KR20230034895A - Polycyclic aromatic compounds - Google Patents

Abstract

The present invention relates to a polycyclic aromatic compound. The polycyclic aromatic compound has a structure consisting of one or two or more structural units represented by Formula (1). According to the present invention, a novel polycyclic aromatic compound, which is useful as a material for organic devices such as organic electroluminescent elements, is provided.

Description

Polycyclic aromatic compounds {POLYCYCLIC AROMATIC COMPOUNDS}

The present invention relates to polycyclic aromatic compounds. The present invention particularly relates to polycyclic aromatic compounds containing nitrogen and boron. The present invention also relates to a material for an organic device, an organic electroluminescent device, and a display device and a lighting device including the polycyclic aromatic compound.

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

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

Among them, Patent Literature 1 discloses that a boron-containing polycyclic aromatic compound is useful as a material for an organic electroluminescent device or the like. It has been reported that an organic electroluminescent device containing this polycyclic aromatic compound has good external quantum efficiency. Patent Literature 2 and Patent Literature 3 disclose polycyclic aromatic compounds containing boron condensed with heterocycles such as benzothiophene.

Patent Document 1: International Publication No. 2015/102118 Patent Document 2: International Publication No. 2020/111830 Patent Document 3: International Publication No. 2020/251049

As described above, although various materials have been developed as materials used for organic EL devices, development of materials composed of novel compounds is expected in order to increase the options of materials for organic EL devices.

An object of the present invention is to provide a useful novel compound as a material for organic devices such as an organic EL element.

In order to solve the above problems, the inventors of the present invention intensively studied and succeeded in producing a novel polycyclic aromatic compound having more excellent luminescent properties in a polycyclic aromatic compound having a structure similar to that of the compound described in Patent Literature 1. Furthermore, they found that an excellent organic EL device can be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes to constitute an organic EL device, and completed the present invention. That is, the present invention provides a polycyclic aromatic compound as described below, a material for an organic device containing the polycyclic aromatic compound as described below, and the like.

The present invention specifically has the following structures.

<1> A polycyclic aromatic compound having a structure composed of one or two or more structural units represented by the following formula (1);

In formula (1),

ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring;

Ring C is a ring represented by formula (C),

In formula (C),

X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR, the >C(-R) ₂ and the >Si( -R) R in ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and the two R of >Si(-R) ₂ above may be bonded to each other to form a ring;

Any two adjacent Z ^{C '} s are carbon directly bonded to either Y ¹ or X ² ,

other Z ^C are each independently N or CR ^C , and R ^C are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of diarylamino may be bonded to each other via a linking group, and the diheteroaryl The two heteroaryls of amino may be bonded to each other through a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group may be combined through

Two adjacent R ^Cs may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^C2 , and R ^C2 has the same meaning as R ^C , provided that R ^C2 is not hydrogen, and two adjacent R ^C2s do not bond to each other to form an aryl ring or a heteroaryl ring;

The ring represented by formula (C) is R ^C or R ^C2 and is aryl at least substituted with a group represented by formula (D-1) or formula (D-2) or formula (D-1) or formula (D-2). 2) includes a heteroaryl at least substituted with a group represented by;

The groups represented by formulas (D-1) and (D-2) are bonded to two ring-constituting atoms adjacent to each other in the aryl ring or heteroaryl ring in two *,

In the formulas (D-1) and (D-2), R ^D are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted is cycloalkyl, and L is each independently substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R in >NR is hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs of (-R) ₂ may be bonded to each other to form a ring, and R of >NR and/or R of >C(-R) ₂ may be bonded to ring A and/or ring A by a linking group or a single bond. / or may be bonded to the B ring, or the A ring and / or the C ring;

At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium.

<2> The above aryl at least substituted with a group represented by formula (D-1) or formula (D-2), which is R ^C or R ^C2 , or represented by formula (D-1) or formula (D-2) An aryl ring at least substituted with a group represented by formula (D-1) or formula (D-2) and formula (D-1) or formula (D-2) The polycyclic aromatic compound according to <1>, further comprising, as a partial structure, at least one ring selected from the group consisting of heteroaryl rings at least substituted with a group represented by

<3> polycyclic aromatic compound according to <1> or <2>, wherein the structural unit represented by formula (1) is a structural unit represented by formula (2);

In formula (2),

Z is each independently N or CR ¹¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se; R of >NR, >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl. , or a substituted or unsubstituted cycloalkyl, and the two Rs of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;

R ¹¹ of CR ¹¹ is each independently hydrogen, 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, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted of aryloxy, substituted or unsubstituted arylthio, or substituted silyl,

The two aryls of the diarylamino may be bonded to each other through a linking group, and the two heteroaryls of the diheteroarylamino may be bonded to each other through a linking group, and the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other may be bonded through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group;

Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring together with ring a or b, and the formed aryl ring and heteroaryl ring are each unsubstituted, or at least one of R ^11b substituted, R ^1lb has the same meaning as R ¹¹ , provided that R ^1lb is not hydrogen, and two adjacent R ^1lb do not bond to each other to form an aryl ring or a heteroaryl ring;

ring C is a ring represented by formula (C);

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R in >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs in (-R) ₂ may be bonded to each other to form a ring, and R in >NR and/or R in >C(-R) ₂ may form a ring or a ring by a linking group or a single bond. / or may be bonded to the b ring, or the a ring and / or the C ring;

At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium.

<4> The polycyclic aromatic compound according to <3>, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-1);

In formula (2a-1), Y ¹ , X ¹ , X ² , and X ^C have the same meaning as Y ¹ , X ¹ , X ² , and X ^C in formula (2), respectively, and R ^1lb and R ^C2 are , R ^1lb , R ^C2 in formula (2) have the same meaning, respectively,

n1 is an integer of 1 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3,

At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium.

<5> The polycyclic aromatic compound according to <4>, represented by any one of the following formulas.

In the formula, Me is methyl, tBu is t-butyl, and D is deuterium.

<6> polycyclic aromatic compound according to <3>, wherein the structural unit represented by formula (2) is a structural unit represented by formula (2a-2);

In formula (2a-2), Y ¹ , X ¹ , X ² , and X ^C have the same meaning as Y ¹ , X ¹ , X ² , and X ^C in formula (2), respectively, and R ^1lb and R ^C2 are , R ^1lb , R ^C2 in formula (2) have the same meaning, respectively,

X ³ and X ⁴ are each independently a single bond, >O, >NR, >C(-R) ₂ , or >S, provided that X ³ and X ⁴ are not single bonds at the same time;

n1 is an integer of 1 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 2,

At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium.

<7> The polycyclic aromatic compound according to <6>, represented by any one of the following formulas.

In the formula, Me is methyl and tBu is t-butyl.

<8> The polycyclic aromatic compound according to <3>, represented by the following formula.

<9> polycyclic aromatic compounds having a structure composed of one or two or more structural units represented by the following formula (1');

In formula (1'),

ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring;

Ring C is a ring represented by formula (C),

In formula (C),

X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR, the >C(-R) ₂ and the >Si( -R) R in ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and the two R of >Si(-R) ₂ above may be bonded to each other to form a ring;

Any two adjacent Z ^{C '} s are carbon directly bonded to either Y ¹ or X ² ,

other Z ^C are each independently N or CR ^C , and R ^C are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of diarylamino may be bonded to each other via a linking group, and the diheteroaryl The two heteroaryls of amino may be bonded to each other through a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group may be combined through

Two adjacent R ^Cs may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^C2 , and R ^C2 has the same meaning as R ^C , provided that R ^C2 is not hydrogen, and two adjacent R ^C2s do not bond to each other to form an aryl ring or a heteroaryl ring;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R in >NR is hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs of (-R) ₂ may be bonded to each other to form a ring, and R of >NR and/or R of >C(-R) ₂ may be bonded to ring A and/or ring A by a linking group or a single bond. / or may be bonded to the B ring, or the A ring and / or the C ring;

The structure is at least one selected from the group consisting of an aryl ring at least substituted with a group represented by formula (D-1) and a heteroaryl ring substituted at least with a group represented by formula (D-1) as a partial structure. include,

The group represented by formula (D-1) is bonded to two adjacent ring atoms in any aryl ring or heteroaryl ring in the above structure in two *, and in formula (D-1), R ^D is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and L is each independently substituted or unsubstituted alkyl ene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;

At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium.

<10> The polycyclic aromatic compound according to <9>, wherein the group represented by formula (D-1) is a group represented by formula (D-1-1);

R ^D are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

<11> The polycyclic aromatic compound according to <10>, represented by any one of the following formulas.

<12> A material for organic devices containing the polycyclic aromatic compound according to any one of <1> to <11>.

<13> A pair of electrodes composed of an anode and a cathode, and a light emitting layer disposed between the pair of electrodes, wherein the light emitting layer contains the polycyclic aromatic compound according to any one of <1> to <11>. organic electroluminescent device.

<14> The organic electroluminescent device according to <13>, wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant.

<15> The organic electroluminescent device according to <14>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

<16> A display device or lighting device provided with the organic electroluminescent element according to any one of <13> to <15>.

According to the present invention, a novel polycyclic aromatic compound useful as a material for organic devices such as an organic electroluminescence device is provided. The polycyclic aromatic compound of the present invention can be used for manufacturing organic devices such as organic electroluminescent devices.

1 is a schematic cross-sectional view showing an example of an organic electroluminescent device.
2 is an energy level diagram showing energy relationships among a host, an assisting dopant, and an emitting dopant of a TAF device using a typical fluorescent dopant.
3 is an energy level diagram showing an example of an energy relationship among a host, an assisting dopant, and an emitting dopant in an organic electroluminescent device according to one embodiment of the present invention.

Hereinafter, the present invention will be described in detail. The description of the constitutional requirements described below may be made based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range expressed using "-" means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, in this specification, "hydrogen" in description of structural formula means "hydrogen atom (H)", and "carbon" means "carbon atom (C)." In this specification, an organic electroluminescent element is sometimes referred to as an organic EL element.

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

Since the chemical structural formulas described in this specification (including general formulas drawn as Markush structural formulas, such as formula (1) described later) are planar structural formulas, in reality, various compounds such as enantiomers, diastereoisomers, and rotational isomers An isomeric structure may exist. In this specification, unless otherwise limited, the compound described may have any isomer structure conceivable from its planar structural formula, or may be a mixture composed of possible isomers in an arbitrary ratio.

In this specification, many structural formulas of aromatic compounds are described. Although aromatic compounds are described with a combination of a double bond and a single bond, since π electrons actually resonate, even a single substance has a plurality of equivalent resonance structures, such as alternating double bonds and single bonds. . Although only one resonance structural formula is described for one substance in this specification, it is assumed that other resonance structural formulas equivalent organically are also included unless otherwise specified. This is referred to in descriptions such as "Z=Z" described later. That is, it is as follows when an example is shown about "Z=Z" in Formula (2) mentioned later, for example. However, it is not limited to this, and naturally applies to not only one resonance structural formula described, but also other equivalent resonance structural formulas that can be considered.

In addition, in this specification, there are cases in which the expression "you may do" is used, but it has the same meaning as "does not do or is doing".

In this specification, "adjacent" is used for two atoms directly bonded by a covalent bond in the structural formula, or two groups respectively bonded to two atoms directly bonded by a covalent bond.

In this specification, a substituent may be substituted with another substituent. For example, a specific substituent may be described as "substituted or unsubstituted". This means that at least one hydrogen of the specific substituent is substituted with another substituent or is not substituted. In this specification, the specific substituent at this time may be referred to as a "first substituent" and the other substituent described above as a "second substituent".

<1. Polycyclic Aromatic Compounds>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1). Compounds having a basic skeleton represented by formula (1) have conventionally been known to give devices with a narrow emission half-width and excellent color purity. ), it was found that an organic electroluminescent device capable of emitting light at a lower voltage and with higher efficiency could be manufactured by using a compound having a partial structure represented by .

In formula (1), ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. As the substituent, other than the group represented by formula (D-1) or formula (D-2), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted of diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl. wherein, the aryl, the heteroaryl, the diarylamino, the diheteroarylamino, the arylheteroarylamino, the diarylboryl, the alkyl, the cycloalkyl, the alkenyl, the alkoxy, the aryloxy, the Arylthio and the substituted silyl serve as the first substituent. As the substituent (second substituent) in the case of "substitution" in "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, as a substituent (second substituent) in the case of "substitution" in "substituted or unsubstituted aryl" or "substituted or unsubstituted heteroaryl", formula (D-1) or formula (D-2) Prayers can be expressed.

In formula (1), ring C is a ring structure represented by formula (C). In formula (C), two arbitrarily adjacent Z ^C 's are carbon bonded to Y ¹ and X ² . Specifically, one of two arbitrary adjacent Z ^Cs is bonded to Y ¹ , and the other is bonded to X ² . As specific examples are shown below, any two adjacent Z ^Cs on the c1 ring may be carbon bonded to Y ¹ and X ² , and two adjacent Z ^Cs on the c2 ring may be Y ¹ and X ² may be a carbon bonded to

In formula (C), X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein >NR and >C(-R) ₂ and R in >Si(-R) ₂ are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, and the above > Two R's of C(-R) ₂ and >Si(-R) ₂ above may be bonded to each other to form a ring. Here, as the substituent (second substituent) in the case of "substitution" in "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. On the other hand, two aryls of the diarylamino may be bonded to each other. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

In formula (C), Z ^C other than Z ^C which is a carbon bonded to either Y ¹ or X ² is independently N or CR ^C . However, all of Z ^Cs other than Z ^C which is a carbon bonded to either Y ¹ or X ² are not N. R ^C are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylhetero Arylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio or substituted silyl.

Here, as the substituent (second substituent) in the case of "substitution" in "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

In formula (C), two adjacent R ^C 's may be bonded to each other (together with the two carbons to which those R ^C 's are bonded) to form an aryl ring or heteroaryl ring. The formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^C2 . R ^C2 has the same meaning as R ^C , provided that R ^C2 is not hydrogen, and two adjacent R ^C2 groups do not bond to each other to form an aryl ring or heteroaryl ring.

The ring represented by formula (C) is R ^C or R ^C2 and is aryl at least substituted with a group represented by formula (D-1) or formula (D-2) or formula (D-1) or formula (D-2). 2) includes heteroaryl at least substituted with a group represented by

The group represented by formula (D-1) and the group represented by formula (D-2) each bond to two ring atoms adjacent to each other in the aryl ring or heteroaryl ring in two *. R ^D are each independently a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and L is each independently a substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene. Here, it is preferable that the arylene and heteroarylene in L make two adjacent ring constituting atoms of the aryl ring and heteroaryl ring, respectively, as a bonding position.

A condensed ring structure in which at least two rings are condensed is formed by substituting two adjacent ring atoms in an aryl ring or heteroaryl ring with a group represented by formula (D-1) or formula (D-2). For example, a condensed ring in which the benzene ring and cyclohexane are condensed is formed by substituting a benzene ring (phenyl) with a group represented by formula (D-2) in which L is ethylene.

In formulas (D-1) and (D-2), when R ^D is a substituent other than hydrogen, the group represented by formula (D-1) or the group represented by formula (D-2) is an aromatic ring. Substituted structures can be made stable. Each R ^D is independently preferably substituted or unsubstituted aryl or substituted or unsubstituted alkyl, more preferably phenyl optionally substituted with alkyl or alkyl. Most preferably, all R ^D' s are methyl.

In formulas (D-1) and (D-2), L is each independently preferably substituted or unsubstituted alkylene or substituted or unsubstituted arylene, more preferably methylene; It is phenylene (particularly, 1,2-phenylene) which may be substituted with ethylene or alkyl.

Specific examples of the group represented by formula (D-1) are shown below.

Specific examples of the group represented by formula (D-2) are shown below.

Among the formulas (D-1-1) to (D-1-6) and formulas (D-2-1) to (D-2-2), the definition and preferred range of R ^D are in the formula (D- It is the same as the definition and preferable range in 1) and (D-2), respectively. At least one hydrogen in formulas (D-1-1) to (D-1-6) and formulas (D-2-1) to (D-2-2) is a substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl (preferably alkyl (more preferably unsubstituted methyl) or at least one hydrogen replaced by methyl or t-butyl may be substituted with phenyl).

Among formulas (D-1-1) to formula (D-1-6) and formula (D-2-1) to formula (D-2-2), formula (D-1-1) is particularly preferred. By using a polycyclic aromatic compound having an aryl ring or heteroaryl ring structure substituted with a group represented by formula (D-1-1) in the formation of the light emitting layer of an organic EL device, particularly as a dopant material, higher efficiency light emission and longer lifespan can be achieved. An organic EL element can be obtained.

The polycyclic aromatic compound of the present invention is at least substituted with an aryl at least substituted with a group represented by formula (D-1) or formula (D-2) or a group represented by formula (D-1) or formula (D-2) A decrease in melting point or sublimation temperature can be expected by including a heteroaryl that is present. This means that in sublimation purification, which is almost indispensable as a purification method for materials for organic devices such as organic EL elements requiring high purity, since purification can be performed at a relatively low temperature, thermal decomposition of the material can be avoided. In addition, this also applies to the vacuum deposition process, which is an effective means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of materials can be avoided, resulting in high performance. of organic devices can be obtained. In addition, since solubility in organic solvents is improved by introduction of a group represented by formula (D-1) or formula (D-2), it becomes possible to apply it to element fabrication using a coating process. However, the present invention is not particularly limited to these principles.

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1) is R ^C or R ^C2 , a group represented by formula (D-1) or formula (D-2) At a site other than the heteroaryl at least substituted with the aryl substituted or the group represented by formula (D-1) or formula (D-2), in formula (D-1) or formula (D-2) At least one ring selected from the group consisting of an aryl ring at least substituted with the group represented by and a heteroaryl ring at least substituted with the group represented by the formula (D-1) or formula (D-2) is further included as a partial structure You can do it.

For example, the form in which the aryl ring or heteroaryl ring in ring A, ring B, and ring C was substituted with the group represented by formula (D-1) or formula (D-2) is mentioned. In particular, a ring a, b ring, c1 ring, c2 ring (or c3 ring) in a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (2) has the formula (D- 1) or the form substituted with the group represented by formula (D-2). Among these, the form in which the aryl ring or heteroaryl ring in ring B is substituted with a group represented by formula (D-1) or formula (D-2) (particularly, the aryl ring or heteroaryl ring in ring b in formula (2) is The form substituted with the group represented by formula (D-1) or formula (D-2)) is preferable.

The polycyclic aromatic compound of the present invention has a partial structure of at least one aryl ring substituted with a group represented by formula (D-1) or a heteroaryl ring substituted at least with a group represented by formula (D-1) in its structure. It is preferable to include as When the group represented by formula (D-1) is included, the group represented by formula (D-1) or formula (D-2) may or may not be included in R ^C or R ^C2 . In this specification, such a structure is represented by Formula (1'). The polycyclic aromatic compound having a structure containing the structural unit represented by formula (1') is an aryl ring at least substituted with a group represented by formula (D-1-1) in the structure or formula (D-1-1 It is more preferable to include as at least one partial structure a heteroaryl ring at least substituted with a group represented by ).

In formula (C), X ^c is preferably >O, >NR, or >S, more preferably >O or >S, and still more preferably >S. Description of the following specific example can be referred for the preferable range of Z ^C of formula (C).

X ¹ and X ² in Formula (1) are each independently >O, >NR, >Si(-R) ₂ , >C(-R) ₂ , >S, and >Se. It is preferable that one of X ¹ and X ² is >NR, and the other is >NR, >C(-R) ₂ , or >O, and it is more preferable that both X ¹ and X ² are each independently >NR. desirable.

In formula (1), R of >NR which is X ¹ or X ² is hydrogen, optionally substituted aryl (except for amino as a substituent), substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl. R of X ¹ and X ² >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or substituted or unsubstituted It is cycloalkyl. Here, as the substituent (second substituent) in the case of "substitution" in "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

In Formula (1), X ¹ or X ² , R of >Si(-R) ₂ and >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted Heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R's are preferably identical, and two R's may be bonded to form a ring.

In formula (1), X ¹ or X ² For aryl, heteroaryl, alkyl, and cycloalkyl in R in >NR, >Si(-R) ₂ , or >C(-R) ₂ , the description of each group described later can be referred to.

In formula (1), X ¹ or X ² >R of NR is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cycloalkyl, and more preferably a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl desirable. As an example of cycloalkyl, the example mentioned later is mentioned. Here, as aryl, phenyl, biphenylyl (especially 2-biphenylyl), and terphenylyl (especially terphenyl-2'-yl) are preferable, and as heteroaryl, benzothienyl (2-benzo thienyl, 6-benzothienyl, etc.), benzofuranyl (2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl, etc.), dibenzofuranyl (2-dibenzofuranyl, 3-di benzofuranil, 4-dibenzofuranil, 5-dibenzofuranil, etc.) and the like are preferred. As the substituent, tertiary alkyl (especially t-butyl) or cycloalkyl (especially adamantyl) represented by the following formula (tR) is preferable. As for the number of substituents in aryl and heteroaryl, 0-2 are preferable, 1 or 2 are more preferable, and 1 is still more preferable. A group in which the above aryl is substituted with a group represented by formula (D-1) or formula (D-2) is also preferable.

In formula (1), X ¹ or X ² R of >NR is preferably phenyl, naphthyl, biphenylyl, terphenylyl, quaterphenylyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, or carbazolyl, and phenyl, naphthyl , more preferably biphenylyl, terphenylyl, dibenzofuranyl or carbazolyl, and still more preferably phenyl, biphenylyl or dibenzofuranyl. In addition, hydrogen of at least one of the phenyl, the naphthyl, the biphenylyl, the terphenylyl, the quaterphenylyl, the dibenzofuranyl, the dibenzothiophenyl, the fluorenyl and the carbazolyl is , each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or Unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted It may be substituted with arylthio or substituted silyl. In addition, two hydrogen bonded to adjacent carbon may be substituted with a group represented by formula (D-1) or formula (D-2). As the substituent, among the above, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or formula (D-1) or formula (D-2) A group represented by is preferable, and a substituted or unsubstituted aryl, a substituted or unsubstituted alkyl or a substituted or unsubstituted cycloalkyl, or a group represented by formula (D-1) or formula (D-2) is more preferred. , substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or a group represented by formula (D-1) or formula (D-2) is more preferred. And as the said phenyl, the said biphenylyl, the said terphenylyl, and the said quaterphenylyl, any one of the following groups are preferable. In the following formula, * represents the bonding position of X ¹ or X ² >NR with N.

As some of the preferable examples in the case where the phenyl, the biphenylyl, the terphenylyl, or the quaterphenylyl has a substituent, a group represented by the following formula (X-4) is exemplified.

(tBu is t-butyl, * represents a bonding position with N. p and q are each independently an integer from 0 to 3.)

In formula (1), R of >NR which is X ¹ or X ² is preferably an aryl (which may be further substituted) substituted with a group represented by formula (D-1) or formula (D-2) do. As aryl substituted by the group represented by formula (D-1) or formula (D-2), the following are especially preferable.

(Me is methyl, tBu is t-butyl, * represents a bonding position with N. p and q are each independently an integer from 0 to 3.)

In formula (1), X ¹ or X ² are each independently preferably all >NR, and R of at least one of >NR is formula (DX-3), (DX-4), or (DX-5) , or a group represented by (X-4) is preferable. It is also preferable that R in >NR of X ² is a group represented by the formula (DX-3), (DX-4), (DX-5) or (X-4).

In Formula (1), R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ which is X ¹ or X ² is ring A and ring B by a linking group or a single bond. may be bonded to any one of them, or to any one of the A ring and the C ring. That is, R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ that is X ¹ may be bonded to either the A ring or the B ring by a linking group or a single bond. , R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ which is X ² may be bonded to either the A ring or the C ring by a linking group or a single bond. As the linking group, -O-, -S-, or -C(-R ¹³ ) ₂ - is preferable. Although R ¹³ is hydrogen, alkyl or cycloalkyl, the description of each group described later can be referred to as this alkyl or cycloalkyl. In particular, alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

In addition, the above regulation can also be expressed by a structure having a ring structure in which X ¹ of >NR is encapsulated in condensed ring A', which is represented by the following formula (1-3-2). That is, it is a compound having an A' ring formed by adding any one of X ¹ and X ² to ring A, which is, for example, a benzene ring, and condensing the other ring. The formed condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, or a phenothiazine ring.

As an example, R in >N-R is a substituted or unsubstituted cycloalkyl, and is also preferably bonded to the A ring, B ring, or C ring through a single bond. As cycloalkyl, substituted or unsubstituted cyclopentyl or substituted or unsubstituted cyclohexyl is preferable.

A particularly preferable example of the condensed ring formed as described above is a structure represented by formula (A11). In formula (A11), * means “R in at least one of X ¹ or X ² >NR, >Si(-R) ₂ and >C(-R) ₂ is a linking group or a single bond to ring A and In the above stipulation that it may be bonded to any of the B rings or to any of the A and C rings, it corresponds to a form bonded by a single bond. As described above, in this case, the two carbons substituted by methyl are asymmetric carbons, and diastereomers and enantiomers may exist as compounds represented by formula (1), but as compounds represented by formula (1) Any of these isomers may be sufficient, and the form in which possible isomers are mixed in arbitrary ratios may be sufficient.

In formula (A11), Me is methyl, and is bonded to one ring of the two rings to which X ¹ or X ² is bonded at positions * and **, and to the other ring at position ***.

Similarly, the following examples can be presented in which R in >N-R is phenyl and is bonded to the A ring, B ring, or C ring by a single bond.

In formula (A12), X ¹ or X ² is bonded to one ring of the two rings at positions * and ** and to the other ring at position ***.

By using the compound of the present invention having >NR as X ¹ or X ² , which is R within the above preferred range, as a light emitting material for manufacturing a device, the luminous efficiency and lifetime of the device can be further improved.

R of >Si(-R) ₂ which is X ¹ or X ² in formula (1) is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted is a cycloalkyl of As this aryl, heteroaryl, alkyl or cycloalkyl, the description of each group mentioned later can be referred to respectively. In particular, aryls having 6 to 10 carbon atoms (eg, phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (eg, carbazolyl, etc.), and alkyls having 1 to 5 carbon atoms (eg, methyl, ethyl, etc.) or cycloalkyl (preferably cyclohexyl or adamantyl) of 5 to 10 carbon atoms. As the substituent (second substituent) in the case of "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

R of >C(-R) ₂ which is X ¹ or X ² in formula (1) is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl or substituted or unsubstituted is a cycloalkyl of As this aryl, heteroaryl, alkyl or cycloalkyl, the description of each group mentioned later can be referred. In particular, aryls having 6 to 10 carbon atoms (eg, phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (eg, carbazolyl, etc.), and alkyls having 1 to 5 carbon atoms (eg, methyl, ethyl, etc.) or cycloalkyl (preferably cyclohexyl or adamantyl) of 5 to 10 carbon atoms. As the substituent (second substituent) in the case of "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

As a preferable form of the structural unit represented by formula (1), the structural unit represented by following formula (2) is mentioned.

In formula (2), in ring a and ring b, Z is each independently N or CR ¹¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si (-R) ₂ , >S, or >Se, and R of >NR, >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, A substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si(-R) ₂ are two R's bonded to each other to form a ring may be forming. Here, as a substituent (second substituent) in the case of "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

In formula (2), R ¹¹ of CR ¹¹ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, or substituted or unsubstituted diheteroaryl. Amino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy , substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl. Here, as a substituent in the case of "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

As R ¹¹ , hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted silyl is preferable. do.

Next, description of "Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se" is explained. For example, in ring b in Formula (2), the position of "Z=Z" is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se As a ring obtained by being substituted with, a cyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring, etc. are mentioned. In ring b, one Z=Z is >NR, >O, >S, >C(-R) ₂ and the other Z is CH. Further, one Z=Z is >NR, >O, >S, >C(-R) ₂ , the remaining Z is CR ¹¹ , and an example in which adjacent R ¹¹ forms a benzene ring as will be described later is shown below. However, as a form which ring b etc. can take, it is not limited to the following example.

As described above, since the aromatic compound has a resonance structural formula completely equivalent organically, it may be based on any possible resonance structural formula. In addition, R of >NR, >C(-R) ₂ and >Si(-R) ₂ where Z=Z is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, It is substituted or unsubstituted alkyl or substituted or unsubstituted cycloalkyl, and two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. As the substituent (second substituent) in the case of "substituted or unsubstituted", aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferable. In addition, examples of substituents in the case of "substitution" in "substituted or unsubstituted aryl" and "substituted or unsubstituted heteroaryl" include groups represented by formula (D-1) or formula (D-2). there is.

In Formula (2), it is preferable that all of Z are independently CR ¹¹ .

Two adjacent R ¹¹ groups may be bonded to each other to form an aryl ring or heteroaryl ring together with the a ring or the b ring. The formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^11b . R ^11b has the same meaning as R ¹¹ , provided that R ^11b is not hydrogen and two adjacent R ^11s are bonded to each other and do not form an aryl ring or a heteroaryl ring. In addition, as an aryl ring or heteroaryl ring here, the description of each ring mentioned later can be referred.

Examples of the aryl ring formed together with ring a or b include a naphthalene ring, an anthracene ring, a fluorene ring, an indene ring, and a 9,10-dihydroanthrancene ring (especially 9,9,10,10-tetramethyl-9,10- A dihydroanthrancene ring), a dihydroacridine ring, or a xanthene ring is preferable, and examples of the heteroaryl ring formed include a benzothiophene ring, an indole ring, a benzofuran ring, a dibenzothiophene ring, a dibenzofuran ring, or a carcyclic ring. A bazol ring is preferred.

An example in which two adjacent R ¹¹ bonds to each other to form an aryl ring or heteroaryl ring together with the b ring is shown below. In addition, the benzene ring in the following structure may further have at least one ^R1b as a substituent.

As a more preferred form of formula (2), the following formulas (2a), formula (2b), formula (2c), formula (2d), formula (2e), formula (2f), formula (2g) and formula (2h) ) can be heard.

In Formula (2a), Formula (2b), Formula (2c), Formula (2d), Formula (2e), Formula (2f), Formula (2g), and Formula (2h), each Z ^c is independently CR ¹¹ The phosphorus form is preferred, and in formulas (2a), (2b), (2c), (2d), (2e), (2f), (2g) and (2h), c2 It is also preferable to form an aryl ring (preferably a benzene ring) in which each Z ^c of the ring independently represents CR ^c , and as will be described later, adjacent R ^c bonds with each other to form an aryl ring (preferably a benzene ring). Further, in formulas (2a), formulas (2b), formulas (2c), formulas (2d), formulas (2e), formulas (2f), formulas (2g) and formulas (2h), formulas (2a) and formulas (2b) is preferred, and formula (2a) is most preferred. In addition, the description of this specification mentioned later can be referred for description of each code|symbol and phrase.

In formulas (2c), formulas (2d), formulas (2e), formulas (2f), formulas (2g) and formulas (2h), all Z ^C 's of ring c2 are CR ^C 's, and two adjacent R ^C 's are It is preferable that they combine with each other to form an aryl ring or a heteroaryl ring (more preferably an aryl ring, and still more preferably a benzene ring). This preferable form is shown below. Definitions of symbols in formulas (2c-2), formulas (2d-2), formulas (2e-2), formulas (2f-2), formulas (2g-2) and formulas (2h-2), and their preferred Regarding the range, reference can be made to the description of equation (2).

Furthermore, as a structural unit represented by formula (2a), the structural unit represented by the following formula (2a-1) or formula (2a-2) is preferable.

In formula (2a-1) or formula (2a-2), Y ¹ , X ¹ , X ² , and X ^C have the same meaning as Y ¹ , X ¹ , X ² , and X ^C in formula (1), respectively. , R ^1lb , and R ^C2 have the same meaning as R ^1lb and R ^C2 in formula (2), respectively. X ³ and X ⁴ are each independently a single bond, >O, >NR, >C(-R) ₂ , or >S, provided that X ³ and X ⁴ are not single bonds at the same time. n1 is an integer of 0 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, and n4 is an integer of 0 to 2. At least one of the aryl ring or heteroaryl ring in the structure consisting of one or two or more structural units represented by formula (2a-1) or formula (2a-2) is at least one of formula (D-1) or formula It may be substituted with the group represented by (D-2).

In formulas (2a-1) and (2a-2), the preferred ranges of Y ¹ , X ¹ , X ² , and X ^C are Y ¹ , X ¹ , X ² , and X ^C in formula (1). is equal to the preferred range of In formula (2a-2), X ³ and X ⁴ have >C(-R) ₂ on one side and >O, >NR, or >C(-R) ₂ on the other side, or a single bond on one side and a single bond on the other side. is preferably >O or >NR. 1-2 are preferable and, as for n1, 1 is more preferable. 0-2 are preferable and, as for n2, 0 or 1 is more preferable. As for n3, 0 or 1 is preferable. n4 is preferably 0.

The structural unit represented by formula (2a-1) or formula (2a-2) is an aryl or formula (D-2) at least substituted with a group represented by formula (D-1) or formula (D-2) as R ^C2 . 1) or heteroaryl at least substituted with a group represented by formula (D-2). The compound represented by formula (2a-1) or formula (2a-2) is, in at least one of the aryl ring or heteroaryl ring at a site other than R ^C2 of the structure, formula (D-1) or formula (D- It may be substituted with the group represented by 2).

In Formula (1) and in Formula (2), which is a preferred embodiment thereof, Y ¹ is each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge -R, preferably B, P=O or P=S, most preferably B. R in Si-R and Ge-R is aryl of 6 to 12 carbon atoms, alkyl of 1 to 6 carbon atoms, or cycloalkyl of 3 to 14 carbon atoms. R of Si-R and Ge-R in Y ¹ in formula (1) is aryl, alkyl or cycloalkyl, and examples of the aryl, alkyl or cycloalkyl include groups described below. In particular, aryl of 6 to 10 carbon atoms (eg phenyl, naphthyl, etc.), alkyl of 1 to 5 carbon atoms (eg methyl, ethyl, etc.) or cycloalkyl of 5 to 10 carbon atoms (preferably cyclohexyl or adamane). til) is preferred.

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1) or its preferred form, such as formula (2). As a polycyclic aromatic compound which has a structure consisting of one structural unit, the polycyclic aromatic compound represented by Formula (1) (or Formula (2) which is its preferable form) is mentioned. As the polycyclic aromatic compound having a structure composed of two or more structural units represented by formula (1), a compound corresponding to a multimer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1) can be heard As for a multimer, a 2-hexamer is preferable, a 2-3mer is more preferable, and a dimer is especially preferable. The multimer may be in the form of having a plurality of the above unit structures in one compound, and any ring (A ring (a ring), B ring (b ring) or C ring (c1 ring, c2 ring) contained in the above structural unit , c3 ring)) may be shared in a plurality of unit structures and bonded, and any ring (A ring (a ring), B ring (b ring) or C ring (c1 ring) included in the unit structure , c2 ring, c3 ring)) may be in a form in which each other is condensed and bonded. Moreover, the form in which the said unit structure couple|bonded with multiple coupling groups, such as a single bond and C1-C3 alkylene, phenylene, and naphthylene, may be sufficient. Among these, a form in which rings are shared and bonded is preferable.

All or part of the hydrogen in the structural unit represented by Formula (1) and the structure consisting of one or two or more of its preferable forms may be substituted with deuterium, cyano or halogen.

For example, in the structure consisting of the structural unit represented by formula (1) and one or two or more of its preferable form, ring A (ring a), ring B (ring b), ring C (ring c1) , c2 ring, c3 ring), a substituent in A to C ring, R when Y ¹ is Si-R or Ge-R (= alkyl, cycloalkyl, aryl), and one of X ¹ and X ² Hydrogen in R of >NR may be substituted with deuterium, cyano or halogen, but among these, all or part of hydrogen in aryl or heteroaryl is substituted with deuterium, cyano or halogen. can Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and still more preferably fluorine. In particular, a form in which hydrogen is substituted with deuterium is preferable because stability of the compound is improved. When hydrogen is substituted with heavy hydrogen, one hydrogen may be substituted with heavy hydrogen, but it is preferable that a plurality of hydrogens are substituted with heavy hydrogen, and it is more preferable that all the hydrogens in the aromatic part are substituted with heavy hydrogen, and all the hydrogens are heavy hydrogen. It is more preferable to be substituted with .

Details of the rings and substituents used in the present specification are described below.

Examples of the "aryl ring" in the present specification include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and aryl rings having 6 to 12 carbon atoms. An aryl ring of to 10 is particularly preferred.

Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, an indene ring, and a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl). ), condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, 9,10-dihydroanthrancene ring, condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, A chrysene ring, a perylene ring which is a condensed 5-ring system, a pentacene ring, etc. are mentioned. The fluorene ring, benzofluorene ring, and indene ring also include structures in which fluorene rings, benzofluorene rings, cyclopentane rings, and the like are spiro bonded, respectively. In addition, as a fluorene ring, a benzofluorene ring, and an indene ring, two hydrogens of methylene are each substituted with an alkyl such as methyl as a first substituent described later to obtain a dimethylfluorene ring, a dimethylbenzofluorene ring, and a dimethylindene ring Including those that have become etc. In addition, as a 9,10-dihydroanthrancene ring, 4 hydrogens of 2 methylenes are each substituted with an alkyl such as methyl as a first substituent described later to obtain 9,9,10,10-tetramethyl-9,10 - What has become a dihydroanthrancene ring etc. is included.

Examples of the "heteroaryl ring" in the present specification include a heteroaryl ring having 2 to 30 carbon atoms, a heteroaryl ring having 2 to 25 carbon atoms is preferable, and a heteroaryl ring having 2 to 20 carbon atoms is more preferable. A heteroaryl ring having 2 to 15 carbon atoms is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazane ring), a thiadiazole ring, a triazole ring, and a tetracyclic ring. sol ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzo Triazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, carboline ring, acridine ring, fe Noxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, Dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxine ring, dihydroacridine ring, xanthene ring, A thioxanthene ring, a dibenzodioxine ring, etc. are mentioned. Further, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, two of the two hydrogens of methylene are substituted with an alkyl such as methyl as a first substituent described below, respectively, to obtain a dimethyldihydroacridine ring, dimethylxanthene ring, and dimethylthiozane It is also preferable to be a ten ring or the like. Examples of the "heteroaryl ring" include a bipyridine ring, phenylpyridine ring, and pyridylphenyl ring, which are bicyclic rings, and terpyridine rings, bispyridylphenyl rings, and pyridylbiphenyl rings, which are tricyclic rings. In addition, a "heteroaryl ring" shall also include a pyran ring.

In addition, the following formula (BO) is also included in the heteroaryl ring.

On the other hand, ring A and ring B in Formula (1) are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and in the "aryl ring" or "heteroaryl ring" herein At least one hydrogen of is a first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroaryl" arylamino”, substituted or unsubstituted “arylheteroarylamino”, substituted or unsubstituted “diarylboryl”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “alkenyl”, substituted or unsubstituted may be substituted with "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or "substituted silyl".

The "aryl" in the present specification is a monovalent group in which one hydrogen is removed from the above-mentioned "aryl ring", and examples thereof include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, , C6-C20 aryl is more preferable, C6-C16 aryl is still more preferable, C6-C12 aryl is especially preferable, C6-C10 aryl is most preferable.

In addition, "heteroaryl" is a monovalent group obtained by removing one hydrogen from the aforementioned "heteroaryl ring", examples of which include heteroaryl having 2 to 30 carbon atoms, and heteroaryl having 2 to 25 carbon atoms is preferable. A heteroaryl having 2 to 20 carbon atoms is more preferable, a heteroaryl having 2 to 15 carbon atoms is even more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Moreover, as a heteroaryl, the heterocyclic etc. which contain 1-5 hetero atoms selected from oxygen, sulfur, and nitrogen other than carbon as a ring constituting atom are mentioned, for example.

As the aryl or heteroaryl in "substituted or unsubstituted diarylamino", "substituted or unsubstituted diheteroarylamino", or "substituted or unsubstituted arylheteroarylamino" as the first substituent, the above-mentioned "aryl ” or “heteroaryl” can be cited together with its preferred range.

The two aryls in diarylamino as the first substituent may be bonded to each other via a linking group, and the two heteroaryls in diheteroarylamino as the first substituent may be bonded to each other via a linking group. The aryl and heteroaryl of arylheteroarylamino as a substituent may be bonded to each other through a linking group. Here, the description of "bonding via a linking group" indicates that, for example, two phenyls of diphenylamino form a bond with a linking group, as shown below. This statement also applies to diheteroarylamino and arylheteroarylamino, formed from aryls or heteroaryls.

(* indicates the binding position.)

Specifically as a linking group, >O, >NR ^X , >C(-R ^X ) ₂ , -(CR ^X )=(CR ^X )-, >Si(-R ^X ) ₂ , >S, >CO, > CS, >SO, >SO ₂ , and >Se. R ^X is each independently an alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. In addition, >C(-R ^X ) ₂ , -(CR ^X )=(CR ^X )-, >Si(-R ^X ) ₂ , two R ^{X '} s are mutually connected through a single bond or a linking group ^XY They may combine to form a ring. Examples of X ^Y include >O, >NR ^Y , >C(-R ^Y ) ₂ , >Si(-R ^Y ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. and R ^Y are each independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. However, when ^XY is >C(-R ^Y ) ₂ and >Si(-R ^Y ) ₂ , two R ^Y are bonded together to form no further ring. Moreover, alkenylene is also mentioned as a linking group. Any hydrogen of the alkenylene may be each independently substituted with R ^2X , and each R ^2X is independently alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl, which are alkyl, cycloalkyl, substituted silyl, or aryl. may be substituted. Two R ^{X 's} in -(CR ^X )=(CR ^X )- may be bonded to each other to form an aryl (benzene ring, etc.) or heteroaryl ring together with C=C to which they are bonded. That is, -(CR ^X )=(CR ^X )- may be arylene (1,2-phenylene, etc.) or heteroarylene.

In addition, in the present specification, when simply described as “diarylamino,” “diheteroarylamino,” or “arylheteroarylamino,” unless otherwise specified, each “two aryls of diarylamino are a linking group may be bonded through", "the two heteroaryls of the diheteroarylamino may be bonded to each other through a linking group", and "the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group" It is assumed that the explanation of "is added.

As the "alkyl" as the first substituent, either straight-chain or branched chain may be used, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. C1-C18 alkyl (C3-C18 branched chain alkyl) is preferable, C1-C12 alkyl (C3-C12 branched chain alkyl) is more preferable, C1-C8 alkyl (C3 -8 branched chain alkyl) is more preferable, C1-6 alkyl (C3-6 branched chain alkyl) is particularly preferable, C1-5 alkyl (C3-5 branched chain alkyl) this is most 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, 4-methyl-2-pentyl, 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-hepta Decyl, n-octadecyl, n-eicosyl, etc. are mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

As the substituent containing the above "alkyl", tertalkyl represented by the following formula (tR) is a substituent for the aryl ring or heteroaryl ring in the A ring, the B ring, and the C ring, and is particularly preferable. One. This is because the luminescence quantum yield (PLQY) is improved because the intermolecular distance is increased by such a bulky substituent. Further, a substituent in which the tertiary alkyl represented by the formula (tR) is substituted with another substituent as the second substituent is also preferable. Specifically, diarylamino substituted with tertiary alkyl represented by (tR), carbazolyl (preferably N-carbazolyl) substituted with tertiary alkyl represented by (tR), or (tR) benzocarbazolyl (preferably, N-benzocarbazolyl) substituted with tertiaryalkyl represented by About "diarylamino", the group demonstrated as the following "1st substituent" is mentioned. Examples of substitution forms of groups represented by the formula (tR) in diarylamino, carbazolyl and benzocarbazolyl include examples in which some or all hydrogens of the aryl ring or benzene ring in these groups are substituted with groups represented by the formula (tR) can

　

　

In formula (tR), R ^a , R ^b , and R ^c are each independently an alkyl having 1 to 24 carbon atoms, and any -CH ₂ - in the alkyl may be substituted with -O-, and the formula ( The group represented by tR) is substituted with at least one hydrogen in the structure containing the structural unit represented by formula (1) in *.

"C1-C24 alkyl" of R ^a , R ^b and R ^c may be either straight-chain or branched chain, and examples thereof include straight-chain alkyl having 1-24 carbon atoms or branched-chain alkyl having 3-24 carbon atoms; C1-18 alkyl (C3-18 branched chain alkyl), C1-12 alkyl (C3-12 branched chain alkyl), C1-6 alkyl (C3-6 branched chain alkyl) , C1-C4 alkyl (C3-C4 branched chain alkyl).

The total number of carbon atoms of R ^a , R ^b , and R ^c in formula (tR) of formula (1) is preferably 3 to 20 carbon atoms, particularly preferably 3 to 10 carbon atoms.

Specific examples of alkyl of R ^a , R ^b , and R ^c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n -Undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Ecosil etc. can be mentioned.

Examples of the group represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1 -Methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1, 1-Dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl- 1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1 -Ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. are mentioned. Of these, t-butyl and t-amyl are preferred.

Further, as the "cycloalkyl" as the first substituent, cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 5 to 10 carbon atoms. , C5-C8 cycloalkyl, C5-C6 cycloalkyl, C5 cycloalkyl, etc. are mentioned. Cyclohexyl in this specification includes not only monocyclic cyclohexyl and the like, but also polycyclic ones such as adamantyl and the like, as listed below.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[ 2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl (norbornyl), bicyclo [2.2.2] octyl, adamantyl, diamantyl, decahydronaphtharenyl, decahydroazulenyl, and alkyl (particularly methyl) substituents of these having 1 to 5 carbon atoms; and the like.

Examples of "alkenyl" as the first substituent include straight chain alkenyl having 2 to 24 carbon atoms or branched chain alkenyl having 4 to 24 carbon atoms. Alkenyl having 2 to 18 carbon atoms is preferred, alkenyl having 2 to 12 carbon atoms is more preferred, alkenyl having 2 to 6 carbon atoms is even more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred.

Specific examples of "alkenyl" include vinyl, allyl, butadienyl, and the like.

Moreover, as "alkoxy" as a 1st substituent, C1-C24 linear or C3-C24 branched alkoxy is mentioned, for example. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) -6 branched chain alkoxy) is more preferred, and C1-5 alkoxy (C3-5 branched alkoxy) is particularly preferred.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy etc. can be mentioned.

"Aryloxy" as the first substituent is a group in which the hydrogen of the -OH group is substituted with an aryl, and the aryl and its preferable range can be cited as described above.

"Arylthio" as the first substituent is a group in which the hydrogen of the -SH group is substituted with an aryl, and the aryl and its preferable range can be cited as described above.

Examples of the "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

Examples of "trialkylsilyl" include groups in which three hydrogens in silyl are each independently substituted with alkyl, and this alkyl and its preferred range include the group described as "alkyl" in the first substituent described above. can Preferable alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, t-amyl and the like.

Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, and propyldimethyl. Silyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, t-amyldiisopropylsilyl, etc. can

Examples of "tricycloalkylsilyl" include groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl and its preferred range are referred to as "cycloalkyl" in the first substituent described above. The described group can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1 .0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, Decahydroazulenyl etc. are mentioned.

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

Specific examples of dialkylcycloalkylsilyl substituted with 2 alkyl and 1 cycloalkyl and alkyldicycloalkylsilyl substituted with 1 alkyl and 2 cycloalkyl include groups selected from the above specific alkyl and cycloalkyl substituted. silyl.

Specific examples of dialkylarylsilyl in which two alkyls and one aryl are substituted, alkyldiarylsilyl in which one alkyl and two aryls are substituted, and triarylsilyls in which three aryls are substituted are the specific alkyl and aryls described above. and silyl substituted with a group selected from As a specific example of triarylsilyl, especially triphenylsilyl is mentioned.

In addition, the description of the above-mentioned aryl can be cited as "aryl" among "diaryl boryl" of a 1st substituent and its preferable range. 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 in >C(-R) ₂ and >NR is aryl, heteroaryl, diarylamino (two aryls may be bonded to each other through a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (or more , the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent), and specific examples of these groups include aryl and hetero as the first substituent described above. Descriptions of aryl, diarylamino (two aryls may be bonded to each other through a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy may be cited. In addition, when it is simply described as "diaryl boryl" in this specification, unless otherwise specified, explanation is added that "two aryls of diaryl boryl may be bonded to each other through a single bond or a linking group" do as there is

"Cycloalkyl" of "aryl", "heteroaryl", "diarylamino", "diheteroarylamino", "arylheteroarylamino", "diarylboryl", "alkyl" as the first substituent; When "alkenyl", "alkoxy", "aryloxy", and "arylthio" are described as substituted or unsubstituted, at least one hydrogen in them may be substituted with a second substituent. As this second substituent, if there is no special description, preferably, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is mentioned, and specific examples thereof are as the first substituent " Reference can be made to descriptions of "aryl", "heteroaryl", "diarylamino", "alkyl", "cycloalkyl" or "substituted silyl". In addition, in the aryl and heteroaryl as the second substituent, at least one hydrogen in them is aryl such as phenyl (specific examples are groups described above), alkyls such as methyl and t-butyl (specific examples are groups described above ) or cycloalkyl such as cyclohexyl (specific examples are groups described above). One example thereof is a group in which the ninth position of carbazolyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. Furthermore, cycloalkyl as a second substituent includes groups in which at least one hydrogen in them is substituted with an alkyl such as methyl or t-butyl. This description is also applicable to the description of other first substituents and second substituents in this specification. In addition, when two or more hydrogens in the first substituent are substituted with second substituents, those two or more second substituents may be the same or different.

The emission wavelength can be adjusted by the structural steric hindrance, electron donating property, and electron withdrawing property of the substituent. It is preferably a group represented by the following structural formulas, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, dimethyladamantyl, phenyl, o-tolyl, p -Tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t -butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, even more preferably methyl, t-butyl, t -amyl, t-octyl, neopentyl, adamantyl, dimethyladamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolyl amino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a higher steric hindrance is preferred for selective synthesis. Specifically, t-butyl, t-amyl, t-octyl, adamantyl, dimethyladamantyl, o-tolyl, p -Tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl ) amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

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

As a substituent when 2 or 3 hydrogens bonded to consecutive (adjacent) carbon atoms are substituted, in addition to the group represented by the above formula (D-1) or formula (D-2), any of the following Contributions can also be shown.

In each formula, Me is methyl. In each formula, what is necessary is just to couple|bond with two or three consecutive (adjacent) atoms in the ring of any aryl ring or heteroaryl ring of ring A, B ring, and C ring by *.

The polycyclic aromatic compound having a structural unit represented by formula (1) and a structure composed of one or two or more of the preferable forms thereof is a tert-alkyl (t-butyl or t- amyl, etc.), neopentyl or adamantyl, and preferably contains at least one tertiary alkyl represented by the formula (tR) (t-butyl or t-amyl, etc.). This is because the luminescence quantum yield (PLQY) is improved because the intermolecular distance is increased by such a bulky substituent. Further, as the substituent, diarylamino (two aryls may be bonded to each other through a linking group) is also preferable. Furthermore, diarylamino substituted with a group of formula (tR) (two aryls may be bonded to each other via a linking group), carbazolyl substituted with a group of formula (tR) (preferably N-carbazolyl) Or benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a group of formula (tR) is also preferable. As a substitution form of the group of the formula (tR) to diarylamino (provided that the two aryls of the diarylamino may be bonded to each other via a linking group), carbazolyl and benzocarbazolyl, aryl in these groups An example in which some or all of the hydrogens in the ring or benzene ring is substituted with a group represented by the formula (tR) is exemplified.

Further specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium. In addition, the following structure is an example.

The polycyclic aromatic compound of the present invention can be produced in the following procedure.

<Method for producing polycyclic aromatic compound>

A polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1) or formula (2) is basically first ring A (ring a), ring B (ring b) and C A ring (condensed ring composed of ring c1 and c2) is bonded with a linking group (group containing X ¹ or X ² ) to prepare an intermediate (first reaction), and then ring A (ring a), ring B ( Ring b) and ring C (ring c) can be combined with a linking group (group containing Y ¹ ) to produce a final product (second reaction). In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Birchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic electron transfer reaction, hereinafter the same) can be used. Somewhere in the reaction step, by using a raw material having a desired condensed ring or by adding a step of condensing the ring, at least one ring selected from the group consisting of A ring, B ring and C ring is a monocyclic aryl ring, A compound can be produced from a condensed ring composed of two or more rings selected from the group consisting of a monocyclic heteroaryl ring and a cyclopentadiene ring.

<Production method via Intermediate 1>

The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each process below, description of International Publication No. 2015/102118 can be referred.

A reaction step of metallizing a halogen atom (Hal) between X ¹ and X ² in Intermediate 1 below using an organic alkali compound, a halide of Y ¹ , an aminated halide of Y ¹ , and a reaction step of Y ¹ Y 1 by a reaction step of exchanging Y ¹ with the metal using a reagent selected from the group consisting of an alkoxide and an aryloxide of Y ¹ , and a continuous aromatic electron transfer reaction using ^a Bronsted base; The reaction including the reaction step of coupling ring B and ring C with is recorded below.

As the metalation reagent used in the halogen-metal exchange reaction in the scheme described so far, alkyl lithium such as methyl lithium, n-butyl lithium, sec-butyl lithium, t-butyl lithium, isopropyl magnesium chloride, isopropyl bromide and lithium chloride complexes of isopropyl magnesium chloride known as magnesium, phenylmagnesium chloride, phenylmagnesium bromide, and Turbogrignard reagents.

In addition, as the metalation reagent used in the orthometal exchange reaction in the scheme described so far, in addition to the above reagents, lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyl and organic alkali compounds such as disilazide, lithium chloride tetramethylpiperidinylmagnesium/lithium chloride complex, and tri-n-butylmagnesium lithium.

In the case of using alkyllithium as the metallization reagent, as additives that promote the reaction, N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, N ,N-dimethylpropylene urea, etc. are mentioned.

In addition, as Lewis acids used in the schemes described so far, 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 addition, those in which these Lewis acids are supported on a solid can be used similarly.

In addition, as the Bronsted acid used in the scheme described so far, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboranic acid, trifluoroacetic acid, (trifluoromethanesulfonyl) Imide, tris (trifluoromethanesulfonyl) methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc. are mentioned. Examples of solid Bronsted acids include Amberlyst (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and Teicacur (trade name: Teika Co., Ltd.).

In addition, as amines that may be added in the schemes described so far, diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine , N,N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-t-butylamine, and the like.

In addition, as the solvent used in the scheme described so far, o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2, 4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether and the like.

Here, an example in which Y ¹ is B has been described, but compounds in which Y ¹ is P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R are also synthesized by appropriately changing the raw material. can do.

In the above scheme, a Bronsted base or a Lewis acid may be used to promote the tandem hetero Friedel Crafts reaction. However, when a halide of Y ¹ such as trifluoride of Y 1 , trichloride of Y ¹ , tribromide of Y ¹ , or triiodide of ^{Y 1 is} used, along with the progress of the aromatic electron substitution reaction, Since acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, the use of a Bronsted base to capture the acid is effective. On the other hand, when an aminated halide of Y ¹ or an alkoxide of Y ¹ is used, amines and alcohols are formed as the aromatic electron transfer reaction progresses, so in many cases it is not necessary to use a Bronsted base. However, since the ability to release amino or alkoxy is low, the use of a Lewis acid that promotes the release is effective.

The polycyclic aromatic compound of the present invention also includes compounds in which at least part of the hydrogen atoms are substituted with deuterium or cyano, and compounds in which halogens such as fluorine or chlorine are substituted. It can be synthesized in the same manner as above by using cyaninated, fluorinated or chlorinated raw materials.

<2. organic devices>

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

The polycyclic aromatic compound according to the present invention can be used as a material for organic devices. Examples of the organic device include an organic electroluminescent device, an organic field effect transistor, and an organic thin-film solar cell, but an organic electroluminescent device is preferable. The polycyclic aromatic compound according to the present invention is preferably a material for an organic electroluminescent device, more preferably a material for a light emitting layer (light emitting material), and most preferably a dopant material for the light emitting layer.

<2-1. Organic Electroluminescent Device>

<2-1-1. Structure of Organic Electroluminescent Device>

1 is a schematic cross-sectional view showing an example of an organic EL element.

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

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

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

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

<2-1-2. Light emitting layer in organic electroluminescent device>

The polycyclic aromatic compound of the present invention is preferably used as a material for forming one or more arbitrary organic layers in an organic electroluminescent device, and is more preferably used as a material for forming a light emitting layer. The light-emitting layer 105 is a layer that emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light emitting layer 105, any compound (luminescent compound) that is excited by recombination of holes and electrons and emits light can be used, and a stable thin film shape can be formed, and strong light emission (fluorescence) efficiency in a solid state can be obtained. It is preferable that it is a compound which shows. The polycyclic aromatic compound of the present invention can be used as a material for a light emitting layer, may be used as a dopant material, or may be used as a host material, but is preferably used as a material for the light emitting layer, and is more preferably used as a dopant material. .

In addition, as a dopant, there is an example in which an assisting dopant and an emitting dopant are used in combination, but in this specification, when only described as a "dopant", it refers to a light emitting dopant used alone.

The light emitting layer may be a single layer or a plurality of layers, or may be either, and each is formed of a light emitting layer material (host material, dopant material). The host material and the dopant material may be one type, a combination of a plurality of materials, or any of them. The dopant material may be included in the entire host material, may be partially included, or may be any. As a doping method, although it can form by the vapor-codepositing method with a host material, you may vapor-deposit simultaneously after mixing with a host material beforehand. Specific examples of the dopant to be combined with the compound of the present invention in the case of using a plurality of dopants in combination are shown below. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium.

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

The amount of use of the dopant material differs depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The standard for the amount of dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, still more preferably 0.1 to 10% by mass of the total mass of the light emitting layer material. If it is the said range, it is preferable at the point that a concentration quenching phenomenon can be prevented, for example.

<Host Material>

As the host material, condensed ring derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclo A pentadiene derivative, a fluorene derivative, a benzofluorene derivative, etc. are mentioned.

Moreover, as a host material, the compound represented by any one of following formula (H1), (H2), and (H3) can be used, for example.

In formulas (H1), (H2) and (H3), L ¹ represents arylene having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylene arylene having 6 to 24 carbon atoms, and arylene having 6 to 24 carbon atoms. Arylene heteroarylene arylene, preferably arylene having 6 to 16 carbon atoms, more preferably arylene having 6 to 12 carbon atoms, particularly preferably arylene having 6 to 10 carbon atoms, specifically, a benzene ring , bivalent groups such as a biphenyl ring, a terphenyl ring and a fluorene ring. As the heteroarylene, heteroarylene having 2 to 24 carbon atoms is preferable, heteroarylene having 2 to 20 carbon atoms is more preferable, heteroarylene having 2 to 15 carbon atoms is still more preferable, and heteroarylene having 2 to 10 carbon atoms is more preferable. Arylene is particularly preferred, specifically, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazane ring), a thiadiazole ring, a triazole ring, and a tetrazole ring. , Pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzooxazole ring, benzothiazole ring, 1H-benzotria Zol ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, Green ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and thianthrene ring Divalent groups, such as these, are mentioned. At least one hydrogen in the compounds represented by the above formulas may be substituted with C1-C6 alkyl, cyano, halogen or deuterium.

As a preferable specific example, the compound represented by any one of the structural formulas listed below is mentioned. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (for example, methyl or t-butyl), phenyl or naphthyl.

<Anthracene compound>

Examples of the anthracene compound as a host include compounds represented by formula (3-H) and compounds represented by formula (3-H2).

In formula (3-H),

X and Ar ⁴ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroarylamino, substituted or unsubstituted Arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or It is substituted silyl, all X and Ar ⁴ do not become hydrogen at the same time, the two aryls of the diarylamino may be bonded to each other through a linking group, and the two heteroaryls of the diheteroarylamino are linked to each other through a linking group They may be bonded together, and the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group.

At least one hydrogen in the compound represented by formula (3-H) is unsubstituted or substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

Alternatively, a multimer (preferably a double body) may be formed by using the structure represented by formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by formula (3-H) are bonded to each other through X, and examples of this X include single bonds, arylene (phenylene, biphenylene, naphthylene, etc.) and heteroarylene (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 have a divalent bonding value), and the like.

The details of each group in the compound represented by the formula (3-H) can be cited from the description in the above formula (1), and further described in the column of the following preferred embodiments.

Preferred aspects of the anthracene compound are described below. The definition of the symbol in the following structure is the same as the above-mentioned definition.

In formula (3-H), X is each independently a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), formula (3-X1), formula (3- X2) or the group represented by formula (3-X3) bonds with the anthracene ring of formula (3-H) in *. Preferably, there is no case where two X's simultaneously become a group represented by formula (3-X3). More preferably, two X's do not simultaneously become groups represented by formula (3-X2).

Alternatively, a multimer (preferably a double body) may be formed by using the structure represented by formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by formula (3-H) are bonded to each other through X, and examples of this X include single bonds, arylene (phenylene, biphenylene, naphthylene, etc.) and hetero arylene (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 have a divalent bonding value).

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

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

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or Formula (A) are the groups represented (including carbazolyl, benzocarbazolyl and phenyl substituted carbazolyl). 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-H) and the group represented by formula (A) bond directly.

Further, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is selected from alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, and phenane. It may be further substituted with a group represented by tril, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula (A) (including carbazolyl and phenyl substituted carbazolyl). In addition, when the substituent of Ar ³ is a group represented by formula (A), the group represented by formula (A) bonds to Ar ³ in formula (3-X3) at *.

Ar ⁴ is, each independently, hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and/or cycloalkyl having 5 to 10 carbon atoms; It is a silyl substituted with

Alkyl having 1 to 4 carbon atoms substituted for silyl includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are independently , which is substituted with these alkyls.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, and ethyldimethyl Silyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec- Butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropyl Silyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, etc. are mentioned.

Cycloalkyl having 5 to 10 carbon atoms substituted with silyl is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, Cyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, decahydro azulenyl etc. are mentioned, and three hydrogens in silyl are each independently substituted with these cycloalkyls.

Specific examples of "silyl substituted with cycloalkyl of 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

Substituted silyl includes dialkylcycloalkylsilyl substituted with 2 alkyl and 1 cycloalkyl, and alkyldicycloalkylsilyl substituted with 1 alkyl and 2 cycloalkyl. As a specific example, the group mentioned above is mentioned.

In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with a group represented by 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-H) in *.

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

In 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, or optionally substituted aryl. , optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted may be amino, halogen, hydroxy or cyano, adjacent groups of R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring, and R ²⁹ is hydrogen or may be substituted it is aryl

It is preferable that Y in Formula (A) is -O-.

"Alkyl" of "alkyl which may be substituted" in R ²¹ to ^{R 28} may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms or branched chain having 3 to 24 carbon atoms. Alkyl is mentioned. C1-C18 alkyl (C3-C18 branched chain alkyl) is preferable, C1-C12 alkyl (C3-C12 branched chain alkyl) is more preferable, C1-C6 alkyl (C3 -6 branched chain alkyl) is more preferred, and C1-C4 alkyl (C3-C4 branched chain alkyl) is particularly preferred.

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

Examples of the "cycloalkyl" of the "optionally substituted cycloalkyl" in 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 cycloalkyl having 3 to 24 carbon atoms. Cycloalkyl of 14 carbon atoms, cycloalkyl of 5 to 10 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, cycloalkyl of 5 carbon atoms, and the like.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms, and bicyclo[1.1 .0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl ( norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphtharenyl, decahydroazulenyl, and the like.

Examples of the "aryl" of the "optionally substituted aryl" in R ²¹ to ^{R 28} include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, and aryl having 6 to 12 carbon atoms. An aryl of is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), Condensed tricyclic ring system, such as acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, condensed tetracyclic ring system, triphenylenyl, pyrenyl, naphthacenyl, condensed five ring system, perylenyl, pentacenyl and the like. .

Examples of the “heteroaryl” of the “optionally substituted heteroaryl” in R ²¹ to ^{R 28} include heteroaryl having 2 to 30 carbon atoms, and heteroaryl having 2 to 25 carbon atoms is preferable; A heteroaryl having 2 to 20 carbon atoms is more preferable, a heteroaryl having 2 to 15 carbon atoms is even more preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Moreover, as a heteroaryl, the heterocyclic etc. which contain 1-5 hetero atoms selected from oxygen, sulfur, and nitrogen other than carbon as a ring constituting atom are mentioned, for example.

Specific examples of "heteroaryl" include pyrroleyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyr Dill, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindoleyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, sinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, indolizinil, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, thienyl, benzo[b]thienyl, dibenzothienyl, furazanil, thianthrenil, naphthobenzofuranil , naphthobenzothienyl, and the like.

Examples of the "alkoxy" of the "optionally substituted alkoxy" in R ²¹ to ^{R 28} include straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) -6 branched chain alkoxy) is more preferred, and C1-C4 alkoxy (C3-C4 branched alkoxy) is particularly preferred.

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

"Aryloxy" of the "optionally substituted aryloxy" in R ²¹ to ^{R 28} is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is a group in which the above-mentioned "aryloxy in R ²¹ to R ²⁸ " The group described as "aryl" can be cited.

"Arylthio" of the "optionally substituted arylthio" in R ²¹ to ^{R 28} is a group in which hydrogen in the -SH group is substituted with aryl, and this aryl is a group in which the above-mentioned "arylthio" in R ²¹ to ^{R 28} 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 “alkyl silyl” in R ²¹ to R ²⁸ described above. The group described as " can be cited. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl and cyclobutyl.

Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, and isopropyl. dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyl diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, 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 the above-mentioned R ²¹ to R ²⁸ The group described as "cycloalkyl" of can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1 .0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, Decahydroazulenyl etc. are mentioned.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of dialkylcycloalkylsilyl substituted with 2 alkyl and 1 cycloalkyl and alkyldicycloalkylsilyl substituted with 1 alkyl and 2 cycloalkyl include groups selected from the above specific alkyl and cycloalkyl substituted silyl.

Examples of the "substituted amino" of the "optionally substituted amino" in R ²¹ to ^{R 28} include amino in which two hydrogen atoms are substituted with aryl or heteroaryl. Amino in which two hydrogens are substituted with aryl is diaryl (two aryls may be bonded to each other through a linking group) substituted amino, amino in which two hydrogens are substituted with heteroaryl is diheteroaryl substituted amino, Aminos in which two hydrogens are substituted by aryl and heteroaryl are arylheteroaryl substituted aminos. As for this aryl or heteroaryl, groups described as "aryl" or "heteroaryl" for R ²¹ to ^{R 28} can be cited.

Specific examples of "substituted aminos" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

Examples of the "halogen" for R ²¹ to ^{R 28} include fluorine, chlorine, bromine and iodine.

Some of the groups described as R ²¹ to ^{R 28} may be substituted as described above, and examples of substituents in this case include alkyl, cycloalkyl, aryl and heteroaryl. As the alkyl, cycloalkyl, aryl or heteroaryl, groups described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" for R ²¹ to R ²⁸ can be cited.

R ²⁹ in “>NR ²⁹ ” as Y is hydrogen or optionally substituted aryl. Examples of this aryl include groups described as “aryl” in R ²¹ to ^{R 28} described above, and examples of substituents thereof include 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. The case where a ring is not formed is a group represented by the following formula (A-1), and the case where a ring is formed is a group represented by the following formulas (A-2) to (A-14), for example. . 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, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryls may be bonded to each other through a linking group) substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, It may be substituted with hydroxy or cyano.

Examples of the ring formed by bonding adjacent groups to each other include a cyclohexane ring as long as it is a hydrocarbon ring, and examples of the aryl ring and heteroaryl ring include "aryl" and "heteroaryl" for R ²¹ to ^{R 28} described above. The ring structure demonstrated is mentioned, These rings are formed so that one or two benzene rings in Formula (A-1) may condense.

The group represented by formula (A) is a group obtained by removing one hydrogen at any one position of formula (A), and * represents the position. That is, the group represented by Formula (A) may make any one position a bonding position. For example, any one carbon atom on two benzene rings in the structure of formula (A), any one cyclic atom formed by bonding adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A), or Directly with any position of R ²⁹ in ">NR ²⁹ " as Y in the structure of Formula (A), or with N (R ²⁹ becomes a bond) in ">NR ²⁹ " can be a bonding group. The same applies to groups represented by any one of formulas (A-1) to (A-14).

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

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

In the compound represented by formula (3-H), the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), and A form bonded to any one of Ar ³ in (3-X3) is preferable.

In addition, deuterium may be sufficient as all or part of the hydrogen in the chemical structure of the anthracene compound represented by Formula (3-H).

The anthracene compound as a host may be, for example, a compound represented by the following formula (3-H2).

In formula (3-H2), Ar ^c is optionally substituted aryl or optionally substituted heteroaryl, R ^c is hydrogen, alkyl or cycloalkyl, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino (two aryls are connected to each other through a linking group may be bonded), diheteroarylamino which may be substituted (two heteroaryls may be bonded to each other through a linking group), arylheteroarylamino which may be substituted (aryl and heteroaryl are bonded to each other through a linking group, optionally substituted), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl and at least one hydrogen in the compound represented by formula (3-H2) may be substituted with halogen, cyano or deuterium.

In the formula (3-H2), "optionally substituted aryl", "optionally substituted heteroaryl", "optionally substituted diarylamino (two aryls may be bonded to each other via a linking group)", " Diheteroarylamino which may be substituted (two heteroaryls may be bonded to each other via a linking group)", "Arylheteroarylamino which may be substituted (aryl and heteroaryl may be bonded to each other via a linking group)" , "optionally substituted alkyl", "optionally substituted cycloalkyl", "optionally substituted alkenyl", "optionally substituted alkoxy", "optionally substituted aryloxy", "optionally substituted aryl The definition of "thio" or "optionally substituted silyl" is the same as that of the above formula (3-H), and the explanation in the formula (3-H) can be cited.

As "the aryl which may be substituted", it is also preferable that it is a group represented by any one of the following formula (3-H2-X1) - formula (3-H2-X8).

In the formulas (3-H2-X1) to (3-H2-X8), * represents a bonding position. In formulas (3-H2-X1) to (3-H2-X3), Ar ²¹ , Ar ²² , and Ar ²³ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, or quaterphenylyl , naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In addition, in the description of formula (3-H2), the group represented by formula (A) is the same as that described in the anthracene compound represented by formula (3-H).

In formulas (3-H2-X4) to (3-H2-X8), Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ , Ar ²⁸ , Ar ²⁹ , and Ar ³⁰ are each independently hydrogen or phenyl , biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, any one or two or more hydrogens in each of the groups represented by formulas (3-H2-X1) to formulas (3-H2-X8) are alkyl of 1 to 6 carbon atoms (preferably methyl or t-butyl) may be substituted.

Preferred examples of "the aryl which may be substituted" are represented by phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and formula (A) and terphenylyl (particularly m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of groups.

As "heteroaryl which may be substituted", group represented by formula (A) is mentioned. In addition, dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl etc. are mentioned as a specific example of "the aryl which may be substituted" and the "heteroaryl which may be substituted".

At least one hydrogen in the compound represented by formula (3-H2) may be substituted with halogen, cyano or deuterium. As "halogen" in this case, fluorine, chlorine, bromine, and iodine are mentioned. In particular, a compound in which all hydrogens in the compound represented by formula (3-H2) are substituted with heavy hydrogen is preferable.

In formula (3-H2), R ^c is hydrogen, alkyl or cycloalkyl, preferably hydrogen, methyl or t-butyl, more preferably hydrogen.

In formula (3-H2), it is preferable that at least two of Ar ¹¹ to ^{Ar 18} are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryls and optionally substituted heteroaryls are bonded to the anthracene ring.

The anthracene compound represented by formula (3-H2) is an aryl or heteroaryl which may be substituted with two of Ar ¹¹ to ^{Ar 18} , and the other 6 are hydrogen, optionally substituted alkyl, or optionally substituted. It is more preferably cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, the anthracene compound represented by formula (3-H2) more preferably has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

The anthracene compound represented by formula (3-H2) is an aryl which may be substituted with any two of Ar ¹¹ to Ar ¹⁸ or a heteroaryl which may be substituted, and the other 6 are hydrogen, methyl, or t-butyl. desirable.

In formula (3-H2), it is preferable that R ^c is hydrogen and any six of Ar ¹¹ to Ar ¹⁸ are hydrogen.

The anthracene compound represented by formula (3-H2) is the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3- It is preferably an anthracene compound represented by H2-E).

In the formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorene It is a group represented by yl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or formula (A), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quater It may be substituted by phenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when all the hydrogens of the methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be mutually bonded with a single bond. Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' The carbon atoms of the anthracene rings to which they are not bonded have methyl or t-butyl instead of hydrogen. may be combined.

When Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl, respectively , It is preferably a group represented by any one of the formulas (3-H2-X1) to (3-H2-X8).

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are each independently phenyl, biphenylyl (particularly, biphenyl-2-yl) Or biphenyl-4-yl), terphenylyl (particularly, m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or the above formulas (A-1) to (A It is more preferably a group represented by any one of -4), and in this case, at least one hydrogen in these groups is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formula (A -1) - may be substituted with the group represented by any one of formula (A-4).

In addition, in the compound represented by formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E) At least one hydrogen may be substituted with halogen, cyano or deuterium. A deuterated form is preferable, and a form in which all anthracene rings are deuterated or all hydrogen atoms are deuterated is preferable.

As an especially preferable anthracene compound represented by formula (3-H2), the anthracene compound represented by the following formula (3-H2-Aa) is mentioned.

In formula (3-H2-Aa), Ar ^c ′, Ar ¹⁴ ′, and Ar ¹⁵ ′ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or benzofluorene. Nyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the formulas (A-1) to (A-11), and at least one hydrogen in these groups is phenyl or biphenylyl , Terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-11) may be substituted. Here, when all of the methylene hydrogens in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. In addition, carbon atoms on the anthracene ring to which Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are not bonded may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) substituted with deuterium.

In formula (3-H2-Aa), Ar ^c ′, Ar ¹⁴ ′, and Ar ¹⁵ ′ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formula ( It is preferably a group represented by any one of A-1) to formula (A-4), and at least one hydrogen in these groups is phenyl, naphthyl, phenanthryl, fluorenyl, or formula (A-1) -You may be substituted by the group represented by any one of formula (A-4).

In the compound represented by formula (3-H2-Aa), it is preferable that at least the hydrogen bonded to the carbon at position 10 (the carbon to which Arc ^' is bonded is designated as position 9) of the anthracene ring is substituted with deuterium. . That is, it is preferable that the compound represented by formula (3-H2-Aa) is a compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is heavy hydrogen, and Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' have the same definitions as in formula (3-H2-Aa). D in the formula (3-H2-Ab) indicates that at least this position is a deuterium, any one or more hydrogens among the others in the formula (3-H2-Ab) may be a deuterium at the same time, and the formula (3-H2-Ab) It is also preferable that all of the hydrogens in -Ab) are deuterium.

Specific examples of the anthracene compound include compounds represented by formulas (3-131-Y) to (3-182-Y), formulas (3-183-N) and formulas (3-184-Y) to, for example. Formula (3-284-Y), and Formula (3-500) to Formula (3-557), and Formula (3-600) to Formula (3-605), and Formula (3-606-Y) to Formula The compound represented by (3-626-Y) is mentioned. The hydrogen atoms in these formulas may be partially or entirely substituted with deuterium, but particularly preferred forms of deuterium substitution are individually listed. Y in the formula is -O-, -S-, >NR ²⁹ (R ²⁹ is defined as above) or >C(-R ³⁰ ) ₂ (R ³⁰ is aryl or alkyl which may be linked). and R ²⁹ is, for example, phenyl, and R ³⁰ is, for example, methyl. The formula number is, for example, when Y is O, formula (3-131-Y) is expressed as formula (3-131-O), and when Y is -S- or >NR ²⁹ , formula (3 -131-S) or formula (3-131-N).

In the above formula, D is deuterium.

Among these compounds, formula (3-131-Y) to formula (3-134-Y), formula (3-138-Y), formula (3-140-Y) to formula (3-143-Y), formula (3-150-Y), formula (3-153-Y) to formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173- Y), formula (3-177-Y), formula (3-180-Y) to formula (3-183-N), formula (3-185-Y), formula (3-190-Y), formula ( 3-223-Y), Formula (3-241-Y), Formula (3-250-Y), Formula (3-252-Y) to Formula (3-254-Y), Formula (3-270-Y) )∼Formula(3-284-Y), Formula(3-501), Formula(3-507), Formula(3-508), Formula(3-509), Formula(3-513), Formula(3- 514), formula (3-519), formula (3-521), formula (3-538) to formula (3-547) or formula (3-600) to formula (3-605), and formula (3- 606-Y) - the compound represented by formula (3-626-Y) is preferable. Further, Y is preferably -O- or >NR ²⁹ , and more preferably -O-. Moreover, the form of deuterium substitution is also preferable.

The above anthracene compound 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) if it is an anthracene compound represented by formula (3-H) as a starting material, it can be manufactured by applying Suzuki coupling, Negishi coupling, and other well-known coupling reactions. Examples of the reactive group of these reactive compounds include halogen and boronic acid. As a specific manufacturing method, reference can be made to, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725.

<Fluorene compound>

The compound represented by formula (4-H) basically functions as a host.

In formula (4-H),

R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4-H) through a linking group), diarylamino (two Aryl may be bonded to each other through a linking group), diheteroarylamino (two heteroaryls may be bonded to each other through a linking group), arylheteroarylamino (aryl and heteroaryl may be bonded to each other through a linking group) ), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and also R ¹ and R ² , R ² And R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ may be independently bonded to form a condensed ring or spiro ring, At least one hydrogen in the formed ring is aryl, heteroaryl (the heteroaryl may be bonded to the formed ring through a linking group), diarylamino (two aryls may be bonded to each other through a linking group), di Heteroarylamino (two heteroaryls may be bonded to each other through a linking group), arylheteroarylamino (aryl and heteroaryls may be bonded to each other through a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryl It may be substituted with oxy, 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-H) is halogen , cyano or deuterium may be substituted.

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

Examples of alkenyl in R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, and more preferably alkenyl having 2 to 10 carbon atoms. , alkenyl having 2 to 6 carbon atoms is more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred. Preferred alkenyls are 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, any one from the compounds of formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) Monovalent group represented by removing the hydrogen atom of is also mentioned.

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 -Ar1) to formula (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. .

These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton in formula (4-H) and the heteroaryl may not only be directly bonded, but may also be bonded through a linking group therebetween. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. there is.

Further, 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 in the formula (4-H) are each independently bonded A condensed ring may be formed by combining R ⁹ and R ¹⁰ to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed with the benzene ring in the formula (4-H), 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 the benzene ring in Formula (4-H). The spiro ring formed by R ⁹ and R ¹⁰ is a ring that is spiro bonded to the 5-membered ring in Formula (4-H), 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 formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3), respectively. , A compound in which the benzene ring formed by combining R ¹ and R ² in the formula (4-H) is condensed, a compound in which the benzene ring formed by combining R ³ and R ⁴ in the formula (4-H) is condensed, and the compound in the formula (4-H) -H) is a compound in which none of R ¹ to R ⁸ are bonded.

The definitions of R 1 to R 10 in formulas (4-H-1), formulas (4-H-2) and formulas (4-H-3) correspond to corresponding ^{R 1 to} R ¹⁰ in formulas (4-H). The same as R ¹⁰ , and the definitions of R ¹¹ to R ¹⁴ in formulas (4-H-1) and (4-H-2) are also the same as R ¹ to R ¹⁰ in formula (4-H) do.

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

The definitions of R ² to R ⁷ in formulas (4-H-1A), formulas (4-H-2A) and formulas (4-H-3A) are formulas (4-H-1), formulas (4- H-2) and corresponding R ² to R ⁷ in formulas (4-H-3), and R ¹¹ to R in formulas (4-H-1A) and (4-H-2A) The definition of ¹⁴ is also the same as R ¹¹ to R ¹⁴ in formulas (4-H-1) and (4-H-2).

All or part of hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

More specific examples of the fluorene compound as a host of the present invention include compounds represented by the following structural formulas. In addition, "Me" represents methyl.

<Dibenzochrysene compound>

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

In formula (5-H), R ¹ to R ¹⁶ are each independently hydrogen, aryl, or heteroaryl (the heteroaryl is bonded to the dibenzochrysene skeleton in formula (5-H) through a linking group, may be), diarylamino (two aryls may be bonded to each other through a linking group), diheteroarylamino (two heteroaryls may be bonded to each other through a linking group), arylheteroarylamino (aryl and hetero Aryl may be bonded to each other through a linking group), 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 is aryl or heteroaryl (the heteroaryl is bonded to the formed ring through a linking group, may be), diarylamino (two aryls may be bonded to each other through a linking group), diheteroarylamino (two heteroaryls may be bonded to each other through a linking group), arylheteroarylamino (aryl, hetero Aryl may be bonded to each other through a linking group), may be substituted with alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl or at least one hydrogen in the compound represented by formula (5-H) may be substituted with halogen, cyano or deuterium.

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

Examples of alkenyl in the definition of formula (5-H) include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, and alkenyl having 2 to 10 carbon atoms. More preferably, alkenyl having 2 to 6 carbon atoms is still more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls are 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, any one from the compounds of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) Monovalent group represented by removing the hydrogen atom of is also mentioned.

In formulas (5-Ar1) to (5-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 -Ar1) to formula (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. .

These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryl may not only be directly bonded, but may also be bonded through a linking group therebetween. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. there is.

In the compound represented by formula (5-H), 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-H) are each independently hydrogen, phenyl, biphenylyl, naphthyl, Anthracenyl, phenanthrenyl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (corresponding The monovalent group having the structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- through, may be bonded to the dibenzochrysene skeleton in the formula (5-H)), methyl, ethyl, propyl, or butyl is preferable.

The compound represented by formula (5-H) is more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and R ¹⁶ is hydrogen. In this case, at least one (preferably 1 or 2, more preferably 1) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5-H) is a single bond, phenylene, via phenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, formula (5-Ar1), formula ( 5-Ar2), a monovalent group having a structure of formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5), other than at least one of the above (ie, a monovalent group having the above structure is substituted). position) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these is phenyl, biphenylyl, naphthyl, anthracenyl , methyl, ethyl, propyl, or butyl may be substituted.

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

More specific examples of the dibenzochrysene compound as a host of the present invention include compounds represented by the following structural formulas. In addition, "tBu" represents t-butyl.

The above-mentioned materials for the light emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound having a reactive substituent substituted thereto as a monomer, or a cross-linked polymer thereof, or a main chain polymer and the reactive compound. A pendant type polymer compound that has been reacted or a pendant type polymer crosslinked product thereof can also be used as a material for a light emitting layer.

<Emitting layer containing assisting dopant and emitting dopant>

The light emitting layer in the organic electroluminescent element may contain a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. It is also preferable to use the polycyclic aromatic compound of the present invention as an emitting dopant. As the assisting dopant (compound), a thermally activated delayed phosphor can be used.

In the following description, an organic electroluminescent element using a thermally activated delayed phosphor as an assisting dopant is sometimes referred to as a "TAF element" (TADF Assisting Fluorescence element). The "host compound" in the TAF element means that the lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component. high compound.

"Thermally activated delayed phosphor" is a phosphor capable of absorbing thermal energy to cause inverse intersystem crossing from the lowest triplet excited state to the lowest singlet excited state, and radiatively deactivated from the lowest singlet excited state to emit delayed fluorescence. means compound. However, "heat-activated delayed fluorescence" includes those that pass higher-order triplet in the excitation process from the lowest triplet excited state to the lowest singlet excited state. For example, a paper by Monkmans, University of Durham (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038/ncomms13680), a paper by Hosokai et al., Sci.Adv.2017;3: e1603282), a paper by Kyoto University scholars (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7), as well as a conference presentation by Kyoto University scholars (Japan Chemical Society 98th Spring Banquet, Publication No.: 2I4-15, Mechanism of High Efficiency Luminescence in Organic Electroluminescence Using DABNA as a Light-Emitting Molecule, Graduate School of Engineering, Kyoto University), and the like. In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300 K, a slow fluorescence component is observed, and the target compound is determined to be a "heat-activated delayed phosphor". Here, the slow fluorescence component refers to a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (C11367-01 manufactured by Hamamatsu Photonics Co., Ltd.).

The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "heat-activated delayed phosphor" can function as an assisting dopant that assists light emission of the polycyclic aromatic compound of the present invention.

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF device using a general fluorescent dopant as an emitting dopant (ED). In the figure, the ground state energy level of the host is E(1, G), the lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the fluorescence spectrum of the host is E(1, S, Sh), and the short wavelength side of the phosphorescence spectrum of the host is The lowest excitation triplet energy level obtained from the shoulder of E(1, T, Sh), the ground state energy level of the assisting dopant as the second component is E(2, G), and the fluorescence of the assisting dopant as the second component. The lowest excitation singlet energy level obtained from the shoulder on the short wavelength side of the spectrum is E(2, S, Sh), and the lowest excitation triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant as the second component is E( 2, T, Sh), E(3, G), the ground state energy level of the emitting dopant as the third component, the lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the fluorescence spectrum of the emitting dopant as the third component E(3, S, Sh), the lowest excitation triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the third component, the emitting dopant, is E(3, T, Sh), the hole is h+, and the electron is e -, fluorescence resonance energy transfer is FRET (Fluorescence Resonance Energy Transfer). In the TAF device, when a general fluorescent dopant is used as the emitting dopant (ED), energy upconverted from the assisting dopant moves to the lowest excitation singlet energy level E(3, S, Sh) of the assisting dopant and emits light. do. However, part of the excitation triplet energy E(2, T, Sh) on the assisting dopant moves to the lowest excitation triplet energy level E(3, T, Sh) of the emitting dopant, or the lowest excitation work on the emitting dopant. Intersystem crossing occurs from the singlet energy level E(3, S, Sh) to the lowest excited triplet energy level E(3, T, Sh), followed by thermal deactivation to the ground state E(3, G). do. A part of the energy is not used for light emission through this path, and energy is wasted.

In contrast, in the organic EL device of the present embodiment, energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, and thus high light emission efficiency can be realized. This is estimated to be based on the following light emission mechanism.

A preferable energy relationship in the organic electroluminescent device of the present embodiment is shown in FIG. 3 . In the organic electroluminescent device of this embodiment, a compound having a boron atom as an emitter dopant has a high lowest triplet excitation energy level E(3, T, Sh). Because of this, the excitation singlet energy upconverted in the assisting dopant is either upconverted or , recovered with the lowest excitation triplet energy level E(2, T, Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. In addition, by dividing into two types of molecules capable of improving upconversion and light emission functions, respectively, it is expected that the residence time of high energy is reduced and the burden on the compound is reduced.

In this aspect, a known host compound can be used, for example, a compound having at least one of a carbazole ring and a furan ring, and among them, at least one of furanyl and carbazolyl; It is preferable to use a compound in which at least one of arylene and heteroarylene is bonded. As a specific example, mCP, mCBP, etc. are mentioned.

The lowest excitation triplet energy level E (1, T, Sh) determined from the shoulder of the short wavelength side of the peak of the phosphorescence spectrum of the host compound is the highest in the light emitting layer from the viewpoint of promoting the generation of TADF in the light emitting layer without hindering it. The one higher than the lowest excitation triplet energy level E (2, T, Sh), E (3, T, Sh) of the emitting dopant or assisting dopant having the highest lowest excitation triplet energy level is preferable, specifically , the lowest excitation triplet energy level E (1, T, Sh) of the host compound is preferably 0.01 eV or more, and preferably 0.03 eV or more, compared to E (2, T, Sh), E (3, T, Sh). This is more preferable, and 0.1 eV or more is even more preferable. Further, a compound having TADF activity may be used as the host compound.

As the host compound, for example, a compound represented by any one of formulas (H1), (H2) and (H3) can be used.

<Heat activated delayed phosphor (assisting dopant)>

The thermally activated delayed phosphor (TADF compound) used in the TAF device uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to achieve HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied It is preferable to be a donor-acceptor type thermally activated delayed phosphor (D-A type TADF compound) designed to localize molecular orbitals and cause efficient reverse intersystem crossing. Here, in the present specification, "electron-donating substituent" (donor) means a substituent and partial structure in which the HOMO orbit is localized in a thermally activated delayed phosphor molecule, and "electron-accepting substituent" (acceptor), It shall mean the substituent and partial structure in which the LUMO orbital is localized in the thermally activated delayed phosphor molecule.

In general, a thermally activated delayed phosphor using a donor or acceptor has a large spin-orbit coupling (SOC) due to its structure, and at the same time, a small exchange interaction between HOMO and LUMO and a small ΔE(ST) Therefore, a very fast inverse interterminal crossing rate is obtained. On the other hand, thermally activated delayed phosphors using a donor or acceptor have a large structural relaxation in the excited state (since the stable structure is different between the ground state and the excited state in some molecules, it is changed from the ground state to the excited state by external stimulation). When conversion occurs, the structure is then changed to a stable structure in an excited state), providing a wide luminescence spectrum, so there is a possibility of reducing color purity when used as a luminescent material.

However, high color purity can be provided by using a thermally activated delayed phosphor using a donor or acceptor as an assisting dopant together with an appropriate emitting dopant such as a polycyclic aromatic compound of the present invention.

The thermally activated delayed phosphor may be any compound whose emission spectrum overlaps at least partially with the absorption spectrum of the polycyclic aromatic compound of the present invention. Both the polycyclic aromatic compound and the thermally activated delayed phosphor of the present invention may be included in the same layer or in adjacent layers.

As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or through a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used As the donor structure, carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, Phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydroinde Noacridine, diphenyldihydrodibenzoazacillin, etc. are mentioned. As the acceptor structure, sulfonyldibenzene, benzophenone, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole , oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzooxazole, benzobis(oxazole), quinoline, benzoimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide , dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorenedicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyridine midine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthenedioxide, thianthrenetetraoxide and tris(dimethylphenyl)borane. In particular, the compound having thermally activated delayed fluorescence in the TAF element has, as a partial structure, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isop It is preferably a compound having at least one selected from talonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone.

The compound used as the second component of the light emitting layer in the TAF element is a thermally activated delayed phosphor, and it is preferable that the emission spectrum overlaps at least partially with the absorption peak of the emitting dopant. In the following, compounds that can be used as the second component (heat-activated delayed phosphor) of the light emitting layer in the TAF element are exemplified. However, compounds that can be used as thermally activated delayed phosphors in TAF elements are not limitedly interpreted by the following exemplary compounds. In the following formula, Me represents methyl, tBu represents t-butyl, and the broken line represents the bonding position.

Further, as the thermally activated delayed phosphor, a compound represented by any of the following formulas (AD1), (AD2) and (AD3) can also be used.

In the above formulas (AD1), (AD2) and (AD3), M is each independently a single bond, -O-, >N-Ar or >CAr ₂ , and the HOMO depth and lowest excitation of the substructure to be formed From the viewpoint of the height of the singlet energy level and the lowest excited triplet energy level, it is preferably a single bond, -O- or >N-Ar. J is a spacer structure that divides the donor substructure and the acceptor substructure, and each independently is an arylene having 6 to 18 carbon atoms, from the viewpoint of the size of the conjugate exuded from the donor substructure and the acceptor substructure, Arylene having 6 to 12 carbon atoms is preferred. More specifically, phenylene, methylphenylene, and dimethylphenylene are mentioned. Q is, each independently, =C(-H)- or =N-, from the viewpoint of the shallowness of the LUMO of the substructure to be formed and the height of the lowest singlet excitation energy level and the lowest triplet excitation energy level, preferably , =N-. Ar is each independently hydrogen, aryl of 6 to 24 carbon atoms, heteroaryl of 2 to 24 carbon atoms, alkyl of 1 to 12 carbon atoms, or cycloalkyl of 3 to 18 carbon atoms, and the depth and minimum HOMO of the partial structure to be formed From the viewpoint of the height of the singlet excitation energy level and the lowest triplet excitation energy level, preferably hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or carbon atoms 6 to 10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarba zolyl, benzoimidazolyl or phenylbenzoimidazolyl, more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2; n is an integer of (6-m) or less, and is preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance. In addition, at least one hydrogen in the compounds represented by the above formulas may be substituted with halogen or heavy hydrogen.

More specifically, the compounds used as the second component of this embodiment include 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz are preferred.

The compound used as the second component of the present embodiment may be a donor acceptor type TADF compound represented by D-A in which one donor D and one acceptor A are bonded directly or through a linking group, but one acceptor A It is preferable to have a structure represented by the following formula (DAD1) in which a plurality of donors D are bonded directly or through a linking group, because the characteristics of the organic electroluminescent device are more excellent.

(D ¹ -L ¹ )nA ¹ (DAD1)

The formula (DAD1) includes a compound represented by the following formula (DAD2).

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In the formulas (DAD1) and (DAD2), D ¹ , D ² and D ³ each independently represents a donor group. As the donor group, the above donor structure can be employed. A ¹ and A ² each independently represent an acceptor group. As the acceptor group, the above acceptor structure can be employed. L ¹ , L ² and L ³ each independently represent a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates the donor group from the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms. More preferably, L ¹ , L ² and L ³ are each independently phenylene, methylphenylene or dimethylphenylene. n in Formula (DAD1) is 2 or more, and represents an integer equal to or less than the maximum number that A ¹ can substitute. n may be selected within the range of 2-10, for example, or may be selected within the range of 2-6. When n is 2, it becomes a compound represented by formula (DAD2). n pieces of D ¹ may be the same or different, and n pieces of L ¹ may be the same or different. Preferable specific examples of the compounds represented by formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, but the second component employable in the present invention is not limited to these compounds.

In this embodiment, the light emitting layer may be a single layer or a plurality of layers. In addition, the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be included in the same layer or may be included in at least one component each in a plurality of layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention included in the light emitting layer may each be of one kind, a combination of a plurality of them, or any of them. The assisting dopant and the emitting dopant may be included as a whole or partially in the host compound as a matrix. The light emitting layer doped with the assisting dopant and the emitting dopant is deposited simultaneously after mixing the host compound, the assisting dopant, and the emitting dopant by a method of forming a film by a three-way co-deposition method, mixing the host compound, the assisting dopant, and the emitting dopant in advance. It can be formed by, for example, a wet film forming method in which a composition (paint) for forming a light emitting layer prepared by dissolving a host compound, an assisting dopant, and an emitting dopant in an organic solvent is applied.

The amount of host compound used differs depending on the type of host compound, and may be determined according to the characteristics of the host compound. The amount of the host compound used is preferably 40 to 99% by mass, more preferably 50 to 98% by mass, still more preferably 60 to 95% by mass of the total mass of the light emitting layer material. The above range is preferable in terms of, for example, efficient charge transport and efficient energy transfer to the dopant.

The amount of assisting dopant (heat-activated delayed phosphor) used varies depending on the type of assisting dopant, and may be determined according to the characteristics of the assisting dopant. The standard for the amount of assisting dopant used is preferably 1 to 60% by mass, more preferably 2 to 50% by mass, still more preferably 5 to 30% by mass of the total mass of the material for the light emitting layer. The above range is preferable, for example, in that energy is efficiently transferred to the emitting dopant.

The amount of the emitting dopant (compound having a boron atom) used varies depending on the type of the emitting dopant, and may be determined according to the characteristics of the emitting dopant. The amount of the emitting dopant used is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, still more preferably 0.1 to 10% by mass of the total mass of the material for the light emitting layer. The above range is preferable in that, for example, the concentration quenching phenomenon can be prevented.

The amount of the emitting dopant used is preferably low in concentration because concentration quenching can be prevented. A high concentration of the assisting dopant is preferred from the viewpoint of the efficiency of the thermally activated delayed fluorescence device. In addition, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the assisting dopant is used at a low concentration compared to the amount of the assisting dopant.

<2-1-3. Substrates in Organic Electroluminescent Devices>

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

<2-1-4. Anode in Organic Electroluminescent Device>

The anode 102 serves to inject holes into the light emitting layer 105 . On the other hand, when any one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through them.

Materials forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO)) etc.), metal halides (such as copper iodide), copper sulfide, carbon black, ITO glass and Nessa glass. As an organic compound, conductive polymers, such as polythiophene, such as poly(3-methylthiophene), polypyrrole, and polyaniline, etc. are mentioned, for example. In addition, it can be used suitably selected from materials used as anodes of organic EL elements.

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

<2-1-5. Hole Injection Layer and Hole Transport Layer in Organic Electroluminescent Devices>

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

As the hole injection/transport material, it is necessary to efficiently inject/transport holes from the positive electrode between the electrodes to which an electric field is applied, and it is preferable to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable to use a material that has a low ionization potential, high hole mobility, excellent stability, and is difficult to generate trap impurities during production and use.

As the material forming the hole injection layer 103 and the hole transport layer 104, in the photoconductive material, a compound conventionally used as a hole charge transport material, a p-type semiconductor, a hole injection layer of an organic EL device, and a hole Any compound may be selected and used from known compounds used in the transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine Derivative (4,4',4"-tris(N-carbazolyl)triphenylamine, polymer having aromatic tertiary amino in main chain or side chain, 1,1-bis(4-di-p-tolyl Aminophenyl) cyclohexane, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-di Naphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N, N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H -Carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'-tetra[1,1'-biphenyl]-4-yl Triphenylamine derivatives such as )-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1, 4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, and the like. In the polymer system, polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane, etc. having the above monomers in their side chains are preferable, but they can form a thin film necessary for manufacturing a light emitting device, inject holes from an anode, and also It is not particularly limited as long as it is a compound capable of transporting.

It is also known that the conductivity of an organic semiconductor is strongly influenced by its doping. Such an organic semiconductor matrix material is composed of a compound having good electron donating property or a compound having good electron accepting property. For doping of electron donor materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are used. known (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz , M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. As matrix materials having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburstamine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly, zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Publication) Publication No. 2005-167175). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

<2-1-6. Electron blocking layer in organic electroluminescent device>

An electron blocking layer may be provided between the hole injection/transport layer and the light emitting layer to prevent diffusion of electrons from the light emitting layer. A compound represented by any of formulas (H1), (H2) and (H3) described above can be used to form the electron blocking layer. The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

<2-1-7. Electron Injection Layer, Electron Transport Layer in Organic Electroluminescent Device>

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

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

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in photoconductive materials, an electron injection layer and an electron transport layer of an organic EL device. It can be used by selecting it arbitrarily from known compounds in use.

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

In addition, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO 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.), Opene 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, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline- 2-yl)-9,9'-spirofluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives , Thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2': 6',2"-terpyridine-4 '-yl)benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silol derivatives, and azoline derivatives; and the like.

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

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

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

The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or a material for forming an electron transport layer.

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

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

<2-1-8. 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 forming the cathode 108 is not particularly limited as long as it is a material capable of efficiently injecting electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or alloys thereof (magnesium-silver alloy, magnesium -Indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.), etc. are preferable. In order to improve device characteristics by increasing electron injection efficiency, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in air in many cases. In order to improve this point, a method is known in which, for example, an organic layer is doped with a small amount of lithium, cesium or magnesium to use an electrode having high stability. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

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

<2-1-9. Binders that can be used in each layer>

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

<2-1-10. Manufacturing method of organic electroluminescent device>

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

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

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

<2-1-11. Application Examples of Organic Electroluminescent Devices>

Organic EL elements can also be applied to display devices or lighting devices.

A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting an organic EL element and a known drive device, and a known drive method such as direct current drive, pulse drive, or alternating current drive can be used as appropriate. You can drive using it.

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

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

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is illuminated. For example, the time or temperature display in a digital watch or thermometer, the operation state display of an audio device or electric cooker, and the panel display of a car etc. are mentioned.

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

<2-2. Other Organic Devices>

The polycyclic aromatic compound according to the present invention can be used for fabrication of an organic field effect transistor or an organic thin film solar cell in addition to the organic electroluminescent device described above.

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

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

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

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

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

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

The organic field effect transistor configured in this way can be applied as a pixel drive switching element of an active matrix drive type liquid crystal display or an organic light emitting device display.

An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. The organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like other than the above. For organic thin-film solar cells, well-known materials used for organic thin-film solar cells can be appropriately selected and combined.

<3. Wavelength Conversion Materials>

The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

Currently, application of the multi-colorization technology by a color conversion method to liquid crystal displays, organic EL displays, lighting, and the like is actively being studied. Color conversion is wavelength conversion of light emission from a light emitting body into longer wavelength light, and indicates, for example, conversion of ultraviolet light or blue light into green light or red light emission. By forming a film of this wavelength conversion material having a color conversion function and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red, that is, to extract white light from the blue light source. A full-color display can be manufactured by using a white light source obtained by combining such a blue light source and a wavelength conversion film having a color conversion function as a light source unit, and combining a liquid crystal driving part and a color filter. In addition, if there is no liquid crystal driving part, it can be used as a white light source as it is, and can be applied as a white light source such as LED lighting, for example. In addition, by using a blue organic EL element as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to manufacture a full-color organic EL display without using a metal mask. Furthermore, by using a blue micro LED as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to manufacture a low-cost full-color micro LED display.

The polycyclic aromatic compound of the present invention can be used as this wavelength conversion material. Using the wavelength conversion material containing the polycyclic aromatic compound of the present invention, light from a light source or light emitting element that generates ultraviolet light or shorter wavelength blue light is converted into a display device (a display device using an organic EL element or a liquid crystal display device) It can be converted into blue light or green light with high color purity suitable for use in Adjustment of the color to be converted can be performed by appropriately selecting the substituent of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength conversion composition described later, and the like. The wavelength conversion material can be prepared as a composition for wavelength conversion containing the polycyclic aromatic compound of the present invention. Moreover, you may form a wavelength conversion film using this composition for wavelength conversion.

The composition for converting wavelengths may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. As binder resin, what was described in Paragraph 0173 - 0176 of International Publication No. 2016/190283 can be used, for example. As other additives, the compounds described in Paragraphs 0177 to 0181 of International Publication No. 2016/190283 can be used. As the solvent, the description of the solvent contained in the above composition for forming a light emitting layer can be referred to.

The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for producing a wavelength conversion layer from a wavelength conversion composition, a known film formation method can be referred to. The wavelength conversion film may consist only of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, and other wavelength conversion layers (eg, a wavelength conversion layer that converts blue light into green light or red light, blue light or green light). A wavelength conversion layer that converts into red light) may be included. Further, the wavelength conversion film may include a base layer or a barrier layer for preventing deterioration of the color conversion layer due to oxygen, moisture, or heat.

[Example]

Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited thereto.

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

Under nitrogen atmosphere, intermediate (X-1) (52.1 g), 1-t-butyl-3,4,5-trichlorobenzene (23.8 g), dichlorobis[di-t-butyl (4-dimethyl as a palladium catalyst) Aminophenyl)phosphino]palladium(II) (Pd-132, 0.91 g), sodium-t-butoxide (NaOtBu, 14.4 g) and toluene (500 ml) were put in a flask and heated at 110°C for 3 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture and stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified with a silica gel short pass column (eluent: heptane) to obtain 69.2 g of intermediate (X-2).

Under a nitrogen atmosphere, intermediate (X-2) (36.2 g), intermediate (X-3) (29.9 g), Pd-132 (0.719 g), NaOtBu (7.2 g) and toluene (300 ml) as a palladium catalyst were added to a flask. and heated at 110°C for 3 hours. After completion of the reaction, water and ethyl acetate were added to the reaction mixture and stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified with a silica gel short pass column (eluent: toluene/heptane = 1/9 (volume ratio)) to obtain 52.2 g of an intermediate (X-4).

In a flask containing intermediate (X-4) (12.86 g) and tert-butylbenzene ( ^t Bu-benzene, 100 ml), 1.60 M tert-butyllithium pentane solution ( ^t BuLi, 12.5 ml) was added. After completion of the dropwise addition, the temperature was raised to 70°C and stirred for 0.5 hour, and then components having a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. After cooling to -50°C, boron tribromide (2.51 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hour. After that, it was cooled to 0°C again, N,N-diisopropylethylamine (EtN ⁱ Pr ₂ , 1.29g) was added, and the mixture was stirred at room temperature until the exotherm was resolved, then the temperature was raised to 100°C and heated for 1 hour. Stir. The reaction solution was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath and then ethyl acetate were added to separate the mixture. After concentrating the organic layer, it was purified by a silica gel shortpass column (eluent: chlorobenzene). By recrystallizing the obtained crude product from toluene, 7.72 g of compound (1-1) was obtained.

Compound (1-1) was confirmed by MALDI-TOF-MS and ¹ H-NMR.

m/z(M+H)=1259.83

¹ H-NMR (CDCl ₃ ): δ = 8.6 (d, 1H), 8.0 (d, 2H), 8.0 (d, 1H), 7.8 (s, 1H), 7.7 (s, 1H), 7.6 to 7.5 ( m, 5H), 7.4(d, 2H), 7.2(d, 1H), 7.0(m, 3H), 6.9(d, 1H), 6.8(d, 1H), 6.7(s, 1H), 6.6(s) , 1H), 6.5 (d, 2H), 1.9 to 1.8 (m, 4H), 1.8 (s, 4H), 1.6 (s, 4H), 1.5 (s, 3H), 1.5 (s, 3H), 1.4 ( s, 6H), 1.4(s, 6H), 1.3(s, 3H), 1.3(s, 3H), 1.2(s, 9H), 1.2(s, 6H), 1.2(s, 6H), 1.1(s , 9H), 0.9(s, 18H).

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

Compound (1-2) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-2).

The target compound with m/z (M+H) = 1301.79 was confirmed by MALDI-TOF-MS.

Synthesis Example (3): Synthesis of Compound (1-5)

Compound (1-5) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-5).

The target compound with m/z (M+H) = 1127.74 was confirmed by MALDI-TOF-MS.

Synthesis Example (4): Synthesis of Compound (1-6)

Compound (1-6) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-6).

The target compound with m/z (M+H) = 1255.80 was confirmed by MALDI-TOF-MS.

Synthesis Example (5): Synthesis of Compound (1-11)

Compound (1-11) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-11).

The target compound with m/z (M+H) = 1457.88 was confirmed by MALDI-TOF-MS.

Synthesis Example (6): Synthesis of Compound (1-15)

Compound (1-15) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-15).

The target compound with m/z (M+H) = 1347.77 was confirmed by MALDI-TOF-MS.

Synthesis Example (7): Synthesis of Compound (1-16)

Compound (1-16) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-16).

The target compound with m/z (M+H) = 1239.73 was confirmed by MALDI-TOF-MS.

Synthesis Example (8): Synthesis of Compound (1-17)

Compound (1-17) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-17).

The target compound with m/z (M+H) = 1410.87 was confirmed by MALDI-TOF-MS.

Synthesis Example (9): Synthesis of Compound (1-21)

Compound (1-21) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-21).

The target compound with m/z (M+H) = 955.52 was confirmed by MALDI-TOF-MS.

Synthesis Example (10): Synthesis of Compound (1-22)

Compound (1-22) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-22).

The target compound with m/z (M+H) = 1181.70 was confirmed by MALDI-TOF-MS.

Synthesis Example (11): Synthesis of Compound (1-23)

Compound (1-23) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-23).

The target compound with m/z (M+H) = 1192.58 was confirmed by MALDI-TOF-MS.

Synthesis Example (12): Synthesis of Compound (1-24)

Compound (1-24) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-24).

The target compound with m/z (M+H) = 1387.76 was confirmed by MALDI-TOF-MS.

Synthesis Example (13): Synthesis of Compound (1-26)

Compound (1-26) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-26).

The target compound (1-26) with m/z (M+H) = 1385.88 was confirmed by MALDI-TOF-MS.

Synthesis Example (14): Synthesis of Compound (1-30)

Compound (1-30) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-30).

The target compound with m/z (M+H) = 1087.67 was confirmed by MALDI-TOF-MS.

Synthesis Example (15): Synthesis of Compound (1-31)

Compound (1-31) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-31).

The target compound with m/z (M+H) = 1232.72 was confirmed by MALDI-TOF-MS.

Synthesis Example (16): Synthesis of Compound (1-35)

Compound (1-35) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-35).

The target compound with m/z (M+H) = 1257.69 was confirmed by MALDI-TOF-MS.

Synthesis Example (17): Synthesis of Compound (1-41)

Compound (1-41) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-41).

The target compound with m/z (M+H) = 1392.70 was confirmed by MALDI-TOF-MS.

Synthesis Example (18): Synthesis of Compound (1-46)

Compound (1-46) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-46).

The target compound with m/z (M+H) = 1221.87 was confirmed by MALDI-TOF-MS.

Synthesis Example (19): Synthesis of Compound (1-47)

Compound (1-47) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-47).

The target compound (1-4) with m/z (M+H) = 1238.84 was confirmed by MALDI-TOF-MS.

Synthesis Example (20): Synthesis of Compound (1-48)

Compound (1-48) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-48).

The target compound (1-4) with m/z (M+H) = 1143.68 was confirmed by MALDI-TOF-MS.

Synthesis Example (21): Synthesis of Compound (1-50)

Compound (1-50) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-50).

The target compound with m/z (M+H) = 1282.98 was confirmed by MALDI-TOF-MS.

Synthesis Example (22): Synthesis of Compound (1-52)

Compound (1-52) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-52).

The target compound with m/z (M+H) = 1225.81 was confirmed by MALDI-TOF-MS.

Synthesis Example (23): Synthesis of Compound (1-53)

Compound (1-53) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-53).

The target compound with m/z (M+H) = 1049.56 was confirmed by MALDI-TOF-MS.

Synthesis Example (24): Synthesis of Compound (1-54)

Compound (1-54) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-54).

The target compound with m/z (M+H) = 1378.91 was confirmed by MALDI-TOF-MS.

Synthesis Example (25): Synthesis of Compound (1-57)

Compound (1-57) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-57).

The target compound with m/z (M+H) = 1314.78 was confirmed by MALDI-TOF-MS.

Synthesis Example (26): Synthesis of Compound (1-58)

Compound (1-58) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-58).

The target compound with m/z (M+H) = 1408.77 was confirmed by MALDI-TOF-MS.

Synthesis Example (27): Synthesis of Compound (1-59)

Compound (1-59) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-59).

The target compound with m/z (M+H) = 1501.85 was confirmed by MALDI-TOF-MS.

Synthesis Example (28): Synthesis of Compound (1-61)

Compound (1-61) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-61).

The target compound with m/z (M+H) = 1313.69 was confirmed by MALDI-TOF-MS.

Synthesis Example (29): Synthesis of Compound (1-65)

Compound (1-65) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-65).

The target compound with m/z (M+H) = 1243.86 was confirmed by MALDI-TOF-MS.

Synthesis Example (30): Synthesis of Compound (1-66)

Compound (1-66) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-66).

The target compound with m/z (M+H) = 1285.81 was confirmed by MALDI-TOF-MS.

Synthesis Example (31): Synthesis of Compound (1-67)

Compound (1-67) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-67).

The target compound with m/z (M+H) = 1239.82 was confirmed by MALDI-TOF-MS.

Synthesis Example (32): Synthesis of Compound (1-71)

Compound (1-71) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-71).

The target compound with m/z (M+H) = 993, 52 was confirmed by MALDI-TOF-MS.

Synthesis Example (33): Synthesis of Compound (1-72)

Compound (1-72) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-72).

The target compound with m/z (M+H) = 1216.74 was confirmed by MALDI-TOF-MS.

Synthesis Example (34): Synthesis of Compound (1-73)

Compound (1-73) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-73).

The target compound with m/z (M+H) = 1270.81 was confirmed by MALDI-TOF-MS.

Synthesis Example (35): Synthesis of Compound (1-74)

Compound (1-74) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-74).

The target compound with m/z (M+H) = 1123.71 was confirmed by MALDI-TOF-MS.

Synthesis Example (36): Synthesis of Compound (1-75)

Compound (1-75) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-75).

The target compound with m/z (M+H) = 1183.80 was confirmed by MALDI-TOF-MS.

Synthesis Example (37): Synthesis of Compound (1-76)

Compound (1-76) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-76).

The target compound with m/z (M+H) = 1311.86 was confirmed by MALDI-TOF-MS.

Synthesis Example (38): Synthesis of Compound (1-77)

Compound (1-77) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-77).

The target compound with m/z (M+H) = 1229.79 was confirmed by MALDI-TOF-MS.

Synthesis Example (39): Synthesis of Compound (1-78)

Compound (1-78) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-78).

The target compound with m/z (M+H) = 1290.78 was confirmed by MALDI-TOF-MS.

Synthesis Example (40): Synthesis of Compound (1-79)

Compound (1-79) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-79).

The target compound with m/z (M+H) = 1189.66 was confirmed by MALDI-TOF-MS.

Synthesis Example (41): Synthesis of Compound (1-80)

Compound (1-80) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-80).

The target compound with m/z (M+H) = 1183.80 was confirmed by MALDI-TOF-MS.

Synthesis Example (42): Synthesis of Compound (1-85)

Compound (1-85) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-85).

The target compound with m/z (M+H) = 1254.84 was confirmed by MALDI-TOF-MS.

Synthesis Example (43): Synthesis of Compound (1-86)

Compound (1-86) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-86).

The target compound with m/z (M+H) = 1107.73 was confirmed by MALDI-TOF-MS.

Synthesis Example (44): Synthesis of Compound (1-87)

Compound (1-87) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-87).

The target compound with m/z (M+H) = 1167.82 was confirmed by MALDI-TOF-MS.

　

Synthesis Example (45): Synthesis of Compound (1-88)

Compound (1-88) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-88).

The target compound with m/z (M+H) = 1295.89 was confirmed by MALDI-TOF-MS.

　

　

Synthesis Example (46): Synthesis of Compound (1-89)

Compound (1-89) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-89).

The target compound with m/z (M+H) = 1213.81 was confirmed by MALDI-TOF-MS.

Synthesis Example (47): Synthesis of Compound (1-90)

Compound (1-90) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-90).

The target compound with m/z (M+H) = 1274.80 was confirmed by MALDI-TOF-MS.

Synthesis Example (48): Synthesis of Compound (1-91)

Compound (1-91) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-91).

The target compound with m/z (M+H) = 1173.68 was confirmed by MALDI-TOF-MS.

　

　

Synthesis Example (49): Synthesis of Compound (1-92)

Compound (1-92) was obtained in the same manner as in Synthesis Example 1 except for changing compound (X-4) to compound (X-4-92).

The target compound with m/z (M+H) = 1167.82 was confirmed by MALDI-TOF-MS.

　

　

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

<Evaluation method of basic physical properties>

<Preparation of sample>

When evaluating the absorption characteristics and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, there are cases in which the compound to be evaluated is dissolved in a solvent and evaluated in a solvent or in a thin film state. In the case of evaluation in a thin film state, depending on the mode of use of the compound to be evaluated in the organic EL device, the case where only the compound to be evaluated is thinned and evaluated, and the compound to be evaluated is dispersed in an appropriate matrix material to form a thin film. may be evaluated. Here, a thin film obtained by depositing only the compound to be evaluated is referred to as a "single film", and a thin film obtained by applying and drying a coating solution containing the compound to be evaluated and a matrix material is referred to as a "coated film".

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

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

<Evaluation of Absorption Characteristics and Emission Characteristics>

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

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

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

Next, evaluation of basic physical properties of the polycyclic aromatic compound of the present invention will be described.

<Evaluation of fluorescence lifetime (delayed fluorescence)>

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

<Calculation of energy gap (Eg)>

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

<Measurement of ionization potential (Ip)>

A transparent support substrate (28 mm x 26 mm x 0.7 mm) on which ITO (indium tin oxide) is deposited is fixed to a substrate holder of a commercially available evaporation device (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum evaporation boat containing the target compound. After mounting, the vacuum chamber is depressurized to 5×10 ^-4 Pa. Next, the target compound is evaporated by heating the deposition boat to form a single film (neat film) of the target compound.

Using the obtained single film as a sample, the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Machinery Co., Ltd. PYS-201).

<Calculation of Electron Affinity (Ea)>

Electron affinity can be measured from the difference between the ionization potential measured by the above method and the energy gap calculated by the above method.

<Measurement of excitation singlet energy level E(S, Sh) and excitation triplet energy level E(T, Sh)>

For a single film of the compound of interest formed on a glass substrate, at 77 K, the second absorption peak from the long wavelength side of the absorption spectrum was observed in the fluorescence spectrum with excitation light, and the fluorescence spectrum peak was excitation from the shoulder on the short wavelength side. Find the singlet energy level E(S, Sh). In addition, the phosphorescence spectrum was observed with the excitation light of the second absorption peak from the long wavelength side of the absorption spectrum at 77 K for the single film of the target compound formed on the glass substrate, and the phosphorescence spectrum was excited from the shoulder on the short wavelength side. Find the triplet energy level E(T, Sh).

<Evaluation of organic EL element>

Evaluation of the basic physical properties described above confirms that the compound of the present invention has an appropriate energy gap (Eg), a high triplet excitation energy (E _T ), and a small ΔEST. From these results, it can be seen that the compound of the present invention can be expected to be applied to, for example, a light emitting layer and a charge transport layer, and in particular to a light emitting layer.

Next, fabrication and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

<Configuration of organic EL element>

An organic EL device was manufactured using the polycyclic aromatic compound of the present invention.

The material configuration of each layer in the organic EL devices of Examples 1 to 49 and Comparative Examples 1 to 15 is shown in Table 1 below.

"HI", "HAT-CN", "HT-1", "HT-2", "BH", "ET-1", "ET-2", "Liq" in Tables 1 and 2 , "Comparative compound (1)", "Comparative compound (2)", "Comparative compound (3)", "Comparative compound (4)", "Comparative compound (5)", "Comparative compound (6)", " Comparative compound (7)”, “Comparative compound (8)”, “Comparative compound (9)”, “Comparative compound (10)”, “Comparative compound (11)”, “Comparative compound (12)”, “Comparative compound (13)”, the chemical structures of “Comparative Compound (14)” and “Comparative Compound (15)” are shown below.

(Example 1)

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) obtained by polishing ITO film formed to a thickness of 180 nm by sputtering to 150 nm is used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET- A boat for vapor deposition made of molybdenum containing No. 1 and ET-2, and a boat for vapor deposition made of aluminum nitride containing Liq, LiF, and aluminum, respectively, were installed.

Each of the following layers is sequentially formed on the ITO film of the transparent support substrate. Depressurize the vacuum chamber to 5×10 ^-4 Pa, first heat HI to deposit a film thickness of 40 nm, then heat HAT-CN to deposit a film thickness of 5 nm, and then heat HT-1 was heated to deposit a film thickness of 45 nm, and then, HT-2 was heated and deposited to a film thickness of 10 nm to form a four-layered hole layer. Next, BH and compound (1-1) were simultaneously heated and deposited to a film thickness of 25 nm to form a light emitting layer. The deposition rate was adjusted so that the mass ratio of BH and compound (1-1) was about 97:3. Further, ET-1 was heated to deposit a film thickness of 5 nm, and then ET-2 and Liq were simultaneously heated and deposited to a film thickness of 25 nm to form a two-layer electronic layer. The deposition rate was adjusted so that the mass ratio of ET-2 and Liq was about 50:50. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then aluminum was heated and deposited to a film thickness of 100 nm to form a cathode to obtain an organic EL device.

(Examples 2 to 49 and Comparative Examples 1 to 15)

Organic EL devices of Examples 2 to 49 and Comparative Examples 1 to 15 were obtained in the same manner as in Example 1 except that each material listed in Table 2 was used instead of Compound (1-1).

<Evaluation items and evaluation method>

Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. For these evaluation items, for example, values at 1000 cd/m ² light emission can be used.

The quantum efficiency of a light emitting device includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency represents the rate 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 these photons emitted to the outside of the light emitting element, and photons generated in the light emitting layer are partially absorbed or continuously reflected inside the light emitting element, thereby Since it is not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring spectral radiance (emission spectrum) and external quantum efficiency is as follows. Using a voltage/current generator R6144 manufactured by Advantist, a voltage such that the luminance of the element is 1000 cd/m ² is applied to cause the element to emit light. The spectral emission luminance in the visible region was measured from a direction perpendicular to the light emitting surface using a spectroscopic emission luminance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a completely diffusing surface, the measured spectral radiance value of each wavelength component divided by the wavelength energy and multiplied by π is the number of photons at each wavelength. Then, the number of photons in the entire observed wavelength range is integrated, and the total number of photons emitted from the device is taken. The value obtained by dividing the applied current value by the basic charge is the number of carriers injected into the device, and the value 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. In addition, the half width of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity is 50% with the maximum emission wavelength as the center.

For the organic EL devices of Examples 1 to 49 and Comparative Examples 1 to 15, direct current voltage was applied using the ITO electrode as the anode and the LiF/aluminum electrode as the cathode, and the characteristics at 1000 cd/m ² emission and 1000 cd/m ² emission By continuously driving at a voltage of 95%, the time to maintain luminance of 95% or more of the initial luminance was measured.

The results are shown in Table 2.

The polycyclic aromatic compound of the present invention is useful as a material for an organic device, particularly a material for a light emitting layer for forming a light emitting layer of an organic electroluminescent device. By using the polycyclic aromatic compound of the present invention as a dopant for a light emitting layer, an organic electroluminescent device capable of emitting light with low voltage and high efficiency can be obtained.

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 (16)

polycyclic aromatic compounds having a structure composed of one or two or more structural units represented by the following formula (1);

In formula (1),
ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring;
Ring C is a ring represented by formula (C),
In formula (C),
X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR, the >C(-R) ₂ and the >Si( -R) R in ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and the two R of >Si(-R) ₂ above may be bonded to each other to form a ring;
Any two adjacent Z ^{C '} s are carbon directly bonded to either Y ¹ or X ² ,
other Z ^C are each independently N or CR ^C , and R ^C are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of diarylamino may be bonded to each other via a linking group, and the diheteroaryl The two heteroaryls of amino may be bonded to each other through a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group may be combined through
Two adjacent R ^Cs may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^C2 , and R ^C2 has the same meaning as R ^C , provided that R ^C2 is not hydrogen, and two adjacent R ^C2s do not bond to each other to form an aryl ring or a heteroaryl ring;
The ring represented by formula (C) is R ^C or R ^C2 and is aryl at least substituted with a group represented by formula (D-1) or formula (D-2) or formula (D-1) or formula (D-2). 2) includes a heteroaryl at least substituted with a group represented by;
The groups represented by formulas (D-1) and (D-2) are bonded to two ring-constituting atoms adjacent to each other in the aryl ring or heteroaryl ring in two *,
In the formulas (D-1) and (D-2), R ^D are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted is cycloalkyl, and L is each independently substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R in >NR is hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs of (-R) ₂ may be bonded to each other to form a ring, and R of >NR and/or R of >C(-R) ₂ may be bonded to ring A and/or ring A by a linking group or a single bond. / or may be bonded to the B ring, or the A ring and / or the C ring;
At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium. According to claim 1,
R ^C or R ^C2 is at least substituted with the aryl at least substituted with a group represented by formula (D-1) or formula (D-2) or a group represented by formula (D-1) or formula (D-2) An aryl ring at least substituted with a group represented by formula (D-1) or formula (D-2) at a site other than the heteroaryl and represented by formula (D-1) or formula (D-2) A polycyclic aromatic compound further comprising, as a partial structure, at least one ring selected from the group consisting of heteroaryl rings at least substituted with groups. According to claim 1 or 2,
polycyclic aromatic compounds in which the structural unit represented by formula (1) is a structural unit represented by formula (2);

In formula (2),
Z is each independently N or CR ¹¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se; R of >NR, >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl. , or a substituted or unsubstituted cycloalkyl, and the two Rs of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
R ¹¹ of CR ¹¹ is each independently hydrogen, 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, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted of aryloxy, substituted or unsubstituted arylthio, or substituted silyl,
The two aryls of the diarylamino may be bonded to each other through a linking group, and the two heteroaryls of the diheteroarylamino may be bonded to each other through a linking group, and the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other may be bonded through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group;
Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring together with ring a or b, and the formed aryl ring and heteroaryl ring are each unsubstituted, or at least one of R ^11b substituted, R ^1lb has the same meaning as R ¹¹ , provided that R ^1lb is not hydrogen, and two adjacent R ^1lb do not bond to each other to form an aryl ring or a heteroaryl ring;
ring C is a ring represented by formula (C);
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R)2, >S, or >Se, wherein R in >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs in (-R) ₂ may be bonded to each other to form a ring, and R in >NR and/or R in >C(-R) ₂ may form a ring or a ring by a linking group or a single bond. / or may be bonded to the b ring, or the a ring and / or the C ring;
At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium. According to claim 3,
polycyclic aromatic compounds in which the structural unit represented by formula (2) is a structural unit represented by formula (2a-1);

In formula (2a-1), Y ¹ , X ¹ , X ² , and X ^C have the same meaning as Y ¹ , X ¹ , X ² , and X ^C in formula (2), respectively, and R ^1lb and R ^C2 are , R ^1lb , R ^C2 in formula (2) have the same meaning, respectively,
n1 is an integer of 1 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3,
At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium. According to claim 4,
A polycyclic aromatic compound represented by any one of the following formulas.

In the formula, Me is methyl, tBu is t-butyl, and D is deuterium. According to claim 3,
polycyclic aromatic compounds in which the structural unit represented by formula (2) is a structural unit represented by formula (2a-2);

In formula (2a-2), Y ¹ , X ¹ , X ² , and X ^C have the same meaning as Y ¹ , X ¹ , X ² , and X ^C in formula (2), respectively, and R ^1lb and R ^C2 are , R ^1lb , R ^C2 in formula (2) have the same meaning, respectively,
X ³ and X ⁴ are each independently a single bond, >O, >NR, >C(-R) ₂ , or >S, provided that X ³ and X ⁴ are not single bonds at the same time;
n1 is an integer of 1 to 4, n2 is an integer of 0 to 4, n3 is an integer of 0 to 3, n4 is an integer of 0 to 2,
At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium. According to claim 6,
A polycyclic aromatic compound represented by any one of the following formulas.

In the formula, Me is methyl and tBu is t-butyl. According to claim 3,
A polycyclic aromatic compound represented by the following formula.

polycyclic aromatic compounds having a structure composed of one or two or more structural units represented by the following formula (1');

In formula (1'),
ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring;
Ring C is a ring represented by formula (C),
In formula (C),
X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR, the >C(-R) ₂ and the >Si( -R) R in ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and the two R of >Si(-R) ₂ above may be bonded to each other to form a ring;
Any two adjacent Z ^{C '} s are carbon directly bonded to either Y ¹ or X ² ,
other Z ^C are each independently N or CR ^C , and R ^C are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted Unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of diarylamino may be bonded to each other via a linking group, and the diheteroaryl The two heteroaryls of amino may be bonded to each other through a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded to each other through a linking group, and the two aryls of the diarylboryl may be bonded to each other through a single bond or a linking group may be combined through
Two adjacent R ^Cs may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are each unsubstituted or substituted with at least one R ^C2 , and R ^C2 has the same meaning as R ^C , provided that R ^C2 is not hydrogen, and two adjacent R ^C2s do not bond to each other to form an aryl ring or a heteroaryl ring;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
X ¹ and X ² are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R in >NR is hydrogen, substituted Or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein R in >C(-R) ₂ and >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >C(-R) ₂ and >Si The two Rs of (-R) ₂ may be bonded to each other to form a ring, and R of >NR and/or R of >C(-R) ₂ may be bonded to ring A and/or ring A by a linking group or a single bond. / or may be bonded to the B ring, or the A ring and / or the C ring;
The structure is at least one selected from the group consisting of an aryl ring at least substituted with a group represented by formula (D-1) and a heteroaryl ring substituted at least with a group represented by formula (D-1) as a partial structure. include,
The group represented by formula (D-1) is bonded to two adjacent ring atoms in any aryl ring or heteroaryl ring in the above structure in two *, and in formula (D-1), R ^D is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and L is each independently substituted or unsubstituted alkyl ene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene;
At least one hydrogen in the above structure may be substituted with cyano, halogen or deuterium. According to claim 9,
polycyclic aromatic compounds in which the group represented by formula (D-1) is a group represented by formula (D-1-1);

R ^D are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. According to claim 10,
A polycyclic aromatic compound represented by any one of the following formulas.

A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 11. An organic electric field comprising a pair of electrodes comprising an anode and a cathode, and a light emitting layer disposed between the pair of electrodes, wherein the light emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 11. light emitting element. According to claim 13,
The organic electroluminescent element in which the said light emitting layer contains a host and the said polycyclic aromatic compound as a dopant. According to claim 14,
The organic electroluminescent device in which the said host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound. A display device or lighting device provided with the organic electroluminescent element according to any one of claims 13 to 15.

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