JP2023138328A - Polycyclic aromatic compound - Google Patents

Abstract

To provide a novel compound useful as a material for an organic device such as an organic electroluminescent element.SOLUTION: There is provided a polycyclic aromatic compound having a structure containing a structural unit of formula (1) or formula (2). (B to I rings are substituted/unsubstituted aryl rings or substituted/unsubstituted heteroaryl rings; Z is -CH= or -N=; x is independently >N-RNX (RNX is aryl or the like); Y is >B-; at least one selected from the group consisting of an aryl ring or a heteroaryl ring in the structure may be condensed with at least one cycloalkane and at least one hydrogen may be replaced with cyano, halogen or deuterium.)SELECTED DRAWING: None

Description

The present invention relates to polycyclic aromatic compounds. The present invention also relates to organic devices using the polycyclic aromatic compound, such as organic electroluminescent elements, organic field effect transistors, and organic thin film solar cells, as well as display devices and lighting devices.

Conventionally, display devices using light-emitting elements that emit electroluminescence have been studied in various ways because they can save power and be made thinner.Furthermore, organic electroluminescent elements made of organic materials can be easily made lighter and larger. As a result, it has been actively considered. In particular, we are developing organic materials that emit light such as blue, which is one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (which have the potential to become semiconductors and superconductors). Regarding development, research has been active so far, regardless of whether it is a high-molecular compound or a low-molecular compound.

An organic electroluminescent device has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound and disposed between the pair of electrodes. 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 Documents 1 to 3 disclose that polycyclic aromatic compounds containing boron are useful as materials for organic electroluminescent devices and the like. It has been reported that organic electroluminescent devices containing this polycyclic aromatic compound have good external quantum efficiency.

International Publication No. 2015/102118 International Publication No. 2020/162600 International Publication No. 2022/034916

As mentioned above, various materials have been developed for use in organic EL devices, but in order to increase the selection of materials for organic EL devices, it is desired to develop materials made of compounds different from conventional ones. There is.
An object of the present invention is to provide a novel compound useful as a material for organic devices such as organic EL elements.

The present inventors have made extensive studies to solve the above problems, and have discovered a novel compound that has a boron-containing structure similar to the compounds described in Patent Documents 1 to 3, has excellent light-emitting properties, and has a unique emission wavelength. Successfully produced ring aromatic compounds. They also discovered that an excellent organic EL device can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes, thereby completing the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and furthermore, organic device materials containing the following polycyclic aromatic compounds.

<1> A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2);

In formula (1),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
Y is independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R ^Y )- , >Si(-R ^Y )-, or >Ge(-R ^Y )-, and R ^Y is each independently an optionally substituted aryl, an optionally substituted heteroaryl, or an unsubstituted heteroaryl. an optionally substituted alkyl or an optionally substituted cycloalkyl,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the above structure may be fused with at least one cycloalkane, and the cycloalkane may be substituted with at least one substituent. , at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium.

<2> When ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I are each a substituted aryl ring or a substituted heteroaryl ring, the substituent is a substituent group Z and at least one substituent selected from the group consisting of substituents represented by formula (A30),
The substituent group Z is
Aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
Diarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group);
Diheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, and cycloalkyl (two heteroaryls may be bonded to each other via a linking group) ;
Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group) );
Diarylboryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group);
alkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
aryloxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl; and substituted silyl,

In formula (A30),
Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl, and at least one of the alkyl, alkenyl, cycloalkyl, and cycloalkenyl -CH ₂ - may be replaced with -O- or -S-,
R ^Ak is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^Ak is bonded to Ak through a linking group or a single bond. The polycyclic aromatic compound according to <1>, wherein * is a bonding position.
<3> The polycyclic aromatic compound according to <2>, represented by formula (1).

<4> The polycyclic aromatic compound according to <3> represented by the following formula (1-b);

In formula (1-b),
Z is each independently -C(-R ^Z )= or -N=,
R ^Z is each independently hydrogen or a substituent,
When R ^Z is a substituent, the substituent is any substituent selected from substituent group Z or a substituent represented by formula (A30),
Two adjacent R ^Z may be bonded to each other to form an aryl ring or a heteroaryl ring, and each of the formed aryl rings or heteroaryl rings has one of the substituents selected from the substituent group Z. may be substituted with a group,
Z=Z may each independently be >NR, >O, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the above >NR, R in >C(-R) ₂ and >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
Each X is independently >NR ^NX , >O, >C(-R ^CX ) ₂ , >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted is heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or Substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, R ^NX and R ^CX are Z bonded to the carbon atom to which X, including itself, is bonded. May be combined with one or more of
L is a single bond, >NR ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se, and R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or It is an unsubstituted cycloalkyl, and two R ^CL may be bonded to each other to form a ring, and each of R ^NL and R ^CL is one of Z bonded to the carbon atom to which L, including itself, is bonded. It may be combined with one or two or more,
At least one of the aryl rings or heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and the cycloalkane may be substituted with at least one substituent. At least one -CH ₂ - may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium.

<5> All Zs are -C-(R ^Z )=,
The polycyclic aromatic compound according to <4>, wherein each X is independently >O, >NR ^NX , or >S.
<6> R ^Z is each independently hydrogen, alkyl, phenyl optionally substituted with alkyl, diphenylamino optionally substituted with alkyl, or carbazolyl optionally substituted with alkyl, <4> or the polycyclic aromatic compound described in <5>.

式中、Ｍｅはメチルである。
＜８＞ 式（２）で表される＜２＞に記載の多環芳香族化合物。 <7> The polycyclic aromatic compound according to <3> represented by the following formula;

In the formula, Me is methyl.
<8> The polycyclic aromatic compound according to <2>, represented by formula (2).

<9> The polycyclic aromatic compound according to <8> represented by the following formula (2-b);

In formula (2-b),
Z is each independently -C(-R ^Z )= or -N=,
R ^Z is each independently hydrogen or a substituent,
When R ^Z is a substituent, the substituent is any substituent selected from substituent group Z or a substituent represented by formula (A30),
Two adjacent R ^Z may be bonded to each other to form an aryl ring or a heteroaryl ring, and each of the formed aryl rings or heteroaryl rings has one of the substituents selected from the substituent group Z. may be substituted with a group,
Z=Z may each independently be >NR, >O, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the above >NR, R in >C(-R) ₂ and >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
Each X is independently >NR ^NX , >O, >C(-R ^CX ) ₂ , >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted is heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or Substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, R ^NX and R ^CX are Z bonded to the carbon atom to which X, including itself, is bonded. May be combined with one or more of
L is a single bond, >NR ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se, and R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or It is an unsubstituted cycloalkyl, and two R ^CL may be bonded to each other to form a ring, and each of R ^NL and R ^CL is one of Z bonded to the carbon atom to which X, including itself, is bonded. It may be combined with one or two or more,
At least one of the aryl rings or heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and the cycloalkane may be substituted with at least one substituent. At least one -CH ₂ - may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium.

<10> The polycyclic aromatic compound according to <9>, wherein all Zs are -C-(R ^Z )=, and each X is independently >O, >N-R ^NX , or >S .
<11> R ^Z is each independently hydrogen, alkyl, phenyl optionally substituted with alkyl, diphenylamino optionally substituted with alkyl, or carbazolyl optionally substituted with alkyl, <9> or the polycyclic aromatic compound described in <10>.

式中、Ｍｅはメチルである。 <12> The polycyclic aromatic compound according to <8> represented by the following formula;

In the formula, Me is methyl.

<13> A reactive compound obtained by substituting a reactive substituent on the polycyclic aromatic compound according to any one of <1> to <12> is polymerized as a monomer and has a number average molecular weight of 2000 to 1.0×10 ⁸ polymer compounds.
<14> An organic device material containing the polycyclic aromatic compound according to any one of <1> to <12>.
<15> The organic device material according to <14>, wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, an organic thin film solar cell material, or a wavelength conversion filter material. .
<16> The polycyclic aromatic compound according to any one of <1> to <12>, comprising a pair of electrodes consisting of an anode and a cathode and an organic layer disposed between the pair of electrodes, wherein the organic layer is An organic electroluminescent device containing.
<17> The organic electroluminescent device according to <16>, wherein the organic layer is a light emitting layer.
<18> A display device or a lighting device comprising the organic electroluminescent element according to <16> or <17>.

<19> A method for producing a polycyclic aromatic compound according to any one of <1> to <12>, comprising:
By adding a boronating agent and a Brønsted base to the compound represented by the formula (Int) and making them react, a polycyclic aromatic compound represented by the formula (1) and a polycyclic aromatic compound represented by the formula (2) are prepared. A manufacturing method comprising obtaining a mixture with a group compound;

In the formula (Int),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (Int) may be fused with at least one cycloalkane, and the cycloalkane is substituted with at least one substituent. and at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in formula (Int) may be replaced with cyano, halogen, or deuterium.

<20> Compound represented by formula (Int);

In the formula (Int),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (Int) may be fused with at least one cycloalkane, and the cycloalkane is substituted with at least one substituent. and at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in formula (Int) may be replaced with cyano, halogen, or deuterium.

The present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used for manufacturing organic devices such as organic electroluminescent elements.

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

In the following, the present invention will be explained in detail. Although the constituent elements described below may be explained based on typical embodiments and specific examples, the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "~" means a range that includes the numerical values written before and after the "~" as lower and upper limits. Further, in this specification, "hydrogen" in the explanation of the structural formula means "hydrogen atom (H)". Similarly, a "carbon atom (C)" is sometimes referred to as "carbon."
As used herein, the term "adjacent groups" refers to two groups each bonding to two adjacent atoms (two atoms directly bonded by a covalent bond) in the structural formula.

In this specification, "Me" is methyl, "Et" is ethyl, "nBu" is n-butyl (normal butyl), "tBu" is t-butyl (tertiary butyl), "iBu" is isobutyl, "secBu" is secondary butyl, "nPr" is n-propyl (normal propyl), "iPr" is isopropyl, "tAm" is t-amyl, "2EH" is 2-ethylhexyl, "tOct" is t-octyl, "Ph" is phenyl, "Mes" represents mesityl (2,4,6-trimethylphenyl), "Ad" represents 1-adamantyl, "Tf" represents trifluoromethanesulfonyl, "TMS" represents trimethylsilyl, and "D" represents deuterium.
In this specification, an organic electroluminescent device may be referred to as an organic EL device.

In this specification, chemical structures and substituents may be expressed by the number of carbon atoms, but when a chemical structure is substituted with a substituent, or when a substituent is further substituted with a substituent, the number of carbon atoms is It refers to the number of carbon atoms in each group, and does not mean the total number of carbon atoms in the chemical structure and substituents, or the total number of carbon atoms in the substituents. For example, "substituent B having a carbon number Y substituted with a substituent A having a carbon number X" means that "substituent B having a carbon number Y" is substituted with "substituent A having a carbon number X". However, the carbon number Y is not the total carbon number of substituent A and substituent B. For example, "substituent B having carbon number Y and substituted by substituent A" means that "substituent B having carbon number Y" is substituted with "substituent A (of which the number of carbon atoms is not limited)". However, the carbon number Y is not the total carbon number of substituent A and substituent B.

0. Description of Rings and Substituents First, details of the rings and substituents used in this specification will be explained below.
As used herein, the "aryl ring" includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and Particularly preferred are 6 to 10 aryl rings.

Specific "aryl rings" include a monocyclic benzene ring, a biphenyl ring, a fused bicyclic naphthalene ring, an indene ring, and a tricyclic terphenyl ring (m-terphenyl ring). phenyl, o-terphenyl, p-terphenyl), fused tricyclic ring systems such as acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, fused tetracyclic ring system such as triphenylene ring, pyrene ring, naphthacene ring, Examples include chrysene ring, perylene ring which is a fused pentacyclic ring, and pentacene ring. Furthermore, the fluorene ring, benzofluorene ring, and indene ring include structures in which fluorene rings, benzofluorene rings, cyclopentane rings, and the like are spiro-bonded, respectively. In addition, in the fluorene ring, benzofluorene ring, and indene ring, two of the two hydrogens of methylene in the structure are respectively replaced with alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorene ring, Also included are dimethylbenzofluorene rings, dimethylindene rings, etc.

As used herein, the "heteroaryl ring" includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, and more preferably a heteroaryl ring having 2 to 20 carbon atoms. Preferably, a heteroaryl ring having 2 to 15 carbon atoms is more preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable. Examples of the "heteroaryl ring" include a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, selenium, phosphorus, and tellurium as ring constituent atoms.

Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring (furazane ring, etc.), thiadiazole ring, triazole ring, and tetrazole ring. ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzopyrrole ring, benzoxazole ring, benzothiazole ring, 1H- Benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, benzoxazinophenoxylene ring Sadine ring, phenothiazine ring, phenazine ring, phenazacyline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzindro Carbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxine ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, dioxaboranaphthoanthracene ring (5,9-dioxa-13b-bora-13bH- (naphtho[3,2,1-de]anthracene ring, etc.), benzoselenophene ring, etc. In addition, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, two of the two hydrogens of methylene in the structure are each replaced with alkyl such as methyl as the first substituent described below, and the dimethyldihydroacridine ring is , dimethylxanthene ring, dimethylthioxanthene ring, etc. are also preferred. Bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, which are bicyclic rings, and terpyridyl rings, bispyridylphenyl rings, and pyridyl biphenyl rings, which are tricyclic rings, are also included as "heteroaryl rings." Furthermore, the term "heteroaryl ring" includes a pyran ring.

Substituents herein may be substituted with further substituents. For example, a specific substituent may be described as "substituted or unsubstituted." This means that the specified substituent is substituted with at least one further substituent or is unsubstituted. In a similar sense, it may also be said that it "may be substituted." In this specification, the above-mentioned specific substituent at this time may be referred to as a "first substituent", and the above-mentioned further substituent may be referred to as a "second substituent".

In this specification, the substituent group Z is
Aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl,
heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
Diarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group),
Diheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, and cycloalkyl (two heteroaryls may be bonded to each other via a linking group) ,
Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group) ),
Diarylboryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group),
alkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
Cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl,
alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
It consists of aryloxy, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, and cycloalkyl, and substituted silyl.
Aryl, which is the second substituent in each group of substituent group Z, may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Similarly, heteroaryl, which is the second substituent, is aryl, Optionally substituted with heteroaryl, alkyl, or cycloalkyl.

In the present specification, when the term "substituent" is used, unless there is a separate explanation (for example, a separate explanation about a substituent such as an aryl ring in ring A, etc., or about R ^Z ), it refers to a substituent selected from substituent group Z. Any group may be used. For example, when a group defined as "substituted or unsubstituted" is substituted, the group may be substituted with at least one group selected from substituent group Z.

As used herein, "aryl" is, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 12 carbon atoms. These include aryls of numbers 6 to 10.

Specific examples of "aryl" include monovalent groups of the above-mentioned "aryl ring", such as phenyl, which is a monocyclic system, and biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), which is a bicyclic system. biphenylyl), fused bicyclic ring systems naphthyl (1-naphthyl or 2-naphthyl), tricyclic ring systems terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl), Phenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl -3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl or p-terphenyl-4-yl), acenaphthylene-(1-, 3-, 4-, or 5-)yl, fluorene-(1- , 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene -(1-, 2-, or 9-)yl, the tetracyclic system quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), triphenylene-(1- or 2-)yl, pyrene-(1-, 2- or 4-)yl, or naphthacen-(1-, 2-, or 5-)yl, or perylene-(1-, 2-, or 3-)yl, or pentacen-yl, which is a fused pentacyclic ring system. (1-, 2-, 5-, or 6-)yl, etc. Other examples include monovalent groups such as spirofluorene.

In addition, the aryl as a second substituent includes aryl such as phenyl (specific examples are the groups mentioned above), alkyl such as methyl (specific examples are the groups mentioned below), and cycloalkyl such as cyclohexyl or adamantyl. Also included are structures substituted with at least one group selected from the group consisting of (specific examples will be described later).
An example thereof is a group in which the 9-position of fluorenyl as a second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl.

"Arylene" is, for example, arylene having 6 to 30 carbon atoms, preferably arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or arylene having 6 to 10 carbon atoms. Such as Arylen.
A specific example of "arylene" is a divalent group obtained by removing one hydrogen from the above-mentioned "aryl" (monovalent group).

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms. Such as a heteroaryl having a number of 2 to 10. "Heteroaryl" contains one or more, preferably 1 to 5, heteroatoms selected from oxygen, sulfur, nitrogen, etc. in addition to carbon as ring constituent atoms.

Specific examples of "heteroaryl" include monovalent groups of the "heteroaryl ring" described above, such as pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, Pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, Isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoin These include dorocarbazolyl, dibenzoindrocarbazolyl, imidazolinyl, or oxazolinyl. Other examples include a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobi[silafluorene], and a monovalent group of benzoselenophene.

In addition, the heteroaryl as a second substituent includes an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups mentioned later), and a cyclo such as cyclohexyl or adamantyl. Also included are structures substituted with at least one group selected from the group consisting of alkyl (specific examples of which will be described later).
An example thereof is a group in which the 9-position of carbazolyl as a second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl. Further, a group in which a nitrogen-containing heteroaryl such as pyridyl, pyrimidinyl, triazinyl, or carbazolyl is further substituted with phenyl or biphenylyl is also included in the heteroaryl as a second substituent.

"Heteroarylene" is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, heteroarylene having 2 to 15 carbon atoms, or carbon Examples include heteroarylene of numbers 2 to 10. Further, "heteroarylene" is a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.
A specific example of "heteroarylene" is a divalent group obtained by removing one hydrogen from the above-mentioned "heteroaryl" (monovalent group).

"Diarylamino" is an amino substituted with two aryls, and the above explanation of "aryl" can be cited for details of this aryl.
"Diheteroarylamino" is an amino group substituted with two heteroaryls, and for details of this heteroaryl, the above explanation of "heteroaryl" can be cited.
"Arylheteroarylamino" is an amino group substituted with aryl and heteroaryl, and the above explanation of "aryl" and "heteroaryl" can be cited for details of this aryl and heteroaryl.

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

Specifically, the linking group includes >O, >N-R ^x , >C(-R ^x ) ₂ , -C(-R ^x )=C(-R ^x )-, >Si(-R ^x ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. Each R ^x is independently alkyl, cycloalkyl, aryl, or heteroaryl, which may be optionally substituted with alkyl, cycloalkyl, aryl, or heteroaryl. In addition, the _two R ^X in each ^of >C(-R ^x ) ₂ ^{, -C(-R x )} =C( ^-R may be bonded to each other to form a ring. X ^Y is >O, >N- ^RY , >C( ^-RY ) ₂ , >Si( ^-RY ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. and each R ^Y is independently alkyl, cycloalkyl, aryl, or heteroaryl, which may be optionally substituted with alkyl, cycloalkyl, aryl, or heteroaryl. However, when X ^Y is >C(-R ^Y ) ₂ and >Si(-R ^Y ) ₂ , the two R ^Y do not combine to form a further ring. Further examples of the linking group include alkenylene. 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, It may be substituted with substituted silyl or aryl. -C(-R ^x )=C(-R ^{x )} -, even if the two R good. That is, -C(-R ^x )=C(-R ^x )- may be arylene (such as 1,2-phenylene) or heteroarylene.

In addition, in this specification, when it is simply described as "diarylamino," "diheteroarylamino," or "arylheteroarylamino," unless otherwise specified, "the two aryls of diarylamino are "The two heteroaryls of the diheteroarylamino may be bonded to each other via a linking group," and "The aryl and heteroaryl of the arylheteroarylamino may be bonded to each other via a linking group." The aryl may be bonded to each other via a linking group.''

"Diarylboryl" is boryl substituted with two aryls, and the above explanation of "aryl" can be cited for details of this aryl. In addition, these two aryls can be a single bond or a linking group (for example, -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R ) ₂ , >Si(-R) ₂ , or >Se). Here, R in -CR=CR-, R in >N-R, R in >C(-R) ₂ , and R in >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Furthermore, two adjacent R's may be bonded to each other to form a ring to form cycloalkylene, arylene, or heteroarylene. For details of the substituents listed here, please refer to the explanations of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" mentioned above, as well as the "alkyl" and "alkenyl" mentioned below. , "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" may be cited. In addition, in the case where "diarylboryl" is simply described in this specification, unless otherwise specified, "the two aryls of diarylboryl may be bonded to each other via a single bond or a linking group." It is assumed that the following explanation is added.

"Alkyl" may be either straight chain or branched chain, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, preferably alkyl having 1 to 18 carbon atoms (carbon Branched chain alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), carbon number These include alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms), alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms), and the like.

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

"Alkylene" is a divalent group obtained by removing any hydrogen from "alkyl", such as methylene, ethylene, and propylene.

Regarding "alkenyl", the above explanation of "alkyl" can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is replaced with a C=C double bond, and only one It also includes groups in which two or more single bonds are substituted with double bonds (also called alkadien-yl or alkatrien-yl).

"Alkenylene" is a divalent group obtained by removing any hydrogen from "alkenyl", and includes, for example, vinylene.

Regarding "alkynyl", the above explanation of "alkyl" can be referred to, and it is a group in which the C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and only one is required. It also includes groups in which two or more single bonds are substituted with triple bonds (also called alkadiin-yl or alkatriin-yl).

"Cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Examples include cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyls thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms (especially methyl). Substituents, , 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, decahydronaphthalenyl, or decahydroazulenyl.

"Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, or cycloalkylene having 3 to 14 carbon atoms. Examples include cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, and cycloalkylene having 5 carbon atoms.
A specific example of "cycloalkylene" is a structure in which one hydrogen is removed from the above-mentioned "cycloalkyl" (monovalent group) to make it a divalent group.

"Cycloalkenyl" is a group having a structure in which at least one single bond between two carbon atoms in the above-mentioned "cycloalkyl" becomes a double bond (for example, -CH ₂ -CH ₂ - is -CH= (a group substituted with CH-) which does not correspond to aryl. Specific examples include 1-cyclohexenyl and 1-cyclopentenyl.

"Alkoxy" is a group represented by "Alk-O--(Alk is alkyl)", and for details of this alkyl, the above explanation of "alkyl" can be cited.

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

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

"Triarylsilyl" is a silyl group substituted with three aryls, and the above explanation of "aryl" can be cited for details of this aryl.
Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

"Trialkylsilyl" is a silyl group substituted with three alkyl groups, and for details of this alkyl, the above explanation of "alkyl" can be cited.
Specific "trialkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-Propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethyl Silyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, Examples include methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups, and for details of this cycloalkyl, the above explanation of "cycloalkyl" can be cited.
Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

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

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl, and the above explanation of "alkyl" and "cycloalkyl" can be cited for details of this alkyl and cycloalkyl. .

<When two groups bonded to the same atom bond to each other>
In this specification, when two groups bond to the same atom are bonded to each other to form a ring, it means that the atom and the two groups form a ring. The two groups may be bonded by a single bond or a linking group (these are also collectively referred to as a linking group), and the linking group includes -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ - CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si( -R) ₂ - or -Se-, and examples thereof include the following structures. In addition, the R of -CHR-CHR-, the R of -CR ₂ -CR ₂ -, the R of -CR=CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and R in -Si(-R) ₂ - each independently represents hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, or cycloalkyl. Alkyl which may be substituted, alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. . Furthermore, two adjacent R's may be bonded to each other to form a ring to form cycloalkylene, arylene, or heteroarylene.

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

The position where two R's are bonded by the bonding group is not particularly limited as long as it is a bondable position, but it is preferable that they bond at the most adjacent position. For example, when the two groups are phenyl, "C" in phenyl It is preferable that the ortho (2nd position) positions are bonded to each other with respect to the bonding position (1st position) of "Si" or "Si" (see the above structural formula).

1. Polycyclic aromatic compound <Description of the overall structure of the compound>
The polycyclic aromatic compound of the present invention has a structure containing a structural unit represented by formula (1) or formula (2).

In formulas (1) and (2), rings B to I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.
The polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) is preferably represented by any formula selected from the group consisting of the following formulas (1-a) to (1-l). It is a compound that has the structure Further, the polycyclic aromatic compound having a structure including a structural unit represented by formula (2) is preferably one of formulas selected from the group consisting of formulas (2-a) to (2-l). A compound having the structure shown below. In this sense, each ring in each formula is represented by a lowercase letter "b", "c", "d", "e", "f", "g", "h", and "i".

Definitions and preferred ranges of the symbols in each of the above formulas will be described later.

A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) has a structure in which aromatic rings are connected with a hetero element such as boron, nitrogen, oxygen, or sulfur, and has a large It has a HOMO-LUMO gap (band gap Eg in a thin film). This is because a 6-membered ring containing a hetero element has low aromaticity, and a decrease in the HOMO-LUMO gap due to expansion of the conjugated system is suppressed. In a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2), the HOMO-LUMO gap can be arbitrarily changed depending on the type of hetero element and the connection method. . This is thought to be due to the fact that the energies of the HOMO and LUMO can be moved arbitrarily according to the spatial extent and energy of the empty orbital or lone pair of the hetero element. For example, a compound in which Y is B (boron) as a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) is a polycyclic aromatic compound having a smaller amount of B (Y). Compared to the compound, the LUMO is deeper and the band gap Eg is narrower, and it emits green light.

These polycyclic aromatic compounds have a narrow half-value width of the fluorescence emission peak due to the localization of excited states SOMO1 and SOMO2 on each atom due to the electronic perturbation of the hetero element, making them suitable as dopants for organic EL devices. When used, luminescence with high color purity can be obtained. For the same reason, ΔE _S1T1 becomes small, exhibiting thermally activated delayed fluorescence, and high efficiency can be obtained when used as an emitting dopant in an organic EL device.
Furthermore, by introducing a substituent, the energies of HOMO and LUMO can be changed arbitrarily, so it is possible to optimize the ionization potential and electron affinity depending on the surrounding materials. However, the present invention is not particularly limited to these principles.

<Explanation of ring structures in compounds>
In formula (1) and formula (2), "B", "C", "D", "E", "F", "G", "H", and "I" in the circles are each circle. This is a code indicating the ring structure shown in . The structure represented by formula (1) or formula (2) has at least nine aromatic rings as a ring, B ring, C ring, D ring, E ring, F ring, G ring, H ring, and I ring. It has a structure in which a ring structure is formed by connecting rings with a hetero element such as boron, oxygen, nitrogen, or sulfur. The formed ring structure is a condensed ring structure composed of at least 17 rings in formula (1) and 19 rings in formula (2).

In each of formula (1) and formula (2), ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I each independently represent a substituted or unsubstituted aryl ring. or a substituted or unsubstituted heteroaryl ring. Substituted or unsubstituted aryl ring or substitution in the B ring, C ring, D ring, E ring, F ring, G ring, H ring, and I ring of the structures represented by formula (1) and formula (2), respectively Or in an unsubstituted heteroaryl ring, the substituent when "substituted or unsubstituted (substituted or unsubstituted)" is a substituent represented by the following formula (A30) added to the substituent group Z. and at least one substituent selected from the group. Further, the substituent may be substituted or unsubstituted diarylphosphino such as diphenylphosphino. Regarding the preferred range of the substituent, reference can be made to the preferred range of R ^Z described later. When a plurality of substituents are present, the plurality of substituents may be the same or different from each other.

In each of formula (1) and formula (2), the broken line connecting the C ring and the D ring indicates that the C ring and the D ring are not bonded at the position of the broken line, or there is a single bond or a connecting group at the position of the broken line. Indicates that they are connected via. When bonded via a single bond or a linking group at the position of the broken line in Formula (1) and Formula (2), the single bond or linking group may be indicated by "L". When ring C and ring D are bonded via a linking group, examples of the linking group include >NR ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se. R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, Substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CL may be bonded to each other to form a ring, and R ^NL and R ^CL are Each of them may be bonded to one or more of Z bonded to the carbon atom to which the linking group containing itself is bonded. It is preferable that the C ring and the D ring are bonded to each other through a single bond at the position of the broken line, or that they are not bonded to each other at the position of the broken line.

Ring B and ring E in formula (1) and formula (2) each form a trivalent group having bonds at three consecutive carbon atoms on the aryl ring or heteroaryl ring in the structure. ing. These three bonds bond to N and two Y, respectively. In the B ring and the E ring, the ring having carbon as a ring constituent element and having the above three bonds is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. This ring may be further fused with another ring. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of a 6-membered ring further fused with another ring include a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring. Examples of the 5-membered ring include a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of a 5-membered ring further fused with another ring include a benzofuran ring, a benzothiophene ring, and an indole ring.

Ring F and ring G in formula (1) each form a trivalent group having bonds at three consecutive carbon atoms on the aryl ring or heteroaryl ring in its structure. These three bonds bond to N, Y, and X, respectively. When ring F and ring G are bonded to R ^NX , R ^CX or R ^IX , they may form a tetravalent group. In the F ring and the G ring, the ring whose ring constituent element is carbon having the above three bonds is preferably a 5-membered ring or a 6-membered ring, and more preferably a 6-membered ring. This ring may be further fused with another ring. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of a 6-membered ring further fused with another ring include a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring. Examples of the 5-membered ring include a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of a 5-membered ring further fused with another ring include a benzofuran ring, a benzothiophene ring, and an indole ring.

Ring F and ring G in formula (2) each form a tetravalent group having bonds at four consecutive carbon atoms on the aryl ring or heteroaryl ring in its structure. These three bonds bond to N, two Y, and X, respectively. When ring F and ring G are bonded to R ^NX , R ^CX or R ^IX , they may form a pentavalent group. The ring having carbon as a ring constituent element and having the above four bonds in the F ring and the G ring is preferably a 6-membered ring. This ring may be further fused with another ring. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of a 6-membered ring further fused with another ring include a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring.

The C ring, D ring, H ring, and I ring in formula (1) and formula (2) each have a bond on two carbon atoms adjacent to each other on the aryl ring or heteroaryl ring in the structure. It suffices if it forms a divalent group. The C ring and the D ring are each bonded to N and Y through the above two bonds, and the H ring and the I ring are bonded to Y and X through the above two bonds, respectively. When ring C and ring D are bonded to each other via L, they may each be a trivalent group. When ring H and ring I are each further bonded to R ^NX , R ^CX or R ^IX , they may form a trivalent group. In the C ring, D ring, H ring, and I ring, the ring whose ring constituent element is carbon having the above two bonds is preferably a 5-membered ring or a 6-membered ring, and is a 6-membered ring. is more preferable. This ring may be further fused with another ring. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of a 6-membered ring further fused with another ring include a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring. Examples of the 5-membered ring include a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of a 5-membered ring further fused with another ring include a benzofuran ring, a benzothiophene ring, and an indole ring.

Furthermore, the F ring, the G ring, the H ring, and the I ring each have a condensed ring in their structure, and may each have one bond on a different ring atom in the condensed ring. For example, it may contain a benzimidazole ring or a benzopyrrole ring, and one carbon on the benzene ring is bonded to either X or Y, and one carbon or nitrogen on the imidazole ring or pyrrole ring is bonded to the other. good. At this time, it is preferable that X is a single bond.

In formula (1), preferred ring structures of ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I are represented by formulas (1-a) to (1-l), respectively. It is represented as ring b, ring c, ring d, ring e, ring f, ring g, ring h, and ring i. In formula (2), preferred ring structures of ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I are represented by formulas (2-a) to (2-l), respectively. It is represented as ring b, ring c, ring d, ring e, ring f, ring g, ring h, and ring i.

<Explanation of Z>
Z in ring a in formulas (1) and (2) is -C(-R ^Z )= or -N=, respectively. Each R ^Z is independently hydrogen or a substituent. Examples of the substituent include at least one substituent selected from the substituent group Z plus a substituent represented by the formula (A30) described below, preferably unsubstituted alkyl, and more preferably methyl. . Preferably R ^Z is hydrogen. Z in ring a is preferably -C(-H)= or -N=, and more preferably -C(-H)=.

Z in ring a in formulas (1-a) to (1-l) and formulas (2-a) to formula (2-l) is Z in ring a in formulas (1) and (2); and the preferred ranges are also the same.

In formulas (1-a) to (1-l) and formulas (2-a) to formula (2-l), Z other than Z in ring a has the same meaning as Z in ring a, and the substituted Examples of the group include at least one substituent selected from the group consisting of substituent group Z plus a substituent represented by formula (A30) described below. Further, the substituent may be substituted or unsubstituted diarylphosphino such as diphenylphosphino. Preferred substituents include those described below. In addition, adjacent Z's can have the following structure in total.

First, when both Zs in Z=Z are -C(-R ^Z )=, two R ^Zs may be bonded to each other to form an aryl ring or a heteroaryl ring. The formed aryl ring or heteroaryl ring may each have a substituent. Examples of the substituent at this time include at least one substituent selected from the group consisting of substituent group Z plus a substituent represented by formula (A30) described below. Further, the substituent may be substituted or unsubstituted diarylphosphino such as diphenylphosphino. The preferred range is the same as the preferred range of R ^Z . Further, Z=Z may each independently be >NR, >O, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se. In this case, R in >NR, >C(-R) ₂ and >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Substituted alkyl, or substituted or unsubstituted cycloalkyl. The two Rs in >C(-R) ₂ may be bonded to each other to form a ring, and the two Rs in >Si(-R) ₂ may be bonded to each other to form a ring.

Structural examples of rings containing Z in each of formulas (1-a) to formula (1-l) and formulas (2-a) to formula (2-l) include four Zs and are bonded to X and Y. An example of the structure is shown below. In addition, in the following formula, R has the same meaning as R ^Z , but does not mean hydrogen and does not mean a bond between R's. Further, n is an integer of 0 to 4, and R ^N and R ^c are hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, cycloalkyl or cycloalkyl which may be substituted with alkyl, and two R ^c may be bonded to each other to form a ring.

In each of the above partial structures, R is preferably alkyl, phenyl optionally substituted with alkyl, or a substituent represented by formula (A30). n is preferably 0 or 1, more preferably 0.
Similar structural examples can be given for structures bonded to N and Y and structures containing three or two Zs.

In each of rings a to i of formulas (1-a) to (1-l) and formulas (2-a) to (2-l), 0 to 2 of Z are -N=; It is preferable that the remainder is -C(-R ^Z )=, and it is more preferable that 0 to 1 are -N= and the rest are -C(-R ^Z )=, and all of them are -C(-R It is further preferable that ^Z )=. In each formula, it is preferable that 0 to 8 of Z be -N= and the rest be -C(-R ^Z )=, and 0 to 3 be -N= and the rest be -C(-R ^Z )=, more preferably 0 to 1 are -N= and the rest are -C(-R ^Z )=, and all of them are -C(-R ^Z )=. Particularly preferred. Any substituent selected from substituent group Z which is R ^Z includes alkyl, phenyl optionally substituted with alkyl, diphenylamino optionally substituted with alkyl or phenyl, substituted with alkyl or phenyl Preferred is carbazolyl, which may be For the substituent R ^Z , reference can also be made to the description of preferred substituents described below. In each formula, it is preferable that 0 to 3 of R ^Z are substituents and the others are hydrogen. In particular, the substituent R ^Z is preferably located at the para position of B.

<Structure containing a structural unit represented by formula (1) or formula (2)>
The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2). Examples of the polycyclic aromatic compound having a structure containing the above structural unit include polycyclic aromatic compounds represented by formula (1) or formula (2). Furthermore, as a polycyclic aromatic compound having a structure containing the above-mentioned structural unit, a form in which any ring (single or plural) contained in the above-mentioned structural unit is shared by a plurality of unit structures, and a form in which the above-mentioned unit structure An example is a form in which any rings contained in are bonded together in a condensed manner. Further, any ring contained in the above structural unit and the X bonded thereto may be bonded so as to be shared by a plurality of unit structures. The above unit structure may be in the form of a single bond or a plurality of linking groups such as alkylene having 1 to 3 carbon atoms, phenylene, naphthylene, etc. Among these, preferred is a form in which they are bonded so as to share a plurality of rings.

<Explanation of L>
L in formula (1-b), formula (1-d), formula (1-f), formula (2-b), formula (2-d), and formula (2-f) is a single bond, >N -R ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se. R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, Substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CL may be bonded to each other to form a ring, and R ^NL and R ^CL are Each may be bonded to one or more of Z bonded to the carbon atom to which L, including itself, is bonded. R ^NL is preferably aryl which may be substituted with alkyl or aryl, or heteroaryl which may be substituted with alkyl or aryl. R ^CL is preferably alkyl, more preferably methyl. L is preferably a single bond.

<Explanation of X ^C >
Formula (1-c) Formula (1-d), Formula (1-e), Formula (1-f), Formula (1-g), Formula (1-h), Formula (1-i), Formula ( 1-j), formula (1-k), formula (1-l), formula (2-c) formula (2-d), formula (2-e), formula (2-f), formula (2- g), formula (2-h), formula (2-i), formula (2-j), formula (2-k), and formula (2-l), each of X ^C is independently >O, >NR, >C(-R) ₂ , >S, or >Se, and R in >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted Substituted alkyl, substituted or unsubstituted cycloalkyl, and each R in >C(-R) ₂ above is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted or substituted or unsubstituted cycloalkyl, and the above >NR and the above >C(-R) ₂ are one or more of Z bonded to the same carbon atom, and in R May be combined. X ^C is preferably >O or >S.

<Explanation of Y>
In each of formula (1) and formula (2), Y is independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga -, >As-, >C(-R ^Y )-, >Si(-R ^Y )-, or >Ge(-R ^Y )-. R ^Y is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. Each Y is preferably >B-, >P-, >P(=O)-, or >P(=S)-, and each is more preferably >B-.

<Explanation of X>
In each of formula (1) and formula (2), X independently represents a single bond, >NR ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ , > S, or >Se. R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, Substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and two R ^CX may be bonded to each other to form a ring. , and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded. .

X is preferably >N-R ^NX , >O, >C(-R ^CX ) ₂ , >S, or >Se, and >O, >N-R ^NX , or >S It is more preferable that R ^NX in >NR ^NX is preferably substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and preferably substituted or unsubstituted phenyl. In a structure where all Y's are B, in order to obtain green light emission, it is preferable that at least one of X is >N-R ^NX , and it is more preferable that all X's are >N-R ^NX . From the viewpoint of TADF properties, it is preferable that at least one of them is S.

<Explanation of the change in ring structure due to the bond between X and ring>
R ^NX , R ^CX and R ^IX in X may each be bonded to one or two rings to which X is bonded, including itself, through a single bond or a linking group. Specifically, in formulas (1) and (2), R ^NX , R ^CX and R ^IX in X bonded to ring F and ring H are bonded to ring F or ring H through a single bond or a linking group. R ^NX , R ^CX and R ^IX in X that are bonded to the G ring and the I ring may be bonded to at least one of the G ring or the I ring through a single bond or a linking group. You may do so. In formula (1B), R ^NX , R ^CX and R ^IX in X bonded to ring f and ring h are bonded to Z (to which R ^NX , R ^CX and R ^IX in X, which may be bonded to Z) adjacent to carbon and bonded to ring g and ring i, are bonded to at least one of ring g or ring i through a single bond or a linking group. It may be bonded to Z on one side (Z adjacent to the carbon to which X is bonded).

When R ^NX , R ^CX and R ^IX each bond to a ring, the linking groups include -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, - CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, etc. can be given. Among these, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are preferred, and -CH=CH-, -CR=CR-, -N(-R)-, -O-, and -S- are more preferred, and -CR=CR-, -N(-R)-, -O-, and -S- are further preferable. R of the above "-CHR-CHR-", R of "-CR ₂ -CR ₂ -", R of "-CR=CR-", R of "-N(-R)-", "-C(- R in "R) ₂ -" and R in "-Si(-R) ₂ -" are each independently substituted with hydrogen, aryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl. heteroaryl optionally substituted with alkyl or cycloalkyl; alkenyl optionally substituted with alkyl or cycloalkyl; alkynyl optionally substituted with alkyl or cycloalkyl; Cycloalkyl optionally substituted with alkyl. Furthermore, two R's bonding to the same element may bond to each other to form a ring. Furthermore, two adjacent R's may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. These rings may also be substituted with alkyl or cycloalkyl.

An example of a structure in which R ^NX , R ^CX and R ^IX are each bonded to a ring is a compound having a ring structure in which X is incorporated into the condensed ring I', represented by the following formula (1'-I). , and a compound having a ring structure in which X is incorporated into a condensed ring F', which is represented by the following formula (2'-F). Examples of the fused ring formed include a carbazole ring, a phenoxazine ring, and a phenothiazine ring.

At least one of the Xs connecting the ring structures is >N-R ^NX , and R ^NX is an optionally substituted alkyl or an optionally substituted cycloalkyl, and a linking group Alternatively, it may have a structure connected to an aryl ring or a heteroaryl ring in ring F, ring H, ring G, or ring I through a single bond.

For example, the following partial structure (A10) may be formed by the above connection.

In formula (A10), R ^A1 to R ^A4 are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any 2 to 4 of R ^A1 to R ^A4 may be bonded to each other by a linking group or a single bond, and is bonded to one ring of the two rings to which X is bonded at the two * positions and to the other ring at the ** position. That is, N in formula (A10) is N of >N-R ^NX when X is >N-R ^NX . The atoms on the ring bonded at the two * positions may be atoms (preferably carbon atoms) that are adjacent to each other. The partial structure represented by formula (A10) contains an N-C bond with a weak bond dissociation energy (BDE), but because there is another bond forming the ring, the reverse reaction ( (recombination reaction) is promoted, resulting in a more stable structure. Therefore, an organic EL device manufactured using a polycyclic aromatic compound having such a structure is expected to have a long device life. When the polycyclic aromatic compound contains the structure represented by formula (A10), the number may be one or two.

In formula (A10), any 2 to 4 of R ^A1 to R ^A4 may be connected to each other via a linking group.
R ^A1 to R ^A4 are any two (R ^A1 and R ^A4 , R ^{A1 and} R ^A4 and R A2 and R ^A3 , R ^A1 and R ^A2 , R ^A3 and R ^A4 , R ^A1 and R ^A2 and R ^A3 and R ^A4 ) are preferably bonded to each other via a linking group or a single bond, and it is more preferable that R ^A1 and R ^A4 are bonded to each other via a linking group or a single bond. Examples of divalent groups formed by bonding with each other include alkylene. At least one hydrogen in the alkylene may be substituted with alkyl or cycloalkyl, and at least one (preferably one) -CH ₂ - in the alkylene is substituted with -O- and -S-. Good too. The divalent groups formed by bonding with each other are preferably straight-chain alkylene having 2 to 5 carbon atoms, more preferably straight-chain alkylene having 3 or 4 carbon atoms, and straight-chain alkylene having 4 carbon atoms (-( CH ₂ ) ₄ -) is more preferred. It is particularly preferable that the linear alkylene having 4 carbon atoms (-(CH ₂ ) ₄ -) is unsubstituted.

It is preferable that the remaining R ^A1 to R ^A4 not participating in the connection by the linking group are each independently hydrogen or an optionally substituted alkyl group, and an optionally substituted alkyl group having 1 to 6 carbon atoms. It is more preferably alkyl, even more preferably unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably methyl.
That is, as the partial structure represented by formula (A10), a structure represented by formula (A11) below is preferable.

式（Ａ１１）中、Ｍｅはメチルであり、２つの＊の位置でＸが結合する２つの環の一方の環に、＊＊の位置で他方の環に結合している。

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

<Preferred substituents>
In a polycyclic aromatic compound used as an emitting dopant (in other compounds used as a dopant), as a substituent containing "alkyl", tertiary alkyl represented by the following formula (tR) is one of the particularly preferable ones. It is. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Also preferred is a substituent in which a tertiary alkyl represented by formula (tR) is substituted with another substituent as a second substituent. Specifically, diarylamino substituted with tertiary alkyl represented by (tR), carbazolyl (preferably N-carbazolyl) substituted with tertiary alkyl represented by (tR), or (tR) Examples include benzocarbazolyl (preferably N-benzocarbazolyl) substituted with the tertiary alkyl represented by the formula. The substitution form of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl is that some or all hydrogens of the aryl ring or benzene ring in these groups are replaced with the group of formula (tR). An example can be given.

In formula (tR), R ^a , R ^b , and R ^c are each independently alkyl having 1 to 24 carbon atoms, and any -CH ₂ - in the alkyl may be substituted with -O-. , the group represented by formula (tR) has * as the bonding position.

The "alkyl having 1 to 24 carbon atoms" for R ^a , R ^b and R ^c may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. Chain alkyl, alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons), alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons), alkyl having 1 to 6 carbons (branched alkyl having 3 to 12 carbons) (branched alkyl having 3 to 6 carbon atoms) and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

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

Specific alkyls 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, Examples include 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 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- Examples include 1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl. Among these, t-butyl and t-amyl are preferred.

As the substituent, a substituent represented by formula (A30) is also preferable.

In formula (A30),
Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl, and at least one -CH in the alkyl, cycloalkyl, and cycloalkenyl ₂ - may be replaced with -O- or -S-,
R ^Ak is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^Ak is bonded to Ak through a linking group or a single bond. * is the bonding position.

In formula (A30), since Ak is the above-mentioned substituent, it does not conjugate with the lone pair on N, so the lone pair can be conjugated with the π electron of the bonding destination, and aryl etc. Larger wavelength changes are possible than in the case where there is Further, the same applies to the influence on the multiple resonance effect, and a greater improvement in thermally activated delayed fluorescence (TADF) properties is possible.

R ^Ak is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, aryl optionally substituted with alkyl, It is more preferably heteroaryl, alkyl or cycloalkyl which may be substituted with alkyl, even more preferably aryl which may be substituted with alkyl, and phenyl which may be substituted with methyl. is particularly preferred.

In formula (A30), Ak is preferably an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and is preferably an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 8 carbon atoms. It is preferably alkyl having 1 to 4 carbon atoms, and even more preferably methyl.

R ^Ak and Ak may be the same or different, and are preferably different.

R ^Ak may be bonded to Ak through a linking group or a single bond. Examples of the linking group in this case include >O, >S, or >Si(-R) ₂ . R in >Si(-R) ₂ is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Examples of structures in which R ^Ak is bonded to Ak through a linking group or a single bond include the following.

上記各式中、＊は結合位置である。

In each of the above formulas, * is a bonding position.

The emission wavelength can be adjusted by the steric hindrance, electron donating and electron withdrawing properties of the structure of the substituent of the compound used as a dopant (assisting dopant or emitting dopant). Preferably it is a group represented by the following structural formula, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4- Xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6- Dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 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 tribenzazepinyl. From the viewpoint of ease of synthesis, those with greater steric hindrance are preferable for selective synthesis; specifically, t-butyl, t-amyl, t-octyl, adamantyl, 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 formula below, * represents the bonding position.

The polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) is a tertiary alkyl compound (such as t-butyl or t-amyl) represented by the above formula (tR). , neopentyl, or adamantyl, and preferably a tertiary alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylamino is also preferred as a substituent. Further, diarylamino substituted with a group of formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a group of formula (tR), or benzocarbazolyl (preferably N-carbazolyl) substituted with a group of formula (tR) Preferably, N-benzocarbazolyl) is also preferred. The substitution form of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl is such that some or all hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of formula (tR). An example can be given.

In the structure containing the structural unit represented by formula (1) or formula (2), the substituent on the aryl ring or heteroaryl ring may be a substituent represented by the following formula (A20).

The substituent represented by formula (A20) is bonded to two atoms adjacent to each other on the ring of the aryl ring or heteroaryl ring through two *. In formula (A20), L is >NR, >O, >Si(-R) ₂ or >S, and R in >NR is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R in the above >Si(-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted alkyl, or It is a cycloalkyl which may be substituted and may be bonded to each other through a linking group, and at least one of R in the above >NR and above >Si(-R) ₂ is a linking group or a single It may be bonded to the aryl ring or heteroaryl ring through a bond,
r is an integer from 1 to 4,
R ^A is each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and any R ^A may be bonded to any other R ^A by a linking group or a single bond. good.

Examples of the above substituents include substituents represented by any of the following.

In each formula, * may be bonded to two or three consecutive (adjacent) atoms on any aryl ring or heteroaryl ring.

<Cycloalkane condensation>
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) is at least one cycloalkane. May be condensed. The same applies to polycyclic aromatic compounds represented by any formula selected from the group consisting of formulas (1-a) to (1-l) and formulas (2-a) to (2-l). The following explanation applies equally to polycyclic aromatic compounds represented by any of these formulas.

The cycloalkane may be any cycloalkane having 3 to 24 carbon atoms. At least one hydrogen in the cycloalkane is substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alternatively, at least one -CH ₂ - in the cycloalkane may be replaced with -O-.

A cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, or an alkyl having 1 to 12 carbon atoms. Alternatively, it is preferably a cycloalkane which may be substituted with a cycloalkyl having 3 to 16 carbon atoms.

"Cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, and cycloalkanes with 5 to 10 carbon atoms. Examples include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), and bicyclo[1.1.0]butane. , bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.2]octane , adamantane, diamantane, decahydronaphthalene and decahydroazulene, as well as alkyl (especially methyl) substituted products having 1 to 5 carbon atoms, halogen (especially fluorine) substituted products and deuterium substituted products thereof.

Among the above examples, for example, as shown in the structural formula below, at least one A structure having one substituent is preferable, a structure having two substituents on the α-position carbon is more preferable, and a structure having two substituents on each of the two α-position carbons (having a total of four substituents) is even more preferable. Examples of the substituent include alkyl having 1 to 5 carbon atoms (especially methyl), halogen (especially fluorine), and deuterium. In particular, a structure in which a partial structure represented by the following formula (B) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring is preferable.

式（Ｂ）中、＊は結合位置を示す。

In formula (B), * indicates the bonding position.

The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl) is shown below. * indicates a bonding position, and the position may be any carbon that constitutes a benzene ring and does not constitute a cycloalkane. Condensed cycloalkanes as shown in formula (Cy-1-4) and formula (Cy-2-4) may be condensed with each other. Even if the ring (group) to be condensed is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, The same is true.

At least one --CH ₂ -- in the cycloalkane may be substituted with --O-. For example, an example in which one or more -CH ₂ - groups in a cycloalkane fused to one benzene ring (phenyl) is substituted with -O- is shown below. Even if the ring (group) to be condensed is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, The same is true.

The cycloalkane may be substituted with at least one substituent, and examples of this substituent include any substituent selected from substituent group Z. Among these substituents, alkyl (eg, alkyl having 1 to 6 carbon atoms) and cycloalkyl (eg, cycloalkyl having 3 to 14 carbon atoms) are preferred. It is also preferred that any hydrogen is replaced with a halogen (eg fluorine) or deuterium. In addition, when cycloalkyl is substituted, a substitution form forming a spiro structure may be used. For example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl) is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and a bond substituting in the skeletal structure of the compound when it is phenyl.

As a form of cycloalkane condensation, first, the B ring, C ring, D ring, E ring, F ring in a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2). , a form in which the aryl ring and heteroaryl ring in each of the G, H, and I rings are condensed with a cycloalkane.

As another form of cycloalkane condensation, a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2), for example, where R ^NX is an aryl fused with a cycloalkane, >NR ^NX , diarylamino fused with a cycloalkane (fused to this aryl moiety), carbazolyl fused with a cycloalkane (fused to this benzene ring moiety) or benzocarbazolyl fused with a cycloalkane (fused to this benzene ring moiety) An example having a benzene ring moiety (condensed to this benzene ring portion) is given.

Note that by introducing a cycloalkane structure into a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2), further reduction in the melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, thermal decomposition of the material can be avoided because purification can be performed at a relatively low temperature. means. This also applies to the vacuum evaporation process, which is an effective means for producing organic devices such as organic EL elements, and because the process can be carried out at relatively low temperatures, thermal decomposition of the material can be avoided. As a result, a high-performance organic device can be obtained. Furthermore, since the solubility in organic solvents is improved by introducing the cycloalkane structure, it can also be applied to device fabrication using a coating process. However, the present invention is not particularly limited to these principles.

<Replacement with deuterium, cyano, or halogen>
All or part of hydrogen in the structure containing the structural unit represented by formula (1) or formula (2) may be deuterium, cyano, or halogen. The same applies to the structure represented by any formula selected from the group consisting of formulas (1-a) to (1-l) and formulas (2-a) to (2-l); is a polycyclic aromatic compound represented by any formula selected from the group consisting of formulas (1-a) to (1-l) and formulas (2-a) to (2-l). The same applies to

For example, in a structure containing a structural unit represented by formula (1) or formula (2), the aryl ring in ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I or a substituent of the aryl ring or heteroaryl ring in the heteroaryl ring, B ring, C ring, D ring, E ring, F ring, G ring, H ring, and I ring, and X is >N-R ^NX , >C(-R ^CX ) ₂ , or >Si(-R ^IX ) ₂ , hydrogen in R ^NX , R ^CX , or R ^IX (=alkyl, cycloalkyl, aryl, or heteroaryl) is deuterium , cyano, or halogen, and examples include embodiments in which all or part of hydrogen in aryl or heteroaryl is replaced with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, even more preferably fluorine. From the viewpoint of durability, it is also preferable that all or part of the hydrogen in the structure containing the structural unit represented by formula (1) or formula (2) is deuterated.

<Specific examples of polycyclic aromatic compounds of the present invention>
Specific examples of the polycyclic aromatic compound of the present invention include compounds represented by any of the following structural formulas.

<Explanation of increasing the molecular weight of polycyclic aromatic compounds>
A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer. (the monomer for obtaining this polymer compound has a polymerizable substituent), or a polymer crosslinked product obtained by further crosslinking the polymer compound (the polymer compound for obtaining this polymer crosslinked product is crosslinked) (having a reactive substituent), or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound (the reactive compound to obtain the pendant polymer compound has a reactive substituent); ), or as a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound (the pendant-type polymer compound for obtaining this pendant-type crosslinked polymer has a crosslinkable substituent), It can be used for materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field effect transistors, materials for organic thin film solar cells, or wavelength conversion filters.

In addition, in this specification, a "polymer compound" has a molecular weight distribution and a number average molecular weight of 1×10 ³ to 1×10 ⁸ (1×10^3 to 1×10^8) in terms of polystyrene. ) means a polymer that is The number average molecular weight (Mn) of a polymer compound in terms of polystyrene can be determined by size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase. Specifically, the polymer compound to be measured is dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL is injected into the SEC. The flow rate of the mobile phase is 1.0 mL/min, and PLgel MIXED_B (manufactured by Polymer Laboratories) is used as the column. A UV_VIS detector (manufactured by Tosoh, trade name: UV-8320GPC) can be used as the detector.
The polymer compound of the present invention preferably has a number average molecular weight of 2,000 to 1×10 ⁸ , more preferably 5,000 to 1×10 ⁸ .

The above-mentioned reactive substituents (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also simply referred to as "reactive substituents") are: , a substituent that can increase the molecular weight of the polycyclic aromatic compound, a substituent that can further crosslink the polymer compound thus obtained, and a substituent that can react pendantly to the main chain polymer. Although not particularly limited, substituents having the following structures are preferred. * in each structural formula indicates the bonding position.

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

Such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers are composed of one or more structural units represented by formula (1) or formula (2). In addition to repeating units of polycyclic aromatic compounds having the structure, substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazines, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted It may contain at least one member selected from the group consisting of dibenzofurans as a repeating unit.

Substituents in these repeating units include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (even if two aryls are bonded via a single bond or a linking group). Examples include alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the "aryl" of triarylamine and these substituents, the explanations in formula (1) and formula (2) can be cited.

<Method for producing polycyclic aromatic compound>
Basically, a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) first connects ring a and rings B to I (rings b to i) with a linking group. Intermediate 1 is produced by combining (first reaction), B ring (b ring), G ring (g ring), I ring (i ring), E ring (e ring) and F ring (f ring). Ring) and H ring (h ring) are bonded with boron to form a condensed ring to obtain intermediate 2 (second reaction), and then a ring and B to I rings (b to i ring ) The final product can be produced by bonding a condensed ring containing the following with boron (third reaction).

For the first reaction, common reactions such as Buchwald-Hartwig reaction, nucleophilic substitution reaction, and Goldberg reaction can be used. Further, in the second reaction and the third reaction, a tandem hetero Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. An example is shown in scheme (0).

In the second reaction, as shown in schemes (1) and (2) below, ring B (ring b), ring G (ring g), ring I (ring i), ring E (ring e), and ring F This is a reaction that introduces boron that bonds the (f ring) and H ring (h ring). The intermediate halogen is subjected to halogen-metal exchange with n-butyllithium, sec-butyllithium, t-butyllithium, etc., and then a boronating agent is added to perform lithium-boron metal exchange, followed by a Bronsted base. The addition causes a tandem bola-Friedel-Crafts reaction to yield intermediate 2, which becomes a precursor for the third reaction.

The third reaction, as shown in schemes (1) and (2) below, is a reaction in which boron is introduced to bond a condensed ring containing ring a and rings B to I (rings b to i). By adding a boronating agent such as boron tribromide or boron triiodide, and a Brønsted base such as N,N-diisopropylethylamine or 2,6-di-tert-butylpyridine to the intermediate, tandem bora-Friedel can be obtained. The desired product can be obtained through a Crafts reaction. In the third reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.
Note that the halogen atom (Hal) in the above scheme (0) and the following scheme may be any of F, Cl, Br, and I, and can be appropriately selected in consideration of the reactivity of the substrate.

In the B-ring, C-ring, D-ring, E-ring, F-ring, G-ring, H-ring, and I-ring in the formula representing an intermediate, etc., a portion that does not show a bond as in the arrow part of the following formula (IntC1) It is assumed that hydrogen is bonded to as shown in the following formula (IntC2).

The above schemes (1) and (2) mainly show methods for producing polycyclic aromatic compounds having a structure containing one structural unit represented by formula (1) or formula (2). A polycyclic aromatic compound containing two or more structural units can be produced by using an intermediate having multiple a rings and B to I rings (b to i rings).

By appropriately selecting the raw materials to be used, a polycyclic aromatic compound having a substituent at a desired position can be synthesized.

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

The orthometalation reagents used in the above schemes (1) and (2) include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, lithium diisopropylamide, and lithium tetramethyl. Examples include organic alkali metal compounds such as piperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

The metal-boron metal exchange reagent used in the above schemes (1) and (2) includes boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide; Examples include alkoxylated products of boron, aryloxylated products of boron, etc.

The Bronsted bases used in the above schemes (1) and (2) include 2,6-di-tert-butylpyridine, N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethyl Piperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenyl Examples include borane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, and Ar ₄ Si (Ar is aryl such as phenyl).

The Lewis acids used in the above schemes (1) and (2) include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ .OEt ₂ , BCl ₃ , BBr 3 , BI 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 etc. can be mentioned.

In schemes (1) and (2) above, a Brønsted base or a Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide are used, as the aromatic electrophilic substitution reaction progresses, hydrogen fluoride, hydrogen chloride, and Since acids such as hydrogen chloride and hydrogen iodide are produced, it is effective to use a Brønsted base to scavenge the acids. On the other hand, when boron aminated halides or boron alkoxides are used, amines and alcohols are generated as the aromatic electrophilic substitution reaction progresses, so in many cases it is not necessary to use a Brønsted base. However, since the elimination ability of amino and alkoxy is low, it is effective to use a Lewis acid that promotes their elimination.

Furthermore, the polycyclic aromatic compounds of the present invention include those in which at least some of the hydrogen atoms are substituted with deuterium or those in which halogens such as fluorine and chlorine are substituted; however, such compounds etc. can be synthesized in the same manner as above by using raw materials that are deuterated, fluorinated, or chlorinated at desired locations.

2. Organic Device The polycyclic aromatic compound of the present invention can be used as a material for organic devices. Examples of the organic device include an organic electroluminescent element, an organic field effect transistor, and an organic thin film solar cell.

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, an organic thin film solar cell, etc., but an organic electroluminescent device is preferable. The polycyclic aromatic compound according to the present invention is preferably an organic electroluminescent device material, more preferably a light-emitting layer material (light-emitting material), and most preferably a dopant material for the light-emitting layer.

2-1. Organic electroluminescent device An organic electroluminescent device has a pair of electrodes consisting of an anode and a cathode, and a light emitting layer disposed between the pair of electrodes. The organic electroluminescent device may further include other organic layers.
2-1-1. Structure of organic electroluminescent device
FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
The organic EL element 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 A hole transport layer 104 provided, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, and a light emitting layer 105 provided on the electron transport layer 106. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

Note that the organic EL element 100 can be manufactured in the reverse order, for example, by forming a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, and an electron injection layer 107. an electron transport layer 106 provided on the electron transport layer 106; a light emitting layer 105 provided on the electron transport layer 106; a hole transport layer 104 provided on the light emitting layer 105; It is also possible to have a configuration including a hole injection layer 103 provided on the hole injection layer 103 and an anode 102 provided on the hole injection layer 103.

All of the above layers are not indispensable, and the minimum structural unit is the anode 102, the light emitting layer 105, and the cathode 108. Layer 107 is an optional layer. Moreover, each of the above layers may be composed of a single layer or a plurality of layers.

In addition to the above-mentioned configuration of "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", examples of the layers constituting the organic EL element include " "Substrate/Anode/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/Anode/Hole injection layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/ Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode", "substrate / Anode/Emissive layer/Electron transport layer/Electron injecting layer/Cathode", "Substrate/Anode/Hole transport layer/Emissive layer/Electron injecting layer/Cathode", "Substrate/Anode/Hole transport layer/Emissive 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.

The organic EL device may further include one or both selected from an electron blocking layer (electron blocking layer) and a hole blocking layer (hole blocking layer). The electron blocking layer has a LUMO shallower than the light emitting layer and a HOMO close to the light emitting layer or the hole transport layer, and is disposed between the light emitting layer and the hole transport layer. Since the electrons remain in the light emitting layer and do not leak out to the hole transport layer, it is possible to prevent a short life due to deterioration of the hole transport layer and a decrease in efficiency due to a decrease in recombination efficiency. The hole blocking layer has a HOMO deeper than the emissive layer and a LUMO close to the emissive layer or the hole transport layer, and is disposed between the emissive layer and the electron transport layer. Since the holes remain in the light emitting layer and do not leak out to the electron transport layer, it is possible to prevent a short life due to deterioration of the electron transport layer and a decrease in efficiency due to a decrease in recombination efficiency. The hole injection/transport layer may also serve as an electron blocking layer. The electron injection/transport layer may also serve as a hole blocking layer.

The organic EL device may further include a high T1 layer. A high T1 layer has a T1 higher than the host compound, assisting dopant compound, or emitting dopant compound used in the emissive layer and is between the emissive layer and the hole transport layer and/or between the emissive layer and the electron blocking layer. Placed. The value of T1 energy varies depending on the light emitting mechanism of the device, but it has a higher T1 than the compound used as the host. By having a high T1 layer around the light-emitting layer, it is possible to confine triplet energy and convert triplet energy, which normally does not lead to light emission with fluorescent molecules, into singlet energy, thereby achieving high efficiency. The hole injection/transport layer or the electron blocking layer may also serve as the high T1 layer. The electron injection/transport layer or the hole blocking layer may also serve as the high T1 layer.

2-1-2. Substrate in the organic electroluminescent device The substrate 101 is a support for the organic EL device 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape depending on the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. are used. Among these, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If the substrate is a glass substrate, soda lime glass or alkali-free glass may be used, and the thickness may be sufficient to maintain mechanical strength. In addition, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side of the substrate 101 in order to improve gas barrier properties. In particular, a synthetic resin plate, film, or sheet with low gas barrier properties may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

2-1-3. The anode anode 102 in the organic electroluminescent device plays the role of injecting holes into the light emitting layer 105. Note that when at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. It turns out.

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

2-1-4. Hole injection layer and hole transport layer in the organic electroluminescent device The hole injection layer 103 plays the role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or into the hole transport layer 104. Fulfill. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating or mixing one or more hole injection/transport materials. Alternatively, the layer may be formed by adding an inorganic salt such as iron(III) chloride to the hole injection/transport material.

As a hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes where an electric field is applied, and the material has high hole injection efficiency and efficiently transports the injected holes. It is desirable to do so. For this purpose, it is preferable to use a substance that has a low ionization potential, high hole mobility, excellent stability, and does not easily generate trapping impurities during production and use.

Materials for forming the hole injection layer 103 and the hole transport layer 104 include compounds conventionally used as hole charge transport materials in photoconductive materials, p-type semiconductors, and hole injection layers of organic EL devices. Any compound can be selected and used from among the known compounds used in the hole transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (aromatic tertiary Polymer with amino in main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 ,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 , 4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N ⁴ ,N ^4' -diphenyl- N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N ⁴ ,N ⁴ ,N ^4' ,N ^{4 '} -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl) triphenylamine derivatives (such as amino) triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives , quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. As for polymer systems, polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane, etc., which have the above-mentioned monomer in the side chain, are preferable, but they can form a thin film necessary for producing a light emitting device, and holes can be injected from the anode. Further, the compound is not particularly limited as long as it can transport holes.

It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such an organic semiconductor matrix material is composed of a compound with good electron donating properties or a compound with good electron accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known. (For example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)). These generate so-called holes by electron transfer processes in electron-donating base materials (hole-transporting materials). 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 starburst amine derivatives (TDATA etc.) or certain metal phthalocyanines (in particular zinc phthalocyanine (ZnPc) etc.) are known ( (Japanese Patent Application Publication No. 2005-167175).

The hole injection layer material and the hole transport layer material described above are a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a polymer crosslinked product thereof, or A pendant polymer compound obtained by reacting a main chain polymer with the above-mentioned reactive compound, or a pendant polymer crosslinked product thereof can also be used as a hole layer material.

2-1-5. The light-emitting layer 105 in an organic electroluminescent device is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is applied. . The material forming the light-emitting layer 105 may be any compound (luminescent compound) that emits light when excited by the recombination of holes and electrons, can form a stable thin film shape, and is in a solid state. Compounds exhibiting strong luminescence (fluorescence) efficiency are preferred and used.

The light emitting layer preferably contains an emitting dopant and at least two selected from the group consisting of a hole transporting host material, an electron transporting host material, and an assisting dopant material. The light-emitting layer may be a single layer or composed of multiple layers, and each is formed from a material for the light-emitting layer. When the light emitting layer consists of multiple layers, it is preferable that any one layer contains the polycyclic aromatic compound of the present invention. Preferably, the light-emitting layer is a single layer. The emitting dopant may be contained entirely or partially in the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

The amount of host material used varies depending on the type of host material, and may be determined depending on the characteristics of the host material. The amount of the host material to be used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass of the total mass of the materials for the light emitting layer. %. When the host material is a combination of a hole-transporting host material and an electron-transporting host material, the amount of the host material used is equal to the amount of the hole-transporting host material used and the amount of the electron-transporting host material used. This is the combined mass. The ratio of the amounts of the hole-transporting host material to the electron-transporting host material may be 1:9 to 9:1 by mass, preferably 4:6 to 6:4, and approximately 1:1. More preferably, it is 1.

The amount of the emitting dopant to be used varies depending on the type of the emitting dopant, and may be determined according to its characteristics. The amount of the emitting dopant to be used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total mass of the material for the emitting layer. Mass%. The above range is preferable in that, for example, concentration quenching phenomenon can be prevented.

In organic electroluminescent devices that use an assisting dopant (thermally activated delayed phosphor or phosphorescent material) in addition to an emitting dopant, the concentration quenching phenomenon can be prevented by using a low concentration of the emitting dopant material. It is preferable in this respect. It is preferable for the assisting dopant to be used in a high concentration from the viewpoint of energy transfer efficiency. It is preferable that the assisting dopant be used in a high concentration from the viewpoint of efficiency of the thermally activated delayed fluorescence mechanism. In an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, the amount of emitting dopant used is smaller than the amount of assisting dopant used. It is preferable that the amount used is low concentration.

When an assisting dopant material is used, the approximate usage amounts of the host material, assisting dopant material, and emitting dopant material are 40 to 99% by mass and 59 to 1% by mass, respectively, based on the total mass of the material for the light emitting layer. % and 20-0.001% by weight, preferably 60-95% by weight, 39-5% by weight and 10-0.01% by weight, more preferably 70-90% by weight, 29% by weight, respectively. -10% by weight and 5-0.05% by weight.

The polycyclic aromatic compound of the present invention is more preferably used as a material for forming a light-emitting layer, and particularly preferably used as a dopant.

A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) is used as a "thermally activated delayed phosphor" in an organic EL device that exhibits thermally activated delayed fluorescence (TADF). It may be used as an emitting dopant for a TADF element (hereinafter sometimes referred to as a "TADF element"). In "thermally activated delayed phosphor", by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, the transition probability from the lowest excited triplet state to the lowest excited singlet state, which normally has a low transition probability, is reduced. Reverse intersystem crossing occurs with high efficiency, and light emission from singlets (thermally activated delayed fluorescence, TADF) is expressed. In normal fluorescence emission, 75% of triplet excitons generated by current excitation pass through a heat deactivation path and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL device can be realized.

A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) can be used as an emitting dopant for a "TADF element", as an emitting dopant for a TADF element using two types of hosts, or as an emitting dopant for a TADF element using two types of hosts. An emitting dopant for an organic electroluminescent device (TAF device) using a thermally activated delayed phosphor as an assisting dopant, an organic electroluminescent device (phosphorescent assist device: phosphorescence-sensitized fluorescence It can be used as an emitting dopant for (phosphor-sensitized fluorescent) devices, PSF devices). From the viewpoint that the less material used in the element, the easier it is to manufacture, it is preferable to use two types of emitting dopants or hosts for the TADF element as the emitting dopant for the TADF element, and the former is more preferable. From the viewpoint of efficiency, it is preferably used as an emitting dopant for a TAF element and a phosphorescent assist element, and more preferably used as an emitting dopant for a TAF element.

Generally, the faster the delayed fluorescence, the better the TADF properties. Specifically, when a light-emitting material having a delayed fluorescence lifetime of 20 μsec or less is used as an emitting dopant in a light-emitting device, high device efficiency and long device life can be provided. The delayed fluorescence lifetime is preferably less than 20 μsec, more preferably 10 μsec or less, and most preferably 5 μsec or less.

Further, generally, the smaller the value of ΔE _S1T1 is, the better the TADF properties are. Note that ΔE _S1T1 is the energy difference between the lowest excited singlet energy level (E _S1 ) and the lowest excited triplet energy level (E _T1 ). Specifically, the value of ΔE _S1T1 is preferably 0.20 eV or less, more preferably 0.15 eV or less, and particularly preferably 0.10 eV or less.

<Host material>
Examples of host materials include fused ring derivatives such as anthracene and pyrene, which have long been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzene derivatives. Examples include fluorene derivatives, N-phenylcarbazole derivatives, and carbazonitrile derivatives.

The lowest excited triplet energy level (E _T1 ) of the host material is determined by the E of the dopant or assisting dopant having the highest E _T1 in the light emitting layer, from the viewpoint of promoting rather than inhibiting the generation of TADF in the light emitting layer. E _T1 of the host material is preferably higher than E _T1 of the above dopant or assisting dopant by 0.01 eV or more, and preferably 0.03 eV or more higher than E _T1 of the above dopant or assisting dopant. More preferably, it is higher than 0.1 eV. Moreover, E _T1 of the host material is preferably 2.55 eV or more, more preferably 2.58 eV or more, and even more preferably 2.650 eV or more.
A TADF active compound may be used as the host material.

The number of host materials may be one type or a combination of multiple types. In the case of a plurality of combinations, it is preferably a combination of a hole-transporting host material and an electron-transporting host material.

The hole-transporting host material (HH) and the electron-transporting host material (EH) satisfy the following relationships for HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital).
The HOMO of the hole-transporting host material (HH) is shallower than the HOMO of the electron-transporting host material (EH), and the LUMO of the electron-transporting host material (EH) is deeper than the LUMO of the hole-transporting host material (HH). .
Further, it is preferable that the HOMO of the emitting dopant is shallower than the HOMO of the hole-transporting host material (HH), or that the LUMO of the emitting dopant is deeper than the LUMO of the electron-transporting host material (EH).

In addition, the lowest excited triplet energy level ( _ET1 ) of the hole-transporting host material (HH) and the electron-transporting host material (EH) is determined from the viewpoint of promoting the generation of TADF in the light-emitting layer without inhibiting it. , is preferably higher than the E T1 of the emitting dopant or assisting dopant having the highest E _T1 in the light emitting layer. Specifically, the E _T1 of the host material is higher than the E _T1 of the above-mentioned emitting dopant or assisting dopant. is preferably 0.01 eV or more higher than E _T1 , more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. Moreover, E _T1 of the host material is preferably 2.47 eV or more, more preferably 2.49 eV or more, and even more preferably 2.56 eV or more.

Note that it is also preferable to use a hole-transporting host material in the hole-transporting layer adjacent to the light-emitting layer, and to use an electron-transporting host material in the electron-transporting layer adjacent to the light-emitting layer. This is because carrier leakage and energy leakage from the light-emitting layer to adjacent layers becomes less likely to occur, and a highly efficient organic EL device can be obtained. The host material (hole-transporting host material) in the light-emitting layer and the hole-transporting layer material may be the same or different. Further, the host material in the light-emitting layer (electron-transporting host material) and the material of the electron-transporting layer may be the same or different.

[Hole transporting host material (HH)]
Examples of preferable hole-transporting host materials (HH) are represented by formula (HH-1) or have a partial structure represented by formula (HH-1), and include an aryl ring and a heteroaryl ring. Compounds having a structure containing at least three rings selected from the group consisting of: This compound preferably does not contain any of an imine structure (-N=C-; including a partial structure of a heteroaryl ring), boron (>B-), and cyano (CN).

In formula (HH-1),
Q is >O, >S, or >NA ^H ;
One carbon atom next to the carbon atom to which Q is bonded in each of the two phenyls in formula (HH-1) may be bonded to each other by L,
L is a single bond, >O, >S, or >C(-A ^H ) ₂ ;
A ^H is hydrogen, aryl, or heteroaryl, and two A ^H at >C(-A ^H ) ₂ may be bonded to each other.

When the hole-transporting host material contains a structure represented by formula (HH-1) as a partial structure, it may contain one partial structure, but it is also preferable to contain two or more partial structures. When two or more partial structures are included, the two or more partial structures may be the same or different from each other. Two or more partial structures may be bonded to each other with a single bond, or may be bonded so as to share any ring contained in the partial structure, or any rings contained in the partial structure may be fused together. They may be combined in this way. The moiety may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy.

The compound represented by the above formula (HH-1) or having a partial structure represented by the formula (HH-1) contains at least three rings selected from the group consisting of an aryl ring and a heteroaryl ring. Has a structure. The number of rings included is preferably 6 or more, more preferably 8 or more. Further, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings, and for condensed rings, the number includes the single rings constituting the condensed ring.

The hole-transporting host material is a compound containing one or more partial structures selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a fused polycyclic ring containing phenoxazine or phenothiazine. It is preferable that there be. The hole-transporting host material may contain one such partial structure, but preferably contains two or more. When two or more partial structures are included, the two or more partial structures may be the same or different from each other.

Specific examples of hole-transporting host materials include the following compounds.

Among the above, HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1- 24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92, HH-1-106 to HH-1-108, and HH-1-109 ~HH-1-113 are preferred.

[Electron transporting host material (EH)]
Examples of electron-transporting host materials (EH) include formulas (EH-1A) to (EH-1D) or partial structures represented by formulas (EH-1A) to (EH-1D). Examples include compounds having a structure containing at least three rings selected from the group consisting of an aryl ring and a heteroaryl ring.

In formulas (EH-1A) to (EH-1D),
Ar is a heteroaryl ring containing N=C as a partial structure constituting the ring,
Z is a single bond, -O-, -S-, or -N(-A ^E )-,
The carbon atom next to the carbon atom to which Z is bonded and A ^E to which Z is bonded may be bonded to each other with L,
L is a single bond, >O, >S or >C(-A ^E ) ₂ ;
A ^E is aryl, heteroaryl, or triarylsilyl, and two A ^E in >C(-A ^E ) ₂ may be bonded to each other,
X is C, P or S;
When X is C, n=2, m=1,
When X is P, n=3, m=1,
When X is S, n=2 and m=1 to 2.

Compounds represented by the above formulas (EH-1A) to (EH-1D) or having a partial structure represented by the formulas (EH-1A) to (EH-1D) are composed of an aryl ring and a heteroaryl ring. It has a structure containing at least three rings selected from the group consisting of: The number of included rings is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. Further, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings, and for condensed rings, the number includes the single rings constituting the condensed ring.

When the electron-transporting host material contains a structure represented by formulas (EH-1A) to (EH-1D) as a partial structure, it may contain one partial structure, but it may also contain two or more partial structures. preferable. When two or more partial structures are included, the two or more partial structures may be the same or different from each other. Two or more partial structures may be bonded to each other with a single bond, or may be bonded so as to share any ring contained in the partial structure, or any rings contained in the partial structure may be fused together. They may be combined in this way. The moiety may further have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy.

Specific examples of electron-transporting host materials include the following compounds.

Another preferred example of the electron-transporting host material (a compound having a partial structure represented by the formula (EH-1)) is a polycyclic aromatic compound represented by the following formula (EH-1b) or the following formula ( Examples include multimers of polycyclic aromatic compounds having a plurality of structures represented by EH-1b).

In formula (EH-1b),
R ¹ , R ² , R ³ , R ⁴ and R ⁵ (hereinafter also referred to as "R ¹ etc.") are each independently hydrogen or a substituent. This substituent may be one selected from substituent group Z.
In formula (EH-1b), X ¹ and X ² are each independently >NR (amine nitrogen), >O, >C(-R) ₂ , >S or >Se, and ¹ and X ² cannot both be >C(-R) ₂ ,
R in the above >NR and >C(-R) ₂ is each independently hydrogen or a substituent selected from substituent group Z, and furthermore, aryl, heteroaryl, alkyl, or cycloalkyl ( , a second substituent), and each of the R's of >N-R and >C(-R) ₂ is independently substituted with a linking group or a single bond of the a-ring, b-ring and c-ring. It may be bonded to at least one ring.
Y ¹ , Y ² , Y ³ , Y ⁴ , Y ⁵ and Y ⁶ (hereinafter also referred to as "Y ¹ etc.") each independently represents =C(-R)- or =N-(pyridine nitrogen ), and at least one is =N- (pyridine nitrogen).
Each R in the above =C(-R)- is independently hydrogen or a substituent selected from substituent group Z.
Adjacent groups of R ¹ , R ² , R ³ , R ⁴ and R ⁵ and R of =C(-R)- as Y ¹ to Y ⁶ are bonded to each other to form ring a, b The ring and at least one ring of the c ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetero May be substituted with arylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents) , at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (hereinafter referred to as the second substituent).
At least one hydrogen in the compound and structure represented by formula (EH-1b) may be substituted with cyano, halogen, or deuterium.

In formula (EH-1b), R ¹ , R ² , R ³ , R ⁴ and R ⁵ are all hydrogen, or R ³ and R ⁴ are both hydrogen, and R ¹ , R ² It is preferable that at least one selected from the group consisting of and R ⁵ is a substituent other than hydrogen, and the others are hydrogen. The substituent is preferably alkyl, aryl optionally substituted with alkyl or heteroaryl, heteroaryl optionally substituted with alkyl or aryl, or diarylamino optionally substituted with alkyl or aryl. In this case, the alkyl is preferably an alkyl having 1 to 6 carbon atoms (methyl, t-butyl, etc.), the aryl is preferably phenyl or biphenyl, and the heteroaryl is triazinyl, carbazolyl (2-carbazolyl, 3-carbazolyl, etc.). , 9-carbazolyl, etc.), pyrimidinyl, pyridinyl, dibenzofuranyl or dibenzothienyl. Specific examples include phenyl, biphenyl, diphenyltriazinyl, carbazolyltriazinyl, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazolyltriazinyl, pyridinyl, dibenzofuranyl and dibenzothienyl.

Y ¹ etc. are each independently =C(-R)- or =N-, and at least one is =N-. Any of Y ¹ to Y ⁶ may be =N-. Preferably, Y ¹ and Y ⁶ are =N- (ring a is a pyrimidine ring), Y ¹ or Y ⁶ is =N- (ring a is a pyridine ring), and Y ² and Y ⁵ are =N- (ring b and ring c is a pyridine ring), Y ³ and Y ⁴ are =N- (rings b and c are pyridine rings), Y ² to Y ⁵ are =N- (ring b and c are pyrimidine rings), Y ¹ , Y ³ , Y ⁴ and Y ⁶ are =N- (ring a is a pyrimidine ring, rings b and c are pyridine rings), Y ¹ , Y ² , Y ⁵ and Y ⁶ are =N- (ring a is a pyrimidine ring); , rings b and c are pyridine rings), Y ¹ to Y ⁶ are =N- (rings a, b and c are pyrimidine rings), Y ² or Y ⁵ is =N- (ring b or c is a pyrimidine ring), pyridine ring).

Further, in addition to the above configurational relationship of =N-, it is preferable that X ¹ and X ² are >O, and a polycyclic aromatic compound containing a partial structure represented by any of the following formulas is preferable.

In particular, a polycyclic aromatic compound containing a partial structure represented by the formula (EH-1b-N1) has a higher E _S1 , a higher E _T1 , and a smaller ΔE _S1T1 than a structure without N.
Specific examples of the polycyclic aromatic compound represented by formula (EH-1b) are shown below.

Of the above, EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1- 51~EH-1-59, EH-1-61, EH-1-66, EH-1-68, EH-1-71, EH-1-72, EH-1-90, EH-1-94~ EH-1-98, EH-1-100, EH-1-101, EH-1-104, EH-1-115, EH-1-117, EH-1-120, EH-1-122, EH- 1-123, EH-1-127 to EH-1-130 are preferred.

[Combination of hole transporting host material and electron transporting host material]
The combination of hole transporting host material and electron transporting host material is selected according to the HOMO, LUMO and lowest excited triplet energy level (E _T1 ) of the hole transporting host material, electron transporting host material and dopant material. Ru.
Regarding HOMO and LUMO, the HOMO (HH) of the hole-transporting host material is shallower than the HOMO (EH) of the electron-transporting host material, and the LUMO (EH) of the electron-transporting host material is shallower than the LUMO of the hole-transporting host material. Select a combination that is deeper than (HH), more specifically, a combination in which HOMO (HH) is 0.10 eV or more shallower than HOMO (EH), and LUMO (HH) is 0.10 eV or more deeper than HOMO (EH), A more preferable combination is that HOMO (HH) is 0.20 eV or more shallower than HOMO (EH), LUMO (HH) is 0.20 eV or more deeper than HOMO (EH), and HOMO (HH) is 0.25 eV or more than HOMO (EH). More preferred is a combination in which the LUMO (HH) is shallow and the LUMO (HH) is 0.25 eV or more deeper than the HOMO (EH).

The hole-transporting host material and the electron-transporting host material may be combined to form an association called an exciplex. It is generally known that an exciplex is likely to be formed between a material having a relatively deep LUMO level and a material having a shallow HOMO level. The interaction between the hole-transporting host material and the electron-transporting host material, specifically whether or not an exciplex is formed, is determined by determining whether a monolayer film consisting of only the hole-transporting host material and the electron-transporting host material is formed. The light emitting layer is formed under the same conditions as the light emitting layer, and the emission spectrum (fluorescence, phosphorescence spectrum) is measured. This can be determined by comparing it with the spectrum. The spectrum of the mixed film containing the hole-transporting host material and the electron-transporting host material exhibits an emission wavelength that is different from both the spectrum of the film of the hole-transporting host material and the spectrum of the film of the electron-transporting host material. It can be determined by Specifically, the fact that the peak wavelengths of the spectra differ by 10 nm or more may be used as an index.

Specific examples of combinations of hole-transporting host materials and electron-transporting host materials that do not form exciplexes include the following combinations. In order to satisfy the physical property values of HOMO, LUMO and E _T1 described above, the hole transporting host material has carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole and benzoxazinophenoxazine as partial structures. Compounds are preferred, compounds having carbazole, dibenzofuran and dibenzothiophene as a partial structure are more preferred, and compounds having carbazole as a partial structure are even more preferred. Similarly, in the electron-transporting host material, compounds having pyridine, triazine, phosphine oxide, benzofuropyridine, and dibenzoxacillin as partial structures are preferable, and compounds having triazine, phosphine oxide, benzofuropyridine, and dibenzoxacillin as partial structures are preferable. are more preferred, and compounds having triazine are even more preferred.

More specifically, the hole-transporting host materials include HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH- The electron transporting host material is preferably selected from the group consisting of EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25. , EH-1-32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-71, EH-1-72, EH-1-90, EH -1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH- Preferably, it is selected from the group consisting of 1-130. Preferred examples of the combination include compound HH-1-1 and compound EH-1-22, compound HH-1-1 and compound EH-1-23, compound HH-1-1 and compound EH-1-24, and compound HH-1-2 and compound EH-1-22, compound HH-1-2 and compound EH-1-23, compound HH-1-2 and compound EH-1-24, or compound HH-1-1 and compound EH-1-128 is mentioned.

Specific examples of combinations of hole-transporting host materials and electron-transporting host materials that form exciplexes include the following combinations. In order to satisfy the above-mentioned physical property values of HOMO, LUMO, and _E Compounds having lylamine, indolocarbazole, and benzoxazinophenoxazine as partial structures are more preferred, and compounds having triarylamine as a partial structure are even more preferred. Similarly, in the electron-transporting host material, compounds having pyridine, triazine, phosphine oxide, and benzofuropyridine as partial structures are preferable, and compounds having triazine, phosphine oxide, benzofuropyridine, and dibenzoxacillin as partial structures are more preferable. More preferred are compounds having , phosphine oxide and triazine.

More specifically, the hole-transporting host materials include HH-1-1, HH-1-2, HH-1-11, HH-1-12, HH-1-17, HH-1-18, Preferably, it is selected from the group consisting of HH-1-23 and HH-1-24, and the electron transporting host material is selected from the group consisting of EH-1-1 to EH-1-4, EH-1-21 to EH-1. -25, EH-1-51 to EH-1-57, EH-1-59, EH-1-66, EH-1-68, EH-1-90, EH-1-94, EH-1-100 , EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and from EH-1-127 to EH-1-130 Preferably, it is selected from the group consisting of: Preferred examples of the combination include compound HH-1-1 and compound EH-1-21, compound HH-1-2 and compound EH-1-21, compound HH-1-12 and compound EH-1-94, and compound HH-1-12 and compound EH-1-117, compound HH-1-1 and compound EH-1-130, compound HH-1-33 and compound EH-1-117, compound HH-1-48 and compound EH -1-117 or compound HH-1-49 and compound EH-1-117.

For other specific combinations of hole-transporting host materials and electron-transporting host materials, see Organic Electronics 66 (2019) 227-24, Advanced. Functional Materials 25 (2015) 361-366. , Advanced Materials 26 (2014) 4730-4734. , ACS Applied Materials and Interfaces 8 (2016) 32984-32991. , ACS Applied Materials and Interfaces 2016, 8, 9806-9810, ACS Applied Materials and Interfaces 2016, 8, 32984-32991, Journal of Materials Chemistry C, 2018, 6, 8784-8792, Angewante Chemie International Edition. 2018, 57, 12380-12384, Advanced Functional Materials, 24, 2014, 3970, Advanced Materials, 26, 2014, 5684, and Synthetic Metals, 201, 201 5, 49, etc. can be referred to.

<Assisting dopant (thermally activated delayed phosphor or phosphorescent material)>
Preferably, the emissive layer includes an assisting dopant along with an emitting dopant and a host material. The assisting dopant is preferably a thermally activated delayed phosphor or a phosphorescent material.

In this embodiment, known host compounds can be used, such as compounds having at least one of a carbazole ring and a furan ring, and among them, at least one of furanyl and carbazolyl, and arylene and heteroarylene. It is preferable to use a compound bound to at least one of the following. Specific examples include mCP and mCBP. Further, a TADF-active compound may be used as the host compound. In this embodiment, it is also preferable to use a combination of a hole-transporting host material and an electron-transporting host material as the host.

The lowest excited triplet energy level E (1, T, Sh) determined from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum of the host compound is determined from the viewpoint of promoting the generation of TADF in the light emitting layer without inhibiting it. Compared to the lowest excited triplet energy level E (2, T, Sh), E (3, T, Sh) of the emitting dopant or assisting dopant that has the highest lowest excited triplet energy level in the light emitting layer. It is preferable that the lowest excited triplet energy level E (1, T, Sh) of the host compound is higher than E (2, T, Sh) and E (3, T, Sh). It is preferably higher than 0.01 eV, more preferably higher than 0.03 eV, even more preferably higher than 0.1 eV.

[Thermally activated delayed phosphor]
A "thermally activated delayed phosphor" absorbs thermal energy to cause reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and then radiatively deactivates from the lowest excited singlet state to cause a delay. A compound that can emit fluorescence. However, "thermally activated delayed fluorescence" also includes fluorescence that passes through a higher-order triplet during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, a paper by Monkman et al., Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038/ncomms13680), a paper by Hosokai et al., National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3:e1603282), Kyoto Paper by Sato et al., University (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7), conference presentation by Sato et al., also Kyoto University (98th Spring Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15) , Mechanism of highly efficient light emission in organic electroluminescence using DABNA as a light-emitting molecule, Graduate School of Engineering, Kyoto University), Review by Bui et al. (DOI:10.3762/bjoc.14.18), Review by Duan et al. (DOI:10.1063/1.5143501) ), reviews by Ding et al. (DOI:10.1088/1674-4926/42/5/050201), and reviews by Xie et al. (DOI:10.1002/adom.202002204). In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300 K, the target compound is determined to be a "thermally activated delayed phosphor" based on the observation of a slow fluorescence component. Here, the slow fluorescence component refers to one whose fluorescence lifetime is 0.1 μsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01).

In a light emitting layer that further contains a "thermally activated delayed phosphor" as an assisting dopant, the polycyclic aromatic compound of the present invention can function as an emitting dopant. That is, the "thermally activated delayed phosphor" can function as an assisting dopant that assists the polycyclic aromatic compound of the present invention to emit light.
In this specification, an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant is sometimes referred to as a "TADF device" (TADF Assisting Fluorescence device).
The "host compound" in a TAF element is one in which the lowest excited singlet energy level determined from the shoulder on the short wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally activated delayed phosphor as an assisting dopant and the emitting dopant. It means a compound with a high concentration.

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF element 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 excited singlet energy level determined from the shoulder on the short wavelength side of the fluorescence spectrum of the host is E(1,S,Sh), and the host The lowest excited triplet energy level determined from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant is E(1,T,Sh), and the energy level of the ground state of the assisting dopant is E(2,G). The lowest excited singlet energy level determined from the shoulder on the short wavelength side of the fluorescence spectrum of the dopant is E(2,S,Sh), and the lowest excited triplet energy level determined from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant is E(2,S,Sh). The energy level is E (2, T, Sh), the energy level of the ground state of the emitting dopant is E (3, G), and the lowest excited singlet determined from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant. The energy level is E (3, S, Sh), the lowest excited triplet energy level determined from the shoulder on the short wavelength side of the phosphorescence spectrum of the emitting dopant is E (3, T, Sh), and the hole is h + , electron is e-, and fluorescence resonance energy transfer is FRET (Fluorescence Resonance Energy Transfer). In a TAF element, when a general fluorescent dopant is used as an emitting dopant (ED), the energy upconverted by the assisting dopant is at the lowest excited singlet energy level E (3, S, Sh) of the emitting dopant. and emits light. However, some of the lowest excited triplet energy levels E (2, T, Sh) on the assisting dopant move to the lowest excited triplet energy levels E (3, T, Sh) of the emitting dopant, An intersystem crossing occurs on the emitting dopant from the lowest excited singlet energy level E(3,S,Sh) to the lowest excited triplet energy level E(3,T,Sh), followed by the ground state E( 3, thermally inactivated to G). Due to this path, some energy is not used for light emission, resulting in wasted energy.

In contrast, in the organic electroluminescent device of this embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, thereby achieving high luminous efficiency. This is presumed to be due to the following light emission mechanism.
A preferable energy relationship in the organic electroluminescent device of this embodiment is shown in FIG. In the organic electroluminescent device of this embodiment, the compound having a boron atom as an emitting dopant has a high lowest excited triplet energy level E (3, T, Sh). Therefore, even if the lowest excited singlet energy upconverted by the assisting dopant intersystem-crosses to the lowest excited triplet energy level E (3, T, Sh) in the emitting dopant, the emitting dopant or is recovered to the lowest excited 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 wasting it. It is also expected that by separating the upconversion and luminescence functions into two types of molecules, each with its own strengths, the residence time of high energy will be reduced and the burden on the compound will be reduced.

The thermally activated delayed phosphor (TADF compound) used in TAF elements uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to combine intramolecular HOMO (Highest Occupied Molecular Orbital) and LUMO. A donor-acceptor thermally activated delayed phosphor (DA-type TADF compound) designed to localize the Lowest Unoccupied Molecular Orbital and cause efficient reverse intersystem crossing. ) is preferable.

Here, in this specification, the term "electron-donating substituent" (donor) means a substituent and a partial structure in which a HOMO is localized in a heat-activated delayed phosphor molecule, and an "electron-accepting substituent" (donor) The term "acceptor" means a substituent and a partial structure in which LUMO is localized in a heat-activated delayed phosphor molecule.

In general, thermally activated delayed phosphors using donors and acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a small ΔE _S1T1 . Due to its small size, very fast inverse intersystem crossing velocities are obtained. On the other hand, thermally activated delayed fluorophores that use donors and acceptors have a large structural relaxation in the excited state (for some molecules, the stable structure is different between the ground state and the excited state, so external stimuli can cause the structure to be excited from the ground state). When the conversion occurs, the structure changes to a stable structure in the excited state), giving a broad emission spectrum, which may reduce color purity when used as a luminescent material.
However, by simultaneously using the polycyclic aromatic compound of the present invention, the polycyclic aromatic compound of the present invention functions as an emitting dopant, and the TADF material functions as an assisting dopant, making it possible to provide high color purity. The TADF material may be any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention. Both the polycyclic aromatic compound and the TADF material of the present invention may be contained in the same layer, or in adjacent or other adjacent layers.

As a thermally activated delayed phosphor in a TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used. Examples of the electron donating group (donor structure) and electron accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention include those described in Chemistry of Materials, 2017, 29, 1946-1963. The structures described can be used. Donor structures include 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-dihydroindenoacridine, and diphenyldihydrodibenzazacilline. Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis (phenylmethone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole. , benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b :5,4-b']dipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, Mention may be made of dimethylthioxanthene dioxide, thianthrene tetraoxide and tris(dimethylphenyl)borane. In particular, compounds having thermally activated delayed fluorescence in TAF elements include carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, A compound having at least one selected from oxadiazole, thiadiazole and benzophenone is preferred.

The compound used as an assisting dopant in the emitting layer of the TAF element is preferably a thermally activated delayed phosphor, and the emission spectrum thereof at least partially overlaps with the absorption peak of the emitting dopant.

[Phosphorescent material (assisting dopant)]
In the light emitting layer, a phosphorescent material may be used as an assisting dopant. In this specification, an organic electroluminescent device using a phosphorescent material as an assisting dopant may be referred to as a phosphor-assisted device, a phosphor-sensitized fluorescent device, or a PSF device. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) caused by metal atoms to emit light from an excited triplet state. As such a phosphorescent material, for example, a luminescent metal complex can be used. Examples of the luminescent metal complex include compounds represented by the following formula (B-1) and the following formula (B-2).

In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu, n is an integer from 1 to 3, and "XY'' are each independently bidentate ligands.
In formula (B-2), M is at least one selected from the group consisting of Pt, Re and Cu, and "WXYZ" is a tetradentate ligand.
In formula (B-1), M is preferably Ir and n is preferably 3 from the viewpoint of efficiency and life.
In formula (B-2), M is preferably Pt from the viewpoint of efficiency and life.
The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of: The ligand (WXYZ) in formula (B-2) has as a part at least one ligand selected from the group consisting of:

During the ceremony,
--- combines with the central metal M,
Y is each independently BR _e , NR _e , PR _e , O, S, Se, C=O, S=O, SO2, CR _e R _f , SiR _e R _f , or GeR _e R _f Each aromatic carbon C-H in the ring may be independently substituted with N,
R _e and R _f may optionally be fused or combined to form a ring,
R _a , R _b , R _c , and R _d may each independently be unsubstituted or substituted from 1 to the maximum number that can be substituted;
R _a , R _b , R _c , R _d , R _e , and R _f each independently represent hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof;
However, any two adjacent substituents in R _a , R _b , R _c , and R _d may be fused or bonded to form a ring or a multidentate ligand.

Examples of the compound represented by formula (B-1) include Ir(ppy) ₃ , Ir(ppy) ₂ (acac), Ir(mppy) ₃ , Ir(PPy) ₂ (m-bppy), BtpIr( acac), Ir(btp) ₂ (acac), Ir(2-phq) ₃ , Hex-Ir(phq) ₃ , Ir(fbi) ₂ (acac), fac-Tris(2-(3-p-xylyl) phenyl)pyridine iridium (III), Eu(dbm) ₃ (Phen), Ir(piq) ₃ , Ir(piq) ₂ (acac), Ir(Fliq) ₂ (acac), Ir(Fliq) ₂ (acac), Ru(dtb-bpy) ₃・2(PF ₆ ), Ir(2-phq) ₃ , Ir(BT) ₂ (acac), Ir(DMP) ₃ , Ir(Mphq) ₃ IR(phq) ₂ tpy, fac -Ir(ppy) ₂ Pc, Ir(dp)PQ ₂ , Ir(Dpm)(Piq) ₂ , Hex-Ir(piq) ₂ (acac), Hex-Ir(piq) ₃ , Ir(dmpq) ₃ , Ir (dmpq) ₂ (acac), FPQIrpic, etc.

Other examples of the compound represented by formula (B-1) include the following compounds.

Also, JP 2006-089398, JP 2006-080419, JP 2005-298483, JP 2005-097263, and JP 2004-111379, US Patent Application Publication No. 2019/ Iridium complexes described in 0051845 specification etc., or Advanced Materials, 26: 7116-7121, NPG Asia Materials 13, 53 (2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode - An Platinum complexes described in Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may also be used.

<Other dopant materials>
The above emitting dopants may be used in combination with other dopant materials. However, the amount of other dopant materials in one light-emitting layer is preferably less than 100% by mass, more preferably 50% by mass or less, and 30% by mass or less based on the total mass of the above-mentioned emitting dopant. It is more preferable that the amount is at most 10% by mass, particularly preferably 10% by mass or less. Known compounds can be used as other dopant materials, and can be selected from various materials depending on the desired emission color. Specifically, for example, fused ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP 1-245087), bisstyrylarylene derivatives (JP 2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl) Isobenzofuran derivatives such as isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7- Coumarin derivatives such as methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine Derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1 , 2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

As other dopant materials, polycyclic aromatic compounds containing boron described in paragraphs 0097 to 0269 of International Publication No. 2015/102118, International Publication No. 2020/162600, JP 2021-077890, etc. may be used. is also preferable.

2-1-6. Electron injection layer and electron transport layer in the organic electroluminescent device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer that is in charge of injecting electrons from the cathode and further transporting electrons, and it is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapping impurities during production and use. However, when considering the transport balance of holes and electrons, if the role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, the electron transport capacity is not so great. Even if it is not high, it has the same effect of improving luminous efficiency as a material with high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 may be a compound conventionally used as an electron transport compound in photoconductive materials, or a compound used in the electron injection layer and electron transport layer of an organic EL device. Any known compound may be selected and used.

Materials used for the electron transport layer or electron injection layer include compounds consisting of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; It is preferable to contain at least one selected from pyrrole derivatives, fused ring derivatives thereof, and metal complexes having electron-accepting nitrogen. Specifically, fused 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, aryl nitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, and oxadiazoles. derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinolines derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole- (2-yl)benzene, etc.), benzoxazole 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, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc.

Further, metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. can give.

The above-mentioned materials can be used alone, but they can also be used in combination with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol derivatives Metal complexes are preferred.

<Reducing substance>
The electron transport layer or the electron injection layer may further contain a substance that can reduce the material forming the electron transport layer or the electron injection layer. A variety of substances can be used as this reducing substance as long as it has a certain reducing property, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, and alkali metals. From the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes At least one selected can be suitably used.

Preferred reducing substances include alkali metals such as Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), or Cs (work function: 1.95 eV), and Ca (work function: 2.3 eV). Examples include alkaline earth metals such as Sr (2.0 to 2.5 eV), Sr (2.0 to 2.5 eV), and Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferable reducing substances are alkali metals such as K, Rb, or Cs, still more preferably Rb or Cs, and most preferable is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the life of the organic EL element can be extended. Further, as a reducing substance with a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, and in particular, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of light emission and the longevity of the organic EL element can be improved.

2-1-7. The cathode 108 in the organic electroluminescent device plays the role of injecting electrons into the light emitting layer 105 via 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 can efficiently inject 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 their alloys (magnesium-silver alloy, magnesium - indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum), etc.) are preferred. In order to increase electron injection efficiency and improve device characteristics, 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 the atmosphere. In order to improve this point, a method is known in which, for example, the organic layer is doped with a trace amount of lithium, cesium, or magnesium to use a highly stable electrode. Other dopants that can also be used are inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, it is not limited to these.

Additionally, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys of these metals, as well as inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, and vinyl chloride, are used to protect the electrodes. A preferred example is to laminate a hydrocarbon polymer compound or the like. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

2-1-8. Method for manufacturing an organic electroluminescent device Each layer constituting an organic EL device is prepared by depositing the materials to constitute each layer using a vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method, or casting method. It can be formed by forming a thin film using a method such as a coating method. The thickness of each layer formed in this way is not particularly limited and can be set appropriately depending on the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a crystal oscillation type film thickness measuring device. When forming a thin film using an evaporation method, the evaporation conditions vary depending on the type of material, the intended crystal structure and association structure of the film, and so on. Generally, the deposition conditions are: 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, and film thickness 2 nm to 5 μm. It is preferable to set it appropriately within a range.

When applying a direct current voltage to the organic EL element obtained in this way, it is sufficient to apply it with the anode as + polarity and the cathode as - polarity. Luminescence can be observed from the sides (anode or cathode, or both). This organic EL element also emits light when pulsed current or alternating current is applied. Note that the waveform of the applied alternating current may be arbitrary.

Next, as an example of a method for producing an organic EL device, an organic EL device consisting of an anode/hole injection layer/hole transport layer/light emitting layer made of a host material and dopant material/electron transport layer/electron injection layer/cathode will be described. The manufacturing method will be explained.

<Vapor deposition method>
After a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on this anode. On top of this, a host material and a dopant material are co-deposited to form a thin film to form a light-emitting layer, an electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like. By forming it and using it as a cathode, the desired organic EL element can be obtained. In addition, in the production of the above-mentioned organic EL element, it is also possible to reverse the production order and produce the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode in this order. It is.

<Wet film formation method>
The wet film-forming method is carried out by preparing a liquid organic layer-forming composition containing a low-molecular compound capable of forming each organic layer of an organic EL element. If there is no suitable organic solvent to dissolve this low-molecular-weight compound, the low-molecular-weight compound is substituted with a reactive substituent and becomes a polymer together with other monomers and main chain polymers that have a solubility function. The composition for forming an organic layer may be prepared from a molecularized polymer compound or the like.

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

The wet film forming method is a film forming method using a solution, and includes, for example, some printing methods (inkjet method), spin coating method, casting method, coating method, and the like. Unlike the vacuum evaporation method, the wet film formation method does not require the use of an expensive vacuum evaporation device and can form a film under atmospheric pressure. In addition, the wet film formation method allows for large-area production and continuous production, leading to reductions in manufacturing costs.

On the other hand, when compared with the vacuum evaporation method, the wet film formation method may have difficulty in laminating layers. When producing a laminated film using a wet film formation method, it is necessary to prevent the composition of the upper layer from dissolving the lower layer. solvents) are used. However, even with these techniques, it may be difficult to use a wet film formation method for coating all films.

Therefore, a method is generally adopted in which an organic EL element is fabricated using a wet film forming method for only some layers and using a vacuum evaporation method for the remaining layers.

For example, a procedure for manufacturing an organic EL element by partially applying a wet film forming method is shown below.
(Procedure 1) Film formation by vacuum evaporation of anode (Procedure 2) Film formation by wet film formation of hole injection layer forming composition containing material for hole injection layer (Procedure 3) Material for hole transport layer Forming a film by a wet film forming method of a composition for forming a hole transport layer containing a host material and a dopant material (Step 4) Forming a film by a wet film forming method of a composition for forming a light emitting layer containing a host material and a dopant material (Step 5) Electron transport layer Film formation by vacuum evaporation method (Step 6) Electron injection layer film formation by vacuum evaporation method (Step 7) Film formation by vacuum evaporation method of cathode By going through this procedure, the anode/hole injection layer/hole transport An organic EL device consisting of a layer/a light-emitting layer made of a host material and a dopant material/an electron transport layer/an electron injection layer/a cathode is obtained.
Of course, the electron transport layer and the electron injection layer may also be formed by a wet film forming method using a layer forming composition containing a material for the electron transport layer and a material for the electron injection layer, respectively. In this case, it is preferable to use a means for preventing dissolution of the lower light emitting layer, or a means for forming a film from the cathode side, contrary to the above procedure.

<Other film formation methods>
Laser thermal lithography (LITI) can be used to form a film from the composition for forming an organic layer. LITI is a method in which a compound attached to a base material is heated and vapor-deposited using a laser, and an organic layer-forming composition can be used as the material applied to the base material.

<Optional process>
Appropriate treatment steps, cleaning steps, and drying steps may be performed as appropriate before and after each step of film formation. Examples of the treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for producing banks can also be mentioned.

Photolithography technology can be used to create the banks. As bank materials that can be used in photolithography, positive resist materials and negative resist materials can be used. Patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, a permanent resist material can also be used.

Materials used for banks include polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrene, polyimides, polyamideimides, and polyetherimides. , polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyurethane, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (ABS), silicone resin, polyvinyl chloride, chlorine Examples include fluorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, fluoroolefin-hydrocarbon olefin copolymers, and fluorocarbon polymers. However, it is not limited to that.

<Organic layer forming composition used in wet film forming method>
The composition for forming an organic layer is obtained by dissolving in an organic solvent a low-molecular compound capable of forming each organic layer of an organic EL element, or a high-molecular compound obtained by polymerizing the low-molecular compound. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or its polymer compound) which is at least one dopant material as a first component, at least one host material as a second component, and a third component. It contains at least one organic solvent as a component. The first component functions as a dopant component of the emissive layer obtained from the composition, and the second component functions as the host component of the emissive layer. The third component functions as a solvent that dissolves the first and second components in the composition, and provides a smooth and uniform surface shape during application due to the controlled evaporation rate of the third component itself.

<Organic solvent>
The composition for forming an organic layer contains at least one kind of organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film formability, the presence or absence of defects in the coating, surface roughness, and smoothness. Furthermore, when forming a film using an inkjet method, it is possible to control meniscus stability in a pinhole of an inkjet head and to control and improve ejection performance. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescence properties, efficiency, and life of an organic EL device having an organic layer obtained from the composition for forming an organic layer. I can do it.

(1) Physical properties of organic solvent The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, even more preferably 150°C to 250°C. When the boiling point is higher than 130° C., it is preferable from the viewpoint of inkjet ejection properties. Moreover, when the boiling point is lower than 300° C., it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. The organic solvent preferably contains two or more types of organic solvents from the viewpoint of good inkjet ejection properties, film formability, smoothness, and low residual solvent. On the other hand, depending on the case, the composition may be made into a solid state by removing the solvent from the organic layer forming composition in consideration of transportability and the like.

Furthermore, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one solute, and the boiling point (BP GS ) of the good solvent (GS) is lower than the boiling point (BP _PS ) of the poor solvent ( _PS ). Particularly preferred are configurations in which the
By adding a poor solvent with a high boiling point, the good solvent with a low boiling point evaporates first during film formation, increasing the concentration of the substances contained in the composition and the concentration of the poor solvent, thereby promoting rapid film formation. As a result, a highly smooth coating film with few defects and low surface roughness can be obtained.

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

After film formation, the organic solvent is removed from the coating film through a drying process such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to perform the heating at a temperature not higher than the glass transition temperature (Tg) of at least one of the solutes +30° C. from the viewpoint of improving coating film formation properties. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at least one of the solutes at a glass transition point (Tg) of −30° C. or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent can be sufficiently removed because the film is thin. Further, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

(2) Specific examples of organic solvents Examples of organic solvents used in the organic layer forming composition include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, and monocyclic solvents. Examples include ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, Heptane-2-ol, octan-2-ol, decan-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol Monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol Dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene , o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoro Anisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Anisole, phenethole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene , 2-fluorobenzonitrile, 4-fluoroberatrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2 , 4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolnitrile, n- Amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene , 2,2'-bitryl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4 -(Butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, Examples include, but are not limited to, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether, and the like. Moreover, a single solvent may be used or a mixture may be used.

<Optional ingredients>
The composition for forming an organic layer may contain optional components within a range that does not impair its properties. Optional components include binders, surfactants, and the like.

(1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and also bonds the obtained film to the substrate. It also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

Examples of the binder used in the organic layer forming composition include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, Ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile - Styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

The number of binders used in the composition for forming an organic layer may be one type or a mixture of multiple types may be used.

(2) Surfactant The composition for forming an organic layer may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the film surface. Good too. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic groups, and further classified into alkyl-based, silicone-based, and fluorine-based based on the structure of their hydrophobic groups. In addition, based on the structure of the molecule, it is classified into monomolecular systems with a relatively small molecular weight and a simple structure, and polymer systems with a large molecular weight and side chains and branches. Also, based on the composition, they are classified into single type and mixed type, which is a mixture of two or more types of surfactants and base materials. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

As the surfactant, for example, Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (product name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbyk 180, Disperbake 181, Disperbyk Bake 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (product name, manufactured by BYK Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF -50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 ( EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F- 470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, DIC Corporation) ), fluoroalkyl benzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis (fluoroalkyl polyoxyethylene ether) , fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stear rate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, poly Mention may be made of oxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates and alkyl diphenyl ether disulfonates.

Moreover, one type of surfactant may be used, or two or more types may be used in combination.

<Composition and physical properties of organic layer forming composition>
The content of each component in the organic layer-forming composition is determined by the good solubility, storage stability and film formability of each component in the organic layer-forming composition, as well as the organic layer-forming composition. Good film quality of the coating film, good ejection properties when using an inkjet method, and good electrical properties, light emitting properties, efficiency, and life of an organic EL device having an organic layer produced using the composition. The decision is made taking into account the following points of view. For example, in the case of a composition for forming a light emitting layer, the first component is 0.0001% to 2.0% by mass based on the total mass of the composition for forming a light emitting layer, and the second component is for forming a light emitting layer. The third component is 0.0999% by mass to 8.0% by mass based on the total mass of the composition, and the third component is 90.0% by mass to 99.9% by mass based on the total mass of the composition for forming a light emitting layer. preferable.

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

The composition for forming an organic layer can be manufactured by appropriately selecting and performing stirring, mixing, heating, cooling, dissolving, dispersing, etc., the above-mentioned components using known methods. Further, after preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas substitution/enclosure treatment, etc. may be appropriately selected and carried out.

As for the viscosity of the composition for forming an organic layer, the higher the viscosity, the better the film forming property and the better the ejection property when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. From this, the viscosity of the organic layer forming composition at 25° C. is preferably 0.3 to 3 mPa·s, more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate rotational viscometer (cone-plate type).

As for the surface tension of the composition for forming an organic layer, the lower the surface tension, the better the film formability and the coating film free of defects can be obtained. On the other hand, the higher the value, the better the inkjet ejection performance. From this, the surface tension of the organic layer forming composition at 25° C. is preferably 20 to 40 mN/m, more preferably 20 to 30 mN/m. In the present invention, surface tension is a value measured using a hanging drop method.

式（ＸＬＰ－１）において、
ＭＵはそれぞれ独立して芳香族化合物から任意の２つの水素原子を除いて表される２価の基、ＥＣはそれぞれ独立して芳香族化合物から任意の１つの水素原子を除いて表される１価の基または水素であり、ＭＵ中の２つの水素がＥＣまたはＭＵと置換され、ｋは２～５００００の整数である。ただし、式（ＸＬＰ－１）で表される化合物は少なくとも１つの架橋性置換基（ＸＬＳ）を有し、好ましくは架橋性置換基を有する１価または２価の芳香族化合物の含有量は、分子中０．１～８０質量％である。 <Crosslinkable polymer compound: compound represented by formula (XLP-1)>
Next, a case where the above-mentioned polymer compound has a crosslinkable substituent will be explained. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

In formula (XLP-1),
MU is a divalent group each independently represented by removing any two hydrogen atoms from an aromatic compound, and EC is each independently represented by removing any one hydrogen atom from an aromatic compound. is a valent group or hydrogen, two hydrogens in MU are replaced with EC or MU, and k is an integer from 2 to 50,000. However, the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is It is 0.1 to 80% by mass in the molecule.

More specifically,
MU is each independently arylene, heteroarylene, diarylenearylamino, diarylenearylboryl, oxaboline-diyl, azaboline-diyl,
EC is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy;
At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl,
k is an integer from 2 to 50,000.
k is preferably an integer from 20 to 50,000, more preferably from 100 to 50,000.

At least one hydrogen in MU and EC in formula (XLP-1) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen or deuterium, and further, the above-mentioned Any -CH ₂ - in the alkyl may be substituted with -O- or -Si(CH ₃ ) ₂ -, and the -CH ₂ - directly connected to EC in formula (XLP-1) in the alkyl Any -CH ₂ - except for may be substituted with arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

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

More specifically, divalent groups represented by any of the following structures can be mentioned. In these, MUs combine with other MUs or ECs at *.

Furthermore, examples of EC include monovalent groups represented by any of the following structures. In these, EC joins MU at *.

In the compound represented by formula (XLP-1), from the viewpoint of solubility and coating film forming properties, 10 to 100% of the total number of MUs (k) in the molecule has an alkyl group having 1 to 24 carbon atoms. is preferable, and it is more preferable that 30 to 100% of the total number of MU in the molecule (k) has alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms); It is further preferred that 50 to 100% of MU in k) has alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have alkyl atoms having 7 to 24 carbon atoms; It is more preferable that 30 to 100% of MU of ) has an alkyl having 7 to 24 carbon atoms (branched alkyl having 7 to 24 carbon atoms).

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

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structure are preferred. * in each structural formula indicates the bonding position.

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

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure. * in the following structural formula represents the bonding position.

<Production method of polymer compound and crosslinkable polymer compound>
The method for producing a polymer compound and a crosslinkable polymer compound will be explained using the compound represented by the above-mentioned formula (XLP-1) as an example. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include aromatic solvents, saturated/unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-methoxyethoxy)ethane, -ethoxyethoxy)ethane, etc.

Moreover, the reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

When producing the compound of formula (XLP-1), it may be produced in one step or in multiple steps. Alternatively, it may be carried out by a batch polymerization method in which the reaction is started after all of the raw materials are put into the reaction vessel, or by a dropwise polymerization method in which the raw materials are added dropwise into the reaction vessel, or the product may be added to the reaction vessel to prevent the progress of the reaction. It may be carried out by a precipitation polymerization method that involves precipitation, or it can be synthesized by appropriately combining these methods. For example, when synthesizing the compound represented by formula (XLP-1) in one step, a monomer with a polymerizable group bonded to the monomer unit (MU) and a monomer with a polymerizable group bonded to the end cap unit (EC) are used. The target product is obtained by carrying out the reaction while added to the reaction vessel. In addition, when synthesizing the compound represented by formula (XLP-1) in multiple steps, after polymerizing the monomer in which a polymerizable group is bonded to the monomer unit (MU) to the desired molecular weight, the end cap unit (EC) is The desired product is obtained by adding a monomer to which a polymerizable group is bonded and causing a reaction. If a monomer to which a polymerizable group is bonded is added to different types of monomer units (MU) in multiple steps and the reaction is carried out, a polymer having a concentration gradient in the structure of the monomer units can be produced. Moreover, after preparing the precursor polymer, the target polymer can be obtained by post-reaction.

Further, by selecting the polymerizable group of the monomer unit (MU), the primary structure of the polymer can be controlled. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize polymers with random primary structures (Synthesis Scheme 1), polymers with regular primary structures (Synthesis Schemes 2 and 3), etc. They can be used in appropriate combinations depending on the object. Furthermore, by using a monomer having three or more polymerizable groups, hyperbranched polymers and dendrimers can be synthesized.

Monomers that can be used in the present invention include JP2010-189630A, WO2012/086671, WO2013/191088, WO2002/045184, WO2011/049241, WO 2013/146806, WO 2005/049546, WO 2015/145871, JP 2010-215886, JP 2008-106241, WO 2016/031639, JP 2011 It can be synthesized according to the method described in JP-A-174062.

For specific polymer synthesis procedures, please refer to JP 2012-036388, WO 2015/008851, JP 2012-36381, JP 2012-144722, and WO 2015/194448. , International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2011/049241 can be referred to. .

2-1-9. Application example of organic electroluminescent device The present invention can also be applied to a display device equipped with an organic EL device or a lighting device equipped with an organic EL device.
A display device or a lighting device equipped with an organic EL element can be manufactured by a known method such as connecting the organic EL element according to this embodiment with a known drive device, and can be manufactured by a known method such as direct current drive, pulse drive, alternating current drive, etc. It can be driven using a known driving method as appropriate.

Examples of display devices include panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (Refer to Japanese Patent Publication No. 2004-281086, etc.). Furthermore, examples of the display method include a matrix method and a segment method. Note that matrix display and segment display may coexist in the same panel.

In a matrix, display pixels are arranged two-dimensionally in a grid or mosaic pattern, and characters or images are displayed as a collection of pixels. The shape and size of pixels are determined by the application. For example, rectangular pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and in the case of large displays such as display panels, pixels with sides of mm order are used. become. 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 displayed side by side. In this case, there are typically delta types and striped types. As a driving method for this matrix, either a line sequential driving method or an active matrix driving method may be used. Line sequential driving has the advantage of a simpler structure, but when considering operating characteristics, active matrix driving may be superior in some cases, so it is necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is caused to emit light. Examples include time and temperature displays on digital clocks and thermometers, operating status displays on audio equipment and electromagnetic cookers, and panel displays on automobiles.

Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light by themselves, and are used in liquid crystal display devices, watches, audio devices, automobile panels, display boards, signs, and the like. In particular, considering that it is difficult to reduce the thickness of liquid crystal display devices, especially backlights for personal computers where thinning is an issue, since conventional systems consist of fluorescent lamps and light guide plates, this embodiment A backlight using a light emitting element according to the above is characterized by being thin and lightweight.

2-2. Other Organic Devices The polycyclic aromatic compound according to the present invention can be used in the production of organic field effect transistors, organic thin film solar cells, etc. in addition to the organic electroluminescent devices described above.

An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and is provided with 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 and drain electrodes can be 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 an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a source electrode and a drain electrode are further provided in contact with the organic semiconductor active layer. A gate electrode may be provided with an insulating layer (dielectric layer) sandwiched therebetween. Examples of the device structure include the following structure.
(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 is It can be applied as a pixel drive switching element for active matrix drive type liquid crystal displays and organic electroluminescent displays.

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 laminated 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, etc. in addition to the above. For the organic thin film solar cell, known materials used for organic thin film solar cells can be appropriately selected and used in combination.

3. Wavelength Conversion Material The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material. Currently, the application of multicolor technology using color conversion methods to liquid crystal displays, organic EL displays, lighting, etc. is being actively studied. Color conversion refers to converting the wavelength of light emitted from a light emitter into light with a longer wavelength, and represents, for example, converting ultraviolet light or blue light into green light or red light. By forming a wavelength conversion material having this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By using a white light source that is a combination of such a blue light source and a wavelength conversion film having a color conversion function as a light source unit, and combining it with a liquid crystal drive part and a color filter, it becomes possible to produce a full-color display. 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 for, for example, LED lighting. Further, 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 becomes possible to produce 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 becomes possible to produce a full-color micro-LED display at low cost.

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

The wavelength conversion composition may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Publication No. 2016/190283 can be used. As other additives, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016/190283 can be used. As for the solvent, the description of the solvent contained in the above-mentioned 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 forming 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 may include other wavelength conversion layers (for example, converting blue light into green light or red light). A wavelength conversion layer, a wavelength conversion layer that converts blue light or green light into red light) may be included. Furthermore, the wavelength conversion film may include a barrier layer for preventing deterioration of the base layer and color conversion layer due to oxygen, moisture, or heat.

Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

<<Synthesis example>>
Synthesis example (1):
Synthesis of compound (1-1) and compound (2-1)

A 1.6M tert-butyllithium pentane solution (1.6 ml) was added to a flask containing compound (I-1) (1.09 g) and tert-butylbenzene (7.0 ml) at -30°C under a nitrogen atmosphere. ) was added. After completion of the dropwise addition, the temperature was raised to 60°C and the mixture was stirred for 2 hours, after which components with boiling points lower than tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −30° C., boron tribromide (0.63 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled to 0° C. again, N,N-diisopropylethylamine (0.43 ml) was added, and the mixture was stirred at room temperature until the heat generation subsided, then heated to 120° C. and stirred for 3 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by heptane to separate the layers. Next, after purification with a silica gel short-pass column (developing solution: toluene), the solvent was distilled off under reduced pressure, and the resulting solid was dissolved in toluene, and heptane was added to reprecipitate it to give compound (I-2) (0. 35g) was obtained.

Compound (I-2) (78.1 mg, 0.075 mmol), boron triiodide (470.3 mg, 1.20 mmol), 2,6-di-tert-butylpyridine (102 μL, 0.45 mmol) and toluene ( 2.0 ml) was stirred at 60° C. for 4 hours. Thereafter, phosphate buffer solution (pH=6.8, 10 ml) was added to the reaction mixture at 0° C., and the aqueous layer was separated and extracted with toluene (20 ml, 3 times). Thereafter, the obtained crude product was subjected to silica gel column chromatography (developing solvent: hexane/dichloromethane = 4/1, 3/1, 3/2, ethyl acetate) to separate the products, and the respective solvents were distilled off under reduced pressure. After washing with hexane (10 ml), compound (2-1) (2.9 mg) was obtained as a yellow solid. At the same time, compound (1-1) (3.4 mg) was obtained as a red solid.

The structure of compound (2-1) obtained was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 2.41 (s, 6H), 2.58 (s, 6H), 2.73 (s, 6H), 2.86 (s, 6H), 6 .29 (d, 2H), 6.71 (d, 2H), 7.13 (d, 2H), 7.22 (d, 4H), 7.32 (d, 4H), 7.47 (t, 2H), 7.53 (d, 2H), 7.78 (s, 1H), 8.21 (s, 2H), 8.30 (s, 2H), 8.48 (s, 2H), 8. 69 (s, 2H), 8.83 (s, 2H).

The structure of compound (1-1) obtained was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 2.41 (s, 6H), 2.58 (s, 6H), 2.73 (s, 6H), 2.86 (s, 6H), 6 .29 (d, 2H), 6.71 (d, 2H), 7.13 (d, 2H), 7.22 (d, 4H), 7.32 (d, 4H), 7.47 (t, 2H), 7.53 (d, 2H), 7.78 (s, 1H), 8.21 (s, 2H), 8.30 (s, 2H), 8.48 (s, 2H), 8. 69 (s, 2H), 8.83 (s, 2H).

By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the above-mentioned synthesis example.

<<Evaluation of absorption characteristics and emission characteristics>>
The absorption spectrum of the sample was measured using an ultraviolet-visible-near-infrared spectrophotometer (Shimadzu Corporation, UV-2600). Further, the fluorescence spectrum or phosphorescence spectrum of the sample was measured using a spectrofluorophotometer (manufactured by Hitachi High-Tech Corporation, F-7000).

For measurement of fluorescence spectra, photoluminescence was measured at room temperature with excitation at an appropriate excitation wavelength. The phosphorescence spectrum was measured while the sample was immersed in liquid nitrogen (temperature 77 K) 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 the start of measurement. The samples were excited at the appropriate excitation wavelength and photoluminescence was measured.

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

Evaluation of fluorescence lifetime (delayed fluorescence) Fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, we observed an emission component with a fast fluorescence lifetime and an emission component with a slow fluorescence lifetime at the maximum emission wavelength measured at an appropriate excitation wavelength. In fluorescence lifetime measurements at room temperature of general organic EL materials that emit fluorescence, slow emission components involving triplet components derived from phosphorescence are rarely observed due to deactivation of triplet components due to heat. If a slow emission component is observed in the compound to be evaluated, this indicates that triplet energy with a long excitation lifetime has been transferred to singlet energy due to thermal activation and observed as delayed fluorescence.

Calculation of energy gap (Eg) Calculated from the long wavelength end A (nm) of the absorption spectrum obtained by the method described above as Eg=1240/A.

Calculation of E(S, Sh), E(T, Sh) and ΔE(ST) The lowest excited singlet energy level E(S, Sh) is based on the tangent line passing through the inflection point on the shorter wavelength side of the peak of the fluorescence spectrum. From the wavelength B _Sh (nm) at the intersection with the line, it was calculated as E(S, Sh)=1240/B _Sh . Moreover, the lowest excited triplet energy level E(T, Sh) is calculated from the wavelength C _Sh (nm) at the intersection of the baseline and the tangent passing through the inflection point on the short wavelength side of the peak of the phosphorescence spectrum. Sh)=1240/C _Sh .

ΔE(ST) is defined as the energy difference between E(S, Sh) and E(T, Sh), ΔE(ST)=E(S, Sh)−E(T, Sh). In addition, ΔE(ST) is, for example, "Purely organic electroluminescent material realizing 100% conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo,T It can also be calculated using the method described in Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015, 6, 8476.

<Example A1>
Evaluation of basic physical properties of compound (1-1)
A solution of compound (1-1) dissolved in toluene at a concentration of 1E-5M was prepared, and its absorption and luminescence properties were measured. After removing dissolved oxygen by bubbling the solution with nitrogen, PLQY and fluorescence lifetime were measured.

<Example A2, Comparative Example A1>
In the evaluation of Example A1, the evaluation was carried out under the same conditions except that compound (1-1) was changed to compound (2-1), new-DABNA. The results are summarized in Table 1.

<<Preparation and evaluation of vapor-deposited organic EL device>>
Next, the preparation and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.
Evaluation items include drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), and half-width (nm). . For these evaluation items, values at appropriate emission brightness can be used.

There are two types of quantum efficiency for light-emitting devices: internal quantum efficiency and external quantum efficiency.Internal quantum efficiency is when external energy injected as electrons (or holes) into the light-emitting layer of a light-emitting device is converted purely into photons. It shows the percentage of On the other hand, external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light emitting element, and some of the photons generated in the light emitting layer are absorbed inside the light emitting element or continue to be reflected. Since the light is not emitted to the outside of the light emitting device, 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. The device was caused to emit light by applying a voltage using a voltage/current generator R6144 manufactured by Advantest. Spectral radiance in the visible light region was measured in the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light-emitting surface is a completely diffusing surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying it by π. Next, the number of photons was integrated over the entire observed wavelength range to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary 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. Further, the half-width of the emission spectrum is determined as the width between the upper and lower wavelengths at which the intensity is 50%, centering on the maximum emission wavelength.

[Comparative example 1-1]
A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.), in which ITO was formed into a 200 nm thick film by sputtering and polished to 120 nm, was 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 Shinku Co., Ltd.), and molybdenum vapor deposition containing HAT-CN, HTL-1, TcTa, ETL-1, new-DABNA, and ET7, respectively. A tungsten deposition boat containing LiF and aluminum was installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The pressure in the vacuum chamber was reduced to 5×10 ⁻⁴ Pa, and HAT-CN was first heated and deposited to a thickness of 5 nm to form a hole injection layer. Next, HTL-1 is heated and deposited to a thickness of 90 nm to form a hole transport layer 1, and TcTa is further heated and deposited to a thickness of 10 nm to form a hole transport layer 2. was formed. Next, ETL-1 and new-DABNA were simultaneously heated and deposited to a thickness of 20 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of ETL-1 to new-DABNA was approximately 99:1. Next, ETL-1 is heated and deposited to a thickness of 20 nm to form an electron transport layer 1, and ET7 is further heated and deposited to a thickness of 10 nm to form an electron transport layer 2. did. The deposition rate of each layer was 0.01-1 nm/sec. Thereafter, LiF is heated and deposited to a thickness of 1 nm at a deposition rate of 0.01 to 0.1 nm/sec, and then aluminum is heated and deposited to a thickness of 100 nm to form a cathode. An organic EL device was obtained. At this time, the aluminum deposition rate was adjusted to 1 to 10 nm/sec.

[Example 1-1 and Example 2-1]
Organic EL devices of Examples 1-1 and 1-2 were obtained in the same manner as in Comparative Example 1-1 except that new-DABNA in Comparative Example 1-1 was changed to the compound listed in Table 2.

[Examples 2-1 to 2, Examples 3-1 to 2, Examples 4-1 to 2, Comparative Example 2-1, Comparative Example 3-1, and Comparative Example 4-1]
ETL-1 (host) of Comparative Example 1-1 was replaced with TcTa and ETL-1 (host 1 and host 2) listed in Table 3, and new-DABNA was replaced with the emitting dopant or assisting dopant listed in Table 3. Example 2-1~2, Example 3-1~2, Example 4-1~2, Comparative Example 2-1, Comparison Organic EL devices of Example 3-1 and Comparative Example 4-1 were obtained.
In Table 3, "Host 1" corresponds to a hole-transporting host material, and "Host 2" corresponds to an electron-transporting host material.

The chemical structures of the compounds used to manufacture each of the above devices are shown below.

Examples 1-1 to 2, Examples 2-1 to 2, Examples 3-1 to 2, Examples 4-1 to 2, Comparative Example 1-1, Comparative Example 2-1, Comparative Example 3-1 and For the organic EL element of Comparative Example 4-1, a DC voltage was applied using the ITO electrode as the anode and the LiF/aluminum electrode as the ^cathode , and the maximum emission wavelength (EL), external quantum efficiency (EQE), and LT50 (time taken to reach 500 cd/m ² when continuously driven at a current density at an initial brightness of 1000 cd/m ² ) was measured.
Table 4 shows the evaluation results for each element.

Comparison with comparative examples shows that organic EL devices using polycyclic aromatic compounds having the structure represented by formula (1) or formula (2) emit green light with high efficiency and have a long life. It can be seen that

<<Preparation and evaluation of coating type organic EL device>>
Next, an organic EL element obtained by coating and forming an organic layer will be described.

<Synthesis of polymeric host compound: SPH-101>
SPH-101 was synthesized according to the method described in International Publication No. 2015/008851. A copolymer in which M2 or M3 is bonded next to M1 is obtained, and it is estimated from the charging ratio that each unit is 50:26:24 (molar ratio). In the structural formula below, Bpin is pinacolatoboryl, and * is the connection point of each unit.

<Synthesis of polymeric hole transport compound: XLP-101>
XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 was bonded next to M4 was obtained, and it is estimated from the charging ratio that each unit was 40:10:50 (molar ratio). Bpin is pinacolatoboryl, and * is the connection point of each unit.

<Example 5-1 to Example 5-9>
A coating-type organic EL device is manufactured by preparing a coating solution of materials forming each layer.

<Production of organic EL devices of Examples 5-1 to 5-3>
Table 5 shows the material composition of each layer in the organic EL element.

The structure of "ET1" in Table 5 is shown below.

<Preparation of composition for forming light emitting layer (1)>
A luminescent layer forming composition (1) is prepared by stirring the following components until a uniform solution is obtained. By spin-coating the prepared luminescent layer-forming composition onto a glass substrate and heating and drying it under reduced pressure, a coated film with no film defects and excellent smoothness can be obtained.
Compound (A) 0.04% by mass
SPH-101 1.96 Mass%
Xylene 69.00% by mass
Decalin 29.00% by mass

In addition, compound (A) is a polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2) (for example, compound (1-1)), the polycyclic aromatic compound This is a polymer compound obtained by polymerizing the polymer as a monomer (that is, the monomer has a reactive substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound. A polymer compound for obtaining a crosslinked polymer has a crosslinkable substituent.

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

<Preparation of OTPD solution>
OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, manufactured by San-Apro Inc.) were dissolved in toluene, and the OTPD concentration was 0.7% by mass and the IK-2 concentration was 0.007% by mass. Prepare an OTPD solution of

<Preparation of XLP-101 solution>
XLP-101 is dissolved in xylene at a concentration of 0.6% by mass to prepare a 0.6% by mass XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7% by mass PCz solution.

<Example 5-1>
A PEDOT:PSS solution is spin-coated on a glass substrate on which ITO is deposited to a thickness of 150 nm, and then baked on a hot plate at 200°C for 1 hour to form a PEDOT:PSS film with a thickness of 40 nm. (hole injection layer). Next, the OTPD solution was spin-coated, dried on a hot plate at 80°C for 10 minutes, exposed to light using an exposure machine at an exposure intensity of 100 mJ/cm ² , and baked on a hot plate at 100°C for 1 hour. An OTPD film with a thickness of 30 nm that is insoluble in is formed (hole transport layer). Next, the luminescent layer forming composition (1) is spin-coated and baked on a hot plate at 120° C. for 1 hour to form a luminescent layer with a thickness of 20 nm.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing ET1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, ET1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 5-2>
An organic EL device is obtained in the same manner as in Example 5-1. Note that the hole transport layer is formed by spin coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film with a thickness of 30 nm.

<Example 5-3>
An organic EL device is obtained in the same manner as in Example 5-1. Note that the hole transport layer is formed by spin coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film with a thickness of 30 nm.

<Evaluation of organic EL devices of Examples 5-1 to 5-3>
It can be expected that the coated organic EL device obtained as described above will also have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL device.

<Production of organic EL devices of Examples 5-4 to 5-6>
Table 6 shows the material composition of each layer in the organic EL element.

<Preparation of light-emitting layer forming compositions (2) to (4)>
A composition for forming a light emitting layer (2) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
mCBP 1.98 mass%
Toluene 98.00% by mass

A composition for forming a light emitting layer (3) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
SPH-101 1.98 mass%
Xylene 98.00% by mass

A luminescent layer forming composition (4) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
DOBNA 1.98% by mass
Toluene 98.00% by mass

In Table 6, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b. -boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structure is shown below.

<Example 5-4>
After spin-coating ND-3202 (manufactured by Nissan Chemical Industries) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, it was heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes. By heating for a minute, an ND-3202 film with a thickness of 50 nm is formed (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the luminescent layer forming composition (2) is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm luminescent layer.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 5-5 and Example 5-6>
An organic EL device is obtained in the same manner as in Example 5-4 using the composition for forming a light emitting layer (3) or (4).

<Evaluation of organic EL devices of Examples 5-4 to 5-6>
It can be expected that the coated organic EL device obtained as described above will also have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL device.

<Production of organic EL devices of Examples 5-7 to 5-9>
Table 7 shows the material composition of each layer in the organic EL element.

<Preparation of light-emitting layer forming compositions (5) to (7)>
A luminescent layer forming composition (5) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
2PXZ-TAZ 0.18 mass%
mCBP 1.80 mass%
Toluene 98.00% by mass

A luminescent layer forming composition (6) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
2PXZ-TAZ 0.18 mass%
SPH-101 1.80 mass%
Xylene 98.00% by mass

A luminescent layer forming composition (7) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by mass
2PXZ-TAZ 0.18 mass%
DOBNA 1.80 mass%
Toluene 98.00% by mass

In Table 7, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene))bis(10H- phenoxazine). The chemical structure is shown below.

<Example 5-7>
After spin-coating ND-3202 (manufactured by Nissan Chemical Industries) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, it was heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes. By heating for a minute, an ND-3202 film with a thickness of 50 nm is formed (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the luminescent layer forming composition (5) is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm luminescent layer.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 5-8 and Example 5-9>
An organic EL device is obtained in the same manner as in Example 5-7 using the composition for forming a light emitting layer (6) or (7).

<Evaluation of organic EL devices of Examples 5-7 to 5-9>
It can be expected that the coated organic EL device obtained as described above will also have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL device.

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 (20)

A polycyclic aromatic compound having a structure containing a structural unit represented by formula (1) or formula (2);

In formula (1),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
Y is independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R ^Y )- , >Si(-R ^Y )-, or >Ge(-R ^Y )-, and R ^Y is each independently an optionally substituted aryl, an optionally substituted heteroaryl, or an unsubstituted heteroaryl. an optionally substituted alkyl or an optionally substituted cycloalkyl,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the above structure may be fused with at least one cycloalkane, and the cycloalkane may be substituted with at least one substituent. , at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium. When ring B, ring C, ring D, ring E, ring F, ring G, ring H, and ring I are each a substituted aryl ring or a substituted heteroaryl ring, the substituents are substituent group Z and the formula ( At least one substituent selected from the group consisting of substituents represented by A30),
The substituent group Z is
Aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
Diarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded to each other via a linking group);
Diheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, and cycloalkyl (two heteroaryls may be bonded to each other via a linking group) ;
Arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (aryl and heteroaryl may be bonded to each other via a linking group) );
Diarylboryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl (two aryls may be bonded via a single bond or a linking group);
alkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl;
alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl and cycloalkyl;
aryloxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl and cycloalkyl; and substituted silyl;

In formula (A30),
Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl, and at least one of the alkyl, alkenyl, cycloalkyl, and cycloalkenyl -CH ₂ - may be replaced with -O- or -S-,
R ^Ak is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^Ak is bonded to Ak through a linking group or a single bond. * is the bond position,
The polycyclic aromatic compound according to claim 1. The polycyclic aromatic compound according to claim 2, represented by formula (1). The polycyclic aromatic compound according to claim 3, represented by the following formula (1-b);

In formula (1-b),
Z is each independently -C(-R ^Z )= or -N=,
R ^Z is each independently hydrogen or a substituent,
When R ^Z is a substituent, the substituent is any substituent selected from substituent group Z or a substituent represented by formula (A30),
Two adjacent R ^Z may be bonded to each other to form an aryl ring or a heteroaryl ring, and each of the formed aryl rings or heteroaryl rings has one of the substituents selected from the substituent group Z. may be substituted with a group,
Z=Z may each independently be >NR, >O, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the above >NR, R in >C(-R) ₂ and >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
Each X is independently >NR ^NX , >O, >C(-R ^CX ) ₂ , >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted is heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or Substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, R ^NX and R ^CX are Z bonded to the carbon atom to which X, including itself, is bonded. May be combined with one or more of
L is a single bond, >NR ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se, and R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or It is an unsubstituted cycloalkyl, and two R ^CL may be bonded to each other to form a ring, and each of R ^NL and R ^CL is one of Z bonded to the carbon atom to which L, including itself, is bonded. It may be combined with one or two or more,
At least one of the aryl rings or heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and the cycloalkane may be substituted with at least one substituent. At least one -CH ₂ - may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium. All Z are -C-(R ^Z )=,
5. The polycyclic aromatic compound of claim 4, wherein each X is independently >O, >NR ^NX , or >S. Claim 5, wherein R ^Z is each independently hydrogen, alkyl, phenyl optionally substituted with alkyl, diphenylamino optionally substituted with alkyl, or carbazolyl optionally substituted with alkyl. The polycyclic aromatic compound described. The polycyclic aromatic compound according to claim 3 represented by the following formula;

In the formula, Me is methyl. The polycyclic aromatic compound according to claim 2, represented by formula (2). The polycyclic aromatic compound according to claim 8, represented by the following formula (2-b);

In formula (2-b),
Z is each independently -C(-R ^Z )= or -N=,
R ^Z is each independently hydrogen or a substituent,
When R ^Z is a substituent, the substituent is any substituent selected from substituent group Z or a substituent represented by formula (A30),
Two adjacent R ^Z may be bonded to each other to form an aryl ring or a heteroaryl ring, and each of the formed aryl rings or heteroaryl rings has one of the substituents selected from the substituent group Z. may be substituted with a group,
Z=Z may each independently be >NR, >O, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the above >NR, R in >C(-R) ₂ and >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
Each X is independently >NR ^NX , >O, >C(-R ^CX ) ₂ , >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted is heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or Substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, R ^NX and R ^CX are Z bonded to the carbon atom to which X, including itself, is bonded. May be combined with one or more of
L is a single bond, >NR ^NL , >O, >C(-R ^CL ) ₂ , >S, or >Se, and R ^NL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CL is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or It is an unsubstituted cycloalkyl, and two R ^CL may be bonded to each other to form a ring, and each of R ^NL and R ^CL is one of Z bonded to the carbon atom to which X, including itself, is bonded. It may be combined with one or two or more,
At least one of the aryl rings or heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and the cycloalkane may be substituted with at least one substituent. At least one -CH ₂ - may be replaced with -O-,
At least one hydrogen in the structure may be replaced with cyano, halogen, or deuterium. All Z are -C-(R ^Z )=,
10. The polycyclic aromatic compound of claim 9, wherein each X is independently >O, >NR ^NX , or >S. Claim 10, wherein R ^Z is each independently hydrogen, alkyl, phenyl optionally substituted with alkyl, diphenylamino optionally substituted with alkyl, or carbazolyl optionally substituted with alkyl. The polycyclic aromatic compound described. The polycyclic aromatic compound according to claim 8, represented by the following formula;

In the formula, Me is methyl. A high polymer having a number average molecular weight of 2000 to 1.0×10 ⁸ obtained by polymerizing a reactive compound obtained by substituting a reactive substituent on the polycyclic aromatic compound according to any one of claims 1 to 12 as a monomer. molecular compound. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 12. The organic device material according to claim 14, wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, an organic thin film solar cell material, or a wavelength conversion filter material. It has a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, the organic layer containing the polycyclic aromatic compound according to any one of claims 1 to 12. , organic electroluminescent device. The organic electroluminescent device according to claim 16, wherein the organic layer is a light emitting layer. A display device or a lighting device comprising the organic electroluminescent element according to claim 16. A method for producing a polycyclic aromatic compound according to any one of claims 1 to 12, comprising:
By adding a boronating agent and a Brønsted base to the compound represented by the formula (Int) and making them react, a polycyclic aromatic compound represented by the formula (1) and a polycyclic aromatic compound represented by the formula (2) are prepared. A manufacturing method comprising obtaining a mixture with a group compound;

In the formula (Int),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (Int) may be fused with at least one cycloalkane, and the cycloalkane is substituted with at least one substituent. and at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in formula (Int) may be replaced with cyano, halogen, or deuterium. A compound represented by the formula (Int);

In the formula (Int),
Ring B, Ring C, Ring D, Ring E, Ring F, Ring G, Ring H, and Ring I are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
A broken line connecting ring C and ring D indicates that ring C and ring D are not bonded at the position of the broken line, or are bonded via a single bond or a linking group at the position of the broken line. ,
Z is -C(-R ^Z )= or -N=, R ^Z is hydrogen or a substituent,
X is each independently a single bond, >N-R ^NX , >O, >C(-R ^CX ) ₂ , >Si(-R ^IX ) ₂ >S, or >Se, and R ^NX is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R ^CX and R ^IX are each independently hydrogen, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R ^CX may be bonded to each other to form a ring, and two R ^IX may be bonded to each other to form a ring, and R ^NX , R ^CX and R ^IX may each be bonded to one or two rings to which X, including itself, is bonded,
At least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (Int) may be fused with at least one cycloalkane, and the cycloalkane is substituted with at least one substituent. and at least one -CH ₂ - in the cycloalkane may be replaced with -O-,
At least one hydrogen in formula (Int) may be replaced with cyano, halogen, or deuterium.