to R ⁴ are not simultaneously hydrogen, and m is 1 or 2, and when m is 2, the group formed by the azoline ring and L is the same.

As a specific example of the azoline derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

More preferably, Φ is in the group consisting of divalent groups represented by the following equations (Φ2-1), equations (Φ2-31), equations (Φ2-32), equations (Φ2-33) and equations (Φ2-34) Is selected, at least one hydrogen of Φ may be substituted with aryl having 6 to 18 carbon atoms, and * in each structural formula represents a bonding position,

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine and triazine, and at least one hydrogen of L is an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms. , May be substituted with C6-C10 aryl or C2-C14 heteroaryl,

Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, wherein at least one hydrogen of Ar has 1 to 4 carbon atoms. It may be substituted with alkyl, C5-C10 cycloalkyl, or C6-C10 aryl,

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 are hydrogen at the same time, and,

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

As another specific example of the azoline derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

For details of the alkyl, cycloalkyl, aryl or heteroaryl in each of the above formulas defining this azoline derivative, the description in the above formulas (1) and (2) can be cited.

This azoline derivative can be produced using a known raw material and a known synthesis method.

5. Specific description of the organic electroluminescent device

Hereinafter, the organic EL device 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 device according to the present embodiment.

<Structure of organic electroluminescent device>

The 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 ( 103), the hole transport layer 104 provided on the hole transport layer 104, 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 electron injection provided on the electron transport layer 106 It has a layer 107 and a cathode 108 provided on the electron injection layer 107.

In addition, the organic EL element 100 reverses the order of fabrication, for example, the substrate 101, the cathode 108 provided on the substrate 101, and the electron injection layer provided on the cathode 108 ( 107), the electron transport layer 106 provided on the electron injection layer 107, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer A configuration including a hole injection layer 103 provided on 104 and an anode 102 provided on the hole injection layer 103 may be employed.

Not all of the above layers are indispensable, and the minimum structural units are 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 arbitrary layer. In addition, each of the above layers may be composed of a single layer or may be composed of multiple layers.

As the form of the layer constituting the organic EL element, in addition to the configuration form 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/light-emitting layer” /Electron transport layer/electron injection layer/cathode", ``substrate/anode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/cathode”, ``substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron injection layer/ Cathode", "Substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode", "substrate/anode/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light emitting layer/ Electron injection layer/cathode”, “substrate/anode/hole 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/ The configuration of a light emitting layer/electron transport layer/cathode", "substrate/anode/light emitting layer/electron transport layer/cathode", and "substrate/anode/light emitting layer/electron injection layer/cathode" may be used.

<Substrate in organic electroluminescent 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 a plate shape, a film shape, or a sheet shape depending on the purpose, and, for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. If it is a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness needs only to have sufficient thickness to maintain the mechanical strength, so it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. As for the material of the glass, an alkali-free glass is preferable because it is better to have less ions eluted from the glass, but soda lime glass having a barrier coating such as SiO _{2 is} also commercially available, and thus can be used. Further, in order to increase the gas barrier property, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side. In particular, a plate, film or sheet made of a synthetic resin having low gas barrier property is used as the substrate 101. In the case of using as a gas barrier film, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescent 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 emission layer 105, holes are injected into the emission layer 105 through them.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO)) Etc.), a metal halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. are mentioned. Examples of the organic compound include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from materials used as anodes of organic EL devices.

The resistance of the transparent electrode is not limited since it is sufficient to 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, if an ITO substrate of 300 Ω/□ or less, it functions as an element electrode, but at present, it is possible to supply a substrate of about 10 Ω/□, for example, 100 to 5 Ω/□, preferably 50 It is particularly preferable to use a low resistance product of ~5Ω/□. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

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

As the hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is preferable that the hole injection efficiency is high and the injected holes are efficiently transported. For this, it is preferable that the ionization potential is small, the hole mobility is large, the stability is excellent, and the impurities used as traps are difficult to occur during manufacture and use.

As the material for forming the hole injection layer 103 and the hole transport layer 104, a compound conventionally used as a charge transport material for holes in a photoconductive material, a p-type semiconductor, a hole injection layer and a hole in an organic EL device Arbitrary compounds can be selected and used from known compounds used in the transport layer. These specific examples are 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 the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3- Methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N, N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl- 1,1'-diamine, N ^4, N ^{4 '-} diphenyl -N ^4, N ^4' - bis (9-phenyl -9H- carbazole-3-yl) [1,1'-biphenyl] - ^{4,4'-diamine, N 4, N 4, N} 4 ', N 4' - tetrahydro [1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -4,4 Triphenylamine derivatives such as'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper Phthalocyanine, etc.), pyrazoline derivatives, hydrazone 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, polycarbonate or styrene derivatives having the above monomers in the side chain, polyvinylcar Bazole, polysilane, and the like are preferable, but the compound is not particularly limited as long as it is a compound capable of forming a thin film required for fabrication of a light emitting device, injecting holes from the 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 donation or a compound having good electron acceptability. For the doping of electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are used. It is known (e.g., 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)). They generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number of holes and the mobility, the conductivity of the base material changes considerably. As a matrix material having hole transport properties, for example, a benzidine derivative (TPD, etc.), a starburst amine derivative (TDATA, etc.), or a specific metal phthalocyanine (in particular, zinc phthalocyanine (ZnPc), etc.) is known (Japanese Patent Laid-Open 2005). -167175).

<Light emitting layer in organic electroluminescent element>

The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes applied with an electric field. The material for forming the light-emitting layer 105 may be a compound (luminescent compound) that is excited by recombination of holes and electrons to emit light, and a stable thin film shape can be formed, and strong light emission (fluorescence) efficiency in a solid state. It is preferably a visible compound.

The light-emitting layer may be a single layer or a plurality of layers, and each is formed of a light-emitting layer material (host material, dopant material). The host material and the dopant material may be either one type or a combination of a plurality of them. The dopant material may be included in the entire host material or partially included in the host material. As the doping method, it can be formed by a co-deposition method with a host material, but may be simultaneously evaporated after mixing with the host material in advance.

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

The amount of the dopant material used depends on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The basis of the amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight of the total material for the light emitting layer. In the above range, for example, concentration quenching is preferable in that it can be prevented.

As host materials, condensed cyclic derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, which have been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclo Pentadiene derivatives, etc. are mentioned. In particular, an anthracene-based compound, a fluorene-based compound, or a dibenzochrysen-based compound is preferable.

<Anthracene compound>

The anthracene compound as a host is, for example, a compound represented by the following general formula (3).

In equation (3),

X and Ar ⁴ are each independently hydrogen, may be substituted aryl, may be substituted heteroaryl, may be substituted diarylamino, may be substituted diheteroarylamino, may be substituted aryl heteroarylamino, Alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, or silyl which may be substituted, all X and Ar ⁴ does not become hydrogen at the same time,

At least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

Further, a multimer (preferably a dimer) may be formed by using the structure represented by formula (3) as a unit structure. In this case, for example, a form in which unit structures represented by formula (3) are bonded through X can be exemplified, and examples of this X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroaryl Rene (a group in which a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl substituted carbazole ring has a divalent bonding value), and the like.

Details of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl will be described in the following preferred form column. . In addition, examples of the substituents thereto include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl, and the like, These details are also described in the column of the following preferred modes.

The preferred form of the anthracene compound is described below. The definition of the sign in the following structure is the same as the definition mentioned above.

In general formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and formula (3-X1) and formula (3-X2 ) Or a group represented by formula (3-X3) is bonded to the anthracene ring of formula (3) in *. Preferably, two Xs do not simultaneously become groups represented by formula (3-X3). More preferably, two Xs do not simultaneously become a group represented by formula (3-X2).

Further, a multimer (preferably a dimer) may be formed by using the structure represented by formula (3) as a unit structure. In this case, for example, a form in which unit structures represented by formula (3) are bonded through X can be exemplified, and examples of this X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroaryl Rene (a group in which a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl substituted carbazole ring has a divalent bonding value), and the like.

The naphthylene moiety in formula (3-X1) and formula (3-X2) may be condensed by one benzene ring. The structure condensed in this way is as follows.

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

Ar ³ is phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or the formula (A) It is a group that appears (including a carbazolyl group, a benzocarbazolyl group, and a phenyl substituted carbazolyl group). In addition, when Ar ³ is a group represented by formula (A), the group represented by formula (A) bonds with a single bond represented by a straight line in formula (3-X3) in *. That is, the anthracene ring of formula (3) and the group represented by formula (A) are directly bonded.

In addition, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is further alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, It may be substituted with phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl substituted carbazolyl group). In addition, when the substituent which Ar ³ has is a group represented by formula (A), the group represented by formula (A) is bonded to Ar ³ in formula (3-X3) in *.

Ar ⁴ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) or substituted with a cycloalkyl having 5 to 10 carbon atoms, It's Silyl.

Examples of alkyl having 1 to 4 carbon atoms substituted for silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and the three hydrogens in silyl are each independently Is substituted with these alkyl.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyl Dimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl , sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldii-propylsilyl , Ethyldii-propylsilyl, butyldii-propylsilyl, sec-butyldii-propylsilyl, t-butyldii-propylsilyl, and the like.

Cycloalkyl having 5 to 10 carbon atoms substituted for silyl is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1 ]Pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, deca Hydroazulenyl and the like, and the three hydrogens in silyl are each independently substituted with these cycloalkyls.

Specific examples of "silyl substituted with a cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Substituted silyls include dialkylcycloalkylsilyls substituted by two alkyls and 1 cycloalkyl, and alkyldicycloalkylsilyls substituted by 1 alkyl and 2 cycloalkyls. As a specific example, the group mentioned above is mentioned.

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

The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) may have.

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

As the "alkyl" of the "alkyl which may be substituted" in R ²¹ to R ²⁸ , either straight chain or branched chain may be used, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. Can be mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, and alkyl having 1 to 6 carbon atoms (3 carbon atoms Branched chain alkyl of ~6) is more preferable, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable.

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, etc. are mentioned.

Examples of the "cycloalkyl" of the "cycloalkyl which may be substituted" for R ²¹ to R ²⁸ include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and 3 to carbon atoms. 14 cycloalkyl, C5-C10 cycloalkyl, C5-C8 cycloalkyl, C5-C6 cycloalkyl, C5 cycloalkyl, etc. are mentioned.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents having 1 to 4 carbon atoms, norbornenyl, Bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1. 2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

As the "aryl" of the "optionally substituted aryl" in R ²¹ to R ²⁸ , for example, aryl having 6 to 30 carbon atoms is exemplified, aryl having 6 to 16 carbon atoms is preferable, and 6 to 12 carbon atoms Of aryl is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, and tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), Condensed tricyclic systems, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, condensed tetracyclic systems triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic systems perylenyl, pentacenyl, and the like. .

Examples of the "heteroaryl" of the "heteroaryl which may be substituted" in R ²¹ to R ²⁸ include, for example, heteroaryl having 2 to 30 carbon atoms, and heteroaryl having 2 to 25 carbon atoms is preferable, Heteroaryl having 2 to 20 carbon atoms is more preferable, heteroaryl having 2 to 15 carbon atoms is still more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. In addition, examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as a ring constituent atom.

As a specific "heteroaryl", for example, pyrroleyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyri Dill, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, Isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naph Tobenzofuranyl, naphthobenzothienyl, etc. are mentioned.

As the "alkoxy" of the "optionally substituted alkoxy" for R ²¹ to R ²⁸ , for example, a straight chain having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms can be mentioned. C1-C18 alkoxy (C3-C18 branched chain alkoxy) is preferable, C1-C12 alkoxy (C3-C12 branched chain alkoxy) is more preferable, and C1-C6 alkoxy ( Branched chain alkoxy having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferable.

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

Examples of R ²¹ ~ R ²⁸ "aryloxy group" of "aryloxy which may be substituted" in, a group of the -OH group is hydrogen-substituted in the aryl, the aryl is in the R ²¹ ~ R ²⁸ above " The group described as "aryl" can be cited.

The "arylthio" of the "optionally substituted arylthio" in R ²¹ to R ²⁸ is a group in which hydrogen of the -SH group is substituted with an aryl, and this aryl is "arylthio" in R ²¹ to R ²⁸ described above. The group described as "aryl" can be cited.

Examples of the "trialkylsilyl" in R ²¹ to R ²⁸ include groups in which three hydrogens in the silyl group are each independently substituted with alkyl, and this alkyl is the "alkylsilyl" in R ²¹ to R ²⁸ described above. The group described as ”can be cited. Preferred alkyl for substitution is alkyl having 1 to 4 carbon atoms, and specifically, methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, and the like are mentioned.

Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i -Propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldii-propylsilyl, ethyldii-propylsilyl, Butyldii-propylsilyl, sec-butyldii-propylsilyl, t-butyldii-propylsilyl, etc. are mentioned.

Examples of the "tricycloalkylsilyl" in R ²¹ to R ²⁸ include groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl is represented by R ²¹ to R ²⁸ described above. The group described as "cycloalkyl" of can be cited. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo [2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaph Thalenyl, decahydroazulenyl, and the like.

As a specific "tricycloalkylsilyl", tricyclopentylsilyl, tricyclohexylsilyl, etc. are mentioned.

As a specific example of the dialkylcycloalkylsilyl substituted by two alkyl and one cycloalkyl, and the alkyldicycloalkylsilyl substituted by one alkyl and two cycloalkyl, a group selected from the specific alkyl and cycloalkyl described above is substituted. One can be lifted.

Examples of the "substituted amino" of "amino which may be substituted" in R ²¹ to R ²⁸ include an amino group in which two hydrogens are substituted with aryl or heteroaryl. Amino in which two hydrogens are substituted with aryl is diaryl substituted amino, amino in which two hydrogens are substituted with heteroaryl is diheteroaryl substituted amino, and amino in which two hydrogens are substituted with aryl and heteroaryl is arylheteroaryl Is substituted amino. As the aryl or heteroaryl, the groups described as "aryl" or "heteroaryl" in R ²¹ to R ²⁸ described above can be cited.

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

Examples of "halogen" in R ²¹ to R ²⁸ include fluorine, chlorine, bromine, and iodine.

Among the groups described as R ²¹ to R ²⁸ , some may be substituted as described above, and examples of the substituent in this case include alkyl, cycloalkyl, aryl or heteroaryl. As the aryl, cycloalkyl, aryl or heteroaryl, the groups described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in R ²¹ to R ²⁸ described above can be cited.

R ²⁹ in ">NR ²⁹ " as Y is hydrogen or aryl which may be substituted, and as this aryl, the group described as "aryl" in R ²¹ to R ²⁸ described above can be cited, and as the substituent The groups described as substituents for R ²¹ to R ²⁸ can be cited.

Adjacent groups among R ²¹ to R ^{28 may} be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. When not forming a ring is a group represented by the following formula (A-1), and when forming a ring, for example, a group represented by any one of the following formulas (A-2) to (A-14) is mentioned. . In addition, at least one hydrogen in the group represented by any one of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, trialkyl. It may be substituted with cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxy or cyano. Y and * in the formula are the same definitions as above.

Examples of the ring formed by bonding of adjacent groups to each other include a cyclohexane ring as long as it is a hydrocarbon ring, and examples of the aryl ring or heteroaryl ring include "aryl" or "heteroaryl" in R ²¹ to R ²⁸ described above. The ring structures described above are mentioned, and these rings are formed so as to condense with one or two benzene rings in the formula (A-1).

Examples of the group represented by formula (A) include groups represented by any one of formulas (A-1) to (A-14), and formulas (A-1) to (A-5) and A group represented by any one of formulas (A-12) to (A-14) is preferred, a group represented by any one of formulas (A-1) to (A-4) is more preferred, and the formula (A-1 ), a group represented by any one of formulas (A-3) and (A-4) is more preferred, and a group represented by the formula (A-1) is particularly preferred.

The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2) in * in formula (A), a single bond in formula (3-X3), and formula (3-X3) Combining with Ar ³ in and substituting with at least one hydrogen in the compound represented by Formula (3) is as described above, but among these bonding forms, in Formula (3-X1) or Formula (3-X2) A naphthalene ring, a single bond in formula (3-X3), and a form in which at least one of Ar ³ in formula (3-X3) is bonded to each other are preferred.

In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), single bond in formula (3-X3), and Ar ³ in formula (3-X3) are In the bonded position and the structure of the group represented by formula (A), the position substituted with at least one hydrogen in the compound represented by formula (3) may be any position in the structure of formula (A). For example, any one of two benzene rings in the structure of formula (A), any one ring formed by bonding of adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A), or the structure of formula (A) It can bond at any one of R ²⁹ in ">NR ²⁹ " as Y in

As a group represented by formula (A), the following groups are mentioned, for example. Y and * in the formula are the same definitions as above.

In addition, all or part of hydrogen in the chemical structure of the anthracene compound represented by the general formula (3) may be deuterium.

As a specific example of an anthracene compound, a compound represented by any one of following formula (3-1)-formula (3-142) is mentioned, for example. In the following structural formula, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

The anthracene-based compound represented by formula (3) is a compound having a reactive group at a desired position of the anthracene skeleton, and a compound having a reactive group in a partial structure such as the structure of X, Ar ⁴ and formula (A) as starting materials, and Suzuki It can be produced by applying coupling, Negishi coupling, and other known coupling reactions. As a reactive group of these reactive compounds, halogen, boronic acid, etc. are mentioned. As a specific manufacturing method, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to, for example.

<Fluorene compound>

The compound represented by the general formula (4) basically functions as a host.

In the above formula (4),

R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in Formula (4) through a linking group), diarylamino, diheteroarylamino , Arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl,

In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ are each independently bonded and condensed A ring or a spiro ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl (the heteroaryl may be bonded to the ring formed through a linking group), diarylamino, diheteroarylamino, Arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy may be substituted, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and,

At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of the above formula (4), the description in the polycyclic aromatic compound of the above formula (1) or (2) can be cited.

Examples of the alkenyl in R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms is preferable, and alkenyl having 2 to 10 carbon atoms are more preferable, Alkenyl having 2 to 6 carbon atoms is more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-phen Tenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

In addition, as a specific example of the heteroaryl, a monovalent group having a structure of the formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) Can be lifted.

In formulas (4-Ar1) to (4-Ar5), Y ¹ is each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,

At least one hydrogen in the structures of the formulas (4-Ar1) to (4-Ar5) is substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. You may have it.

These heteroaryl may be bonded to the fluorene skeleton in the formula (4) through a linking group. That is, not only the fluorene skeleton in formula (4) and the heteroaryl are directly bonded, but may be bonded therebetween through a linking group. As this linking group, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, etc. are mentioned.

In addition, in formula (4), R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ are each independently bonded to each other to form a condensed ring And R ⁹ and R ¹⁰ may be bonded to each other to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed with the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and a naphthalene ring, a phenanthrene ring, etc. are mentioned as a structure containing a benzene ring in Formula (4). The spiro ring formed by R ⁹ and R ¹⁰ is a ring spiro bonded to the 5-membered ring in formula (4), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and a fluorene ring etc. are mentioned.

The compound represented by general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2), or formula (4-3), and in each general formula (4), R ¹ A compound in which a benzene ring formed by bonding of and R ² is condensed, a compound in which a benzene ring formed by bonding of R ³ and R ⁴ in general formula (4) is condensed, and all of R ¹ to R ⁸ in general formula (4) are bonded It is a compound not doing.

Equation (4-1), the definition of R ¹ ~ R ¹⁰ in the formula (4-2) and (4-3) are the same as R ¹ ~ R ^10, which corresponds in the formula (4), formula ( The definitions of R ¹¹ to R ¹⁴ in 4-1) and formula (4-2) are also the same as those of R ¹ to R ¹⁰ in formula (4).

The compound represented by general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), and is a compound represented by formula (4-1) and formula ( In 4-1) or formula (4-3), R ⁹ and R ¹⁰ are bonded to each other to form a spiro-fluorene ring.

The definitions of R ² to R ⁷ in formulas (4-1A), (4-2A) and (4-3A) include formulas (4-1), (4-2), and (4-3). ) In the corresponding R ² to R ^7, and definitions of R ¹¹ to R ¹⁴ in formulas (4-1A) and (4-2A) are also defined in formulas (4-1) and (4-2). ) In R ¹¹ to R ¹⁴ .

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

As a specific example of a fluorene-type compound, the compound represented by any one of following formula (4-4)-formula (4-22) is mentioned, for example. In addition, "Me" in the following structural formula represents a methyl group.

<Dibenzochrysene compound>

The dibenzochrysene compound as a host is a compound represented by the following general formula (5), for example.

In the above formula (5),

R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl (this heteroaryl may be bonded to the dibenzochrysene skeleton in formula (5) through a linking group), diarylamino, dihetero Arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl,

In addition, adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring may be aryl or heteroaryl (the heteroaryl is bonded to the ring formed in question through a linking group, May be), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be aryl, heteroaryl, It may be substituted with alkyl or cycloalkyl, and,

At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of the above formula (5), the description of the polycyclic aromatic compound of the above formula (1) or (2) can be cited.

As the alkenyl in the definition of the formula (5), for example, alkenyl having 2 to 30 carbon atoms is exemplified, alkenyl having 2 to 20 carbon atoms is preferable, and alkenyl having 2 to 10 carbon atoms is more It is preferable, alkenyl having 2 to 6 carbon atoms is more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-phen Tenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

In addition, as a specific example of heteroaryl, a monovalent having a structure of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) You can pray.

In formulas (5-Ar1) to (5-Ar5), Y ¹ is each independently O, S or NR, and R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,

At least one hydrogen in the structures of the formulas (5-Ar1) to (5-Ar5) is substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. You may have it.

These heteroaryl may be bonded to the dibenzochrysene skeleton in the formula (5) via a linking group. That is, not only the dibenzochrysene skeleton in formula (5) and the heteroaryl are directly bonded, but may be bonded therebetween through a linking group. As this linking group, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, etc. are mentioned.

As for the compound represented by general formula (5), Preferably R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are hydrogen. In this case, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5) are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, Phenanthrenyl, a monovalent group having a structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) The monovalent group has, through phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O- or -OCH ₂ CH ₂ O-, the above formula It may be bonded with the dibenzochrysene skeleton in (5)), and it is preferable that it is methyl, ethyl, propyl, or butyl.

The compound represented by the general formula (5) is more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and R ¹⁶ It is hydrogen. In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5) is a single bond, phenylene, biphenylene, Naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O- or -OCH ₂ CH ₂ O- through the above formula (5-Ar1), formula (5-Ar2) , Is a monovalent group having the structure of formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5),

Other than the at least one (i.e., other than the position where the monovalent group having the above structure is substituted) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one in these The hydrogen of the dog may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl.

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

As a specific example of the dibenzochrysene type compound, the compound represented by any one of following formula (5-1)-formula (5-39) is mentioned, for example. In addition, "tBu" in the following structural formula represents a t-butyl group.

<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 and mixing one or two or more types of electron transport/injection materials, respectively, or a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting electrons. It is preferable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferable that the material has high electron affinity, high electron mobility, excellent stability, and difficult to generate trapping impurities during manufacture and use. However, in the case of considering the transport balance of holes and electrons, in the case where the main role is to effectively block the flow of holes from the anode to the cathode side without recombination, the luminous efficiency is improved even if the electron transport capacity is not very high. It has the same effect as a material having a high electron transport ability. Therefore, the electron injection/transport layer in the present embodiment may also contain a function of a layer capable of effectively preventing the movement of holes.

As a material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a polycyclic aromatic compound represented by the general formula (1) as the first component described above or a structure represented by the general formula (1) In addition to a multimer of a polycyclic aromatic compound having a plurality of and a compound as a second component, a compound conventionally used as an electron transfer compound in a photoconductive material, a known compound used in an electron injection layer and an electron transport layer of an organic EL device It can be arbitrarily selected and used.

As the material used for the electron transport layer or the electron injection layer, a compound consisting of an aromatic ring or a heteroaromatic ring consisting of at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, a pyrrole derivative and a condensed ring derivative thereof, and It is preferable to contain at least one type selected from metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives , Quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of 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. These materials may be used alone, but may be used by mixing 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 Compound, gallium complex, pyrazole derivative, perfluorinated phenylene derivative, triazine derivative, pyrazine derivative, benzoquinoline derivative (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -Spirobifluorene), 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, phosphor oxide derivatives, bisstyryl derivatives, etc. Can be lifted.

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

The above-described materials may be used alone, but may be used by mixing with other materials.

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

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (copper 2.28 eV), Rb (copper 2.16 eV) or Cs (copper 1.95 eV), Ca (copper 2.9 eV), Sr (copper 2.0 -2.5 eV) or Ba (copper 2.52 eV), and other alkaline earth metals, and a material having a work function of 2.9 eV or less is particularly preferable. Among these, a more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferable is Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to a material forming the electron transport layer or the electron injection layer, the luminance of light emission in the organic EL device and the lifespan thereof are increased. In addition, as a reducing material 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 containing Cs, the reducing ability can be exhibited efficiently, and by addition to a material for forming an electron transport layer or an electron injection layer, the luminance of light emission in the organic EL device is improved and the lifespan thereof is increased.

<Cathode in organic electroluminescent device>

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

The material for 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 for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium -Indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.) and the like are preferable. In order to increase the electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, these low work function metals are generally unstable in the atmosphere in many cases. In order to improve this point, for example, a method of using an electrode having high stability by doping an organic layer with a trace amount of lithium, cesium or magnesium is known. 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, for electrode protection, 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, hydrocarbon-based Laminating a polymer compound or the like is exemplified as a preferred example. The manufacturing method of these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam vapor deposition, sputtering, ion plating and coating.

<Binder that can be used in each layer>

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 independently, but polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcar) as a polymer binder Bazol), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS Disperse in solvent-soluble resins such as resins and polyurethane resins, and curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. It is also possible to do.

<Method of manufacturing organic electroluminescent device>

Each layer constituting the organic EL device is a thin film using a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coat method, cast method, coating method, etc. It can be formed by setting it as. The film thickness of each layer thus formed is not particularly limited, and can be appropriately set according to the properties 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 vapor 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~+400℃, vacuum degree 10 ^-6 ~10 ^-3 Pa, deposition rate 0.01~50nm/sec, substrate temperature -150~+300℃, film thickness 2nm~5㎛ It is desirable to set appropriately within the range of.

Next, as an example of a method of manufacturing an organic EL device, a method of manufacturing an organic EL device comprising an anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode made of a host material and a dopant material will be described. do. On a suitable substrate, a thin film of an anode material is formed by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. On this, a host material and a dopant material are co-deposited to form a thin film to form a light emitting layer, and an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed as a cathode by evaporation or the like. An EL element is obtained. Further, in the fabrication of the organic EL device described above, it is also possible to reverse the fabrication order and fabricate in the order of a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode.

In the case of applying a DC voltage to the organic EL device thus obtained, it is sufficient to apply the anode with the polarity of + and the cathode with the polarity of -. When a voltage of about 2 to 40 V is applied, the transparent or semi-transparent electrode side (anode or cathode and Light emission from both) can be observed. Further, 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 be applied may be arbitrary.

<Application example of organic electroluminescent device>

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

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

Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (for example, Japanese Unexamined Patent Publication No. Hei 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281086, etc.). Moreover, as a display system of a display, a matrix, a segment system, etc. are mentioned, for example. Further, the matrix display and the segment display may coexist in the same panel.

In a matrix, pixels for display are arranged two-dimensionally, such as a grid or a mosaic, and characters and images are displayed as a set of pixels. The shape or size of the pixel is determined according to the application. For example, in PCs, monitors, and television images and characters, a square pixel with a side of 300 μm or less is usually used, and in the case of a large display such as a display panel, a pixel of the order of mm is used. do. In the case of a monochrome display, pixels of the same color may be arranged, but in the case of a color display, red, green, and blue pixels are arranged and displayed. In this case, there are typically a delta type and a stripe type. As a driving method of this matrix, either a linear-sequential driving method or an active matrix may be used. Line-sequential driving has the advantage that the structure is simple, but when the operation characteristics are taken into consideration, the active matrix may be excellent, and thus it is necessary to use differently depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is emitted. For example, display of time and temperature on a digital clock or thermometer, display of operating states of audio equipment and electronic cookers, and panel display of automobiles are exemplified.

Examples of the lighting device include lighting devices such as indoor lighting, backlights for liquid crystal displays, and the like (for example, Japanese Unexamined Patent Publication No. 2003-257621, Japanese Unexamined Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, and a sign. In particular, as a backlight for a liquid crystal display device, especially for a PC whose thickness reduction is a problem, considering that it is difficult to reduce the thickness since 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. It is characterized by light weight.

[Example]

Next, in order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention are shown, but the present invention is not limited thereto. First, a synthesis example of a polycyclic aromatic compound is described below.

Synthesis Example (1): Synthesis of Compound (1-501)

1,3-dibromo-5-fluorobenzene (50.0 g), carbazole (36.2 g), potassium carbonate (54.0 g) and N-methylpyrrolidone (NMP, 250 ml) were put into a flask under a nitrogen atmosphere. And stirred at 170°C for 6 hours. After the reaction, the reaction solution was cooled, water was added, and the precipitate was filtered. The precipitate was washed with water and methanol and dried, followed by purification with a silica gel column (eluent: toluene/heptane = 2/8 (volume ratio)), and further dissolving the crude body in toluene and reprecipitating with heptane. (A) was obtained (55.3 g).

Compound (A) (25.0 g), 3-(2-methylphenyl) phenol (25.2 g), copper iodide (0.60 g), tris (acetylacetonato) iron (2.20 g), potassium carbonate (34.0 g) and N- Methylpyrrolidone (NMP, 100 ml) was placed in a flask under a nitrogen atmosphere, and stirred at 150°C for 3 hours. After the reaction, the reaction solution was cooled, NMP was distilled off under reduced pressure, water and ethyl acetate were added to the residue, stirred, and then filtered through Celite (registered trademark). Ammonia water was added to the filtrate, the water layer was removed after stirring, and the organic layer was washed with water twice, and the organic layer was concentrated under reduced pressure. The obtained crude product was purified by a silica gel column (eluent: toluene/heptane = 3/7 (volume ratio)) to obtain compound (B) (28.1 g).

In a flask containing compound (B) (25.0 g) and xylene (140 ml), while cooling with an ice bath under a nitrogen atmosphere, s-butyllithium/cyclohexane, n-hexane solution (1.05M, 41.1ml) ) Was added. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 3 hours, and then the low boiling point component was distilled off under reduced pressure. It cooled to -50 degreeC, boron tribromide (12.4 g) was added, and it heated up to room temperature and stirred for 0.5 hours. Then, it cooled again with an ice bath, and N,N-diisopropylethylamine (10.6 g) was added. After stirring at room temperature until heat generation subsided, it heated up to 120 degreeC, and heated and stirred for 4 hours, aluminum chloride (12.1 g) was further added, and it heated and stirred for 2 hours. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled with an ice bath, followed by addition of ethyl acetate, followed by stirring for 1 hour to precipitate a precipitate, and after adding heptane further, the precipitate was filtered. Subsequently, the precipitate was purified by a silica gel short column (eluent: toluene), further dissolved in toluene, reprecipitated with heptane, and finally sublimated and purified to obtain compound (1-501) (16.0 g).

The structure of the compound obtained from NMR measurement was confirmed.

¹ H NMR (? ppm in CDCl ₃ ); 2.4(s,6H), 7.3~7.4(m,10H), 7.4(m,2H), 7.5(m,2H), 7.5(s,2H), 7.6(d,2H), 7.7(d,2H) , 8.2(d,2H), 8.8(d,2H).

Synthesis Example (2): Synthesis of Compound (1-601)

1,3-dibromo-5-fluorobenzene (80.0g), 4-(9H-carbazol-9-yl)phenylboronic acid (130.9g), dichlorobis[(di-t-butyl) as a palladium catalyst (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 1.47 g), potassium phosphate (176 g), toluene (600 ml), isopropyl alcohol (IPA, 150 ml) and water (70 ml) were added to a flask in a nitrogen atmosphere. Then, it stirred at reflux temperature for 2 hours. After cooling the reaction liquid, water was added and stirred, and toluene was added to perform liquid separation and extraction to remove the water layer, and then the organic layer was washed with water. The crude product obtained by concentrating the organic layer under reduced pressure was further washed with a mixed solution of heptane/ethyl acetate = 4/1 (volume ratio) to obtain compound (C) (166 g).

Compound (C) (25.0g), 3-(2-methylphenyl)phenol (28.5g), potassium carbonate (39.0g) and NMP (150ml) were put in a flask under a nitrogen atmosphere, and stirred at 200°C for 2 hours, Further, potassium phosphate (37 g) was added, followed by stirring at 200°C for 4 hours. After cooling the reaction solution, NMP was distilled off under reduced pressure, toluene and water were added and stirred, and then the water layer was removed. Further, after washing the organic layer with water twice, the organic layer was concentrated under reduced pressure. The obtained crude was purified by a silica gel column (eluent: toluene/heptane = 3/7 (volume ratio), then changed to 4/6 (volume ratio)) to obtain compound (D) (40 g).

To a flask containing compound (D) (39.0 g) and xylene (190 ml), s-butyllithium/cyclohexane and n-hexane solution (1.05M, 57.0 ml) were added while cooling with an ice bath under a nitrogen atmosphere. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 3 hours, and then the component having a low boiling point was distilled off under reduced pressure. It cooled to -50 degreeC, boron tribromide (17.1 g) was added, and it heated up to room temperature and stirred for 0.5 hours. Then, it cooled again with an ice bath, and N,N-diisopropylethylamine (14.7 g) was added. After stirring at room temperature until heat generation subsided, it heated up to 130 degreeC and stirred for 4 hours after heating. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled with an ice bath, followed by addition of ethyl acetate, followed by stirring for 1 hour to precipitate a precipitate, and after adding heptane further, the precipitate was filtered. The precipitate was washed with methanol, water, ethyl acetate, and heptane in that order, and then the solid was dried, further suspended in ethyl acetate, washed by refluxing, further dissolved in hot chlorobenzene, concentrated and reprecipitated, and finally By sublimation purification, a compound (1-601) was obtained (27.0 g).

The structure of the compound obtained from NMR measurement was confirmed.

¹ H NMR (? ppm in CDCl ₃ ); 2.4(s,6H), 7.3~7.4(m,8H), 7.4(m,4H), 7.4~7.5(m,2H), 7.5(d,2H), 7.6(d,2H), 7.6(s, 2H), 7.7(d,2H), 8.0(d,2H), 8.2(d,2H), 8.8(d,2H).

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

Synthesis Example (3): Synthesis of a compound of formula ETM-1-(4)

1-Bromo-4-dimesitylborylnaphthalene (14g), bis(pinacolato)diboron(9.5g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II)dichloro A dimethyl sulfoxide solution (175 ml) containing lead (760 mg) and potassium acetate (9.1 g) was heated at 80°C and stirred for 2 hours. After completion of the reaction, it was cooled to room temperature, pure water was added, and the organic layer was extracted. The organic layer was concentrated by an evaporator and column-purified to obtain 1-dimesitylboryl-4-(4,4,5,5-tetramethyl-1,3-dioxaboran-2-yl)naphthalene (13 g ).

A dimethyl sulfoxide solution (100 ml) containing nitrogen gas flow, carbazole (3.1 g), 1-bromo-4-fluoronaphthalene (5 g) and cesium carbonate (7.2 g) was heated to 150° C., It stirred for 3 hours. After completion of the reaction, it was cooled to room temperature, the precipitated precipitate was separated by filtration, and the filtrate was concentrated with an evaporator. Then, by purifying by column and recrystallization, 9-(4-bromonaphthalen-1-yl)-carbazole was obtained (5.8 g).

1-Dimesitylboryl-4-(4,4,5,5-tetramethyl-1,3-dioxaboran-2-yl)naphthalene (2g), 9-(4-bromonaphthalen-1-yl) )-Carbazole (1.5 g), palladium acetate (54 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (198 mg) and potassium phosphate (3.4 g) containing toluene (40 ml) ), ethanol (10 ml) and pure water (10 ml) were stirred at reflux for 16 hours. After completion of the reaction, it was cooled to room temperature, pure water was added, and the organic layer was extracted. This organic layer was concentrated by an evaporator and purified by column and recrystallization to obtain a compound of formula ETM-1-(4) (1.4 g).

Synthesis Example (4): Synthesis of a compound of formula ETM-1-(2)

It synthesized by the method according to the synthesis example (3).

Synthesis Example (5): Synthesis of a compound of formula ETM-2-(2)

First, 2-chloroanthracene (5.00g), phenylboronic acid (4.3g), tris (dibenzylideneacetone) 2 palladium (0) (538 mg), tricyclohexylphosphine (494 mg), 3 potassium phosphate (9.98 g) ) And toluene (75 ml) were put into a flask, and stirred at reflux temperature under an argon atmosphere for 2 hours. After completion of the heating, toluene (1.5 L) was added to the reaction solution, cooled to room temperature, filtered and separated, and the filtrate was purified by a silica gel column (eluent: toluene). The solvent was distilled off under reduced pressure, and the concentrate was recrystallized from toluene to obtain 2-phenylanthracene (5.0 g).

Next, 2-phenylanthracene (3.32 g) was dissolved in dichloromethane (400 ml) in a flask under a nitrogen atmosphere. A carbon tetrachloride solution (30 ml) of bromine (5.00 g) was dripped there over 15 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, and the reaction was stopped with an aqueous sodium thiosulfate solution. The organic layer was extracted with a separating funnel, concentrated with an evaporator, and the concentrate was recrystallized with toluene (50 ml) to obtain 9,10-dibromo-2-phenylanthracene (4.4 g).

Next, 9,10-dibromo-2-phenylanthracene (10.0 g), bis (pinacolato) diboron (14.8 g), bis (dibenzylideneacetone) palladium (0) (838 mg), tricyclo Hexylphosphine (1.02 g), potassium acetate (7.15 g), and 1,4-dioxane (50 ml) were put into a flask, and the mixture was stirred under an argon atmosphere at reflux temperature for 8 hours. After completion of the heating, toluene was added to the reaction solution, cooled to room temperature, filtered and separated, and the filtrate was concentrated by an evaporator. The concentrate was purified by a silica gel column (eluent: toluene), and then recrystallized from a tetrahydrofuran/heptane mixed solution to obtain 9,10-bis(4,4,5,5-tetramethyl-1,3,2- Dioxaborolanyl)-2-phenylanthracene was obtained (8.3 g).

Finally, 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-2-phenylanthracene (0.80g), 5-bromo-2, 2'-bipyridine (0.83 g), tris (dibenzylideneacetone) 2 palladium (0) (88 mg), tricyclohexylphosphine (81 mg), 3 potassium phosphate (1.36 g) and toluene (35 ml) were added to a flask. Then, the mixture was stirred for 27 hours and a half at reflux temperature under an argon atmosphere. After the completion of heating, the reaction solution was cooled to room temperature, pure water was added, and the organic layer was extracted. The organic layer was concentrated by an evaporator, the concentrate was purified by an activated alumina column (eluent: toluene), and further recrystallized with a mixed solvent of chloroform/ethyl acetate to obtain the compound (9,10-bis) of the formula ETM-2-(2). (2,2'-bipyridin-5-yl)-2-phenylanthracene) was obtained (198 mg).

The structure of the obtained compound was confirmed by NMR measurement.

¹ H-NMR (CDCl ₃ ): δ=7.3(t,1H), 7.4(m,6H), 7.6(d,2H), 7.7(m,3H), 7.8(d,1H), 7.9(m, 3H), 8.0(m,2H), 8.6(d,2H), 8.7(d,2H), 8.8(m,2H), 8.9(m,2H).

Synthesis Example (6): Synthesis of a compound of formula ETM-2-(4)

It synthesized by the method according to the synthesis example (5).

Synthesis Example (7): Synthesis of a compound of formula ETM-8-(2)

Synthesis Example (8): Synthesis of a compound of formula ETM-8-(5)

These pyrimidine derivatives were synthesized by known raw materials and known synthesis methods with reference to International Publication No. 2011/021689.

Synthesis Example (9): Synthesis of a compound of formula ETM-16-(12)

2,6-dichloropyridin-4-ylboronic acid (1.7 g), 4-iodine-1,1'-biphenyl (5.0 g), dichlorobis (triphenylphosphine) palladium (0.06 g), potassium carbonate (2.5 g), tetra-n-butylammonium bromide (0.6 g), toluene (20 ml) and water (2 ml) were placed in a flask, and stirred for 5 hours while heating to reflux under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and toluene was further added to perform liquid separation extraction. The organic layer was separated, dried and concentrated, and the crude product was purified by a silica gel column (eluent: toluene/heptane = 1/1 (volume ratio), then 3/1 (volume ratio)), thereby 4-([1,1'- Biphenyl]-4-yl)-2,6-dichloropyridine was obtained (1.8 g).

4-([1,1'-biphenyl]-4-yl)-2,6-dichloropyridine (1.4g), 4,4-dimethyl-2-(4-(4,4,5,5-tetra Methyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazoline (4.2g), bis(dit-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (0.1g), Potassium carbonate (2.6 g), tetra-n-butylammonium bromide (0.3 g), cyclopentylmethyl ether (20 ml), and water (2 ml) were placed in a flask and stirred for 7 hours while heating to reflux under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and toluene was further added to perform liquid separation extraction. The organic layer was separated, dried, concentrated, and the crude product was purified by a silica gel column (eluent: toluene/ethyl acetate = 7/3 (volume ratio)), followed by sublimation purification to obtain a compound of formula ETM-16-(12) ( 4-([1,1'-biphenyl]-4-yl)-2,6-bis(4-(4,4-dimethyloxazolin-2-yl)phenyl)pyridine) was obtained (1.1 g).

The structure of the obtained compound was confirmed by NMR measurement.

¹ H-NMR(CDCl ₃ ): δ=8.3(d,4H), 8.1(d,4H), 8.0(s,2H), 7.8(d,2H), 7.8(d,2H), 7.7(m, 2H), 7.5 (t, 2H), 7.4 (tt, 1H), 4.2 (s, 4H), 1.4 (s, 12H).

Synthesis Example (10): Synthesis of a compound of formula ETM-16-(15)

4-([1.1'-biphenyl]-4-yl)-2,6-dichloropyrimidine (1.6 g), 4,4-dimethyl-2- synthesized by the method described in International Publication No. 2012/096263 (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazoline (4.8g), bis(dit-butyl(4-dimethyl) Aminophenyl (phosphine) dichloropalladium (0.1 g), potassium carbonate (2.9 g), tetra-n-butylammonium bromide (0.3 g), cyclopentylmethyl ether (20 ml) and water (2 ml) were added to a flask, and nitrogen The reaction mixture was stirred for 10 hours while heating and refluxing in an atmosphere, the reaction solution was cooled to room temperature, water was added, and toluene was further added to perform liquid separation extraction After separating the organic layer, it was dried and concentrated, and the crude product was subjected to a silica gel column (eluent : After purification with toluene/ethyl acetate = 4/1 (volume ratio)), by sublimation purification, the compound of formula ETM-16-(15) (6-([1,1'-biphenyl]-4-yl) -2,4-bis(4-(4,4-dimethyloxazolin-2-yl)phenyl)pyrimidine) was obtained (1.2 g).

The structure of the obtained compound was confirmed by NMR measurement.

¹ H-NMR(CDCl ₃ ): δ=8.8(d,2H), 8.4(d,2H), 8.3(d,2H), 8.1(m,5H), 7.8(d,2H), 7.7(d, 2H), 7.4 (t, 2H), 7.4 (t, 1H), 4.2 (s, 4H), 1.4 (s, 12H).

By appropriately changing the compound of the raw material, the derivative (second component) of the present invention can be synthesized by a method according to the synthesis example described above.

<Evaluation of organic EL device>

The organic EL devices according to Examples 1-1 to 1-9, Comparative Examples 1-1 and 1-2 were fabricated, and the voltage (V), the emission wavelength (nm), which are characteristics at the time of 1000 cd/m ² light emission, The external quantum efficiency (%) was measured, and then the time to maintain the luminance of 95% or more of the initial luminance when the constant current was driven at a current density of 22.5 mA/cm 2 was measured.

Quantum efficiency of a light emitting device includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency represents a ratio at which external energy injected as electrons (or holes) into the light emitting layer of the light emitting device is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of this photon emitted to the outside of the light-emitting element, and the photons generated in the light-emitting layer are partially absorbed inside the light-emitting element or are continuously reflected. Since it is not emitted to the outside, the external quantum efficiency becomes lower than the internal quantum efficiency.

The method of measuring the external quantum efficiency is as follows. Using the voltage/current generator R6144 manufactured by Advantest, the device was made to emit light by applying a voltage such that the luminance of the device is 1000 cd/m ² . Using a spectroscopic radiation luminance meter SR-3AR manufactured by TOPCON, the spectral radiation luminance in the visible light region was measured from the direction perpendicular to the light-emitting surface. Assuming that the light-emitting surface is a fully diffused surface, a value obtained by dividing the measured value of the spectral radiation luminance of each wavelength component by the wavelength energy and multiplied by π is the number of photons at each wavelength. Subsequently, the number of photons was accumulated over the entire observed wavelength range to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the small charge is the number of carriers injected into the device, and the number obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

Fabrication of organic EL device

Organic EL devices according to Examples and Comparative Examples were fabricated according to the layer structure shown in Table 1 below. However, the present invention is not limited to the layer structure shown in Table 1, and the film thickness and material of each layer can be appropriately changed according to the basic physical properties of the compound to be combined.

Precision
Injection layer 1
40nm
Precision
Injection layer 2
5nm
Precision
Transport layer 1
45nm
Precision
Transport layer 2
10nm
Emitting layer
25nm

Electronic
Transport layer
30nm
Weight ratio 1:1
cathode
1nm/
100nm
Host
Dopant
Example 1
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-501)
+
ETM-1-(2)
Liq/
MgAg
Example 2
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-601)
+
ETM-1-(4)
Liq/
MgAg
Example 3
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-501)
+
ETM-2-(2)
Liq/
MgAg
Example 4
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-601)
+
ETM-2-(7)
Liq/
MgAg
Example 5
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-601)
+
ETM-2-(4)
Liq/
MgAg
Example 6
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-501)
+
ETM-8-(2)
Liq/
MgAg
Example 7
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-601)
+
ETM-8-(5)
Liq/
MgAg
Example 8
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-501)
+
ETM-16-(12)
Liq/
MgAg
Example 9
HI
IL
HT-1
HT-2
BH1
BD1 compound
(1-601)
+
ETM-16-(15)
Liq/
MgAg
Comparative Example 1
HI
IL
HT-1
HT-2
BH1
BD1
compound
(1-501)
Liq/
MgAg
Comparative Example 2
HI
IL
HT-1
HT-2
BH1
BD1
compound
(1-601)
Liq/
MgAg

In Table 1, "HI" is N ^4, N ^{4 '-} diphenyl -N ^4, N ^4' - bis (9-phenyl -9H- carbazole-3-yl) [1,1'-biphenyl ]-4,4'-diamine, "IL" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile, "HT-1" is N-([1,1' -Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and "HT -2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine, "BH1" is 2-(10-phenylanthracene-9-yl)naphtho[2,3-b]benzofuran, and "BD1" is 2,12-di-t-butyl-5,9-bis(4 -(t-butyl)phenyl)-7-methyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene together with "Liq" Show the chemical structure in

In addition, the compounds used in the electron transport layer in Table 1 are the compounds of the general formula (1) and the compounds of the second component used together, and their chemical structures are the description of the general formula (1) and the second component. It is shown in the description column of the compound.

<Example 1>

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) was used as a transparent support substrate by polishing ITO formed by sputtering to a thickness of 200 nm to 120 nm. This transparent support substrate was fixed to a substrate holder of a commercial vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and HI, IL, HT-1, HT-2, BH1, BD1, Compound (1-501) and ETM-1 The tantalum evaporation boat containing -(2), respectively, and the aluminum nitride evaporation boat containing Liq, Mg, and Ag respectively, were attached.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum bath was decompressed to 5×10 ^-4 Pa, first, HI was heated to evaporate to a film thickness of 40 nm, and then, IL was heated to evaporate to a film thickness of 5 nm, and then, HT-1 Was heated to evaporate to have a film thickness of 45 nm, and then, HT-2 was heated to evaporate to have a film thickness of 10 nm to form a hole layer consisting of four layers. Next, BH1 and BD1 were simultaneously heated and vapor-deposited to have a thickness of 25 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of BH1 and BD1 was approximately 98 to 2. Further, compound (1-501) and ETM-1-(2) were simultaneously heated to evaporate to have a thickness of 30 nm to form an electron transport layer (which also serves as an electron injection layer). The deposition rate was adjusted so that the weight ratio of compound (1-501) and ETM-1-(2) was approximately 50 to 50. The deposition rate of each layer is 0.01 to 1 nm/sec. Thereafter, Liq is heated to evaporate at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness becomes 1 nm, and then, magnesium and silver are simultaneously heated to evaporate to a film thickness of 100 nm to form a cathode, and an organic EL device Got it. At this time, the deposition rate was adjusted between 0.1 and 10 nm/sec so that the atomic ratio of magnesium and silver was 10 to 1.

As a result of applying a DC voltage using the ITO electrode as the anode and the Mg/Ag electrode as the cathode, and measuring the characteristics at 1000 cd/m2 light emission, blue light emission was obtained, the driving voltage was 4.90V, and the external quantum efficiency was 6.23%. . In addition, the device life was 120 hours.

<Examples 2 to 9, Comparative Examples 1 to 2>

In the same manner as in Example 1, elements of Examples 2 to 9 and Comparative Examples 1 to 2 were produced, and EL characteristics were measured. The obtained properties are combined and shown in Table 2 below.

Voltage
(V) External quantum efficiency
(%) Device life
(time) Example 1 4.90 6.23 120 Example 2 4.82 6.30 110 Example 3 3.67 6.47 200 Example 4 3.62 7.02 140 Example 5 3.85 6.53 150 Example 6 3.80 7.56 220 Example 7 3.75 7.35 250 Example 8 3.92 6.90 220 Example 9 3.95 6.95 190 Comparative Example 1 6.18 5.79 80 Comparative Example 2 5.95 6.02 50

As described above, some of the compounds according to the present invention were evaluated as materials for organic EL devices, and were shown to be excellent materials, but other compounds that were not evaluated also have the same basic skeleton and are compounds having a similar structure as a whole. It can be understood that, for those skilled in the art, it is an excellent material for an organic EL device.

According to a preferred embodiment of the present invention, by producing an organic EL device using at least one of an electron transport layer and an electron injection layer formed by combining a polycyclic aromatic compound represented by formula (1) and a specific compound, quantum efficiency and driving voltage And it is possible to provide an organic EL device excellent in any one or more of the device life, particularly the device life.

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 (21)

An organic electroluminescent device having at least one of a pair of electrodes consisting of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, and an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, At least one of the electron transport layer and the electron injection layer is a polycyclic aromatic compound represented by the following general formula (1) as a first component or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1), and a second As a component, borane derivative, pyridine derivative, fluoranthene derivative, BO derivative, anthracene derivative, benzofluorene derivative, phosphine oxide derivative, pyrimidine derivative, carbazole derivative, triazine derivative, benzoimidazole derivative, phenanthroline An organic electroluminescent device comprising at least one compound selected from the group consisting of derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives.

(In the above formula (1),
A ring, B ring, and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is aryl, alkyl or cycloalkyl. ,
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S, or >Se, and R of >NR is an optionally substituted aryl or optionally substituted heteroaryl , Optionally substituted alkyl or optionally substituted cycloalkyl, wherein R in >C(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or substituted Cycloalkyl which may be present, and at least one R of the >NR and the >C(-R) ₂ is bonded to at least one of the A ring, the B ring and the C ring by a linking group or a single bond, May be,
At least one of ring A, ring B, ring C, aryl, and heteroaryl in the compound or structure represented by formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane Hydrogen of the dog may be substituted, at least one of -CH ₂ -in the cycloalkane may be substituted with -O-, and,
At least one hydrogen in the compound or structure represented by formula (1) may be substituted with cyano, halogen, or deuterium.) The method according to claim 1, wherein in the formula (1),
Ring A, Ring B, and Ring C are each independently an aryl ring or heteroaryl ring, and at least one hydrogen in these rings is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Of diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded through a single bond or a linking group), Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy or substituted silyl may be substituted, and these rings are Y ¹ , X ¹ and X ^It has a 5-membered ring or a 6-membered ring that shares a bond with the condensed bicyclic structure of the above formula consisting of 2,
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is aryl, alkyl or cycloalkyl. ,
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >S or >Se, and R of >NR is an aryl or alkyl which may be substituted with alkyl or cycloalkyl. Or heteroaryl, alkyl or cycloalkyl which may be substituted with cycloalkyl, and R of >C(-R) ₂ may be substituted with aryl, alkyl or cycloalkyl which may be substituted with hydrogen, alkyl or cycloalkyl. Is heteroaryl, alkyl, or cycloalkyl, and at least one of R of the >NR and >C(-R) ₂ is -O-, -S-, -C(-R) ₂ -or a single bond May be bonded to at least one of the ring A, ring B, and ring C, and R of -C(-R) ₂ -is hydrogen, alkyl or cycloalkyl,
At least one of ring A, ring B, ring C, aryl, and heteroaryl in the compound or structure represented by formula (1) may be condensed with at least one cycloalkane, and at least one in the cycloalkane Hydrogen may be substituted, at least one -CH ₂ -in the cycloalkane may be substituted with -0-,
In the case of a multimer, it is a dimer or trimer having two or three structures represented by general formula (1), and,
An organic electroluminescent device, wherein at least one hydrogen in the compound or structure represented by formula (1) may be substituted with cyano, halogen or deuterium. The polycyclic aromatic compound according to claim 1, wherein the polycyclic aromatic compound represented by the formula (1) is a polycyclic aromatic compound represented by the following general formula (2), and a multimer of the polycyclic aromatic compound having a plurality of structures represented by the formula (1) is An organic electroluminescent device, characterized in that it is a multimer of polycyclic aromatic compounds having a plurality of structures represented by (2).

(In the above formula (2),
Arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) may be substituted with "-N=" , Arbitrary ``-C(-R)=C(-R)-'' (where R is R <sup>1</sup> to R <sup>11</sup> in formula (2)), ``-N(-R)-'', ``-O -" or "-S-" may be substituted, and R of "-N(-R)-" is an aryl, alkyl or cycloalkyl,
R <sup>1</sup> to R <sup>11</sup> are each independently hydrogen, 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, and at least one hydrogen in these is aryl, hetero Aryl, alkyl or cycloalkyl may be substituted, and adjacent groups of R <sup>1</sup> to R <sup>11</sup> may be bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring, and the formed ring At least one hydrogen in is 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 may be substituted, and at least one hydrogen in them is aryl, May be substituted with heteroaryl, alkyl or cycloalkyl,
Y <sup>1</sup> is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, C1-C6 alkyl or C3-C14 cycloalkyl,
X <sup>1</sup> and X <sup>2</sup> are each independently >O, >NR, >C(-R) <sub>2</sub> , >S or >Se, and R of >NR is an aryl having 6 to 12 carbon atoms, and having 2 to 15 carbon atoms. Heteroaryl, C1-C6 alkyl or C3-C14 cycloalkyl, and R of >C(-R) <sub>2</sub> is hydrogen, C6-C12 aryl, C2-C15 heteroaryl, C1 -6 alkyl or C3-C14 cycloalkyl, and at least one R of >NR and >C(-R) <sub>2</sub> is -O-, -S-, -C(-R) <sub>2</sub> -Or by a single bond, it may be bonded to at least one of the ring a, ring b, and ring c, and R of -C(-R) <sub>2</sub> -is an alkyl having 1 to 6 carbon atoms or 3 to 14 carbon atoms. Cycloalkyl,
At least one of the a ring, the b ring, the c ring, the formed ring, aryl, and heteroaryl in the compound or structure represented by formula (2) is at least one cycloalkane having 3 to 24 carbon atoms. Condensation may be sufficient, and at least one hydrogen in the cycloalkane may be substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a C1-C24 alkyl, or a C3-C24 cycloalkyl And at least one of -CH <sub>2</sub> -in the cycloalkane may be substituted with -O-,
In the case of a multimer, it is a dimer or trimer having two or three structures represented by formula (2), and,
At least one hydrogen in the compound or structure represented by formula (2) may be substituted with cyano, halogen or deuterium.) The method according to claim 3, wherein in formula (2),
Arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R <sup>1</sup> to R <sup>11</sup> in formula (2)) may be substituted with "-N=" , Arbitrary ``-C(-R)=C(-R)-'' (where R is R ¹ to R ¹¹ in formula (2)), ``-N(-R)-'', ``-O -" or "-S-" may be substituted, and R of "-N(-R)-" is a C6-C12 aryl, a C1-C6 alkyl, or a C3-C14 cycloalkyl, ,
R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 12 carbon atoms), diaryl boryl (however, aryl Is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (however, aryl is 6 carbon atoms -12 aryl) or trialkylsilyl (however, alkyl is an alkyl having 1 to 6 carbon atoms), and adjacent groups among R ¹ to R ¹¹ are bonded to each other to form a ring a, a ring b, or a ring c together with 9 to carbon atoms. A 16 aryl ring or a C6-C15 heteroaryl ring may be formed, and at least one hydrogen in the formed ring is a C6-C30 aryl, a C2-C30 heteroaryl, or a diarylamino (provided , Aryl is an aryl having 6 to 12 carbon atoms), diaryl boryl (however, aryl is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded through a single bond or a linking group), alkyl having 1 to 24 carbon atoms, C3-C24 cycloalkyl, triarylsilyl (however, aryl is a C6-C12 aryl) or trialkylsilyl (however, alkyl is a C1-C6 alkyl) may be substituted,
Y ¹ is B, P, P=O, P=S or Si-R, and R of Si-R is a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl Is,
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , or >S, and R of >NR is aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or It is a C5-C10 cycloalkyl, wherein R of >C(-R) ₂ is hydrogen, a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl,
At least one of the a ring, the b ring, the c ring, the formed ring, aryl, and heteroaryl in the compound or structure represented by formula (2) is at least one cycloalkane having 3 to 20 carbon atoms. Condensation may be performed, and at least one hydrogen in the cycloalkane may be substituted with a C6-C16 aryl, a C2-C22 heteroaryl, a C1-C12 alkyl, or a C3-C16 cycloalkyl. Become,
In the case of a multimer, it is a dimer having two structures represented by formula (2), and,
An organic electroluminescent device, wherein at least one hydrogen in the compound or structure represented by formula (2) may be substituted with cyano, halogen or deuterium. The method according to claim 3, wherein in formula (2),
Even if arbitrary "-C(-R)=" in ring a, ring b, and ring c (where R is R ¹ to R ¹¹ in formula (2)) is substituted with "-N=" And arbitrary "-C(-R)=C(-R)-" (where R is R ¹ to R ¹¹ in Formula (2)) is "-N(-R)-", "- O-" or "-S-" may be substituted, and R of "-N(-R)-" is a C6-C10 aryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl Is,
R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 10 carbon atoms), diaryl boryl (however, aryl Is a C6-C10 aryl, the two aryl may be bonded through a single bond or a linking group), C1-C12 alkyl or C3-C16 cycloalkyl,
Y ¹ is B, P, P=O or P=S,
X ¹ and X ² are each independently >O or >NR, and R of >NR is an aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,
At least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R in the compound or structure represented by formula (2) is at least 1 having 3 to 16 carbon atoms. May be condensed with two cycloalkanes, and at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
In the case of a multimer, it is a dimer having two structures represented by formula (2), and,
An organic electroluminescent device, wherein at least one hydrogen in the compound or structure represented by formula (2) may be substituted with cyano, halogen or deuterium. The method according to claim 3, wherein in formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (however, aryl is an aryl having 6 to 10 carbon atoms), diaryl boryl (however, aryl is an aryl having 6 to 10 carbon atoms, , Two aryl may be bonded through a single bond or a linking group), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms,
Y ¹ is B,
X ¹ and X ² are each independently >O or >NR, and R of >NR is an aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,
At least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R in the compound or structure represented by formula (2) is a cycloalkane having 3 to 14 carbon atoms. May be condensed with, at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 5 carbon atoms,
In the case of a multimer, it is a dimer having two structures represented by formula (2), and,
An organic electroluminescent device, wherein at least one hydrogen in the compound represented by formula (2) may be substituted with cyano, halogen or deuterium. The organic electroluminescent device according to claim 1, wherein the polycyclic aromatic compound as the first component is a compound represented by any one of the following formulas.

"Me" in the above structural formula represents a methyl group. The organic electroluminescent device according to any one of claims 1 to 7, wherein the borane derivative as the second component is a compound represented by the following general formula (ETM-1-1).

In formula (ETM-1-1),
R ¹¹ and R ¹² are each independently aryl, heteroaryl, alkyl, cycloalkyl, triarylsilyl, trialkylsilyl, or cyano, and n is each independently an integer of 0 to 3,
R ¹³ to R ¹⁶ are each independently aryl, alkyl, or cycloalkyl,
R ²¹ and R ²² are each independently aryl, heteroaryl, alkyl, cycloalkyl, triarylsilyl, trialkylsilyl, or cyano, and m is each independently an integer of 0-4,
X ¹ is a divalent group represented by any one of the following formulas (X-1) to (X-9), and * in each structural formula represents a bonding position,

In the formulas (X-1) to (X-9), each of R is independently alkyl, cycloalkyl, or aryl which may be substituted with alkyl,
At least one hydrogen in the compound represented by the formula (ETM-1-1) may be substituted with deuterium. The method according to claim 8, wherein in formula (ETM-1-1),
R ¹¹ and R ¹² are each independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (however, aryl is Aryl of ~ 10), trialkylsilyl (however, alkyl is an alkyl having 1 to 5 carbon atoms), or cyano, and n is each independently an integer of 0 to 2,
R ¹³ to R ¹⁶ are each independently aryl having 6 to 16 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,
R ²¹ and R ²² are each independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (however, aryl is Aryl of ~ 10), trialkylsilyl (however, alkyl is an alkyl having 1 to 5 carbon atoms), or cyano, m is each independently an integer of 0-2,
X ¹ is a divalent group represented by any one of formulas (X-1) to (X-9), and * in each structural formula represents a bonding position,
In the above formulas (X-1) to (X-9), R is each independently a number of carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or alkyl having 1 to 5 carbon atoms. 6-10 aryl,
An organic electroluminescent device, wherein at least one hydrogen in the compound represented by the formula (ETM-1-1) may be substituted with deuterium. The organic electroluminescent device according to claim 8, wherein the borane derivative as the second component is a compound represented by any one of the following formulas.

"Me" in the above structural formula represents a methyl group. The organic electroluminescent device according to any one of claims 1 to 7, wherein the pyridine derivative as the second component is a compound represented by the following general formula (ETM-2-1).

In the above formula (ETM-2-1),
R ¹¹ to R ¹⁸ are each independently hydrogen, aryl, alkyl, or cycloalkyl,
Py is each independently a group represented by any one of the following formulas (Py-1) to (Py to 15), and at least one hydrogen in this group may be substituted with alkyl or cycloalkyl, and * in each structural formula Represents the bonding position,

Py may be bonded to the anthracene ring in the formula (ETM-2-1) via a phenylene group or a naphthylene group,
At least one of two Py in the formula (ETM-2-1) is a group represented by any one of the formulas (Py-1) to (Py-15), the other may be aryl, and the aryl is alkyl or May be substituted with cycloalkyl,
At least one hydrogen in the compound represented by the above formula (ETM-2-1) may be substituted with deuterium. The method according to claim 11, wherein in formula (ETM-2-1),
R ¹¹ to R ¹⁸ are each independently hydrogen, aryl having 6 to 16 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,
Py is each independently a group represented by any one of the following formulas (Py-21) to (Py-44), and at least one hydrogen in this group is an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. May be substituted with, and * in each structural formula represents a bonding position,

Py may be bonded to the anthracene ring in the formula (ETM-2-1) via a 1,4-phenylene group or a 1,4-naphthylene group,
At least one of two Py in the formula (ETM-2-1) is a group represented by any one of the formulas (Py-21) to (Py-44), and the other may be aryl having 6 to 16 carbon atoms, The said aryl may be substituted with C1-C12 alkyl or C3-C16 cycloalkyl,
An organic electroluminescent device, wherein at least one hydrogen in the compound represented by the formula (ETM-2-1) may be substituted with deuterium. The organic electroluminescent device according to claim 11, wherein the pyridine derivative as the second component is a compound represented by any one of the following formulas.

The organic electroluminescent device according to any one of claims 1 to 7, wherein the pyrimidine derivative as the second component is a compound represented by the following general formula (ETM-8-1).

In the above formula (ETM-8-1),
Ar is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these may be substituted with alkyl, cycloalkyl, or halogen,
At least one hydrogen in the compound represented by the formula (ETM-8-1) may be substituted with deuterium. The method according to claim 14, wherein in formula (ETM-8-1),
Ar is each independently a C6-C16 aryl, a C2-C15 heteroaryl, a C1-C12 alkyl, or a C3-C16 cycloalkyl, and at least one hydrogen in these is C1 It may be substituted with ~12 alkyl, C3-C16 cycloalkyl, or halogen,
An organic electroluminescent device, wherein at least one hydrogen in the compound represented by the formula (ETM-8-1) may be substituted with deuterium. The organic electroluminescent device according to claim 14, wherein the pyrimidine derivative as the second component is a compound represented by any one of the following formulas.

The method according to any one of claims 1 to 7, wherein the azoline derivative as the second component is a compound represented by the following general formula (ETM-16-1) or (ETM-16-2). Organic electroluminescent device.

In formula (ETM-16-1) and formula (ETM-16-2),
Φ is a divalent group represented by the following formula (Φ2-1), formula (Φ2-31), formula (Φ2-32), formula (Φ2-33), or formula (Φ2-34), in Φ At least one hydrogen may be substituted with C1-C6 alkyl, C6-C18 aryl, or C2-C18 heteroaryl, and * in each structural formula represents a bonding position,

m is 2,
Y is each independently -O-, -S-, or >N-Ar, Ar is a C6-C12 aryl or a C2-C12 heteroaryl, and at least one hydrogen in Ar is a C1 May be substituted with alkyl of ~4, aryl of 6 to 12 carbon atoms, or heteroaryl of 2 to 12 carbon atoms
R ¹ to R ⁵ are each independently hydrogen or alkyl having 1 to 4 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same,
L is selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline and pteridine. It is a divalent group of the ring, and at least one hydrogen in L may be substituted with an alkyl having 1 to 4 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms,
At least one hydrogen in the compound represented by the above formula (ETM-16-1) or (ETM-16-2) may be substituted with deuterium. The method according to claim 17, wherein in formulas (ETM-16-1) and (ETM-16-2),
Φ is a divalent group represented by the above formula (Φ2-31), formula (Φ2-32), formula (Φ2-33), or formula (Φ2-34), and at least one hydrogen in Φ has 6 carbon atoms May be substituted with aryl of ~18,
m is 2,
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 in Ar has 1 carbon number. It may be substituted with an alkyl of ~4 or aryl of 6 to 10 carbon atoms,
R ¹ to R ⁴ are each independently hydrogen or alkyl having 1 to 4 carbon atoms, provided that R ¹ and R ² are the same, R ³ and R ⁴ are the same, and all of R ¹ to R ⁴ are simultaneously hydrogen There is no case,
L is a divalent group of a ring 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, and 6 to carbon atoms. It may be substituted with 10 aryl or C2-C10 heteroaryl,
An organic electroluminescent device, wherein at least one hydrogen in the compound represented by the above formula (ETM-16-1) or (ETM-16-2) may be substituted with deuterium. The organic electroluminescent device according to claim 17, wherein the azoline derivative as the second component is a compound represented by any one of the following formulas.

The method according to any one of claims 1 to 19, wherein at least one of the electron transport layer and the electron injection layer is an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, and an alkaline earth metal. At least one selected from the group consisting of oxides 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. An organic electroluminescent device comprising. A display device or lighting device comprising the organic electroluminescent element according to any one of claims 1 to 20.

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