JPWO2020045681A1 - Organic electroluminescent device using a light emitting material of a polycyclic aromatic compound - Google Patents

Abstract

An organic electroluminescent element having a light emitting layer containing a polycyclic aromatic compound represented by the following general formula (1) as a host as a first component and a polycyclic aromatic compound containing boron as a dopant as a second component. Is excellent in organic EL characteristics such as light emission characteristics. (In the above formula (1), R1 to R11 are independently bonded to hydrogen, aryl, heteroaryl, diarylamino, and diarylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in said aryl, said heteroaryl, and said diarylamino may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. , At least one hydrogen in the compound represented by the formula (1) may be substituted with a cyano, a halogen or a heavy hydrogen.)

Description

The present invention relates to an organic electroluminescent element using a light emitting material of a polycyclic aromatic compound and a multimer thereof (hereinafter, both are also simply referred to as a polycyclic aromatic compound), and a display device and a lighting device.

Conventionally, display devices using an electric field-emitting element have been studied in various ways because they can save power and be thin, and further, an organic electroluminescent element made of an organic material (hereinafter, also referred to as an organic EL element) has been studied. It has been actively studied because it is easy to reduce the weight and size. In particular, the development of organic materials that have emission characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials that have the ability to transport charges such as holes and electrons (which have the potential to become semiconductors and superconductors). Development has been actively studied for both high molecular weight compounds and low molecular weight compounds.

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

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

Further, in recent years, a material obtained by improving a triphenylamine derivative has been reported as a material used for an organic EL element or an organic thin-film solar cell (International Publication No. 2012/118164). This material was prepared with reference to N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD), which had already been put into practical use. It is a material characterized in that its flatness is enhanced by connecting aromatic rings constituting triphenylamine to each other. In this document, for example, the charge transport property of a NO-linking compound (Compound 1 on page 63) is evaluated, but a method for producing a material other than the NO-linking compound is not described, and the element to be linked is not described. Since the electronic states of the entire compound are different if they are different, the properties obtained from materials other than the NO-linking compound are not yet known. Other examples of such compounds can be found (International Publication No. 2011/107186). For example, a compound having a conjugated structure having a large triplet exciton energy (T1) is useful as a material for a blue light emitting layer because it can emit phosphorescence having a shorter wavelength.

The host material for an organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are linked by a single bond or a phosphorus atom or a silicon atom. This is because the large HOMO-LUMO gap (bandgap Eg in the thin film) required for the host material is secured by connecting a large number of relatively small aromatic rings of the conjugated system. In addition, the host material of the organic EL element using a phosphorescent material or a heat activated delayed fluorescent material, high triplet excitation energy (E _T) is also required, the aromatic ring of the donor or acceptor in the molecule and substituted by linking the group, to localize the SOMO1 and SOMO2 triplet excited state (T1), by reducing the exchange interaction between the two orbit, to improve the triplet excitation energy (E _T) It will be possible. However, the small aromatic ring of the conjugated system does not have sufficient redox stability, and the device using the molecule in which the existing aromatic ring is linked as the host material does not have a sufficient lifetime. On the other hand, polycyclic aromatic compounds having an extended π conjugated system, generally, but the redox stability is excellent, because HOMO-LUMO gap and triplet excitation energy (band gap Eg of the thin film) (E _T) is low, It has been considered unsuitable for host materials.

Further, in recent years, compounds in which a plurality of aromatic rings are condensed with boron or the like as a central atom have been reported (International Publication No. 2015/102118). In this document, an organic EL device evaluation using a compound obtained by condensing the plurality of aromatic rings as a dopant material of the light emitting layer is carried out, but the document discloses an extremely large number of compounds, among these. In particular, it is useful to study a compound having excellent organic EL characteristics such as light emission characteristics.

International Publication No. 2004/061047 Japanese Unexamined Patent Publication No. 2001-172232 Japanese Patent Application Laid-Open No. 2005-170911 International Publication No. 2012/118164 International Publication No. 2011/107186 International Publication No. 2015/102118

As described above, various materials have been developed as materials used for organic EL devices, but in order to further enhance organic EL characteristics such as light emitting characteristics and to increase the choices of organic EL materials such as materials for light emitting layers. In addition, the development of compounds that have not been specifically known in the past is desired.

As a result of diligent studies to solve the above problems, the present inventors have obtained an excellent organic EL by using a polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and an oxygen atom as a material for a light emitting layer. We have found that an element can be obtained and completed the present invention.

In the present specification, the chemical structure and the substituent may be represented by the number of carbon atoms, but the number of carbon atoms in the case where the substituent is substituted in the chemical structure or the substituent is further substituted in the substituent is the chemical structure. It means the carbon number of each of the substituents and substituents, and does not mean the total carbon number of the chemical structure and the substituents or the total carbon number of the substituents and the substituents. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted with "substituent B of carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B. Further, for example, "substituent B having a carbon number Y substituted with a substituent A" means that "substituent A (with no limitation on the number of carbon atoms)" is substituted for "substituent B having a carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B.

（上記式（１）中、
Ｒ^１〜Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、
前記アリール、前記ヘテロアリール、前記ジアリールアミノおよび前記ジアリールボリルにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
式（１）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 1.
An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer arranged between the pair of electrodes.
The light emitting layer in the organic electroluminescent device is
As the first component, a polycyclic aromatic compound represented by the following general formula (1) is contained as a host.
An organic electroluminescent device containing a boron-containing polycyclic aromatic compound as a dopant as a second component.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. )

Item 2.
In the above general formula (1), R ^{1 to} R ¹¹ are independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, and diallyl amino (where aryl has 6 to 12 carbon atoms). Aryl), diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and an alkyl having 1 to 24 carbon atoms. 3-12 cycloalkyls, 1-24-carbon alkoxys or 6-30 carbon-carbon aryloxys.
At least one hydrogen in the aryl, the heteroaryl, the diarylamino and the diarylboryl is 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 an alkyl having 3 to 12 carbon atoms. May be substituted with cycloalkyl,
Item 2. The organic electroluminescent device according to Item 1.

Item 3.
In the above general formula (1), R ^{1 to} R ¹¹ are independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and diallyl amino (where aryl has 6 to 10 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms. 6 to 10 cycloalkyl, 1 to 6 carbon alkoxy or 6 to 16 carbon aryloxy.
At least one hydrogen in the aryl, the heteroaryl, the diarylamino and the diarylboryl is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or 6 to 10 carbon atoms. May be substituted with cycloalkyl,
Item 2. The organic electroluminescent device according to Item 1.

（上記式中、＊は結合位置を示し、
式（１−ａ）〜式（１−ｈ）および式（１−ｐ））〜式（１−ｑ）における少なくとも１つの水素は、炭素数６〜３０のアリール、炭素数２〜３０のヘテロアリール、炭素数１〜２４のアルキルまたは炭素数３〜１２のシクロアルキルで置換されていてもよく、
式（１−ｉ）、式（１−ｊ）、式（１−ｋ）および式（１−ｒ）におけるＲは、それぞれ独立して、水素、炭素数６〜３０のアリール、炭素数２〜３０のヘテロアリール、炭素数１〜２４のアルキルまたは炭素数３〜１２のシクロアルキルを示す。）Item 4.
In the above general formula (1), ^{at least one of R 1 to} R ¹¹ is any one of Items 1 to 3 which is a group represented by any of the following formulas (1-a) to (1-s). The organic electroluminescent device according to item 1.

(In the above formula, * indicates the bonding position, and
At least one hydrogen in formulas (1-a) to (1-h) and formulas (1-p) to (1-q) is an aryl having 6 to 30 carbon atoms and a hetero with 2 to 30 carbon atoms. It may be substituted with aryl, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 12 carbon atoms.
R in the formula (1-i), the formula (1-j), the formula (1-k) and the formula (1-r) are independently hydrogen, an aryl having 6 to 30 carbon atoms, and 2 to 2 carbon atoms. It represents 30 heteroaryls, alkyls with 1 to 24 carbon atoms or cycloalkyls with 3 to 12 carbon atoms. )

Item 5.
Item 4. The organic electroluminescent device according to Item 4, wherein in the general formula (1), ^{at least one of R 1 to} R ¹¹ is a group represented by the above formula (1-d).

Item 6.
In the above general formula (1), R ^{1 to} R ¹¹ are independently bonded to hydrogen, aryl, heteroaryl, diarylamino, and diarylboryl (even if the two aryls are bonded via a single bond or a linking group). Good), alkyl, cycloalkyl or alkoxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Item 2. The organic electroluminescent device according to any one of Items 1 to 5.

Item 7.
In the above general formula (1), ^{at least one of R 4 to} R ¹¹ is a heteroaryl, and at least one hydrogen in the heteroaryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Item 2. The organic electroluminescent device according to any one of Items 1 to 6.

Item 8.
In the general formula (1), ^{at least one of R 1 to} R ³ is aryl or dibenzofuranyl, and the aryl and at least one hydrogen in the dibenzofuranyl are aryl, heteroaryl, alkyl or cycloalkyl. The organic electroluminescent device according to any one of Items 1 to 7, which may be substituted.

Item 9.
In the above general formula (1), ^{at least one of R 1 to} R ³ is a heteroaryl (at least one hydrogen in the heteroaryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl). and at least one of R ⁴ to R ¹¹ is aryl (at least one hydrogen in the aryl aryl, optionally substituted heteroaryl, alkyl or cycloalkyl), any term 1-6 The organic electroluminescent element according to item 1.

Item 10.
Item 2. The organic electroluminescent device according to Item 1, wherein the host of the first component is a polycyclic aromatic compound represented by any of the following formulas.

（上記式（２）中、
Ｒ^１〜Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、シアノまたはハロゲンであり、これらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１〜Ｒ^１１のうちの隣接する基同士が結合してａ環、ｂ環またはｃ環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙ^１は、Ｂ（ホウ素）であり、
Ｘ^１およびＸ^２は、それぞれ独立して、＞Ｏ、＞Ｎ−Ｒ、＞Ｓ、＞Ｓｅまたは−Ｃ（−Ｒ）_２−であり（ただし、Ｘ^１およびＸ^２は同時に＞Ｏであることはない）、前記−Ｃ（−Ｒ）_２−のＲは炭素数１〜６のアルキル、炭素数３〜１４のシクロアルキルまたは炭素数６〜１２のアリールであり、前記＞Ｎ−ＲのＲは炭素数６〜１２のアリール、炭素数２〜１５のヘテロアリール、炭素数１〜６のアルキルまたは炭素数３〜６のシクロアルキルであり、また、当該＞Ｎ−ＲのＲは−Ｏ−、−Ｓ−、−Ｃ（−Ｒ’）_２−、単結合または縮合により前記ａ環、ｂ環およびｃ環の少なくとも１つと結合していてもよく（なお、前記「−Ｃ（−Ｒ’）_２−」のＲ’は水素または炭素数１〜５のアルキルまたは炭素数５〜１０のシクロアルキルである）、そして、
式（２）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 11.
Item 2. The organic electroluminescent element according to any one of Items 1 to 10, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (2) or a multimer thereof.

(In the above formula (2),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, ^{adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. Are Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl. It may be substituted with oxy, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Y ¹ is B (boron) and
X ¹ and X ² are independently>O,>N-R,>S,> Se or -C (-R) _2- (where X ¹ and X ² are> O at the same time. The -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the above-mentioned> N-R R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, and the R of> N-R is -O. -, -S-, -C (-R') _2- , may be bonded to at least one of the a ring, b ring and c ring by a single bond or condensation (note that "-C (-R')". ') _2- 'R'is hydrogen or an alkyl with 1 to 5 carbons or a cycloalkyl with 5 to 10 carbons), and
At least one hydrogen in the compound represented by the formula (2) may be substituted with cyano, halogen or deuterium. )

Item 12.
In the above general formula (2), R ⁸ is a halogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
Item 2. The organic electroluminescence according to Item 11, wherein R ⁷ is hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms. element.

Item 13.
The dopant as the second component is a dimer compound composed of two partial structures represented by the above general formula (2) and a linking group L1 connecting the two partial structures.
The linking group L1 is a single bond, an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, and an alkynylene having 1 to 6 carbon atoms. -O-, -S-,> N-R, or a combination thereof, and the R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and 1 to 1 carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms.
Item 2. The organic electroluminescent element according to Item 11, wherein at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium.

（上記式（３）中、
Ｒ^３〜Ｒ^１２、Ｚ^１およびＺ^２は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、シアノまたはハロゲンであり、これらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^５〜Ｒ^７およびＲ^１０〜Ｒ^１２のうちの隣接する基同士が結合してｂ環およびｄ環の少なくとも１つと共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、さらにこれらにおける少なくとも１つの水素は、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｚ^１は連結基または単結合でａ環と結合してもよく、また、Ｚ^２は連結基または単結合でｃ環と結合してもよく、
ＹはＢ（ホウ素）であり、
Ｘ^１、Ｘ^２、Ｘ^３およびＸ^４は、それぞれ独立して、＞Ｏ、＞Ｎ−Ｒ、＞Ｓ、＞Ｓｅまたは−Ｃ（−Ｒ）_２−であり（ただし、Ｘ^１およびＸ^２が同時に＞Ｏであることはなく、また、Ｘ^３およびＸ^４が同時に＞Ｏであることもない）、前記−Ｃ（−Ｒ）_２−のＲは炭素数１〜６のアルキル、炭素数３〜１４のシクロアルキル、または炭素数６〜１２のアリールであり、前記＞Ｎ−ＲのＲは炭素数６〜１２のアリール、炭素数２〜１５のヘテロアリール、炭素数１〜６のアルキルまたは炭素数３〜６のシクロアルキルであり、また、当該＞Ｎ−ＲのＲは−Ｏ−、−Ｓ−、−Ｃ（−Ｒ’）_２−、単結合または縮合により前記ａ環、ｂ環、ｃ環およびｄ環の少なくとも１つと結合していてもよく（なお、前記「−Ｃ（−Ｒ’）_２−」のＲ’は水素または炭素数１〜５のアルキルまたは炭素数５〜１０のシクロアルキルである）、
Ｒ^１およびＲ^２は、それぞれ独立して、水素、炭素数１〜６のアルキル、炭素数３〜１４のシクロアルキル、炭素数６〜１２のアリール、炭素数２〜１５のヘテロアリールまたはジアリールアミノ（ただしアリールは炭素数６〜１２のアリール）、ジアリールボリル（ただしアリールは炭素数６〜１２のアリールであり、２つのアリールは単結合または連結基を介して結合していてもよい）であり、
式（３）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 14.
Item 2. The organic electroluminescent device according to any one of Items 1 to 11, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (3).

(In the above formula (3),
R ^{3 to} R ¹² , Z ¹ and Z ² are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. ,
Further, ^{adjacent groups of R 5 to} R ⁷ and R ^{10 to} R ¹² may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the b ring and the d ring. At least one hydrogen in the ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl. , Cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Z ¹ may be bonded to the a ring with a linking group or a single bond, and Z ² may be bonded to the c ring with a linking group or a single bond.
Y is B (boron),
X ¹ , X ² , X ³ and X ⁴ are independently>O,>N-R,>S,> Se or -C (-R) _2- (where X ¹ and X ^2). There never is> O simultaneously, nor that ^{X 3} and ^{X 4} are> O simultaneously), the -C _{(-R) 2} - in which R is an alkyl of 1 to 6 carbon atoms, carbon atoms It is a cycloalkyl of 3 to 14 or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and an alkyl having 1 to 6 carbon atoms. Alternatively, it is a cycloalkyl having 3 to 6 carbon atoms, and the R of the> N-R is -O-, -S-, -C (-R') _2- , the a ring, b by a single bond or condensation. It may be bonded to at least one of the ring, the c ring and the d ring (note that the R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 5 carbon atoms or 5 to 5 carbon atoms. 10 cycloalkyl),
R ¹ and R ² are independently hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 14 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl or diarylamino with 2 to 15 carbon atoms, respectively. (However, aryl is an aryl having 6 to 12 carbon atoms), and diarylboryl (however, aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group). ,
At least one hydrogen in the compound represented by the formula (3) may be substituted with cyano, halogen or deuterium. )

（上記式（４）中、
Ｒ^１〜Ｒ^３およびＲ^５〜Ｒ^１５は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、シアノまたはハロゲンであり、これらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１〜Ｒ^３、Ｒ^５〜Ｒ^７、Ｒ^８〜Ｒ^１１およびＲ^１２〜Ｒ^１５のうちの隣接する基同士が結合してａ環、ｂ環、ｃ環およびｄ環の少なくとも１つと共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、さらにこれらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙ^１は、Ｂ（ホウ素）であり、
Ｘは、＞Ｏ、＞Ｎ−Ｒ、＞Ｓ、＞Ｓｅまたは−Ｃ（−Ｒ）_２−であり、前記−Ｃ（−Ｒ）_２−のＲは炭素数１〜６のアルキル、炭素数３〜１４のシクロアルキルまたは炭素数６〜１２のアリールであり、前記＞Ｎ−ＲのＲは炭素数６〜１２のアリール、炭素数２〜１５のヘテロアリール、炭素数１〜６のアルキルまたは炭素数３〜６のシクロアルキルであり、
Ｌは、単結合、−Ｃ（−Ｒ）_２−、＞Ｏ、＞Ｓまたは＞Ｎ−Ｒであり、前記−Ｃ（−Ｒ）_２−および＞Ｎ−ＲにおけるＲは、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
ただし、Ｘが＞Ｎ−Ｒであるとき、Ｌが＞Ｏであることはなく、
多量体の場合の式（４）中のＲ^２は水素であり、そして、
一般式（４）で表される化合物および構造における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 15.
Item 2. The organic electroluminescent element according to any one of Items 1 to 11, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (4) or a multimer thereof.

(In the above formula (4),
R ^{1 to} R ³ and R ^{5 to} R ¹⁵ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. ,
In addition, ^{adjacent groups of R 1 to} R ³ , R ^{5 to} R ⁷ , R ^{8 to} R ¹¹ and R ^{12 to} R ¹⁵ are bonded to each other to form at least one of a ring, b ring, c ring and d ring. They may form an aryl ring or a heteroaryl ring together, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls). May be attached via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be aryl, heteroaryl, alkyl or cyclo. May be substituted with alkyl
Y ¹ is B (boron) and
X is>O,>N-R,>S,> Se or -C (-R) _2- , and the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms and a carbon number of carbons. It is a cycloalkyl of 3 to 14 or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or It is a cycloalkyl with 3 to 6 carbon atoms.
L is a single bond, -C (-R) ₂ -,>O,> S or> N-R, and R in -C (-R) _2- and> N-R is independent of each other. , Hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these. One hydrogen may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl,
However, when X is> N-R, L is never> O.
^{R 2} in equation (4) for multimers is hydrogen, and
At least one hydrogen in the compound and structure represented by the general formula (4) may be substituted with cyano, halogen or deuterium. )

（上記式（５）中、
Ｒ^１〜Ｒ^９は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、シアノまたはハロゲンであり、これらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１〜Ｒ^９のうちの隣接する基同士が結合してａ環、ｂ環およびｃ環の少なくとも１つと共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、さらにこれらにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙ^１は、Ｂ（ホウ素）であり、
Ｘ^１、Ｘ^２およびＸ^３は、それぞれ独立して、＞Ｏ、＞Ｎ−Ｒ、＞Ｓ、＞Ｓｅまたは−Ｃ（−Ｒ）_２−であり（Ｘ^１、Ｘ^２およびＸ^３のうちの少なくとも２つはＮ−Ｒである）、前記−Ｃ（−Ｒ）_２−のＲは炭素数１〜６のアルキル、炭素数３〜１４のシクロアルキルまたは炭素数６〜１２のアリールであり、前記＞Ｎ−ＲのＲは炭素数６〜１２のアリール、炭素数２〜１５のヘテロアリール、炭素数１〜６のアルキルまたは炭素数３〜６のシクロアルキルであり、また、当該＞Ｎ−ＲのＲは−Ｏ−、−Ｓ−、−Ｃ（−Ｒ’）_２−、単結合または縮合により前記ａ環、ｂ環およびｃ環の少なくとも１つと結合していてもよく（なお、前記「−Ｃ（−Ｒ’）_２−」のＲ’は水素または炭素数１〜５のアルキルまたは炭素数５〜１０のシクロアルキルである）、そして、
式（５）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 16.
Item 2. The organic electroluminescent element according to any one of Items 1 to 10, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (5) or a multimer thereof.

(In the above formula (5),
R ^{1 to} R ⁹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, ^{adjacent groups of R 1 to} R ⁹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of a ring, b ring and c ring, and the formed ring may be formed. At least one hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Y ¹ is B (boron) and
X ¹ , X ² and X ³ are independently>O,>N-R,>S,> Se or -C (-R) _2- (of X ¹ , X ² and X ³ ). At least two of them are N-R), the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms. R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, and the said> N The R of −R may be bonded to at least one of the a ring, b ring and c ring by a single bond or condensation of −O−, −S−, −C (−R ′) _{2− (note that it should be noted).} The R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), and
At least one hydrogen in the compound represented by the formula (5) may be substituted with cyano, halogen or deuterium. )

Item 17.
Item 2. The organic electroluminescent device according to Item 1, wherein the dopant of the second component is a polycyclic aromatic compound represented by any of the following formulas.

Item 18.
It has at least one of an electron transporting layer and an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or a fluorantene derivative. , BO-based derivative, anthracene derivative, benzofluorene derivative, phosphine oxide derivative, pyrimidine derivative, carbazole derivative, triazine derivative, benzoimidazole derivative, phenanthroline derivative and quinolinol-based metal complex. Item 2. The organic electric field light emitting element according to any one of Items 1 to 17.

Item 19.
At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline earth metal. Contains at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. 18. The organic electric field light emitting element according to 18.

（上記式（１）中、
Ｒ^１〜Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシであり、
前記アリール、前記ヘテロアリール、前記ジアリールアミノおよび前記ジアリールボリルにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｒ^１〜Ｒ^１１の少なくとも１つは、下記式（１−ｄ）で表される基であり、
式（１）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記式中、＊は結合位置を示し、式（１−ｄ）における少なくとも１つの水素はさらにアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよい。）Item 20.
A polycyclic aromatic compound represented by the following general formula (1).

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy, aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At ^{least one of R 1 to} R ¹¹ is a group represented by the following formula (1-d).
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above formula, * indicates a bond position, and at least one hydrogen in the formula (1-d) may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl.)

（上記式（１）中、
Ｒ^１〜Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、
前記アリール、前記ヘテロアリール、前記ジアリールアミノおよび前記ジアリールボリルにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
式（１）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 21.
A reactive compound in which a polycyclic aromatic compound represented by the following general formula (1) is substituted with a reactive substituent.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. )

Item 22.
A polymer compound obtained by polymerizing the reactive compound according to Item 21 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound.

Item 23.
A pendant type polymer compound in which the main chain type polymer is substituted with the reactive compound according to Item 21, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.

Item 24.
As the first component, the reactive compound according to Item 21, the polymer compound or polymer crosslinked product according to Item 22, or the pendant type polymer compound or pendant type polymer crosslinked product according to Item 23 is used as a host. Including
As the second component, a polycyclic aromatic compound containing boron is contained as a dopant.
Contains an organic solvent as the third component,
A composition for forming a light emitting layer.

（上記式（１）中、
Ｒ^１〜Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、
前記アリール、前記ヘテロアリール、前記ジアリールアミノおよび前記ジアリールボリルにおける少なくとも１つの水素はアリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
式（１）で表される化合物における少なくとも１つの水素はシアノ、ハロゲンまたは重水素で置換されていてもよい。）Item 25.
As the first component, a polycyclic aromatic compound represented by the following general formula (1) is contained as a host.
As the second component, a polycyclic aromatic compound containing boron is contained as a dopant.
A composition for forming a light emitting layer, which contains an organic solvent as a third component.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. )

Item 26.
Item 2. The composition for forming a light emitting layer according to Item 24 or 25, wherein the boiling point of at least one organic solvent of the third component is 130 to 350 ° C.

Item 27.
The organic solvent of the third component contains a good solvent (GS) and a poor solvent (PS) for at least one of the host of the first component and the dopant of the second component, and the boiling point (BP _GS ) of the good solvent (GS). There below the boiling point _{(BP PS)} of the poor solvent (PS), light-emitting layer forming composition according to any one of claims 24-26.

Item 28.
The first component is 0.0999% by mass to 8.0% by mass with respect to the total mass of the composition for forming a light emitting layer.
The second component is 0.0001% by mass to 2.0% by mass with respect to the total mass of the composition for forming a light emitting layer.
The third component is 90.0% by mass to 99.9% by mass with respect to the total mass of the composition for forming a light emitting layer.
Item 2. The composition for forming a light emitting layer according to any one of Items 24 to 27.

Item 29.
High having a first structural unit derived from the reactive compound according to Item 21, and a second structural unit derived from a reactive compound in which a reactive substituent is substituted on a boron-containing polycyclic aromatic compound. Molecular compounds,
A polymer crosslinked product obtained by further cross-linking the polymer compound,
A pendant type polymer compound in which the reactive compound according to Item 21 and a polycyclic aromatic compound containing boron are substituted with a reactive compound in which a reactive substituent is substituted in the main chain type polymer, and a pendant type polymer compound.
At least one selected from pendant-type polymer crosslinked products obtained by further cross-linking the pendant-type polymer compound, and
A composition for forming a light emitting layer, which comprises an organic solvent.

Item 30.
A pair of electrodes consisting of an anode and a cathode, and arranged between the pair of electrodes,
An organic electroluminescent device having a light emitting layer formed by using the composition for forming a light emitting layer according to any one of Items 24 to 29.

Item 31.
At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or a polymer compound. , A polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type polymer compound. Item 2. The organic electric field light emitting element according to any one of Items 1 to 19 and 30, further comprising a crosslinked pendant type polymer crosslinked body.

Item 32.
A display device or a lighting device including the organic electroluminescent element according to any one of Items 1 to 19, 30 and 31.

According to a preferred embodiment of the present invention, by using a specific polycyclic aromatic compound as a material for a light emitting layer, organic EL properties such as light emitting properties can be further enhanced.

It is a schematic cross-sectional view which shows the organic EL element which concerns on this embodiment.

1. 1. Organic electroluminescent device The organic EL device of the present invention has a pair of electrodes composed of an anode and a cathode, and a light emitting layer arranged between the pair of electrodes. The light emitting layer is characterized by containing a polycyclic aromatic compound represented by the above general formula (1) as a first component and a boron-containing polycyclic aromatic compound as a second component. do. In the light emitting layer, the first component functions as a host and the second component functions as a dopant.

1-1. Polycyclic aromatic compound represented by the first component (1) has a large HOMO-LUMO gap and high triplet excitation energy (band gap Eg of the thin film) _{(E T).} This is because the 6-membered ring containing the hetero element has a low aromatic attribute, so that the decrease in the HOMO-LUMO gap due to the expansion of the conjugated system is suppressed, and the triplet excited state (T1) is due to the electronic perturbation of the hetero element. The cause is the localization of SOMO1 and SOMO2. The polycyclic aromatic compound represented by the formula (1) has a high triplet energy and is therefore preferable as a host for a thermally activated delayed fluorescent material.

Specifically, the excited triple-term energy level E (1, T, PT) obtained from the peak top of the phosphorescence spectrum of the compound of the first component is a viewpoint of promoting the generation of TADF in the light emitting layer without inhibiting it. Therefore, it is preferable that the excitation triple energy level E (2, T, PT) obtained from the peak top of the phosphorescence spectrum of the second component compound is higher than that of the excitation triple energy level E (2, T, PT). The triple energy level E (1, T, PT) is preferably 0.01 eV or more, more preferably 0.03 eV or more, still more preferably 0.1 eV or more, as compared with E (2, T, PT). Further, a TADF active compound may be used as the host compound.

The first component is a compound used as a host, and generally, the content in the light emitting layer is larger than that of the dopant which is the second component. Therefore, the excitation triplet energy is generally obtained in a state close to the actual usage conditions. For example, the excitation triplet energy of the first component is obtained from the vapor deposition film of the single component, and the excitation of the second component is obtained. The triplet energy can be obtained from a film containing an inert component or a first component as a main component and a low concentration of a second component uniformly dispersed.
On the other hand, the first component used in the present invention has a relatively large flat structure formed by a boron atom, an oxygen atom and rings a to b, as represented by the formula (1). The values of the excitation singlet energy and the excitation triplet energy may be estimated to be lower than those obtained from the above-mentioned single-component vapor deposition film of the first component. Therefore, in the present specification, in order to eliminate the influence of aggregation and interaction between the first components, the excited singlet energy and the excited triplet energy of the first component and the second component are mainly composed of the inactive component. It is determined by a film formed by uniformly dispersing a low-concentration first component or second component. Here, the inert component includes, for example, an optically transparent polymer in the range of excitation and emission of the first component or the second component, and specifically, poly (methyl methacrylate), polystyrene, polyolefin and cyclo. Examples include olefin polymers.

Further, the first component preferably has low cohesiveness from the viewpoint of reducing the interaction and obtaining high excited triplet energy, and specifically, the molecular structure of the first component preferably has an asymmetric structure. It is preferable to have a large dihedral angle in the molecule, or it is preferable to have steric hindrance in the molecule. Further, from the viewpoint of charge transportability and energy transfer, it is preferable that the orbits involved in charge transport can be close to each other. Further, from the viewpoint of the stability of the device characteristics when the device is driven, it is preferable that the glass transition temperature (Tg) of the first component is high, and it is preferable that the molecules interact with each other.

Regarding the cohesiveness between the respective components, a compound having a low cohesiveness for both the first component and the second component may be used, or a compound having a low cohesiveness for either one may be used. Regarding the cohesiveness, the degree of redshift between the low-concentration uniformly dispersed state and the spectrum of the single-component vapor-deposited film, or the spectrum of the co-deposited film of the first component and the second component and the spectrum of the second component in the low-concentration uniformly dispersed state. It can be estimated by the degree of redshift.

In the above formula (1), R ^{1 to} R ¹¹ are independently bonded to hydrogen, aryl, heteroaryl, diarylamino, and diarylboryl (two aryls may be bonded via a single bond or a linking group). ), Alkyl, cycloalkyl, alkoxy or aryloxy (these are first substituents), and at least one hydrogen in the aryl, the heteroaryl, the diarylamino and the diallylboryl is aryl, heteroaryl, alkyl or cyclo. It may be substituted with an alkyl (above, a second substituent).

Examples of the "aryl" as the first substituent include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and 6 to 6 carbon atoms. Aryl of 16 is more preferable, aryl of 6 to 12 carbon atoms is particularly preferable, and aryl of 6 to 10 carbon atoms is most preferable.

Specific examples of the aryl include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Fused tricyclic aryls, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl. ) Il, pentasen- (1-, 2-, 5-, 6-) yl and the like.

The above description of "aryl" as the first substituent includes "aryl" in diarylamino as the first substituent, diarylboryl (two aryls may be attached via a single bond or a linking group). Can also be cited for "aryl" in, "aryl" in aryloxy, and "aryl" as a second substituent.

Examples of the "heteroaryl" as the first substituent include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and more preferably heteroaryl having 2 to 20 carbon atoms. Heteroaryl having 2 to 15 carbon atoms is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, frills, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, frazayl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, benzofuranyl, Isobenzofuranyl, dibenzofuranyl, thiophenyl, benzo [b] thienyl, dibenzothiophenyl, indrill, isoindrill, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl , Kinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxadinyl, phenothiazine, phenazinyl, phenazacilinyl, phenoxatiinyl, thiantrenyl, indolidinyl, indolocarbazolyl, benzoindrocarbazolyl, benzo. Examples include carbazolyl and naphthobenzofuranyl.

The above description of "heteroaryl" as the first substituent can also be cited for "heteroaryl" as the second substituent. Further, in the "heteroaryl" as the second substituent, at least one hydrogen in the heteroaryl is an aryl such as phenyl (specific example is the group described above) or an alkyl such as methyl (specific example is a group described later). The substituted group is also included in the heteroaryl as the second substituent. As an example, when the second substituent is a carbazolyl group, the carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl or an alkyl such as methyl also becomes a heteroaryl as the second substituent. included.

The "alkyl" as the first substituent may be either a straight chain or a branched chain, and examples thereof include alkyl having 1 to 24 carbon atoms (branched chain alkyl having 3 to 24 carbon atoms) and having 1 to 1 carbon atoms. An alkyl having 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms (3 carbon atoms) is preferable. A branched alkyl having 1 to 6 carbon atoms is further preferable, an alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is even more preferable, and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is more preferable. Alkyl) is particularly preferred, and methyl is most preferred.

Specific alkyl examples include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), and the like. n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3) , 3-Tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethyl Hexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl And so on.
Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2- Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3- Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1 -Propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can also be mentioned.

The above description of "alkyl" as the first substituent can also be cited for "alkyl" as the second substituent. The position where the alkyl, which is the second substituent, substitutes for the first substituent is not particularly limited, but is based on the bonding position (1 position) of the first substituent to the a ring, b ring and c ring. The 2nd or 3rd position is preferable, and the 2nd position is more preferable.

The "cycloalkyl" as the first substituent includes a cycloalkyl consisting of one ring, a cycloalkyl consisting of a plurality of rings, a cycloalkyl containing a double bond that is not conjugated within the ring, and a cycloalkyl containing an out-of-ring branch. For example, cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 3 to 12 carbon atoms. Examples thereof include alkyl, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and cycloalkyl having 6 to 10 carbon atoms.

Specific cycloalkyls include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, norbornenyl, and bicyclo. [1.0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexil, Bicyclo [2.1.2] heptyl, bicyclo [2,2,1] heptyl, bicyclo [2.2.2] octyl, decahydronaphthyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, etc. Be done.

The above description of "cycloalkyl" as the first substituent can also be cited for "cycloalkyl" as the second substituent.

Examples of the "alkoxy" (first substituent) include alkoxy having 1 to 24 carbon atoms (alkoxy of a branched chain having 3 to 24 carbon atoms), and alkoxy having 1 to 18 carbon atoms (3 to 18 carbon atoms). (Ekoxy of branched chains of 3 to 12 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (alkoxy of branched chains having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms (alkoxy of branched chains having 3 to 6 carbon atoms). ) Is even more preferable, alkoxy having 1 to 5 carbon atoms (alkoxy of branched chains having 3 to 5 carbon atoms) is even more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of branched chains having 3 to 4 carbon atoms) is particularly preferable. preferable.

Specific alkoxys include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, and t-pentyl. Oxy, n-hexyloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5 -Trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, Examples thereof include n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy and n-eicosyloxy.

Further, as the "aryl" in the "diarylboryl" of the first substituent, the above-mentioned description of aryl can be cited. Further, the two aryls may be bonded via a single bond or a linking group (for example,> C (-R) ₂ ,>O,> S or> N-R). Here, R of> C (-R) ₂ and> N-R are aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), It is alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and the first substituent is further substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent). Also, as specific examples of these groups, the above-mentioned description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy as the first substituent can be cited.

The emission wavelength can be adjusted by the steric hindrance, electron donating property and electron attracting property of the structure of the first substituent, and the group is preferably represented by the following structural formula, more preferably methyl, t-. Butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xsilyl, 2,4,6-mesityl, diphenylamino, di -P-Trillamino, 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, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-) Butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, o-tryl, p-trill, 2 , 4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, 3,6-dimethylcarba Zolyl and 3,6-di-t-butylcarbazolyl are preferred.

In the following structural formula, "Me" stands for methyl, "tBu" stands for t-butyl, "tAm" stands for t-amyl, and "tOct" stands for t-octyl.

At ^{least one of R 1 to} R ¹¹ is preferably a group represented by any of the following formulas (1-a) to (1-s), and is a group represented by the following formula (1-d). Is more preferable.

In the above formula, * indicates the bonding position.
At least one hydrogen in the formulas (1-a) to (1-h) and the formulas (1-p) to (1-q) has 6 to 30 carbon atoms as the above-mentioned "second substituent". It may be substituted with aryl, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 12 carbon atoms.
Further, R in the formula (1-i), the formula (1-j), the formula (1-k) and the formula (1-r) is independently hydrogen or the above-mentioned "second substituent". As, 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 12 carbon atoms is shown.

More specific embodiments of the groups represented by the formulas (1-a) to (1-s) include, for example, the groups shown below. In the formula, * indicates the binding position, Me indicates methyl, and tBu indicates t-butyl.

In the above formula (1), ^{adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring or a c ring, and the formed ring may be formed. At least one hydrogen in is aryl, heteroaryl, diarylamino, diallylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (or more). It may be substituted with a first substituent), and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl (above, a second substituent).
Therefore, the polycyclic aromatic compounds represented by the general formula (1) have the following formulas (1-L1) and (1-L2) depending on the mutual bonding form of the substituents in the a ring, b ring and c ring. As shown in, the ring structure constituting the compound changes. The a'ring, b'ring and c'ring in each formula correspond to the above-mentioned "formed ring (aryl ring or heteroaryl ring)". Each reference numeral in the equation (1-L1) and the equation (1-L2) is the same as the definition in the equation (1).

Although not shown in the above formula, there are some compounds in which all of the a ring, b ring and c ring are changed to a'ring, b'ring and c'ring. Further, as can be seen from the above equations (1-L1) and (1-L2), for example, R ³ of a ring and R ⁴ of c ring, R ⁷ of c ring and R ⁸ of b ring, and b ring. R ¹¹ and R ^{1 of the} a ring do not correspond to "adjacent groups", and they do not bond with each other. That is, the "adjacent group" means an adjacent group on the same ring.

The compounds represented by the above formulas (1-L1) and (1-L2) are, for example, a benzene ring, an indole ring, and a pyrrole with respect to a benzene ring which is an a ring (and at least one of a b ring and a c ring). A compound having an a'ring (and at least one of a b'ring and a c'ring) formed by condensing a ring, a benzofuran ring, a benzothiophene ring, or the like, and the formed fused ring a'(fused ring b). 'Or fused ring c') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, respectively.

Examples of the formed ring "aryl ring" include an aryl ring having 9 to 30 carbon atoms, preferably an aryl ring having 9 to 24 carbon atoms, and more preferably an aryl ring having 9 to 20 carbon atoms. An aryl ring having 9 to 16 carbon atoms is more preferable, an aryl ring having 9 to 12 carbon atoms is particularly preferable, and an aryl ring having 9 to 10 carbon atoms is most preferable. Since the a ring (b ring or c ring) of this "aryl ring" is already composed of a benzene ring having 6 carbon atoms, the total carbon number 9 of the fused ring in which a 5-membered ring is condensed is the lower limit. It becomes the carbon number of.

Specific examples of the "aryl ring" include naphthalene ring, which is a condensed bicyclic system, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, and triphenylene ring, which is a condensed tetracyclic system, and pyrene. Examples thereof include a ring, a naphthalene ring, a perylene ring which is a condensed five-ring system, and a pentacene ring.

Examples of the formed "heteroaryl ring" include a heteroaryl ring having 6 to 30 carbon atoms, preferably a heteroaryl ring having 6 to 25 carbon atoms, and a heteroaryl ring having 6 to 20 carbon atoms. Is more preferable, a heteroaryl ring having 6 to 15 carbon atoms is further preferable, and a heteroaryl ring having 6 to 10 carbon atoms is particularly preferable. Examples of the "heteroaryl ring" include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms. In this "heteroaryl ring", since the a ring (b ring or c ring) is already composed of a benzene ring having 6 carbon atoms, the total carbon number of the fused ring in which a 5-membered ring is condensed is 6 carbon atoms. It is the lower limit of carbon number.

Specific examples of the "heteroaryl ring" include an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, and a cinnoline. Ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclydin ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolein ring, benzofuran ring, isobenzofuran Examples thereof include a ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thiantolen ring.

The formed first substituent and the second substituent to the ring, can be also cited to the description of the first substituent and second substituent groups mentioned in the description of R ¹ to R ^11.

In the general formula (1), ^{a plurality of R 1 to} R ¹¹ may have a first substituent. From the viewpoint of the difficulty of synthesis, the replacement positions are selected so that the steric hindrances are small. Substituents may be located adjacent to each other on the same ring, but in this case, groups with less steric hindrance are preferred.
^{The number of substituents in R 1 to} R ¹¹ of the general formula (1) is not particularly limited, but the total number of carbon atoms of the substituents in ^{R 1 to} R ^{11 is preferably 36 or less.}

In the general formula (1), when R ^{1 to} R ¹¹ have a plurality of first substituents, especially when a synthetic step of introducing boron at the end is used, a ring-B bond is formed from the viewpoint of ease of synthesis. It is preferable to have a substituent so as to be line symmetric with respect to. On the other hand, from the viewpoint of reducing crystallinity and cohesiveness, it is preferable to have a substituent so as to have an asymmetrical structure.

As a preferred host of the first embodiment in the first component, in general formula (1), R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls are simple). At least one hydrogen in the aryl, the heteroaryl, and the diarylamino is an aryl, which may be attached via a bond or a linking group), alkyl, cycloalkyl or alkoxy (above, the first substituent). , Heteroaryl, alkyl or cycloalkyl (above, a polycyclic aromatic compound which may be substituted with a second substituent).
That is, the polycyclic aromatic compound that is the host of the first aspect is a compound that does not have aryloxy as the first substituent, excluding aryloxy such as the group represented by the above formula (1-h). Is.

As a host of a second preferred embodiment of the first component, in the general formula (1), at least one of R ⁴ to R ¹¹ is heteroaryl (or, first substituent), and at least in the heteroaryl 1 Examples thereof include polycyclic aromatic compounds in which one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (hereinafter, a second substituent).
Examples of the polycyclic aromatic compound that is the host of the second aspect include the compound (BO2-0431) and the compound (BO2-0520S) described later.
Polycyclic aromatic compound which is a host of the second ^aspect, at least one of R 4 ^{to R 11,} the formula (1-a), formula (1-b), formula (1-c), formula (1 d), the group represented by any of the formula (1-l), the formula (1-m) and the formula (1-n) is preferable, and the above formulas (1-a) and the formula (1-d) are preferable. ) Is more preferable.

As a preferred host of the third aspect in the first component, in the above general formula (1), ^{at least one of R 1 to} R ³ is an aryl or a dibenzofuranyl (above, the first substituent), and the aryl is said. And the polycyclic aromatic compound in which at least one hydrogen in the dibenzofuranyl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
Examples of the polycyclic aromatic compound that is the host of the third aspect include the compound (BO2-0264 / 0511S) and the compound (BO2-0231) described later.
Polycyclic aromatic compound which is a host of the third ^aspect, at least one of R 1 to R ^3, the formula (1-d), formula (1-f), the formula (1-i), the formula (1 It is preferably a group represented by any of the formulas (1-k) and (j), and more preferably a group represented by any of the above formulas (1-d) and (1-i). preferable.

As a preferred host of the fourth aspect in the first component, in the above general formula (1), ^{at least one of R 1 to} R ³ is a heteroaryl (or the first substituent) (at least in the heteroaryl. one hydrogen aryl, heteroaryl, alkyl or cycloalkyl (more second substituent) may be substituted by), and at least one of R ⁴ to R ¹¹ is aryl (more first replacement Groups) (at least one hydrogen in the aryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent)), polycyclic aromatic compounds.
Examples of the polycyclic aromatic compound that is the host of the fourth aspect include the compound (BO2-0220 / 0510S) and the compound (BO2-0220 / 0511S) described later.
Polycyclic aromatic compound which is a host of the fourth ^aspect, at least one of R 1 to R ^3, the formula (1-a), formula (1-b), formula (1-c), formula (1 d), formula (1-l), a group represented by any one of formulas (1-m) and formula ^(1-n), at least one of R 4 ^{to R 11,} the formula (1-f ), Formula (1-i), formula (1-j) and formula (1-k).

At least one hydrogen in the polycyclic aromatic compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

As the host of the first component, the polycyclic aromatic compound represented by the general formula (1) is preferably a compound represented by any one of the following formulas, for example. In each formula, any hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms (for example, methyl or t-butyl) or a cycloalkyl having 5 to 10 carbon atoms (for example, cyclopentyl or cyclohexyl).

Hereinafter, the polycyclic aromatic compound represented by the general formula (1) will be described in more detail.
When the compound represented by the general formula (1) is associated with the compound number, it is also described as the general formula (BO2-1). Hereinafter, in the general formula representing the general structure of the compound, the reference numerals ^{R 1 to} R ^{11 may be omitted for the sake of simplification of the expression.} Such omissions are not made in formulas that represent the structure of specific compounds rather than general formulas.

For example, in the general formula (BO2-1), when R ^{1 to} R ¹¹ are hydrogen, it is represented by the general formula (BO2-0001).

^{When R 1 to} R ¹¹ in the general formula (BO2-1) have a substituent other than hydrogen, for example, the following structure can be mentioned. From the viewpoint of steric ^{congestion, R 1, R 2, R} 3, R 4, R 5, R 6, R 9, R is ¹⁰ and ^{R 11} can have any substituents, the HOMO and LUMO From a regulatory point of view, when deepening HOMO, it is preferable to introduce an electron-donating substituent into at least one of ^{R 1} , R ³ , R ⁴ , R ⁶ , R ⁹ and R ^11. When making the HOMO shallow, it is preferable to introduce an electron-withdrawing substituent into at least one of ^{R 1} , R ³ , R ⁴ , R ⁶ , R ⁹ and R ^11. Further, when deepening LUMO, it is preferable to introduce an electron-donating substituent into at least one of ^{R 2} , R ⁵ and R ^{10 , and conversely, when making LUMO shallow, R 2} , R It is preferable to introduce an electron-withdrawing substituent into at least one of ⁵ and R ^10.

Also, for aromatic rings formed by rings a to c and boron and oxygen atoms, it is more cohesive and host-to-host or host-host when the substituents ^{R 1 to} R ^{11 have a larger dihedral angle.} Interactions between dopants can be reduced. In particular, since many of the compounds of the first component used in the present invention and the compounds described later that are suitable as the second component have high flatness, it is better to reduce the cohesiveness and interaction to reduce the red shift of the emission spectrum and the red shift of the emission spectrum. It is preferable from the viewpoint of preventing widening, emitting light in deep blue, and achieving high color purity. In the light emitting layer, which is a mixed film in which the first component and the second component are mixed, the dihedral angle of the compound of the first component used in the present invention is difficult to measure. Molecular orbital calculations may be used for discussions on the helix. It does not have to be a strict calculation, and for example, MOPAC or the like can be used.

Specific examples of the polycyclic aromatic compound represented by the general formula (1), which is the host of the first material, include compounds having the following structural formulas. Me is methyl and tBu is butyl.

The polycyclic aromatic compound represented by the general formula (1) is a polymer compound obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer (the monomer for obtaining this polymer compound). Has a polymerizable substituent), or a polymer crosslinked product obtained by further cross-linking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent), or a main chain. A pendant type polymer compound obtained by reacting a type polymer with the above-mentioned reactive compound (the above-mentioned reactive compound for obtaining this pendant type polymer compound has a reactive substituent), or the pendant type polymer compound. Further crosslinked pendant type polymer crosslinked products (the pendant type polymer compound for obtaining this pendant type polymer crosslinked product has a crosslinkable substituent) can also be used as a material for an organic device, for example, an organic electroluminescent element. It can be used as a material for organic field effect transistors or a material for organic thin film solar cells.

As the above-mentioned reactive substituent (including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant type polymer, hereinafter, also simply referred to as “reactive substituent”). , The substituent capable of increasing the molecular weight of the polycyclic aromatic compound, the substituent capable of further cross-linking the polymer compound thus obtained, and the substituent capable of pendant reaction with the main chain type polymer. Although not particularly limited, substituents having the following structure are preferable. * In each structural formula indicates the bonding position.

L is a single bond,> O,> S,> C = O, -OC (= O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene and carbon having 1 to 12 carbon atoms, respectively. It is a polyoxyalkylene of the number 1-12. Among the above substituents, it is represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17). The group represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17) is more preferable.

上記式（ＸＬＳ−１９）中、Ｒ^４１およびＲ^４２は、それぞれ独立して、アルキルであり、Ｒ^４１およびＲ^４２は互いに結合して環を形成してもよい。また、Ｒ^４１およびＲ^４２の合計炭素数は２〜１０であることが好ましい。Further, the reactive substituent other than the above may be chlorine, bromine or iodine, or a boron-containing group represented by the following formula (XLS-19). * In the structural formula indicates the bonding position.

In the above formula (XLS-19), R ⁴¹ and R ⁴² are independently alkyl, and R ⁴¹ and R ⁴² may be bonded to each other to form a ring. Further, the total number of carbon atoms of ^{R 41} and R ^{42 is preferably 2 to 10.}

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

1-2. Method for producing polycyclic aromatic compound represented by general formula (1) For the compound represented by formula (1), an intermediate is first produced by binding rings a to c with a bonding group (−O−). (First reaction), and then the rings a to c are bonded with a binding group (group containing B) to produce the final product (second reaction). In the first reaction, general etherification reactions such as nucleophilic substitution reaction and Ullmann reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. For details of the first and second reactions, the description described in International Publication No. 2015/102118 can be referred to.

The second reaction is a reaction for introducing B (boron) that binds the a ring, the b ring, and the c ring, as shown in the scheme (1) below. First, the hydrogen atom between the two O's is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Next, boron trichloride, boron tribromide, etc. are added, metal exchange of lithium-boron is performed, and then Bronsted bases such as N, N-diisopropylethylamine are added to cause a tandem Bora Friedel-Crafts reaction. You can get things. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.

In the above scheme, lithium was introduced to the desired position by orthometalation, but as in scheme (2) below, a bromine atom or the like was introduced at the position where lithium was to be introduced, and halogen-metal exchange was also performed to bring it to the desired position. Lithium can be introduced.

In order to obtain a compound substituted with halogen or deuterium, these groups may be introduced into the intermediate in advance, or these groups may be introduced after the second reaction.
By appropriately selecting the above-mentioned synthesis method and appropriately selecting the raw material to be used, a compound having a substituent at a desired position and represented by the formula (1) can be synthesized.

1-3. Second Component The organic EL device of the present invention contains a boron-containing polycyclic aromatic compound as a dopant in the light emitting layer as a second component.
The second component contained in the light emitting layer of the organic EL element of the present invention may be a delayed fluorescent substance or a non-delayed fluorescent substance, preferably a delayed fluorescent substance, and more preferably a thermally activated delayed fluorescent substance. preferable.

"Thermal activated delayed fluorescence" absorbs thermal energy to cause an intersystem crossing from the excited triplet state to the excited singlet state, and radiation deactivates from the excited singlet state to cause delayed fluorescence. It means a compound that can emit radiation. However, "thermally activated delayed fluorescence" includes those that undergo higher-order triplets in the excitation process from the excited triplet state to the excited singlet state.
For example, a paper by Monkman et al. Of Durham University (NATURE COMMUNICATIONS, 7: 13680, DOI: 10.1038 / ncomms13680), a paper by Hosogai et al. , A paper by Sato et al. Of Kyoto University (Scientific Reports, 7: 4820, DOI: 10.1038 / s41598-017-05007-7) and a conference presentation by Sato et al. Numbers: 2I4-15, mechanism of high-efficiency luminescence in organic EL using DABNA as a luminescent molecule, Graduate School of Engineering, Kyoto University). In the present invention, when the fluorescence lifetime of a sample containing a target compound is measured at 300 K, a slow fluorescent component is observed, and the target compound is determined to be a “thermally activated delayed fluorescent substance”. .. Here, the slow fluorescence component means a fluorescence component having a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01).

From the molecular orbital calculation, the compound containing a boron atom, which is the second component of the present invention, has the excited triplet energy involved in the forward and reverse intersystem crossing from the excited triplet state to the excited singlet state. It has been pointed out that it may be a higher-order excited triplet energy rather than the excited triplet energy observed by the phosphorescent spectrum (Japan Chemical Society 98th Annual Meeting, Presentation No .: 2I4-15, DABNA). Mechanism of high-efficiency luminescence in organic EL used as a luminescent molecule, presented by Professor Toru Sato of Graduate School of Engineering, Kyoto University). According to the announcement, the inverse intersystem crossing in DABNA2 having a boron atom in the molecule is an FvHT (Fluorescence via Higher Triplet) mechanism using a higher triplet orbit, and the transition from the higher triplet orbit to the ground state is It is suggested that the transition from the higher-order triplet orbital to the excited singlet orbital occurs because it is suppressed.

The excitation singlet energy level obtained from the peak top on the short wavelength side of the fluorescence spectrum of the second component is E (2, S, PT), and the excitation triplet obtained from the peak top on the short wavelength side of the phosphorescence spectrum of the second component. When the term energy level is E (2, T, PT), it is preferable that the singlet triplet energy difference (ΔE (2, ST, PT)) obtained from these has the following relationship.
ΔE (2, ST, PT) = E (2, S, PT) -E (2, T, PT) ≤ 0.20 eV
That is, in the second component, the magnitude of ΔE (ST) is used as an index of TADF activity. The smaller ΔE (ST), the more advantageous it is to exhibit TADF activity.
Here, ΔE (2, ST, PT) is preferably 0.20 eV or less, more preferably 0.15 eV or less, and further preferably 0.10 eV or less.

Intersystem crossing velocity The inverse intersystem crossing velocity indicates the velocity of the inverse intersystem crossing from the excited triplet to the excited singlet. The intersystem crossing velocity of the second component can be calculated by transient fluorescence spectroscopy using the method described in Nat. Commun. 2015, 6, 8476. Or Organic Electronics 2013, 14, 2721-2726. Specifically, reverse intersystem crossing rate of reeds Sting dopant is preferably ¹⁰ 5 ^{s -1} or more, more preferably ¹⁰ 6 ^{s -1} or more.

Luminescence velocity The emission velocity indicates the rate of transition from an excited singlet to the ground state via fluorescence emission without going through the TADF process. The emission velocity of the second component can be calculated using the method described in Nat. Commun. 2015, 6, 8476. Or Organic Electronics 2013, 14, 2721-2726 as in the case of the intersystem crossing velocity. Specifically, the intersystem crossing velocity of the second component is preferably 10 ⁷ s ^-1 or more, and more preferably 10 ⁸ s ^-1 or more.

The polycyclic aromatic compound as the dopant may be a compound other than the one represented by the formula (1), but suitable polycyclic aromatic compounds will be described in detail below.

1-3-1. Polycyclic aromatic compound represented by the general formula (2) and its multimer As one aspect of the dopant which is the second component, the polycyclic aromatic compound represented by the following general formula (2) or its multimer is used. preferable.

In the above formula (3), R ^{1 to} R ¹¹ (hereinafter, ^{also referred to as “R 1} etc.”) are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, respectively. Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen (above, first substituent), at least in these. One hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
Further, ^{adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. Are Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl. It may be substituted with oxy (above, first substituent), and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
Y ¹ is B (boron), and X ¹ and X ² are independently>O,>N-R,>S,> Se or -C (-R) _2- (however. X ¹ and X ² cannot be> O at the same time), the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or 6 to 12 carbon atoms. R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 6 carbon atoms. , The R of> N-R is -O-, -S-, -C (-R') _2- , even if it is bonded to at least one of the a ring, b ring and c ring by a single bond or condensation. Good (note that the R'of the "-C (-R') _2- " is hydrogen, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms).
At least one hydrogen in the compound represented by the general formula (2) may be substituted with cyano, halogen or deuterium.

"Aryl" as a first substituent such as R ^1, "heteroaryl", "diarylamino", "Jiariruboriru (two aryl may be bonded via a single bond or a linking group)", " alkyl "," cycloalkyl "," alkoxy "and" aryloxy ", and" aryl "as a second substituent such as R ^1," heteroaryl "," alkyl "and" cycloalkyl "described above The description of these groups as the first substituent in formula (1) can be cited.
Further, ^{"heteroaryl" in diheteroarylamino as the first substituent of R 1 and the} like and "heteroaryl" in aryl heteroarylamino are descriptions of heteroaryl as the first substituent in the above formula (1). And "aryl" in aryl heteroarylamino can be cited as the description of aryl as the first substituent in the above formula (1).
The ^{"halogen" which is the first substituent such as R 1} is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine.

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron attracting property of the structure of ^{R 1} etc. (first substituent), and at least one of ^{R 1 to} R ^{11 is preferable.} Is a group represented by the following formula, more preferably methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xysilyl, 2,5-. Xyryl, 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, phenyl, o-tolyl, 2,6-xylyl, 2,4. With 6-methicyl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl be. Further, from the viewpoint of ease of synthesis, it is preferable that the steric hindrance is large for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, o-tolyl, and p-tolyl. , 2,4-xylyl, 2,5-xsilyl, 2,6-xsilyl, 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 following structural formula, "Me" stands for methyl, "tBu" stands for t-butyl, "tAm" stands for t-amyl, and "tOct" stands for t-octyl.

^{Adjacent groups of R 1 to} R ¹¹ in the general formula (2) may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of a ring, b ring and c ring, and are generally used. The polycyclic aromatic compound represented by the formula (2) has the following general formulas (2-L1) and (2-L2) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring. As shown, the ring structure constituting the compound changes. The definition of the code in each equation is the same as the definition of the general equation (2).

Formula (2-L1) and a 'ring, b' in the formula (2-L2) rings and c 'ring, the substituents ^R 1 to R ^3, substituents ^R 8 ^{to R 11} and the substituents ^R 4 to R ^{Adjacent groups of 7} are bonded to each other to indicate an aryl ring or a heteroaryl ring formed together with the a ring, the b ring and the c ring, respectively (another ring structure is condensed on the a ring, the b ring or the c ring). It can be said that it is a fused ring. Although not shown in the formula, there are some compounds in which all of the a ring, b ring and c ring are changed to a'ring, b'ring and c'ring. Further, as can be seen from the formulas (2-L1) and (2-L2), for example, R ³ of the a ring and R ^{4 of} the c ring, R ¹¹ of the b ring and R ^{1 of the} a ring are "adjacent". It does not correspond to "groups", and they do not bind. That is, the "adjacent group" means an adjacent group on the same ring. Further, R ⁸ of the b ring and R ⁷ of the c ring do not bond with an adjacent group and do not form a part of the formed aryl ring or heteroaryl ring.

The formed "aryl ring" (a'ring, b'ring or c'ring) or "heteroaryl ring" (a'ring, b'ring or c'ring) is the aryl as the first substituent described above. Or a heteroaryl, unvalued ring. However, since the a ring (or b ring, c ring) forming a part of the a'ring (b'ring or c'ring) is already a benzene ring having 6 carbon atoms, the "aryl ring" is the benzene. The total number of carbon atoms of the condensed ring in which a 5-membered ring is condensed on the ring is 9 as the lower limit, and for the "heteroaryl ring", the total number of carbons of the condensed ring in which the 5-membered ring is condensed on the benzene ring is the lower limit of carbon. It becomes a number.

The compound represented by the formula (2-L1) or the formula (2-L2) is, for example, a benzene ring, an indole ring, a pyrrole ring, or a benzofuran ring, as opposed to a benzene ring which is an a ring (or a b ring or a c ring). Alternatively, it is a compound having an a'ring (or b'ring or c'ring) formed by condensing a benzothiophene ring, and the formed fused ring a'(or fused ring b'or fused ring c') is They are a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

Aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group) that replace the formed aryl ring or heteroaryl ring. (May be), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) that can be further substituted with the first substituent. the), aryl as a first substituent in the above-mentioned R ^1, etc. (first substituent) and the aforementioned equation (1), heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru ( The two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy descriptions can be cited.

^{X 1} and X ² in the general formula (2) are independently>O,>N-R,>S,> Se or -C (-R) _2- , except that X ¹ and X ² Is distinguished from the polycyclic aromatic compound represented by the general formula (1) in that is never> O at the same time.
For X ¹ and X ² , both>N-R,> O and> N-R, or> N-R and> O are preferable, both> O or both> N-R are more preferable, and both> N-R. Is even more preferable.

The R of −C (−R) ₂₋ is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the R of> N—R is carbon. Aryls having 6 to 12 carbon atoms, heteroaryls having 2 to 15 carbon atoms, alkyls having 1 to 6 carbon atoms or cycloalkyls having 3 to 6 carbon atoms can be used as substituents in the above formula (1). A description of aryl, heteroaryl, alkyl or cycloalkyl as the first substituent can be cited.

Further, the R of> N-R is -O-, -S-, -C (-R') _2- , and is bonded to at least one of the a ring, b ring and c ring by a single bond or condensation. May be good. The R of the above-mentioned "-C (-R) _2- " is hydrogen, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
This specification can be expressed by a compound having a ring structure in which N is incorporated into the condensed ring b'and the condensed ring c', which is represented by the following formula (2-L3). That is, for example, it has a b'ring (or c'ring) formed by condensing other rings so as to incorporate N into the benzene ring which is the b-ring (or c-ring) in the general formula (2). It is a compound. The formed fused ring b'(or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.
Further, the above specification can also be expressed by a compound having a ring structure in which N is incorporated into the condensed ring a', which is represented by the following formula (2-L4) or formula (2-L5). That is, for example, it is a compound having an a'ring formed by condensing other rings so as to incorporate N into the benzene ring which is the a ring in the general formula (2). The formed fused ring a'is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring. Each reference numeral in the equations (2-L3) to (2-L5) is the same as the definition in the equation (2).

As the multimer of the polycyclic aromatic compound having a plurality of unit structures represented by the general formula (2), a 2-hexamer is preferable, a 2-3mer is more preferable, and a dimer is further preferable. The multimer may be in a form having a plurality of the above unit structures in one compound, for example, the unit structure is a single bond, an alkylene group having 1 to 3 carbon atoms (for example, a methylene group), a phenylene group, and a naphthylene. In addition to the form in which a plurality of linked groups such as a group are bonded (linked multimer), any ring (a ring, b ring or c ring) included in the unit structure is shared by the plurality of unit structures. It may be in a bonded form (ring-shared multimer), or in a form in which arbitrary rings (a ring, b ring or c ring) included in the unit structure are bonded to each other (ring condensation). It may be a type multimer), but a ring-shared multimer and a ring-condensed multimer are preferable, and a ring-shared multimer is more preferable.
In the unit structure represented by the general formula (1) having a plurality of multimers, R ² is preferably hydrogen.

Examples of such a multimer include the following general formulas (2-4), formulas (2-4-1), formulas (2-4-2), formulas (2-5-1) to formulas (2-5-1). Examples thereof include multimers represented by 5-4) or formula (2-6).
If the multimer represented by the following formula (2-4) is explained by the general formula (2), a plurality of (two in the following structural formula) general formulas are shared so as to share the benzene ring which is the a ring. It is a multimer compound (ring-shared multimer) having a unit structure represented by (2) in one compound.
Further, if the multimer represented by the following formula (2-4-1) is explained by the general formula (2), a plurality of multimers (three in the following structural formula) are shared so as to share the benzene ring which is the a ring. ) Is a multimer compound (ring-shared multimer) having a unit structure represented by the general formula (2) in one compound.
Further, if the multimer represented by the following formula (2-4-2) is explained by the general formula (2), a plurality of multimers (six in the following structural formula) are shared so as to share the benzene ring which is the a ring. ) Is a multimer compound (ring-shared multimer) having a unit structure represented by the general formula (2) in one compound.
Further, the multimeric compounds represented by the following formulas (2-5-1) to (2-5-4) share the benzene ring, which is the c-ring, as described by the general formula (2). Therefore, it is a multimeric compound (ring-shared multimer) having a plurality of unit structures represented by the general formula (2) in one compound.
Further, the multimer represented by the following formula (2-6) is described by the general formula (2), for example, a benzene ring which is a b ring (or a ring or c ring) of a certain unit structure and a certain unit. A multimer compound (ring condensation) having a unit structure represented by a plurality of general formulas (2) in one compound so as to be condensed with a benzene ring which is a b ring (or a ring or c ring) of the structure. Type multimer).
It is preferable that ^{R 2} in each of the following formulas is hydrogen.

The multimer is a quantifier form represented by the formula (2-4), the formula (2-4-1) or the formula (2-4-2), and the formulas (2-5-1) to the formula (2-4-2). It may be a multimer in combination with any of 5-4) or the quantified form represented by the formula (2-6), and formulas (2-5-1) to (2-5-4). ) And the quantified form expressed by the formula (2-6) may be combined, and the quantified form may be a combination of the formulas (2-4) and (2--6). Quantifier form and formula represented by 4-1) or formula (2-4-2) and quantifier form and formula represented by either formula (2-5-1) to formula (2-5-4) It may be a multimer in combination with the quantifier form represented by (2-6).

Further, at least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (2) and its multimer may be substituted with cyano, halogen or deuterium. For example, in the general formula (2), the a ring, the b ring, the c ring, the substituents on these rings, and X ¹ and X ² are> N-R or -C (-R) _2-. At least one hydrogen in R can be replaced with cyano, halogen or deuterium. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

The polycyclic aromatic compound represented by the general formula (2) and its multimer can be produced according to the production method described in International Publication No. 2015/102118. Further, with reference to the method for producing a polycyclic aromatic compound represented by the above formula (1), it is produced by using a general amination reaction such as a Buchwald-Hartwig reaction instead of an etherification reaction in the first reaction. can do.

1-3-2. Preferable Example Example of Polycyclic Aromatic Compound Represented by General Formula (2) and Multimer thereof In one aspect of the dopant which is the second component, in the above general formula (2), R ⁸ is a halogen and has a carbon number of carbon. It is an alkyl of 1 to 6, a cycloalkyl of 3 to 14 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms, and R ⁷ is a hydrogen, an alkyl having 1 to 6 carbon atoms, and a carbon number of carbon atoms. A polycyclic aromatic compound having 3 to 14 cycloalkyls, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms, and a multimer thereof are preferable.

The halogen for R ^8, fluorine, chlorine, bromine or iodine, in view of increasing the spin-orbit interaction by heavy atom effect, large halogen preferably molecular weight, chlorine, bromine and iodine Preferably, chlorine and bromine Is more preferred, and iodine is even more preferred. From the viewpoint of deepening the HOMO / LUMO orbital by introducing an element having a high electronegativity, an element having a high electronegativity is preferable, fluorine, chlorine and bromine are preferable, fluorine and chlorine are more preferable, and fluorine is further preferable.

The alkyl having 1 to 6 carbon atoms of R ⁸ and R ⁷ may be either a straight chain or a branched chain, and an alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is preferable, and the alkyl having 1 to 5 carbon atoms is preferable. Alkyl of 4 (branched chain alkyl having 3 to 4 carbon atoms) is more preferable, and specifically, 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 and the like, with methyl or t-butyl being more preferred. Is even more preferable.
The cycloalkyl having 3 to 14 carbon atoms of R ⁸ and R ⁷ is preferably a cycloalkyl having 3 to 12 carbon atoms, more preferably a cycloalkyl having 5 to 10 carbon atoms, and specifically, cyclopentyl, cyclohexyl, norbornenyl or Adamantyl is preferred, cyclohexyl is more preferred.
The aryls of R ⁸ and R ⁷ having 6 to 10 carbon atoms are preferably phenyl or naphthyl, and more preferably phenyl.
The heteroaryl having 2 to 10 carbon atoms of R ⁸ and R ⁷ includes the same one as the “heteroaryl” of the first substituent of the general formula (1), and has a part structure of a 6-membered ring or a 5-membered ring. Groups are preferred.

As R ^8, and more specifically, the following partial structural formula (m), Formula (e), Formula (v), Formula (t), Formula (h), Formula (p), Formula (q), Formula ( r), Expression (s), Expression (y), Expression (u), Expression (w), Expression (j), Expression (k), Expression (f), Expression (c), Expression (b), Expression ( The groups of i) or formula (n) are preferred, the groups of formula (m), formula (t), formula (p), formula (f) or formula (n) are more preferred, and formula (m) or formula (t). ) Is more preferred.

（上記式中、Ｍｅはメチル、Ｅｔはエチル、ｉＰｒはイソプロピル、ｔＢｕはブチルを示す。）

(In the above formula, Me is methyl, Et is ethyl, iPr is isopropyl, and tBu is butyl.)

For the combination of R ⁸ and R ^{7 , R 8} is a halogen, an alkyl having 1 to 5 (preferably 1 to 4) carbons, a cycloalkyl or phenyl having 5 to 10 carbons, and R ⁷ is. Hydrogen, an alkyl having 1 to 5 (preferably 1 to 4) carbon atoms, a cycloalkyl or phenyl having 5 to 10 carbon atoms is preferable, and the sum of the molecular weights of ^{R 8} and R ^{7 is preferably small.} More preferably, R ⁸ is methyl, t-butyl or phenyl and R ⁷ is hydrogen, methyl, t-butyl or phenyl. It is more preferred that R ⁸ is methyl or t-butyl and R ^{7 is hydrogen or methyl.} It is particularly preferred that R ⁸ is methyl and R ^{7 is hydrogen or methyl.} Most preferably, R ⁸ is methyl and R ⁷ is hydrogen.

From the viewpoint of synthesizing the compound of the general formula (2), ^{it is preferable that R 10} at a symmetrical position of ^{R 8} is a group other than hydrogen, and it is more preferable that ^{R 8} and R ^{10 are the same group.} Similarly, when R ⁷ is a group other than ^{hydrogen, it is preferable that R 5} at a symmetrical position of ^{R 7} is also a group other than hydrogen, and it is more preferable that ^{R 7} and R ^{5 are the same group.}

Further, in this embodiment, when ^{at least one of X 1} and X ² in the general formula (2) is> N-R, the R of> N-R is aryl, heteroaryl, alkyl or cycloalkyl. , The above partial structural formula (m), formula (e), formula (v), formula (t), formula (h), formula (p), formula (q), formula (r), formula (s), formula. It is preferably the basis of (y), formula (u), formula (w), formula (j) or formula (k), of formula (p), formula (q), formula (r), formula (s). , Y, more preferably a group of formula (u) or formula (w), even more preferably a group of formula (p), formula (q) or formula (r), more preferably formula (p). ) Is particularly preferable.

The polycyclic aromatic compound of this embodiment and its multimer can be produced according to the production method described in WO2015 / 102118. Further, with reference to the method for producing a polycyclic aromatic compound represented by the above formula (1), it is produced by using a general amination reaction such as a Buchwald-Hartwig reaction instead of an etherification reaction in the first reaction. can do.

1-3-3. Preferable Example Example of Multimer of Polycyclic Aromatic Compound Represented by General Formula (2) As one aspect of the dopant which is the second component, two partial structures represented by the general formula (2) and the said A dimeric compound consisting of a linking group L1 that connects the two partial structures is preferable.
The linking group L1 is a single bond, an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, and an alkynylene having 1 to 6 carbon atoms. -O-, -S-,> N-R, or a combination thereof, and the R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and 1 to 1 carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in the dimeric compound may be substituted with cyano, halogen or dehydrogen.

Regarding "arylene", "heteroarylene" and "alkylene" in the linking group L1, the description of "aryl", "heteroaryl" and "alkyl" of the first substituent in the above formula (1) will be described from these groups. Further, it can be quoted instead of the explanation as a divalent group represented by excluding any one hydrogen atom.
Also, "alkenylene" is a group having one or more -C = C- groups in the alkylene, and "alkynylene" has one or more -C≡C- groups in the alkylene. _{As a group, one or more -CH 2} -groups can be replaced with -C = C- group or -C≡C- group, respectively, in the above description of "alkylene".

"Aryl", "heteroaryl", "alkyl" and "cycloalkyl" as R> N-R in linking group L1 and "aryl", "heteroaryl" substituted with at least one hydrogen in linking group L1 , "Alkyl" and "Cycloalkyl", the description of the first substituents "aryl", "heteroaryl", "alkyl" and "cycloalkyl" in the above formula (1) can be cited.

The linking group L1 is an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, an alkynylene having 1 to 6 carbon atoms, −O−, and the linking group L1. It may be a group formed by combining at least one group selected from the group consisting of −S− and> N—R.
The bonding location between the connecting group L1 and the partial structure represented by the formula (2) is arbitrary.

Also, at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium. For example, in the formula (2), when the a ring, the b ring, the c ring, the substituents to these rings, and X ¹ and X ² are> N-R or -C (-R) _2-. At least one hydrogen in R of the above can be substituted, and among these, an embodiment in which all or a part of hydrogen in aryl or heteroaryl is substituted can be mentioned.

In the intermediate compound of this embodiment, after producing a polycyclic aromatic compound corresponding to the partial structure represented by the general formula (2), the two polycyclic aromatic compounds are bonded at the linking group L1 by a known method. Alternatively, it is produced by bonding two intermediates for forming a polycyclic aromatic compound with a linking group L1 and then polycyclic aromaticizing the two intermediate portions bonded with the linking group L1. be able to.

1-3-4. Preferable Specific Examples of Polycyclic Aromatic Compounds Represented by General Formula (2) and Multimers thereof Specific examples of the polycyclic aromatic compounds represented by general formula (2) include Japanese Patent Application No. 2017-199617. , Japanese Patent Application No. 2018-107092, International Application No. PCT / JP2015 / 054426, International Application No. PCT / JP2017 / 001089, and the compounds described in the specification are mentioned, and the compounds shown below are preferable.

1-3-5. As one aspect of the dopant which is the second component of the polycyclic aromatic compound represented by the general formula (3), the polycyclic aromatic compound represented by the following general formula (3) is preferable. The polycyclic aromatic compound represented by the general formula (3) corresponds to a dimer of the polycyclic aromatic compound having two unit structures represented by the general formula (2) described above.

In the above formula (3), R ^{3 to} R ¹² , Z ¹ and Z ² (hereinafter, ^{also referred to as “R 3} etc.”) are independently hydrogen, aryl, heteroaryl, diarylamino, and diheteroarylamino. , Aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen (above, first substituent). At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
Further, ^{adjacent groups of R 5 to} R ⁷ and R ^{10 to} R ¹² may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the b ring and the d ring. At least one hydrogen in the ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl. , Cycloalkyl, alkoxy or aryloxy (above, first substituent), at least one hydrogen in these may be aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent). It may be replaced.
Z ¹ may be bonded to the a ring with a linking group or a single bond, and Z ² may be bonded to the c ring with a linking group or a single bond.
Y is B (boron), and X ¹ , X ² , X ³ and X ⁴ are independently>O,>N-R,>S,> Se or -C (-R) _2- . Yes (however, X ¹ and X ² are not> O at the same time, and X ³ and X ⁴ are not> O at the same time), and the R of −C (−R) ₂₋ is carbon. It is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms and a heteroaryl having 2 to 15 carbon atoms. , Alkyl with 1 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms, and the R of the> N-R is -O-, -S-, -C (-R') _2- , single bond. Alternatively, it may be bonded to at least one of the a ring, b ring, c ring and d ring by condensation (note that R'of the "-C (-R') _2- " is hydrogen or 1 to 1 carbon atoms. It is an alkyl of 5 or a cycloalkyl of 5 to 10 carbon atoms).
R ¹ and R ² are independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and diarylamino. (However, aryl is an aryl having 6 to 12 carbon atoms) or diarylboryl (where an aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group). , At least one hydrogen in the compound represented by the formula (3) may be substituted with cyano, halogen or hydrocarbon.

"Aryl" as a first substituent such as R ^3, "heteroaryl", "diarylamino", "Jiariruboriru (two aryl may be bonded via a single bond or a linking group)", " alkyl "," cycloalkyl "," alkoxy "and" aryloxy ", and" aryl "as a second substituent such as R ^1," heteroaryl "," alkyl "and" cycloalkyl "described above The description of these groups as the first substituent in formula (1) can be cited.
Further, "heteroaryl" in "heteroaryl", aryl heteroarylamino in diheteroarylamino as a first substituent such as R ³ is an explanatory heteroaryl as a first substituent in formula (1) described above And "aryl" in aryl heteroarylamino can be cited as the description of aryl as the first substituent in the above formula (1).
A first substituent such as R ³ "halogen", fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

^{Z 1} and Z ² in the above formula (3) are independently aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), at least one hydrogen in these is aryl, heteroaryl, alkyl or cycloalkyl. It may be substituted with (above, the second substituent).

Substituents of ring b in the general formula (3) R ^{5 to} R ⁷ and at least one of ring substituents R ^{10 to} R ¹² Adjacent groups are bonded to each other to form at least one of ring b and ring d. It may form an aryl ring or a heteroaryl ring together with it.
Therefore, the polycyclic aromatic compound represented by the general formula (3) can be represented by the following general formula (3-L1) depending on the mutual bonding form of the substituents on the b ring and the d ring. The constituent ring structure changes. The b'ring and d'ring in the formula (3-L1) correspond to the b-ring and the d-ring in the general formula (3), respectively. Further, the definition of each code in the formula (3-L1) is the same as the code in the general formula (3).

In the b'ring and d'ring in the above formula (3-L1) ^{, adjacent groups of the substituents R 5 to R 7} of the b ring and the substituents R ^{10 to} R ¹² of the d ring are bonded to each other. , An aryl ring or a heteroaryl ring formed together with the b ring and the d ring, respectively (it can also be said to be a fused ring formed by condensing another ring structure with the b ring or the d ring).
Further, as can be seen from the above formula (3-L1), R ⁷ of the b ring and R ¹² of the d ring in the formula (3) do not correspond to "adjacent groups", and they do not bond with each other. .. That is, the "adjacent group" means an adjacent group on the same ring.

Z ¹ may be bonded to the a ring with a linking group or a single bond, and Z ² may be bonded to the c ring with a linking group or a single bond. The ring structure will change in the same way as the d'ring.
The linking group which bonds the Z ¹ and a ring, and, as the linking group which bonds the ^{Z 2} and c rings, each independently, -O -, - S-, or -C (-R _{') 2} - The R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 6 carbon atoms.

The formed "aryl ring" (b'ring or d'ring) or "heteroaryl ring" (b'ring or d'ring) is the unvalued of the aryl or heteroaryl as the first substituent described above. It is a ring. However, since the b ring or c ring that forms part of the b'ring or c'ring is already a benzene ring having 6 carbon atoms, the "aryl ring" is a fused ring in which a 5-membered ring is condensed with the benzene ring. The total number of carbon atoms of 9 is the lower limit of the number of carbon atoms, and for the "heteroaryl ring", the total number of carbon atoms of the fused ring in which a 5-membered ring is condensed with the benzene ring is the lower limit of the number of carbon atoms.

The compound represented by the formula (3-L1) is formed by condensing, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring with a benzene ring which is a b ring or a c ring. It is a compound having a ring or a c'ring, and the formed fused ring b'or fused ring c'is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

Aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group) that replace the formed aryl ring or heteroaryl ring. (May be), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) that can be further substituted with the first substituent. the), aryl as a first substituent in the above-mentioned R ³ or the like (first substituent) and the aforementioned equation (1), heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru ( The two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy descriptions can be cited.

^{X 1} , X ² , X ³ and X ⁴ in the general formula (3) are independently>O,>N-R,>S,> Se or -C (-R) _2- , wherever. , X ¹ and X ² are not> O at the same time, and X ^{3 and X 4} are not> O at the same time.
The -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the R of> N-R has 6 carbon atoms. Aryls having ~ 12 carbon atoms, heteroaryls having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyls having 3 to 6 carbon atoms. A description of aryl, heteroaryl, alkyl or cycloalkyl as substituents can be cited.

Further, R of> N-R is bonded to at least one of the a ring, b ring, c ring and d ring by -O-, -S-, -C (-R') _{2-, single bond or condensation.} You may be doing it. The R'of the "-C (-R') _2- " is hydrogen, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
^{This specification can be expressed by a compound having a ring structure in which X 1} and X ³ are incorporated into the condensed ring b'and the condensed ring d', which are represented by the following formula (3-L2). That is, for example, the b'ring (or ring) formed by condensing other rings so as to incorporate ^{X 1} (or X ³ ) into the benzene ring which is the b ring (or d ring) in the general formula (3). It is a compound having a d'ring).
The formed fused ring b'(or condensed ring d') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, an acridine ring, or the like. The definition of each code in the formula (3-L2) is the same as the definition in the general formula (3).

The formula (3-L2) ^{shows a ring structure in which X 1} and X ³ are incorporated into the fused ring b'and the condensed ring d', but the same applies to R of> N-R as ^{X 2} and X ^4. Can be bonded to the a ring and the c ring, and when bonded, the ring structure changes in the same manner as the b'ring and the d'ring.

^{R 1} and R ² in the general formula (3) are independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 12 carbon atoms, and 2 to 15 carbon atoms, respectively. Heteroaryl, diarylamino (where aryl is an aryl with 6-12 carbons) or diarylboryl (where aryl is an aryl with 6-12 carbons and the two aryls are attached via a single bond or a linking group. However, it is preferably hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms.
These substituents are alkyl, cycloalkyl, aryl, heteroaryl, diarylamino or diarylboryl as the first substituent in the above formula (1) (two aryls are bonded via a single bond or a linking group). You can quote the explanation.

Further, at least one hydrogen in the polycyclic aromatic compound represented by the general formula (3) may be substituted with cyano, halogen or deuterium. For example, in the formula (3), the a ring, the b ring, the c ring, the d ring, the substituents to these rings, and X ^{1 to} X ⁴ are> N-R or -C (-R) _2-. At least one hydrogen in R can be replaced with cyano, halogen or deuterium. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.

Specific examples of the polycyclic aromatic compound represented by the general formula (3) include the compounds described in the specification of International Application No. PCT / JP2018 / 018731, and the compounds shown below are preferable.

The polycyclic aromatic compound represented by the general formula (3) applies the production method described in International Publication No. 2015/102118, and the polycyclic aromatic compound represented by the above formula (1) and It can be produced with reference to the method for producing the multimer.
The polycyclic aromatic compound represented by the general formula (3) basically produces an intermediate by binding the ring structures to each other (first reaction), and then forms each ring structure. The final product can be produced by bonding with a boron atom (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction, or a general amination reaction such as a Buchwald-Hartwig reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction) can be used.

1-3-6. As one aspect of the polycyclic aromatic compound represented by the general formula (4) or the dopant which is the second component of the multimer thereof, the polycyclic aromatic compound represented by the following general formula (4) or a multimer thereof is preferable. .. The polycyclic aromatic compound represented by the general formula (4) is one of the compounds having a ring structure in which N is incorporated into the condensed ring c'as represented by the above-mentioned formula (2-L3). It is one.

In the above formula (4), R ^{1 to} R ³ and R ^{5 to} R ¹⁵ (hereinafter, ^{also referred to as “R 1} etc.”) are independently hydrogen, aryl, heteroaryl, diarylamino, and diheteroarylamino. , Aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen (above, first substituent). At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
In addition, ^{adjacent groups of R 1 to} R ³ , R ^{5 to} R ⁷ , R ^{8 to} R ¹¹ and R ^{12 to} R ¹⁵ are bonded to each other to form at least one of a ring, b ring, c ring and d ring. They may form an aryl ring or a heteroaryl ring together, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls). May be attached via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy (above, the first substituent), and at least one hydrogen in these may be aryl. , Heteroaryl, alkyl or cycloalkyl (above, second substituent) may be substituted.
Y ¹ is B (boron), X is>O,>N-R,>S,> Se or -C (-R) _2- , and R of -C (-R) _2- Is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms and 2 to 15 carbon atoms. Heteroaryl, alkyl with 1 to 6 carbons or cycloalkyl with 3 to 6 carbons,
L is a single bond, -C (-R) ₂ -,>O,> S or> N-R, and R in -C (-R) _2- and> N-R is independent of each other. , Hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent). ), Which may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituents), where L is> O when X is> N-R. There is no such thing.
In the case of multimers, R ² in formula (4) is hydrogen, and even if at least one hydrogen in the compound and structure represented by general formula (4) is substituted with cyano, halogen or deuterium. good.

"Aryl" as a first substituent such as R ¹ in the formula (4), "heteroaryl", "diarylamino", "Jiariruboriru (two aryl is bonded via a single bond or a linking group may also be) "," alkyl "," cycloalkyl "," alkoxy "and" aryloxy ", and" aryl "as a second substituent such as R ^1," heteroaryl "," alkyl "and" cyclo "Aryl" can be cited as a description of these groups as the first substituent in the above formula (1).
Further, the formula "heteroaryl" in diheteroarylamino as a first substituent such as R ¹ in (4), "heteroaryl" in the aryl heteroarylamino, the first substituent in formula (1) described above The description of the heteroaryl as the above can be cited, and the "aryl" in the aryl heteroarylamino can be cited as the description of the aryl as the first substituent in the above formula (1).
A first substituent such as R ¹ in the formula (4) "halogen", fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

As the more preferred group of the first substituent such as R ¹ in the formula (4), it may be cited to the description of preferred groups of the first substituent such as R ¹ in the formula (1) ..

^{Adjacent groups of R 1 to} R ³ , R ^{5 to} R ⁷ , R ^{8 to} R ¹¹ and R ^{12 to} R ^{15 in} the general formula (4) are bonded to each other to form a ring, b ring, c ring and d. An aryl ring or a heteroaryl ring may be formed together with at least one of the rings, and the polycyclic aromatic compound represented by the general formula (4) is a substituent in the a ring, b ring, c ring and d ring. As shown in the following general formulas (4-L1), general formulas (4-L2) and general formulas (4-L3), the ring structure constituting the compound changes depending on the mutual bonding form of the compounds. The definition of the code in each equation is the same as the definition of the general equation (4).

Equation (4-L1) ~ formula (4-L3) in a 'ring, b' ring, c 'ring and d' ring, the substituents ^R 1 to R ^3, substituents ^R 5 to R ^7, substituents An aryl ring or a heteroaryl ring formed by bonding adjacent groups of R ^{8 to} R ¹¹ and substituents R ^{12 to} R ¹⁵ together with at least one of a ring, b ring, c ring and d ring, respectively. (It can also be said to be a fused ring formed by condensing another ring structure on the a ring, b ring, c ring or d ring). Although not shown in the formula, there are other combinations such as compounds in which all of the a ring, b ring, c ring and d ring are changed to a'ring, b'ring, c'ring and d'ring. .. Further, as can be seen from the formulas (4-L1) to (4-L3), for example, R ¹ of the a ring and R ^{11 of} the b ring, R ⁸ of the b ring and R ^{7 of} the c ring, and R of the c ring. ⁵ and R ¹⁵ of d-ring, R ^{12 of d-ring and R 3 of} a-ring do not correspond to "adjacent groups", and they do not bond with each other. That is, the "adjacent group" means an adjacent group on the same ring.

The formed "aryl ring" (a'ring, b'ring, c'ring or d'ring) or "heteroaryl ring" (a'ring, b'ring, c'ring or d'ring) is described above. It is an unvalued ring of aryl or heteroaryl as the first substituent. However, since the a ring (b ring, c ring or d ring) forming a part of the a'ring (b'ring, c'ring or d'ring) is already a benzene ring having 6 carbon atoms, "aryl" is used. For the "ring", the total carbon number of the fused ring in which the 5-membered ring is condensed with the benzene ring is the lower limit of carbon number 9, and for the "heteroaryl ring", the total carbon of the fused ring in which the 5-membered ring is condensed with the benzene ring. The number 6 is the lower limit of the number of carbon atoms.

The compounds represented by the formulas (4-L1) to (4-L3) are, for example, a benzene ring, an indole ring, a pyrrole ring, etc. It is a compound having an a'ring (b'ring, c'ring or d'ring) formed by condensing a benzofuran ring or a benzothiophene ring, and the formed fused ring a'(fused ring b', fused ring). c'or fused ring d') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

Aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group) that replace the formed aryl ring or heteroaryl ring. (May be), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) that can be further substituted with the first substituent. the), aryl as a first substituent in the above-mentioned R ^1, etc. (first substituent) and the aforementioned equation (1), heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru ( The two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy descriptions can be cited.

In the general formula (4), Y ¹ is B (boron), X is>O,>N-R,>S,> Se or -C (-R) _2- , and> O and> N. -R is preferable.
The R of −C (−R) ₂₋ is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the R of> N—R is , Aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms. ), The description of aryl, heteroaryl, alkyl or cycloalkyl as the first substituent can be cited.

L in the general formula (4) is a single bond, -C (-R) ₂ -,>O,> S and> N-R, preferably a single bond,> O or> N-R, and the single bond is preferable. More preferred.
Aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, which are R of -C (-R) _{2- and> N-R.} , Cycloalkyl, alkoxy or aryloxy (above, first substituent), and aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) further substituting for the first substituent are described above. Aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl as the first substituent in formula (1). You can quote the explanation of Oxy.

The compound represented by the formula (4) does not include a compound in which X is> N-R and L is> O.

As the multimer of the polycyclic aromatic compound having a plurality of unit structures represented by the general formula (4), a 2-hexamer is preferable, a 2-3mer is more preferable, and a dimer is further preferable. The multimer may be in the form of having a plurality of the above unit structures in one compound. For example, the multimer has a single bond, an alkylene group having 1 to 3 carbon atoms (for example, a methylene group), a phenylene group, and a naphthylene group. In addition to the form in which a plurality of bonds are bonded by a linking group such as (linked multimer), any ring (a ring, b ring, c ring or d ring) included in the unit structure is shared by the plurality of unit structures. It may be in the form of a bond (ring-shared multimer), or any ring (a ring, b ring, c ring or d ring) contained in the unit structure may be bonded to each other in a condensed manner. The form (ring-condensed multimer) may be used, but a ring-shared multimer and a ring-condensed multimer are preferable, and a ring-condensed multimer is more preferable.
In the unit structure represented by the general formula (4) having a plurality of multimers, R ² is hydrogen.

Examples of such a multimer include the following general formula (4-4), formula (4-5-1), formula (4-5-2), formula (4-6-1) or formula (4-6-1). Examples thereof include multimers represented by 6-2).
If the multimer represented by the following formula (4-4) is explained by the general formula (4), a plurality of (two in the following structural formula) general formulas are shared so as to share the benzene ring which is the a ring. It is a multimer compound (ring-shared multimer) having a unit structure represented by (4) in one compound.
Further, the multimers represented by the following formulas (4-5-1) and (4-5-2) share the benzene ring, which is the b ring, according to the general formula (4). , A multimeric compound (ring-shared multimer) having a plurality of (two in the following structural formula) unit structures represented by the general formula (1) in one compound.
Further, the multimers represented by the following formulas (4-6-1) and (4-6-2) can be described by the general formula (4), for example, a ring (b ring, c) having a certain unit structure. A plurality of (two in the following structural formula) general, such that a benzene ring (ring or d-ring) and a benzene ring (b-ring, c-ring or d-ring) having a certain unit structure are condensed. It is a multimer compound (ring-condensation type multimer) having a unit structure represented by the formula (4) in one compound.
^{R 2} in each of the following equations is hydrogen.

The multimer is a multimer obtained by combining the quantified form represented by the formula (4-4) and the quantified form represented by the formula (4-5-1) or the formula (4-5-2). It may be, and the quantifier form represented by the formula (4-4), the formula (4-5-1) or the formula (4-5-2), and the formula (4-6-1) or the formula ( It may be a multimer in combination with the quantifier form represented by 4-6-2).

Further, at least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (4) and its multimer may be substituted with cyano, halogen or deuterium. For example, in the general formula (4), when the a ring, the b ring, the c ring, the d ring, the substituents to these rings, and X are> N-R or -C (-R) _2-. At least one hydrogen in R when R, L is −C (−R) _2- or> N—R can be replaced with cyano, halogen or deuterium. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

In the above general formula (4), one of R ⁷ and R ⁸ is halogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 10 carbon atoms, or 2 to 2 carbon atoms. Heteroaryl of 10 (hereinafter also referred to as "Z substituent"), the other is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl or aryl having 6 to 10 carbon atoms or carbon number. It is preferably 2 to 10 heteroaryls.
Further, in this case, R ⁸ of the b ring and R ⁷ of the c ring do not bond with the adjacent group and do not form a part of the formed aryl ring or heteroaryl ring. Further, it is preferable that the "one" is R ⁸ and the "other" is R ^7.

The halogens of R ⁷ and R ⁸ are fluorine, chlorine, bromine or iodine. From the viewpoint of increasing spin-orbit interaction due to the heavy atom effect, halogens having a large molecular weight are preferable, chlorine, bromine and iodine are preferable, chlorine and bromine are more preferable, and iodine is further preferable. From the viewpoint of deepening the HOMO / LUMO orbital by introducing an element having a high electronegativity, an element having a high electronegativity is preferable, fluorine, chlorine and bromine are preferable, fluorine and chlorine are more preferable, and fluorine is further preferable.

The alkyl having 1 to 6 carbon atoms of R ⁷ and R ⁸ may be either a straight chain or a branched chain, and an alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is preferable, and the alkyl having 1 to 5 carbon atoms is preferable. Alkyl of 4 (branched chain alkyl having 3 to 4 carbon atoms) is more preferable, and specifically, 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 and the like, with methyl or t-butyl being more preferred. Is even more preferable.
The cycloalkyl having 3 to 14 carbon atoms of R ⁷ and R ⁸ is preferably a cycloalkyl having 3 to 12 carbon atoms, more preferably a cycloalkyl having 5 to 10 carbon atoms, and specifically, cyclopentyl, cyclohexyl, norbornenyl or Adamantyl is preferred, cyclohexyl is more preferred.
The aryls of R ⁷ and R ⁸ having 6 to 10 carbon atoms are preferably phenyl or naphthyl, and more preferably phenyl.
The heteroaryl having 2 to 10 carbon atoms of R ⁷ and R ⁸ includes the same group as the "heteroaryl" of the first substituent of the general formula (1), and has a partial structure of a 6-membered ring or a 5-membered ring. Groups are preferred.

The Z substituents include the following partial structural formulas (m), formulas (e), formulas (v), formulas (t), formulas (h), formulas (p), formulas (q), and formulas (r). , Expression (s), expression (y), expression (u), expression (w), expression (j), expression (k), expression (f), expression (c), expression (b), expression (i). Alternatively, a group of formula (n) is preferred, a group of formula (m), formula (t), formula (p), formula (f) or formula (n) is more preferred, of formula (m) or formula (t). Groups are even more preferred.

（上記式中、Ｍｅはメチル、Ｅｔはエチル、ｉＰｒはイソプロピル、ｔＢｕはブチルを示す。）

(In the above formula, Me is methyl, Et is ethyl, iPr is isopropyl, and tBu is butyl.)

From the viewpoint of shortening the delayed fluorescence lifetime and expressing the TADF mechanism by giving strain to the molecule, it is preferable that both ^{R 7} and R ^{8 are Z substituents.} From the viewpoint of obtaining high PLQY and the stability of the molecule, it is preferable that only one of ^{R 7} and R ^{8 is a Z substituent.} From the viewpoint of ease of synthesis, ^{it is preferable that R 8} is a Z substituent.

From the viewpoint of ease of synthesis, it is preferable to have a substituent at ^{R 10 when R 8} is a Z substituent ^{, and similarly, when R 7} is a Z substituent, it is at least one of ^{R 5} and R ^13. It is preferable to have a substituent, and similarly, when R ⁵ is a Z substituent, it is preferable to have a substituent at at least one of ^{R 7} and R ^14.
Further, from the viewpoint of ease of synthesis and stability, it is preferable that the substituent is small, and the above formulas (m), (e), formula (v), formula (t), formula (h), and formula (p) are preferable. ), Expression (q), Expression (r), Expression (s), Expression (j), Expression (k), Expression (f), Expression (c), Expression (b), Expression (i) and Expression (n). ) Is preferable, and among these, the groups of the formula (m), the formula (e), the formula (v), the formula (t), the formula (p), the formula (f) and the formula (n) are more preferable. The groups of formula (m) and formula (t) are more preferred, and the groups of formula (m) are most preferred.

The combination of R ⁷ and ^{R 8,} among the ^{R 7} and ^{R 8,} one of halogen, alkyl of 1 to 5 carbon atoms (preferably 1 to 4), cycloalkyl, or phenyl having 5 to 10 carbon atoms The other is hydrogen, an alkyl having 1 to 5 (preferably 1 to 4) carbon atoms, a cycloalkyl or phenyl having 5 to 10 carbon atoms, and the sum of the molecular weights of ^{R 7} and R ^{8 is small.} Is preferable. Further, it is more preferable that one is methyl, t-butyl or phenyl and the other is hydrogen, methyl, t-butyl or phenyl. Further, it is more preferable that one is methyl or t-butyl and the other is hydrogen or methyl. Further, it is particularly preferable that one is methyl and the other is hydrogen or methyl. Most preferably, one is methyl and the other is hydrogen. Further, it is preferable that the "one" is R ⁸ and the "other" is R ^7.

From the viewpoint of synthesizing the compound of the general formula (4), ^{it is preferable that R 10} at a symmetrical position of ^{R 8} is a group other than hydrogen, and it is more preferable that ^{R 8} and R ^{10 are the same group.} Similarly, when R ⁷ is a group other than ^{hydrogen, it is preferable that R 5} at a symmetrical position of ^{R 7} is also a group other than hydrogen, and it is more preferable that ^{R 7} and R ^{5 are the same group.}

Specific examples of the polycyclic aromatic compound represented by the general formula (4) and its multimer include the compounds described in the specification of Japanese Patent Application No. 2018-110876, and the compounds shown below are preferable.

The polycyclic aromatic compound represented by the formula (4) and its multimer can be produced by applying the production method described in International Publication No. 2015/102118.
That is, as shown in the scheme below ^{, an intermediate having one} Z group is synthesized and cyclized by a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction) to obtain a desired polycyclic fragrance. Group compounds and their multimers can be synthesized. In the scheme below, Z ¹ represents halogen or hydrogen, and the definitions of the other symbols are the same as those described above.

The pre-cyclization intermediate in the above scheme can also be similarly synthesized by the method shown in International Publication No. 2015/102118 and the like. That is, an intermediate having a desired substituent can be synthesized by appropriately combining a Buchwald-Hartwig reaction, a Suzuki coupling reaction, an etherification reaction by a nucleophilic substitution reaction, an Ullmann reaction, or the like.

1-3-7. As one aspect of the polycyclic aromatic compound represented by the general formula (5) or the dopant which is the second component of the multimer thereof, the polycyclic aromatic compound represented by the following general formula (5) or a multimer thereof is preferable. ..

In the above formula (5), R ^{1 to} R ⁹ (hereinafter, ^{also referred to as “R 1} etc.”) are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, respectively. Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen (above, first substituent), at least in these. One hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent).
Further, ^{adjacent groups of R 1 to} R ⁹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of a ring, b ring and c ring, and the formed ring may be formed. At least one hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy or aryloxy (above, first substituent), and at least one hydrogen in these is substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent). May be good.
Y ¹ is B (boron) and X ¹ , X ² and X ³ are independently>O,>N-R,>S,> Se or -C (-R) _2- . (At ^{least two of X 1} , X ² and X ³ are N-R), the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms and a cyclo having 3 to 14 carbon atoms. It is an alkyl or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or 3 to 6 carbon atoms. The R of the> N-R is -O-, -S-, -C (-R') _2- , at least of the a ring, b ring and c ring by single bond or condensation. It may be bonded to one (note that the R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms).
At least one hydrogen in the compound represented by the general formula (5) may be substituted with cyano, halogen or deuterium.

"Aryl" as a first substituent such as R ¹ in the formula (5), "heteroaryl", "diarylamino", "Jiariruboriru (two aryl is bonded via a single bond or a linking group may also be) "," alkyl "," cycloalkyl "," alkoxy "and" aryloxy ", and" aryl "as a second substituent such as R ^1," heteroaryl "," alkyl "and" cyclo "Aryl" can be cited as a description of these groups as the first substituent in the above formula (1).
Further, the formula "heteroaryl" in diheteroarylamino as a first substituent such as R ¹ in (5), "heteroaryl" in the aryl heteroarylamino, the first substituent in formula (1) described above The description of the heteroaryl as the above can be cited, and the "aryl" in the aryl heteroarylamino can be cited as the description of the aryl as the first substituent in the above formula (1).
A first substituent such as R ¹ in the formula (5) "halogen", fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

^{Adjacent groups of R 1 to} R ⁹ in the general formula (5) may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of a ring, b ring and c ring. The polycyclic aromatic compound represented by the formula (5) has the following general formulas (5-L1) and (5-L2) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring. As shown, the ring structure constituting the compound changes. The definition of the code in each equation is the same as the definition of the general equation (5).

Equation (5-L1) and a 'ring, b' in the formula (5-L2) rings and c 'ring, and adjacent groups are bonded of the substituents ^R 1 to R ^9, respectively a ring , An aryl ring or a heteroaryl ring formed together with the b ring and the c ring (it can also be said to be a fused ring formed by condensing another ring structure with the a ring, the b ring or the c ring). Although not shown in the formula, there are other combinations such as compounds in which all of the a ring, b ring and c ring are changed to a'ring, b'ring and d'ring. As can be seen from the above equation (5-L1) and formula (5-L2), for example, of a ring ^{R 1} and b rings ^R 9, the b ring ^{R 7} and c rings ^R 6, the c ring R ⁴ and R ^{3 of the} a ring do not correspond to "adjacent groups", and they do not bond with each other. That is, the "adjacent group" means an adjacent group on the same ring.

The formed "aryl ring" (a'ring, b'ring or c'ring) or "heteroaryl ring" (a'ring, b'ring or c'ring) is the aryl as the first substituent described above. Or a heteroaryl, unvalued ring. However, since the a ring (b ring or c ring) forming a part of the a'ring (b'ring or c'ring) is already a benzene ring having 6 carbon atoms, the "aryl ring" is the benzene ring. The total number of carbon atoms of the condensed ring in which the 5-membered ring is condensed is the lower limit of carbon number 9, and for the "heteroaryl ring", the total number of carbon atoms of the condensed ring in which the 5-membered ring is condensed with the benzene ring is the lower limit of the number of carbon atoms. It becomes.

The compounds represented by the formulas (5-L1) and (5-L2) are, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzofuran ring with respect to a benzene ring which is an a ring (b ring or c ring). It is a compound having an a'ring (b ring or c ring) formed by condensing a benzothiophene ring, and the formed fused ring a'(fused ring b'or fused ring c') is a naphthalene ring and a carbazole ring, respectively. It is a ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

Aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are attached via a single bond or a linking group) that replace the formed aryl ring or heteroaryl ring. (May be), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) that can be further substituted with the first substituent. the), aryl as a first substituent in the above-mentioned R ^1, etc. (first substituent) and the aforementioned equation (1), heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, Jiariruboriru ( The two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy descriptions can be cited.

^{Y 1} in the general formula (5) is B (boron), and X ¹ , X ² and X ³ are independently>O,>N-R,>S,> Se or -C (-). _{R) 2} - a the proviso ^that at least two of X 1, ^{X 2} and ^{X 3} is ^N-R, it is preferable three of X 1, ^{X 2} and ^{X 3} is a N-R.

The -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the R of> N-R is carbon. Aryls having 6 to 12 carbon atoms, heteroaryls having 2 to 15 carbon atoms, alkyls having 1 to 6 carbon atoms or cycloalkyls having 3 to 6 carbon atoms can be used as substituents in the above formula (1). A description of aryl, heteroaryl, alkyl or cycloalkyl as the first substituent can be cited.

Further, the R of> N-R is -O-, -S-, -C (-R') _2- , and is bonded to at least one of the a ring, b ring and c ring by a single bond or condensation. May be good. The R'of the "-C (-R') _2- " is hydrogen, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
This regulation is a compound having a ring structure in which N at the position of ^{X 2} or X ¹ of the formula (5) is incorporated into the condensed ring b'and the condensed ring c', which is represented by the following formula (5-L3). Can be expressed. That is, for example, b formed by condensing other rings so as to incorporate N at the position of ^{X 1} (or X ² ) with respect to the benzene ring which is the b ring (or c ring) in the general formula (5). A compound having a'ring (or c'ring). The formed fused ring b'(or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or a phenophosfazine ring.
Further, the above specification has a ring structure in which N at at least one position of ^{X 1} and X ² is incorporated into the fused ring a', which is represented by the following formula (5-L4) or formula (5-L5). It can also be expressed as a compound. That is, for example, a'formed by condensing other rings so as to incorporate N at the position of ^{X 1} (and ^{at least one of X 2} ) with respect to the benzene ring which is the a ring in the general formula (5). It is a compound having a ring. The formed fused ring A'is, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or a phenothiazine ring.
Each reference numeral in the equations (5-L3) to (5-L5) is the same as the definition in the equation (5).

Although not described specifically, the above provisions, N-R a R a X ³ is also included at least one bound forms of b rings and c ring linking group or a single bond. For example, compounds having a b ring (or c ring) in which b 'ring (or c' which as capture X ³ with respect to the benzene ring other rings are formed by condensing ring) in the general formula (5) Is. The formed fused ring b'(or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or a phenophosfazine ring.
In addition, the above specification ^{also includes a form in which X 1} , X ² or X ³ is incorporated into any of the fused rings.

As the multimer of the polycyclic aromatic compound having a plurality of unit structures represented by the general formula (5), a 2-hexamer is preferable, a 2-3mer is preferable, and a dimer is more preferable. The multimer may be in a form having a plurality of the above unit structures in one compound, for example, the unit structure is a single bond, an alkylene group having 1 to 3 carbon atoms (for example, a methylene group), a phenylene group, and a naphthylene. In addition to the form in which a plurality of linked groups such as a group are bonded (linked multimer), any ring (a ring, b ring or c ring) included in the unit structure is shared by the plurality of unit structures. It may be in a bonded form (ring-shared multimer), or in a form in which arbitrary rings (a ring, b ring or c ring) included in the unit structure are bonded to each other (ring condensation). It may be a type multimer), but a ring-shared multimer and a ring-condensed multimer are preferable, and a ring-shared multimer is more preferable.
In the unit structure represented by the general formula (5) having a plurality of multimers, R ² is preferably hydrogen.

Examples of such a multimer include a multimer represented by the following formula (5-4), formula (5-5) or formula (5-6).
If the multimer represented by the following formula (5-4) is explained by the general formula (5), the unit represented by the two general formulas (5) shares the benzene ring which is the a ring. It is a dimer compound (ring-shared multimer) having a structure in one compound.
Further, multimer represented by the following formula (5-5), if described in the general formula (5), so as to share the benzene ring and X ² is a ring, three general formula (5) It is a trimer compound (ring-shared multimer) having a unit structure represented by (1) in one compound.
Further, the multimer represented by the following formula (5-6) can be described by the general formula (5), for example, having a certain unit structure with a benzene ring which is an a ring (or b ring or c ring) of a certain unit structure. A dimer compound (ring condensation) having a unit structure represented by the two general formulas (5) in one compound so as to condense with the benzene ring which is the a ring (or b ring, c ring) of the above. Type multimer).
Each reference numeral in the following equation is the same as the definition in the equation (5).

Further, at least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (5) and its multimer may be cyano, halogen or deuterium. For example, in the general formula (5), the a ring, the b ring, the c ring, the substituents to these rings, and X ¹ , X ² and X ³ are> N-R or -C (-R) _2. At least one hydrogen in R when − can be replaced with cyano, halogen or deuterium. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.

Specific examples of the polycyclic aromatic compound represented by the general formula (5) and its multimer include the compounds described in the specification of Japanese Patent Application No. 2017-171324, and the compounds shown below are preferable.

The polycyclic aromatic compound represented by the formula (5) and its multimer can be produced by applying the production method described in International Publication No. 2015/102118. Further, referring to the method for producing a polycyclic aromatic compound represented by the above formula (1) and its multimer, the first reaction is not an etherification reaction but a general amination reaction such as a Buchwald-Hartwig reaction. Can be manufactured using.

1-3-8. Substructure suitable as a polycyclic aromatic compound of the second component The polycyclic aromatic compound containing boron of the second component is preferably a compound containing any of the following formulas.
In addition, at least one hydrogen in the partial structure of the following formula may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, cyano, halogen or deuterium.

1-3-9. Polymer compounds obtained by polymerizing the polycyclic aromatic compound of the second component The polycyclic aromatic compounds represented by any of the general formulas (2) to (5) are substituted with reactive substituents. A polymer compound obtained by polymerizing a reactive compound as a monomer, or a crosslinked polymer thereof, or a pendant type polymer compound obtained by reacting a main chain type polymer with the above-mentioned reactive compound, or a pendant type height thereof. It can also be used as a material for a light emitting layer as a molecular crosslinked product. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited. The details of the uses of such polymer compounds and crosslinked polymers will be described later.

In addition, a polycycle containing a first structural unit derived from a reactive compound (H) in which a reactive substituent is substituted on a polycyclic aromatic compound represented by the general formula (1) and a second component boron. A second structural unit derived from the reactive compound (D) in which the reactive substituent is substituted on the aromatic compound (polycyclic aromatic compound represented by any of the general formulas (2) to (5)) is used. It may be a polymer compound (HD) which is a copolymer having. Further, it may be a polymer crosslinked body (HD) in which the polymer compound (HD) is further crosslinked.
The polymer compound (HD) and the polymer crosslinked product (HD) have a structure having a first structural unit corresponding to a host and a second structural unit corresponding to a dopant in the same main chain.

Further, it may be a pendant type polymer compound (HD) in which the reactive compound (H) and the reactive compound (D) are substituted in the main chain type polymer, and the pendant type polymer compound (HD) is further crosslinked. It may be a pendant type polymer crosslinked body (HD).
The pendant type polymer compound (HD) and the pendant type polymer crosslinked body (HD) have a pendant type structure in which the side chain corresponding to the host and the dopant is substituted with respect to the main chain.

2. More Detailed Description of Organic Electroluminescent Device The organic EL device according to this embodiment will be described in detail below with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL device according to the present embodiment.

2-1. Structure of Organic Electroluminescent 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 holes. The hole transport layer 104 provided on the injection layer 103, the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electron transport layer. It has an electron injection layer 107 provided on the electron injection layer 106 and a cathode 108 provided on the electron injection layer 107.

The organic EL element 100 is manufactured in the reverse order, for example, the substrate 101, the cathode 108 provided on the substrate 101, the electron injection layer 107 provided on the cathode 108, and the electron injection layer 107. Above the electron transport layer 106 provided on the electron transport layer 106, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, and the hole transport layer 104. The hole injection layer 103 provided in the hole injection layer 103 and the anode 102 provided on the hole injection layer 103 may be provided.

Not all of the above layers are required, and the minimum structural unit is composed of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection. The layer 107 is an arbitrarily provided layer. Further, each of the above layers may be composed of a single layer or a plurality of layers.

As the mode of the layer constituting the organic EL element, in addition to the above-mentioned "board / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", " Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / Antenna / 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 / "Anofect / light emitting layer / electron transport layer / electron injection layer / cathode", "board / anode / hole transport layer / light emitting layer / electron injection layer / cathode", "board / anode / hole transport layer / light emitting layer / electron" Transport layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron transport layer / cathode ”,“ substrate / anode The configuration may be "/ light emitting layer / electron transport layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

2-2. The substrate substrate 101 in the organic electroluminescent element is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. As for the glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness may be sufficient to maintain the mechanical strength. Therefore, for example, 0.2 mm or more may be used. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. The material of the glass, so it is better ions eluted from the glass is less is preferred towards the alkali-free glass, the use of this because soda lime glass with a barrier coat such as SiO ₂ are also available commercially can. Further, in order to enhance the gas barrier property, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side, and a synthetic resin plate, film or sheet having a particularly low gas barrier property may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

2-3. The anode-anode 102 in the organic electroluminescent device serves to inject holes into the light emitting layer 105. When at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 via these. Become.

Examples of the material forming the anode 102 include an inorganic compound and an organic compound. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxidation, etc.). (IZO, etc.), metals halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass, nesa glass, etc. Examples of the organic compound include polythiophene such as poly (3-methylthiophene) and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from the substances used as the anode of the organic EL element.

The resistance of the transparent electrode is not limited as long as a sufficient current can be supplied to emit light from the light emitting element, but it is desirable that the resistance is low from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω / □ or less functions as an element electrode, but since it is now possible to supply a substrate of about 10 Ω / □, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω. It is especially desirable to use a low resistance product of / □. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.

2-4. Hole injection layer and hole transport layer in the organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or 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 laminated and mixed with one or more of the hole injection / transport materials, respectively, or by a mixture of the hole injection / transport material and the polymer binder. It is formed. Further, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

As a hole injection / transporting substance, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and the hole injection efficiency is high, and the injected holes are efficiently transported. It is desirable to do. For that purpose, it is preferable that the substance has a small ionization potential, a large hole mobility, excellent stability, and is less likely to generate trap impurities during production and use.

Examples of the material forming the hole injection layer 103 and the hole transport layer 104 include a compound, a p-type semiconductor, and a hole injection layer of an organic EL element that have been conventionally used as a hole charge transport material in a photoconductive material. And can be arbitrarily selected and used from 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), and triarylamine derivatives (aromatic tertiary). Polymers with amino in the main or side chains, 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, starburstamine derivatives, etc.), stillben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives , Kinoxalin derivatives (eg, 1,4,5,8,9,12-hexazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate or styrene derivative having the monomer as a side chain, polyvinylcarbazole, polysilane, or the like is preferable, but a thin film necessary for producing a light emitting element can be formed 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 affected by its doping. Such an organic semiconductor matrix substance is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron donors. (For example, the document "M.Pfeiffer, A.Beyer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (22), 3202-3204 (1998)" and the document "J. Blochwitz, M." See .Pheiffer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (6), 729-731 (1998) "). They generate so-called holes by an electron transfer process in an electron-donating base material (hole-transporting material). Depending on the number of holes and the mobility, the conductivity of the base material changes considerably. As the matrix substance having hole transporting properties, for example, a benzidine derivative (TPD or the like) or a starburst amine derivative (TDATA or the like) or a specific metal phthalocyanine (particularly zinc phthalocyanine ZnPc or the like) is known (Japanese Patent Laid-Open No. 2005-167 No. 175).

The above-mentioned materials for the hole injection layer and the material for the hole transport layer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a polymer crosslinked product thereof. A pendant type polymer compound obtained by reacting a main chain type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a hole layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

2-5. The light emitting layer light emitting layer 105 in the organic electroluminescent element is a layer that emits light by recombining the holes injected from the anode 102 and the electrons injected from the cathode 108 between the electrodes to which an electric field is applied. .. The material for forming the light emitting layer 105 may be a compound (light emitting compound) that is excited by recombination of holes and electrons to emit light, and can form a stable thin film shape and is in a solid state. It is preferable that the compound exhibits a strong emission (fluorescence) efficiency.

The light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting layer material (host material, dopant material). The host material and the dopant material may be one kind or a combination of a plurality of kinds. The dopant material may be included entirely, partially, or partially in the host material.
The light emitting layer of the organic electroluminescent element of the present invention contains a polycyclic aromatic compound represented by the formula (1) as a host material as a first component, and a polycycle containing boron as a second component. Aromatic compounds are included as dopant materials.

The amount of the host material used depends on the type of host material and may be determined according to the characteristics of the host material. The guideline for the amount of the host material used is preferably 50 to 99.99% by weight, more preferably 70 to 99.9% by weight, and further preferably 80 to 99.9% by weight of the entire material for the light emitting layer. It is particularly preferably 90 to 99.9% by weight.

The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The guideline for the amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.1 to 30% by weight, still more preferably 0.1 to 20% by weight of the entire light emitting layer material. Yes, particularly preferably 0.1 to 10% by weight. The above range is preferable in that, for example, the density quenching phenomenon can be prevented.
On the other hand, from the viewpoint of TADF expression, it is preferable that the amount of dopant is large. Further, since it is affected by a layer other than the light emitting layer, the concentration of the dopant is determined not only by the host and the dopant of the light emitting layer but also by the element configuration.

Host materials that can be used in combination with the compound represented by the formula (1) include fused ring derivatives such as anthracene and fluorene, which have long been known as luminescent materials, and bisstyryl such as bisstyryl anthracene derivatives and distyrylbenzene derivatives. Derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives and the like can be mentioned.

The dopant material that can be used in combination with the boron-containing polycyclic aromatic compound is not particularly limited, and a known compound can be used and selected from various materials according to a desired emission color. can do. Specifically, for example, fused ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysen, benzoxazole derivatives, benzothiazole derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxazoles. Bistylyl derivatives such as derivatives, oxaziazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazol derivatives, triazole derivatives, pyrazoline derivatives, stillben derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives. (Japanese Patent Laid-Open No. 1-245087), bisstyrylallylene derivative (Japanese Patent Laid-Open No. 2-247278), diazaindacene derivative, furan derivative, benzofuran derivative, 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- Cumarin derivatives such as methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzoimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine Derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives, acrydin derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrolopyridine derivatives, flopyridine derivatives, Examples thereof include 1,2,5-thiadiazolopylene derivatives, pyromethene derivatives, perinone derivatives, pyrolopyrrole derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

For example, for each coloring light, examples of the blue to blue-green dopant material include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, inden, and chrysen, and derivatives thereof, furan, pyrrole, and thiophene. Aromatic compounds such as silol, 9-silafluolene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indol, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthylidine, quinoxalin, pyrolopyridine, thioxanthene. Ring compounds and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stillben derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thiadiazol, carbazole, oxazole, oxadiazol, triazole and other azole derivatives and their metal complexes and N , N'-diphenyl-N, N'-di (3-methylphenyl) -4,4'-diphenyl-1,1'-diamine and other aromatic amine derivatives.

Examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, naphthacene derivatives such as rubrene, and the above blue. A preferable example is a compound in which a substituent capable of lengthening the wavelength, such as aryl, heteroaryl, arylvinyl, amino, and cyano, is introduced into the compound exemplified as the blue-green dopant material.

Further, as the orange to red dopant material, naphthalimide derivatives such as bis (diisopropylphenyl) perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complex having acetylacetone, benzoylacetone and phenanthroline as ligands, 4 -(Dicyanomethylene) -2-methyl-6- (p-dimethylaminostyryl) -4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone Derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrolopyridine derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, phenoxazone derivatives, thiadiazolopyrene derivatives, etc. are mentioned, and further exemplified as the above-mentioned blue-blue-green and green-yellow dopant materials. A preferable example is a compound in which a substituent capable of lengthening the wavelength, such as aryl, heteroaryl, arylvinyl, amino, and cyano, is introduced into the above-mentioned compound.

In addition, as the dopant, it can be appropriately selected and used from the compounds described in the June 2004 issue of Chemical Industry, page 13, and the references mentioned therein.

当該式中、Ａｒ^１は炭素数６〜３０のアリールからさらに任意のｍ−１個の水素原子を除いて表されるｍ価の基であり、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６〜３０のアリールであるが、Ａｒ^１〜Ａｒ^３の少なくとも１つはスチルベン構造を有し、Ａｒ^１〜Ａｒ^３は置換されていてもよく、そして、ｍは１〜４の整数である。An amine having a stilbene structure is represented by, for example, the following formula.

In the formula, Ar ¹ is an m-valent group represented by removing any m-1 hydrogen atom from an aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ are independently carbons. Although the number 6 to 30 are aryls, ^{at least one of} Ars ^{1 to Ar 3} has a stillben structure, Ars ^{1 to Ar 3} may be substituted, and m is an integer of 1 to 4. ..

当該式中、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６〜３０のアリールであり、Ａｒ^２およびＡｒ^３は置換されていてもよい。The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula.

In the formula, Ar ² and Ar ³ are independently aryls having 6 to 30 carbon atoms, and Ar ² and Ar ³ may be substituted.

Specific examples of aryls having 6 to 30 carbon atoms are benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthalene, perylene, stilben, distyrylbenzene, distyrylbiphenyl, and distyryl. Fluorene and the like can be mentioned.

Specific examples of amines having a stilbene structure are N, N, N', N'-tetra (4-biphenylyl) -4,4'-diaminostilbene, N, N, N', N'-tetra (1-naphthyl). ) -4,4'-diaminostilbene, N, N, N', N'-tetra (2-naphthyl) -4,4'-diaminostilbene, N, N'-di (2-naphthyl) -N, N '-Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis (Diphenylamino) stilbene] -biphenyl, 1,4-bis [4'-bis (diphenylamino) stilbene] -benzene, 2,7-bis [4'-bis (diphenylamino) stilbene] -9,9-dimethyl Examples include fluorene, 4,4'-bis (9-ethyl-3-carbazovinylene) -biphenyl, 4,4'-bis (9-phenyl-3-carbazovinylene) -biphenyl and the like.
Further, amines having a stilbene structure described in JP-A-2003-347056 and JP-A-2001-307884 may be used.

Examples of the perylene derivative include 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, and 3,4-. Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene , 3- (9'-anthril) -8,11-di (t-butyl) perylene, 3,3'-bis (8,11-di (t-butyl) perylenel) and the like.
In addition, JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP-A-2000-34234, JP-A-2001-267075, JP-A-2001-217077, and the like may be used.

Examples of the borane derivative include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9'-anthril) dimesitylborylnaphthalene, 4- (10'). -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4'-(N-carbazolyl) phenyl) -10- (Dimethylboryl) Anthracene and the like can be mentioned.
Further, the borane derivative described in International Publication No. 2000/40586 pamphlet or the like may be used.

当該式中、Ａｒ^４は炭素数６〜３０のアリールからさらに任意のｎ−１個の水素原子を除いて表されるｎ価の基であり、Ａｒ^５およびＡｒ^６はそれぞれ独立して炭素数６〜３０のアリールであり、Ａｒ^４〜Ａｒ^６は置換されていてもよく、そして、ｎは１〜４の整数である。The aromatic amine derivative is represented by, for example, the following formula.

In the formula, Ar ⁴ is an n-valent group represented by removing any n-1 hydrogen atom from an aryl having 6 to 30 carbon atoms, and Ar ⁵ and Ar ⁶ have independent carbon atoms, respectively. It is an aryl of 6 to 30, Ar ^{4 to} Ar ⁶ may be substituted, and n is an integer of 1 to 4.

In particular, Ar ⁴ is a divalent group represented by removing any two hydrogen atoms from anthracene, chrysene, fluorene, benzofluorene or pyrene, and Ar ⁵ and Ar ⁶ are independently 6 to 30 carbon atoms, respectively. Of the aryl, Ar ^{4 to} Ar ⁶ may be substituted, and n is 2, more preferably an aromatic amine derivative.

Specific examples of aryls having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorenephenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthalene, perylene and pentacene.

As the aromatic amine derivative, as a chrysen system, for example, N, N, N', N'-tetraphenylcrisen-6,12-diamine, N, N, N', N'-tetra (p-tolyl) Chrysen-6,12-diamine, N, N, N', N'-tetra (m-tolyl) Chrysen-6,12-diamine, N, N, N', N'-tetrakis (4-isopropylphenyl) chrysen -6,12-diamine, N, N, N', N'-tetra (naphthalen-2-yl) chrysen-6,12-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) ) Chrysen-6,12-diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) Chrysen-6,12-diamine, N, N'-diphenyl-N, N'-bis ( 4-Ethylphenyl) chrysene-6,12-diamine, N, N'-diphenyl-N, N'-bis (4-isopropylphenyl) chrysene-6,12-diamine, N, N'-diphenyl-N, N '-Bis (4-t-butylphenyl) chrysen-6,12-diamine, N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) chrysen-6,12-diamine And so on.

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

The anthracene system includes, for example, N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N', N'-tetra (p-tolyl) anthracene-9,10-diamine. , N, N, N', N'-tetra (m-tolyl) anthracene-9,10-diamine, N, N, N', N'-tetrakis (4-isopropylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-di (m-tolyl) anthracene-9,10- Diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) anthracene- 9,10-diamine, N, N'-diphenyl-N, N'-bis (4-isopropylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-bis (4-t) -Butylphenyl) anthracene-9,10-diamine, N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene-9,10-diamine, 2,6-di- t-butyl-N, N, N', N'-tetra (p-tolyl) anthracene-9,10-diamine, 2,6-di-t-butyl-N, N'-diphenyl-N, N'- Bis (4-isopropylphenyl) anthracene-9,10-diamine, 2,6-di-t-butyl-N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene -9,10-diamine, 2,6-dicyclohexyl-N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene-9,10-diamine, 2,6-dicyclohexyl -N, N'-bis (4-isopropylphenyl) -N, N'-bis (4-t-butylphenyl) anthracene-9,10-diamine, 9,10-bis (4-diphenylamino-phenyl) anthracene , 9,10-bis (4-di (1-naphthylamino) phenyl) anthracene, 9,10-bis (4-di (2-naphthylamino) phenyl) anthracene, 10-di-p-tolylamino-9-( 4-di-p-tolylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (4-diphenylamino-1-naphthyl) anthracene, 10-diphenylamino- Examples thereof include 9- (6-diphenylamino-2-naphthyl) anthracene.

In addition, [4- (4-diphenylamino-phenyl) naphthalene-1-yl] -diphenylamine, [6- (4-diphenylamino-phenyl) naphthalene-2-yl] -diphenylamine, 4,4'. -Bis [4-diphenylaminonaphthalene-1-yl] biphenyl, 4,4'-bis [6-diphenylaminonaphthalen-2-yl] biphenyl, 4,4 "-bis [4-diphenylaminonaphthalen-1-yl] ] -P-Terphenyl, 4,4 "-bis [6-diphenylaminonaphthalen-2-yl] -p-terphenyl and the like.
Further, the aromatic amine derivative described in JP-A-2006-156888 may be used.

Examples of the coumarin derivative include coumarin-6 and coumarin-334.
Further, the coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758 and the like may be used.

また、特開2005-126399号公報、特開2005-097283号公報、特開2002-234892号公報、特開2001-220577号公報、特開2001-081090号公報、および特開2001-052869号公報などに記載されたピラン誘導体を用いてもよい。Examples of the pyran derivative include the following DCM and DCJTB.

Further, JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, and JP-A-2001-052869. The pyran derivative described in the above may be used.

The above-mentioned materials for the light emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a main chain. A pendant type polymer compound obtained by reacting a type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a light emitting layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

2-6. The electron injection layer and the electron transport layer in the organic electroluminescent element 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 the electrons injected from the cathode 108 or the electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating and mixing one or more of the electron transport / injection materials or a mixture of the electron transport / injection material and the polymer binder, respectively.

The electron injection / transport layer is a layer in which electrons are injected from the cathode and is in charge of further transporting electrons, and it is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For that purpose, it is preferable that the substance has a large electron affinity, a high electron mobility, excellent stability, and is less likely to generate trap impurities during production and use. However, when considering the transport balance between holes and electrons, the electron transport capacity is so high when it mainly plays a role of efficiently blocking the holes from the anode from flowing to the cathode side without recombination. Even if it is not high, it has the same effect of improving luminous efficiency as a material having high electron transport capacity. Therefore, the electron injection / transport layer in the present embodiment may also include the function of a layer capable of efficiently blocking the movement of holes.

As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it is used as a compound conventionally used as an electron transfer compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic EL element. It can be arbitrarily selected and used from the known compounds known.

The material used for the electron transport layer or the electron injection layer is a compound composed of an aromatic ring or a complex aromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus. It preferably contains at least one selected from a pyrrole derivative, a condensed ring derivative thereof, and a metal complex having an electron-accepting nitrogen. Specifically, fused ring-based aromatic ring derivatives such as naphthalene and anthracene, styryl-based aromatic ring derivatives typified by 4,4'-bis (diphenylethenyl) biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , Kinone derivatives such as anthraquinone and diphenoquinone, phosphoroxide derivatives, carbazole derivatives and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex and benzoquinoline metal complex. These materials may be used alone, but may be mixed 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 oxadiasols. 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.), thiazazole derivatives, oxine derivative metal complexes, quinolinol-based metal complexes, quinoxalin derivatives, quinoxalin derivative polymers, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline Derivatives (2,2'-bis (benzo [h] quinoline-2-yl) -9,9'-spirobifluorene, etc.), imidazole pyridine derivatives, borane derivatives, benzoimidazole derivatives (tris (N-phenylbenzoimidazole-) 2-yl) benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as telpyridine, bipyridine derivatives, telpyridine derivatives (1,3-bis (4'-(2,2': 6'2)) "-Terpyridinyl)) benzene, etc.), naphthylidine derivatives (bis (1-naphthyl) -4- (1,8-naphthylidine-2-yl) phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indol derivatives, phosphoroxide derivatives , Bistylyl derivatives and the like.

Further, a metal complex having electron-accepting nitrogen can also be used. Can be mentioned.

The above-mentioned materials may be used alone, but may be mixed with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluorantene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, and quinolinol-based metals Derivatives are preferred.

上記式（ＥＴＭ−１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも一つであり、Ｒ^１３〜Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、または置換されていてもよいアリールであり、Ｘは、置換されていてもよいアリーレンであり、Ｙは、置換されていてもよい炭素数１６以下のアリール、置換されているボリル、または置換されていてもよいカルバゾリルであり、そして、ｎはそれぞれ独立して０〜３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。<Borane derivative>
The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.

In the above formula (ETM-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, respectively. Alternatively, at least one of cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl or optionally substituted aryl, and X is optionally substituted arylene. Y is an aryl with 16 or less carbon atoms which may be substituted, a boryl which may be substituted, or a carbazolyl which may be substituted, and n is an integer of 0 to 3 independently. be. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

式（ＥＴＭ−１−１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも一つであり、Ｒ^１３〜Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、または置換されていてもよいアリールであり、Ｒ^２１およびＲ^２２は、それぞれ独立して、水素、アルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも一つであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、ｎはそれぞれ独立して０〜３の整数であり、そして、ｍはそれぞれ独立して０〜４の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。

式（ＥＴＭ−１−２）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも一つであり、Ｒ^１３〜Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、または置換されていてもよいアリールであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、そして、ｎはそれぞれ独立して０〜３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。Among the compounds represented by the above general formula (ETM-1), the compound represented by the following general formula (ETM-1-1) and the compound represented by the following general formula (ETM-1-2) are preferable.

In formula (ETM-1-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, respectively. , Or at least one of cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl or optionally substituted aryl, and R ²¹ and R ²² are independent, respectively. And at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, where X ¹ may be substituted. It is a good arylene with 20 or less carbon atoms, n is an integer of 0 to 3 independently, and m is an integer of 0 to 4 independently. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

In formula (ETM-1-2), R ¹¹ and R ¹² are independently hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, respectively. , Or at least one of cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl or optionally substituted aryl, and X ¹ may be substituted. It is a good arylene with 20 or less carbon atoms, and n is an independently integer of 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

（各式中、Ｒ^ａは、それぞれ独立してアルキル基または置換されていてもよいフェニル基である。）Specific examples of X ¹ include divalent groups represented by any of the following formulas (X-1) to (X-9).

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

Specific examples of this borane derivative include the following.

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

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

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

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

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

In each formula, the "pyridine-based substituent" is any of the following formulas (Py-1) to (Py-15), and the pyridine-based substituent is independently substituted with an alkyl having 1 to 4 carbon atoms. It may have been done. Further, the pyridine-based substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or a naphthylene group.

The pyridine-based substituent is any of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44). Is preferable.

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

The "alkyl" in R ^{11 to} R ¹⁸ may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms and branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2 -Propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, Examples thereof include n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

As the alkyl having 1 to 4 carbon atoms to be substituted with the pyridine-based substituent, the above description of the alkyl can be cited.

Examples of the "cycloalkyl" in R ^{11 to} R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms.
Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As the ^{"aryl" in R 11 to} R ¹⁸ , the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms. Yes, particularly preferably an aryl having 6 to 12 carbon atoms.

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

Preferred "aryls having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl and the like, more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1 −naphthyl or 2-naphthyl can be mentioned.

^{R 11} and R ¹² in the above formula (ETM-2-2) may be combined to form a ring, and as a result, the 5-membered ring of the fluorene skeleton has cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, etc. Cyclohexane, fluorene, indene and the like may be spiro-bonded.

Specific examples of this pyridine derivative include the following.

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

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

In the above formula (ETM-3), X ^{12 to} X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted. Represents a heteroaryl. Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

Specific examples of this fluoranthene derivative include the following.

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

R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these. May be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Further, ^{adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. May be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or It may be substituted with cycloalkyl.

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

For the explanation of the substituent and the form of ring formation in the formula (ETM-4) and the multimer formed by combining a plurality of structures of the formula (ETM-4), the polycyclic aromatic represented by the above general formula (1). Descriptions of compounds and their multimers can be cited.

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

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

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

Ar is independently divalent benzene or naphthalene, and R ^{1 to} R ⁴ are independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or carbon number of carbons, respectively. 6 to 20 aryls.

Ar can be independently selected from divalent benzene or naphthalene, and the two Ars may be different or the same, but they are the same from the viewpoint of easiness of synthesizing the anthracene derivative. Is preferable. Ar binds to pyridine to form a "site consisting of Ar and pyridine", and this site is anthracene as a group represented by any of the following formulas (Py-1) to (Py-12), for example. Is bound to.

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

The alkyl having 1 to 6 carbon atoms in R ^{1 to} R ⁴ may be either a straight chain or a branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched chain alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, Examples thereof include 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl. , Methyl, ethyl, or t-butyl is more preferred.

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

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

Specific examples of "aryls having 6 to 20 carbon atoms" include phenyl, which is a monocyclic aryl, (o-, m-, p-) trill, and (2,3-,2,4-,2,5-). , 2,6-, 3,4-, 3,5-) xsilyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic aryl (2) -, 3-, 4-) Biphenylyl, fused bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4) '-Il, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -Il, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- Telphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracene- (1-, 2-, 9-) yl, acenaphthylene- (1-, 3-, 4-, 5-) aryl, fluoren- (1-, 2-, 3-, 4-, 9-) yl, phenylene- (1-, 2-) yl, (1-, 2-) 2-, 3-, 4-, 9-) phenyl, triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-, 4-) yl, tetracene- (1) -, 2-, 5-) yl, perylene- (1-, 2-, 3-) yl, which is a fused pentacyclic aryl, and the like can be mentioned.

Preferred "aryl of 6-20 carbon atoms" are phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl. More preferably, it is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

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

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

Ar ² is an aryl having 6 to 20 carbon atoms independently, and the same explanation as “aryl having 6 to 20 carbon atoms” in the above formula (ETM-5-1) can be quoted. Aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphtylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetrasenyl, perylenyl and the like.

R ^{1 to} R ⁴ are independently hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 6 carbon atoms, or an aryl having 6 to 20 carbon atoms, respectively, according to the above formula (ETM-5-1). The explanation in can be quoted.

Specific examples of these anthracene derivatives include the following.

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

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

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

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

The "alkyl" in Ar ² may be either a straight chain or a branched chain, and examples thereof include a linear alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific "alkyl" includes 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 and the like can be mentioned.

Examples of the "cycloalkyl" in Ar ² include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. A more preferable "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

As ^{the "aryl" in Ar 2} , a preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, and more preferably an aryl having 6 to 14 carbon atoms, particularly. It is preferably an aryl having 6 to 12 carbon atoms.

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

Two Ar ² may form a ring, as a result, the 5-membered ring of the fluorene skeleton, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene are spiro-linked You may.

Specific examples of this benzofluorene derivative include the following.

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

Ｒ^５は、置換または無置換の、炭素数１〜２０のアルキル、炭素数６〜２０のアリールまたは炭素数５〜２０のヘテロアリールであり、
Ｒ^６は、ＣＮ、置換または無置換の、炭素数１〜２０のアルキル、炭素数１〜２０のヘテロアルキル、炭素数６〜２０のアリール、炭素数５〜２０のヘテロアリール、炭素数１〜２０のアルコキシまたは炭素数６〜２０のアリールオキシであり、
Ｒ^７およびＲ^８は、それぞれ独立して、置換または無置換の、炭素数６〜２０のアリールまたは炭素数５〜２０のヘテロアリールであり、
Ｒ^９は酸素または硫黄であり、
ｊは０または１であり、ｋは０または１であり、ｒは０〜４の整数であり、ｑは１〜３の整数である。
ここで、置換されている場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。<Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/07927.

R ⁵ is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, heteroaryl of aryl or 5 to 20 carbon atoms of 6 to 20 carbon atoms,
R ⁶ is CN, substituted or unsubstituted, alkyl having 1 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, and 1 to 2 carbon atoms. 20 alkoxy or aryloxy with 6 to 20 carbon atoms,
R ⁷ and R ⁸ are independently substituted or unsubstituted aryls having 6 to 20 carbon atoms or heteroaryls having 5 to 20 carbon atoms, respectively.
R ⁹ is oxygen or sulfur
j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

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

R ^{1 to} R ³ may be the same or different, and may be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, arylether group, arylthioether group. , Aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, amino group, nitro group, silyl group, and fused ring formed between adjacent substituents.

Ar ¹ may be the same or different and is an arylene or heteroarylene group. Ar ² may be the same or different and is an aryl group or a heteroaryl group. However, ^{at least one of Ar 1} and Ar ² has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, and when n is 0, the unsaturated structure portion does not exist, and when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group indicates a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group and a butyl group, which may be unsubstituted or substituted. The substituent when substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, and this point is also common to the following description. The number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

Further, the cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group moiety is not particularly limited, but is usually in the range of 3 to 20.

Further, the aralkyl group indicates an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon are substituted without substitution. It doesn't matter. The carbon number of the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, which may be unsubstituted or substituted. The carbon number of the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

The cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted. It doesn't matter.

Further, the alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The carbon number of the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

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

The alkylthio group is a group in which the oxygen atom of the ether bond of the alkoxy group is replaced with a sulfur atom.

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

The arylthioether group is a group in which the oxygen atom of the ether bond of the arylether group is replaced with a sulfur atom.

Further, the aryl group indicates, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group and a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms of the aryl group is not particularly limited, but is usually in the range of 6 to 40.

Further, the heterocyclic group refers to a cyclic structural group having an atom other than carbon such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group and a carbazolyl group, which are substituted even if they are not substituted. It doesn't matter. The number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

The aldehyde group, carbonyl group, and amino group can also include a group substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle, or the like.

Further, the aliphatic hydrocarbon, the alicyclic hydrocarbon, the aromatic hydrocarbon, and the heterocycle may be substituted or substituted.

The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The carbon number of the silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon is usually 1 to 6.

The fused rings formed between the adjacent substituents are, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , and Ar ¹ . It is a conjugated or non-conjugated fused ring formed between Ar ^{2 and the like.} Here, when n is 1, may be formed conjugated or non-conjugated fused ring with two of R ¹ each other. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be condensed with another ring.

Specific examples of this phosphine oxide derivative include the following.

This phosphine oxide derivative can be produced by using a known raw material and a known synthetic method.

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

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific "aryls" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Fused tricyclic aryls, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl. ) Ill, pentasen- (1-, 2-, 5-, 6-) yl, etc.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and so on. Benomidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. Phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoyl, dibenzophosphoryl, benzophosphole Examples thereof include a monovalent group of the oxide ring, a monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantranyl, indolocarbazolyl, benzoindrocarbazolyl and benzobenzoindrocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl and heteroaryl, respectively.

Specific examples of this pyrimidine derivative include the following.

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

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

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. n is independently an integer of 0-4, preferably an integer of 0-3, more preferably 0 or 1.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific "aryls" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Fused tricyclic aryls, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl. ) Ill, pentasen- (1-, 2-, 5-, 6-) yl, etc.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and so on. Benomidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. Phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoyl, dibenzophosphoryl, benzophosphole Examples thereof include a monovalent group of the oxide ring, a monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantranyl, indolocarbazolyl, benzoindrocarbazolyl and benzobenzoindrocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl and heteroaryl, respectively.

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

Specific examples of this carbazole derivative include the following.

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

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/015601.

Ar is an aryl which may be substituted or a heteroaryl which may be substituted independently of each other. n is an integer of 1-3, preferably 2 or 3.

Examples of the "aryl" of the "optionally substituted aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, and more preferably aryls having 6 to 20 carbon atoms. More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific "aryls" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused dicyclic aryl. , Tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -Terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , Fused tricyclic aryls, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1) -, 2-) Il, (1-, 2-, 3-, 4-, 9-) phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, which is a tetracyclic aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2), a fused tetracyclic aryl -) Ill, pyrene- (1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, perylene- (1-, 2-, 3-), which is a fused pentacyclic aryl. ) Ill, pentasen- (1-, 2-, 5-, 6-) yl, etc.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and so on. Benomidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. Phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoyl, dibenzophosphoryl, benzophosphole Examples thereof include a monovalent group of the oxide ring, a monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantranyl, indolocarbazolyl, benzoindrocarbazolyl and benzobenzoindrocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl and heteroaryl, respectively.

Specific examples of this triazine derivative include the following.

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

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

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzfluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. In the "benzimidazole-based substituent", the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is benzo. It is a group that replaces the imidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with fluorene.

^{R 11} in the benzimidazole group is hydrogen, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, or an aryl having 6 to 30 carbon atoms, and is the above formula (ETM-2-1) and the formula (ETM-2-1). It may be cited to the description of ^{R 11} in ETM-2-2).

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the structure of the above formula (ETM-2-1) or formula (ETM-2-2), and each formula can be cited. For R ^{11 to} R ¹⁸ in the above, the explanation in the above formula (ETM-2-1) or formula (ETM-2-2) can be quoted. Further, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described in a bonded form, but when these are replaced with benzoimidazole-based substituents, both are used. The pyridine-based substituent may be replaced with a benzoimidazole-based substituent (that is, n = 2), any one of the pyridine-based substituents may be replaced with a benzoimidazole-based substituent, and the other pyridine-based substituent may be replaced with R ^11. It may be replaced with ~ R ¹⁸ (that is, n = 1). ^{Further, for example, at least one of R 11 to} R ¹⁸ in the above formula (ETM-2-1) may be replaced with a benzimidazole-based substituent, and the “pyridine-based substituent” may be replaced ^{with R 11 to} R ^18.

Specific examples of this benzimidazole derivative include, for example, 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (10-). Naphthalen-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalen-2-yl) anthracene-9-yl) -1,2-diphenyl-1H-benzazole, 1- (4) -(10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)) Anthracene-2-yl) phenyl) -1-phenyl-1H-benzazole, 1-(4- (9,10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -2- Examples thereof include phenyl-1H-benz [d] imidazole and 5- (9,10-di (naphthalen-2-yl) anthracene-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole.

This benzimidazole derivative can be produced by using a known raw material and a known synthetic method.

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

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

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

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

Alkyl in R ¹¹ to R ^18, cycloalkyl and aryl may be cited to the description of ^R 11 ^{to R 18} in the formula (ETM-2). In addition to the above-mentioned structure, φ has, for example, the following structural formula. In addition, R in the following structural formulas is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl.

Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-). Phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9' Examples thereof include −difluoro-bi (1,10-phenanthroline-5-yl), bathocuproine and 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene.

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

式中、Ｒ^１〜Ｒ^６は、それぞれ独立して、水素、フッ素、アルキル、アラルキル、アルケニル、シアノ、アルコキシまたはアリールであり、ＭはＬｉ、Ａｌ、Ｇａ、ＢｅまたはＺｎであり、ｎは１〜３の整数である。<Kinolinol-based metal complex>
The quinolinol-based metal complex is, for example, a compound represented by the following general formula (ETM-13).

In the formula, R ^{1 to} R ⁶ are independently hydrogen, fluorine, alkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al, Ga, Be or Zn, and n is 1. It is an integer of ~ 3.

Specific examples of the quinolinol-based metal complex include 8-quinolinol lithium, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, and tris (3). , 4-Dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) ( Phenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenorate) aluminum, bis (2-methyl-8- Kinolinolate) (4-methylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-Methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) ( 2,6-Dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,4-dimethylphenorate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (3,5-di-t-butylphenolate) Aluminum, bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) Aluminum, bis ( 2-Methyl-8-quinolinolate) (2,4,6-triphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl -8-quinolinolate) (2,4,5,6-tetramethylphenorate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2) -Naftrat) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenylate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) ) (3-Phenylphenorate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) Lat) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-di-t-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate) aluminum-μ-oxo-bis (2) -Methyl-8-quinolinolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-4-ethyl) -8-Kinolinolate) Aluminum-μ-oxo-bis (2-methyl-4-ethyl-8-quinolinolate) Aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) Aluminum-μ-oxo-bis (2) -Methyl-4-methoxy-8-quinolinolate) Aluminum, bis (2-methyl-5-cyano-8-quinolinolate) Aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolate) Aluminum, bis (2-Methyl-5-trifluoromethyl-8-quinolinolate) Aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolate) Aluminum, bis (10-hydroxybenzo [h] quinoline) Berylium and the like can be mentioned.

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

ベンゾチアゾール誘導体は、例えば下記式（ＥＴＭ−１４−２）で表される化合物である。

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

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

Φ of each formula is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 The "thiazole-based substituent" and "benzothiazole-based substituent" are the "pyridine-based" in the above formulas (ETM-2), (ETM-2-1) and (ETM-2-2). The pyridyl group in the "substituent" is a group in which a thiazole group or a benzothiazole group is replaced, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with dehydrogen.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the structure of the above formula (ETM-2-1) or formula (ETM-2-2), and each formula can be cited. For R ^{11 to} R ¹⁸ in the above, the explanation in the above formula (ETM-2-1) or formula (ETM-2-2) can be quoted. Further, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described in a bound form, and these are described as thiazole-based substituents (or benzothiazole-based substituents). When substituting with (group), both pyridine-based substituents may be replaced with thiazole-based substituents (or benzothiazole-based substituents) (that is, n = 2), or any one of the pyridine-based substituents may be replaced with thiazole-based substituents. It may be replaced with a group (or a benzothiazole-based substituent) and the other pyridine-based substituent ^{may be replaced with R 11 to} R ¹⁸ (that is, n = 1). ^{Further, for example, at least one of R 11 to} R ¹⁸ in the above formula (ETM-2-1) is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to replace the "pyridine-based substituent" with R ^{11 to} R ^18. May be replaced with.

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

The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As this reducing substance, various substances are used as long as they have a certain reducing property. For example, alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkali. 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 preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2.95 eV). Examples thereof include alkaline earth metals such as 9 eV), Sr (2.0 to 2.5 eV) and Ba (2.52 eV), and a substance having a work function of 2.9 eV or less is particularly preferable. Of these, the more preferable reducing substance is an alkali metal of K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have a 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 emission brightness and the life of the organic EL device can be extended. Further, as a reducing substance having a work function of 2.9 eV or less, a combination of these two or more kinds of alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By containing Cs, the reducing ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL device can be improved.

The above-mentioned material for the electron transport injection layer and the material for the electron transport layer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or a polymer crosslinked product thereof, or a main component thereof. A pendant type polymer compound obtained by reacting a chain type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for an electron layer. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

2-7. The cathode and cathode 108 in the organic electroluminescent element plays a role of injecting electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material for forming the cathode 108 is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the organic layer, but a material similar to the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium). -Indium alloys, aluminum-lithium alloys such as lithium fluoride / aluminum, etc.) are preferred. Alloys containing lithium, sodium, potassium, cesium, calcium, magnesium or these low work function metals are effective for increasing electron injection efficiency and improving device characteristics. However, these low work function metals are generally often unstable in the atmosphere. In order to improve this point, for example, a method of doping an organic layer with a trace amount of lithium, cesium or magnesium and using a highly stable electrode is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

In addition, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium for electrode protection, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride. , Laminating a hydrocarbon-based polymer compound or the like is given as a preferable example. The method for producing these electrodes is also not particularly limited as long as conduction can be obtained, such as resistance heating, electron beam, sputtering, ion plating and coating.

2-8. The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer, which are higher than the binder that may be used in each layer, can form each layer independently. Polyvinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole), polymethylmethacrylate, polybutylmethacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, Solvent-soluble resins such as vinyl acetate resin, ABS resin and polyurethane resin, curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin and silicone resin. It is also possible to disperse and use it.

2-9. Method for manufacturing organic electroluminescent element For each layer constituting an organic EL element, the material to be composed of each layer is vapor-deposited, resistance-heated 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 by a method such as a coating method. The film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When a thin film is formed by using a thin film deposition method, the vapor deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. The vapor deposition conditions are generally: boat heating temperature +50 to + 400 ° C., vacuum degree ^10-6 to ^10-3 Pa, vapor deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to + 300 ° C., film thickness 2 nm to 5 μm. It is preferable to set appropriately within the range.

When a DC voltage is applied to the organic EL element thus obtained, the anode may be applied with a positive polarity and the cathode may be applied with a negative polarity, and when a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Emission can be observed from the side (anode or cathode, or both). The organic EL element also emits light when a pulse current or an alternating current is applied. The AC waveform to be applied may be arbitrary.

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

2-9-1. The deposition suitable substrate, after forming a thin film of an anode material is formed by a vapor deposition method or the like anode, to form a thin film of the hole injection layer and a hole transport layer on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by a vapor deposition method or the like. By forming it into a cathode, the desired organic EL element can be obtained. In the above-mentioned production of the organic EL element, the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be manufactured in this order. Is.

2-9-2. Wet film forming method The wet film forming method is carried out by preparing a small molecule compound capable of forming each organic layer of an organic EL element as a liquid organic layer forming composition and using the same. If there is no suitable organic solvent to dissolve this low molecular weight compound, it is high together with other monomers having a soluble function as a reactive compound in which the low molecular weight compound is substituted with a reactive substituent and a main chain type polymer. A 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 by 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 by this drying step to form a crosslinked polymer. Depending on the difference in the coating process, the method using a spin coater is the spin coating method, the method using the slit coater is the slit coating method, the method using the plate is gravure, offset, reverse offset, the flexographic printing method, and the method using the inkjet printer is the inkjet method. , The method of spraying in a mist form is called the spray method. The drying step includes methods such as air drying, heating, and vacuum drying. The drying step may be performed only once, or may be performed a plurality of times using different methods and conditions. Further, different methods may be used in combination, for example, firing under reduced pressure.

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

On the other hand, when compared with the vacuum vapor deposition method, the wet film deposition method may be difficult to laminate. When the laminated film is prepared by the wet film forming method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and the composition with controlled solubility, the cross-linking of the lower layer and the orthogonal solvent (Orthogonal solvent) dissolve each other. No solvent) etc. are used. However, even if these techniques are used, it may be difficult to use the wet film forming method for coating all the films.

Therefore, in general, a method is adopted in which only some layers are formed by a wet film forming method and the rest are formed by a vacuum vapor deposition method to produce an organic EL device.

For example, the procedure for manufacturing an organic EL device by partially applying the wet film forming method is shown below.
(Procedure 1) Film formation by vacuum vapor deposition method of anode (Procedure 2) Film formation by wet film formation method of composition for forming hole injection layer containing material for hole injection layer (Procedure 3) Material for hole transport layer Formation of a composition for forming a hole transport layer containing (Procedure 4) Formation of a composition for forming a light emitting layer containing a host material and a dopant material by a wet film formation method (Procedure 5) Electron transport layer (Procedure 6) Film formation by vacuum vapor deposition method of electron injection layer (Procedure 7) Film formation by vacuum vapor deposition method of cathode By going through this procedure, anode / hole injection layer / hole transport An organic EL element composed of a light emitting layer / electron transport layer / electron injection layer / cathode composed of a layer / host material and a dopant material can be obtained.
Of course, there is a means for preventing the dissolution of the light emitting layer of the lower layer, or by using a means for forming a film from the cathode side contrary to the above procedure, a layer containing a material for an electron transport layer and a material for an electron injection layer is formed. It can be prepared as a composition for use and deposited by a wet film forming method.

2-9-3. Other film forming method A laser heating drawing method (LITI) can be used for forming a film of the composition for forming an organic layer. LITI is a method in which a compound adhered to a base material is heated and vapor-deposited with a laser, and an organic layer forming composition can be used as a material to be applied to the base material.

2-9-4. Any step Before and after each step of film formation, an appropriate treatment step, cleaning step and drying step may be appropriately added. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, heat treatment, and the like. Further, a series of steps for producing a bank can be mentioned.

Photolithography technology can be used to create the bank. As the bank material that can be used for photolithography, both an inorganic material and an organic material can be used. Examples of the inorganic material include SiN _x , SiO _x and a mixture thereof. On the other hand, examples of the organic material include a positive resist material and a negative resist material. Further, a patternable printing method such as an inkjet method, a gravure offset printing, a reverse offset printing, and a screen printing can also be used. In that case, a permanent resist material can also be used.

Materials used for banks include polysaccharides and derivatives thereof, homopolymers and copolymers of ethylenic monomers having hydroxyls, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, and polyetherimides. , Polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyurethane, epoxy (meth) acrylate, melamine (meth) acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer polymer (ABS), silicone resin, polyvinyl chloride, chlorine Fluoropolymers such as polyethylene chemicals, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene, fluoroolefin-hydrocarbon olefin copolymer polymer, fluorocarbon polymer, etc. However, it is not limited to that.

For example, as a forming method using an organic material in Bank's photolithography technology,
An organic layer is formed by applying a material exhibiting liquid repellency to the composition for forming an organic layer to an element substrate on which an electrode is formed and drying the material. By performing an exposure step and a developing step on this organic layer using an exposure mask, a bank can be formed on the element substrate on which the electrodes are formed. After that, if necessary, in order to spread the composition for forming the organic layer evenly, steps such as cleaning / drying with a solvent and ultraviolet treatment may be performed to remove impurities on the surface of the bank.

Further, an organic EL element can be produced on a substrate having a bank by using an inkjet method. Specifically, a bank is provided on the element substrate on which an electrode is formed, and an organic EL element is provided between the banks from the inkjet head. A film can be formed by dropping droplets of the layer-forming composition and drying the layers. Then, by repeating this process, laminating the films in sequence, and forming an electron transport layer, an electron injection layer, and an electrode by using a vacuum vapor deposition method, an organic EL device in which the light emitting portion is separated by a bank material can be produced. can.
The organic EL device thus produced is preferably covered with a sealing layer in order to protect it from moisture and oxygen. For example, when water or oxygen infiltrates from the outside, the light emitting function is impaired, the luminous efficiency is lowered, and dark spots (dark spots) that do not emit light are generated. In addition, the light emission life may be shortened.
As the sealing layer, for example, an inorganic insulating material such as silicon oxynitride (SiON), which has low permeability to moisture and oxygen, can be used. Further, the organic EL element may be sealed by attaching a sealing substrate such as transparent glass or opaque ceramic to the element substrate on which the organic EL element is formed via an adhesive.

2-9-5. Composition for forming an organic layer used in a wet film forming method The composition for forming an organic layer is a low molecular weight compound capable of forming each organic layer of an organic EL element, or a polymer obtained by polymerizing the low molecular weight compound. It is obtained by dissolving the compound in an organic solvent. For example, the composition for forming a light emitting layer has a polycyclic aromatic compound (or a polymer compound thereof) represented by the above general formula (1) as a host material as a first component, and a dopant as a second component. It is preferable to contain the above-mentioned polycyclic aromatic compound containing boron (or a polymer compound thereof), which is a material, and at least one organic solvent as a third component. The third component functions as a solvent for dissolving the first component and the second component in the composition, and at the time of application, the third component itself gives a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

The polymer compound includes a first structural unit derived from the reactive compound (H) in which a reactive substituent is substituted on the polycyclic aromatic compound represented by the above general formula (1), and a first structural unit. A reactive compound (D) in which a reactive substituent is substituted for a polycyclic aromatic compound (a polycyclic aromatic compound represented by any of the general formulas (2) to (5)) containing two components of boron. A polymer compound (HD) which is a copolymer having a second structural unit derived from the compound, a crosslinked polymer (HD) obtained by further cross-linking the polymer compound (HD), and a main chain type polymer. , A pendant type polymer compound (HD) in which the reactive compound (H) and the reactive compound (D) are substituted, and a pendant type polymer crosslinked product (HD) in which the pendant type polymer compound (HD) is further crosslinked. Is also included.
That is, formation of an organic layer containing at least one selected from a polymer compound (HD), a polymer crosslinked body (HD), a pendant type polymer compound (HD) and a pendant type polymer crosslinked body (HD), and an organic solvent. Can be a composition for use.
The polymer compound (HD), the polymer crosslinked body (HD), the pendant type polymer compound (HD) and the pendant type polymer crosslinked body (HD) are the host which is the first component and the second component. It has a structure in which a dopant is incorporated in the same molecule.

<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 at the time of film formation, it is possible to control and improve the film forming property, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. Further, at the time of film formation using the inkjet method, the meniscus stability at the pinhole of the inkjet head can be controlled, and the ejection property can be controlled / improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light emission characteristics, efficiency, and life of the organic EL device having the organic layer obtained from the composition for forming the organic layer can be improved. Can be done.

(1) Physical Properties of Organic Solvent The boiling point of at least one organic solvent is 130 to 350 ° C., preferably 140 to 300 ° C., and more preferably 150 to 250 ° C. When the boiling point is 130 ° C. or higher, it is preferable from the viewpoint of inkjet ejection property. Further, when the boiling point is 350 ° C. or lower, it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent and smoothness. The organic solvent is more preferably configured to contain two or more kinds of organic solvents from the viewpoint of good inkjet ejection property, film forming property, smoothness and low residual solvent. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming an organic layer in consideration of transportability and the like.

Further, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the host of the first component and the dopant of the second component, and the boiling point (BP _GS ) of the good solvent (GS) is the poor solvent. It is preferably lower than the boiling point (BP _{PS) of (PS).}
By adding the poor solvent having a high boiling point, the good solvent having a low boiling point volatilizes first at the time of film formation, and the concentration of the content in the composition and the concentration of the poor solvent increase, and rapid film formation is promoted. As a result, a coating film having few defects, a small surface roughness, and high smoothness can be obtained.

Differential solubility _(S GS _{-S PS)} is preferably 1% or more, more preferably 3% or more, 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 the film formation, the organic solvent is removed from the coating film by a drying step such as vacuum, reduced pressure, and heating. When heating is performed, it is preferable to perform heating at a glass transition temperature (Tg) of at least one of the solutes + 30 ° C. or lower from the viewpoint of improving the coating film-forming property. From the viewpoint of reducing the residual solvent, it is preferable to heat the solute at at least one 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 is sufficiently removed because the film is thin. Further, the drying may be performed a plurality of times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific Examples of Organic Solvents Examples of the organic solvent used in the composition for forming an organic layer include an alkylbenzene solvent, a phenyl ether solvent, an alkyl ether solvent, a cyclic ketone solvent, an aliphatic ketone solvent, and a monocyclic solvent. Examples thereof include a ketone solvent, a solvent having a diester skeleton, and a fluorine-containing solvent. Specific examples thereof include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, Heptane-2-ol, octane-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 Anisol, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mecitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Anisol, phenetol, benzodioxol, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methyl Anisole, Simene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, Decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, benzoic acid Methyl, isopentylbenzene, 3,4-dimethylanisole, o-tornitrile, 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'-bitril, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydro Benzofuran, 1-methyl-4- (propoxymethyl) benzene, 1-methyl-4- (butyloxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) ) Benzene, 1-methyl-4- (heptyloxymethyl) benzenebenzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether, nitrobenzene, dimethylnitrobenzene, aminobiphenyl, diphenylamine, etc. Not limited. Further, the solvent may be used alone or may be mixed.

Among these, as the organic solvent, one or more selected from an alkylbenzene solvent and a phenyl ether solvent are preferable, and a mixed solvent of 3-phenoxytoluene and cyclohexylbenzene is more preferable.

<Arbitrary ingredient>
The composition for forming an organic layer may contain an arbitrary component as long as its properties are not impaired. Examples of the optional component include a binder and a surfactant.

(1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film at the time of film formation and joins 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 composition for forming an organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, and the like. 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) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the above resins and polymers, but are not limited thereto.

The binder used in the composition for forming an organic layer may be only one kind or a mixture of a plurality of kinds may be used.

(2) Surfactant The composition for forming an organic layer contains, for example, a surfactant for controlling the film surface uniformity, the solvent-like property and the liquid repellency of the film surface of the composition for forming an organic layer. May be good. Surfactants are classified into ionic and nonionic based on the structure of hydrophilic groups, and further classified into alkyl-based, silicon-based and fluorine-based based on the structure of hydrophobic groups. Further, from the molecular structure, it is classified into a monomolecular system having a relatively small molecular weight and a simple structure and a polymer system having a large molecular weight and having side chains and branches. Further, it is classified into a single system, a mixed system in which two or more kinds of surfactants and a base material are mixed, according to the composition. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbak 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181 and Disper. Bake 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF -50-100CS (trade name, manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Surfron SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futergent 251 and FTX-218 (trade name) Product name, Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (Product name, Mitsubishi Material Co., Ltd.), Megafuck F- 470, Megafuck F-471, Megafuck F-475, Megafuck R-08, Megafuck F-477, Megafuck F-479, Megafuck F-553, Megafuck F-554 (trade name, DIC Co., Ltd.) ), Fluoroalkylbenzene sulfonate, Fluoralkyl 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 Steerate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, Polyoxyethylene sorbitan oleate, polyo Examples thereof include xyethylene naphthyl ether, alkylbenzene sulfonate and alkyldiphenyl ether disulfonate.

Further, the surfactant may be used alone or in combination of two or more.

<Composition and physical properties of composition for forming organic layer>
The content of each component in the composition for forming an organic layer is obtained from the good solubility, storage stability and film forming property of each component in the composition for forming an organic layer, and the composition for forming an organic layer. Good film quality of the coating film, good ejection property when the inkjet method is used, and good electrical characteristics, light emission characteristics, efficiency, and life of the organic EL element having an organic layer produced by using the composition. It is decided in consideration of the viewpoint of. For example, in the case of a light emitting layer forming composition, the host material of the first component is 0.0999 to 8.0% by mass with respect to the total mass of the light emitting layer forming composition, and the dopant material is the second component. Is 0.0001 to 2.0% by mass with respect to the total mass of the light emitting layer forming composition, and the organic solvent as the third component is 90.0 to 99 with respect to the total mass of the light emitting layer forming composition. It is preferably 9.9% by mass.

More preferably, the host material as the first component is 0.095 to 4.0% by mass with respect to the total mass of the light emitting layer forming composition, and the second component is based on the total mass of the light emitting layer forming composition. The amount of the organic solvent as the third component is 0.005 to 1.0% by mass, and the amount of the organic solvent as the third component is 95.0 to 99.9% by mass with respect to the total mass of the composition for forming the light emitting layer.
More preferably, the host material as the first component is 0.25 to 2.5% by mass with respect to the total mass of the light emitting layer forming composition, and the dopant material as the second component is the light emitting layer forming composition. The amount of the organic solvent as the third component is 97.0 to 99.7% by mass with respect to the total mass of the composition for forming a light emitting layer.

The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by a known method such as stirring, mixing, heating, cooling, dissolving, and dispersing. Further, after the preparation, filtration, degassing (also referred to as degas), ion exchange treatment, inert gas replacement / encapsulation treatment and the like may be appropriately selected.

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

The lower the surface tension of the composition for forming an organic layer, the better the film-forming property and the coating film without defects. On the other hand, the higher the value, the better the inkjet ejection property. From this, the viscosity of the composition for forming an organic layer is preferably 20 to 40 mN / m and more preferably 20 to 30 mN / m in surface tension at 25 ° C. In the present invention, the surface tension is a value measured by using the suspension method.

式（ＸＬＰ−１）において、
ＭＵｘ、ＥＣｘおよびｋは上記式（ＳＰＨ−１）におけるＭＵ、ＥＣおよびｋと同定義であり、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。 2-9-6. Crosslinkable Polymer Compound: Compound Represented by the General Formula (XLP-1) Next, a case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

In formula (XLP-1)
MUx, ECx and k have the same definition as MU, EC and k in the above formula (SPH-1), except that the compound represented by the formula (XLP-1) has at least one crosslinkable substituent (XLS). The content of the monovalent or divalent aromatic compound having, preferably having a crosslinkable substituent is 0.1 to 80% by mass in the molecule.

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 capable of further crosslinking the above-mentioned polymer compound, but a substituent having the following structure is preferable. * In each structural formula indicates the bonding position.

L is a single bond, −O−, −S−,> C = O, −OC (= O) −, alkylene having 1 to 12 carbon atoms, and oxyalkylene having 1 to 12 carbon atoms, respectively. And a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, it is represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17). The group represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17) is more preferable.

上記式（ＸＬＳ−１９）中、Ｒ^４１およびＲ^４２は、それぞれ独立して、アルキルであり、Ｒ^４１およびＲ^４２は互いに結合して環を形成してもよい。また、Ｒ^４１およびＲ^４２の合計炭素数は２〜１０であることが好ましい。Further, the crosslinkable substituent other than the above may be chlorine, bromine or iodine, or a boron-containing group represented by the following formula (XLS-19). * In the structural formula indicates the bonding position.

In the above formula (XLS-19), R ⁴¹ and R ⁴² are independently alkyl, and R ⁴¹ and R ⁴² may be bonded to each other to form a ring. Further, the total number of carbon atoms of ^{R 41} and R ^{42 is preferably 2 to 10.}

Examples of the divalent aromatic compound having a crosslinkable substituent include a compound having the following partial structure. * In each structural formula indicates the bonding position.

2-9-7. Method for Producing Polymer Compound and Crosslinkable Polymer Compound Regarding the method for producing the polymer compound and the crosslinkable polymer compound, the compound represented by the above formula (SPH-1) and the compound represented by (XLP-1) described above. Will be described 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 and the like, and examples thereof include dimethoxyethane, 2- (2-methoxyethoxy) ethane, and 2- (2). -Ethoxyethoxy) ethane and the like.

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 the compound of the formula (SPH-1) and the compound of (XLP-1) are produced, they may be produced in one step or in multiple steps. Further, it may be carried out by a batch polymerization method in which the reaction is started after all the raw materials are placed in the reaction vessel, or it may be carried out by a dropping polymerization method in which the raw materials are added dropwise to the reaction vessel, and the product advances the reaction. It may be carried out by a precipitation polymerization method in which the mixture precipitates, and these can be combined and synthesized as appropriate. For example, when the compound represented by the formula (SPH-1) is synthesized in one step, the desired product is obtained by carrying out the reaction with the monomer unit (MU) and the end cap unit (EC) added to the reaction vessel. .. Further, when synthesizing a compound represented by the general formula (SPH-1) in multiple stages, the purpose is to polymerize the monomer unit (MU) to the desired molecular weight and then add the end cap unit (EC) to react. Get things. By adding different types of monomer units (MUs) in multiple stages and carrying out the reaction, a polymer having a concentration gradient in the structure of the monomer units can be produced. In addition, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

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

Examples of the monomer unit that can be used in the present invention include JP-A-2010-189630, International Publication No. 2012/086671, International Publication No. 2013/191088, International Publication No. 2002/045184, and International Publication No. 2011/049241. No., International Publication No. 2013/146806, International Publication No. 2005/049546, International Publication No. 2015/145871, Japanese Patent Application Laid-Open No. 2010-215886, Japanese Patent Application Laid-Open No. 2008-106241, Japanese Patent Application Laid-Open No. 2010-215886, International Publication No. It can be synthesized according to the methods described in Publication No. 2016/031639, Japanese Patent Application Laid-Open No. 2011-174062, International Publication No. 2016/031639, International Publication No. 2016/031639, and International Publication No. 2002/045184. ..

For specific polymer synthesis procedures, see JP2012-036388, International Publication No. 2015/008851, JP2012-36381, JP2012-144722, and International Publication No. 2015/194448. , International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2016/031639, International Publication No. 2016/031639, International It can be synthesized according to the method described in Publication No. 2016/125560, International Publication No. 2015/145871, International Publication No. 2011/049241 and Japanese Patent Application Laid-Open No. 2012-144722.

2-10. Application Examples of Organic Electroluminescent Devices The present invention can also be applied to a display device provided with an organic EL element, a lighting device provided with an organic EL element, and the like. A display device or a lighting device provided with an organic EL element can be manufactured by a known method such as connecting an organic EL element according to the present embodiment to a known drive device, and can be manufactured by a known method such as DC drive, pulse drive, AC drive, or the like. It can be driven by using a known driving method as appropriate.

Examples of the display device include a panel display such as a color flat panel display and a flexible display such as a flexible color organic electroluminescent (EL) display (for example, JP-A-10-335066, JP-A-2003-321546). See Japanese Patent Application Laid-Open No. 2004-281086, etc.). Further, as the display method of the display, for example, at least one of a matrix method and a segment method can be mentioned. The matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally such as in a grid pattern or a mosaic pattern, and characters and images are displayed as a set of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on a personal computer, monitor, or television, quadrangular pixels with a side of 300 μm or less are usually used, and in the case of a large display such as a display panel, pixels with a side on the order of mm should be 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 a delta type and a stripe type. Then, as the driving method of this matrix, either a line sequential driving method or an active matrix may be used. Line sequential drive has the advantage of a simpler structure, but when considering operating characteristics, the active matrix may be superior, so it is also necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed so as to display predetermined information, and a predetermined area is made to emit light. For example, a time and temperature display in a digital clock or a thermometer, an operating state display of an audio device or an electromagnetic cooker, a panel display of an automobile, and the like can be mentioned.

Examples of the lighting device include a lighting device such as an indoor lighting device, a backlight of a liquid crystal display device, and the like (for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211). Etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, the present embodiment considers that it is difficult to reduce the thickness of a liquid crystal display device, especially a backlight for a personal computer for which thinning is an issue, because it is composed of a fluorescent lamp and a light guide plate in the conventional method. The backlight using the light emitting element according to the above is characterized by being thin and lightweight.

At present, application of multicoloring technology by a color conversion method to liquid crystal displays, organic EL displays, lighting, and the like is being actively studied. The color conversion is to convert the light emitted from the light emitter into light having a longer wavelength (wavelength conversion), and represents, for example, to convert blue light emission into green or red light emission. By forming a composition having this wavelength conversion function into a film and combining it with, for example, a blue light source, it is possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. A full-color display can be manufactured by using a white light source, which is a combination of such a blue light source and a film having a wavelength conversion function, as a light source unit, and combining the liquid crystal driving portion and a color filter. Further, if there is no liquid crystal drive portion, it can be used as it is as a white light source, and can be applied as a white light source such as LED lighting. Further, by using a blue organic EL element as a light source in combination with a film that converts green and red, it is possible to manufacture a full-color organic EL display that does not use a metal mask. Further, by using a blue micro LED as a light source in combination with a film that converts green and red, it becomes possible to manufacture a low-cost full-color micro LED display.
The polycyclic aromatic compound represented by the general formula (1) is useful as a fluorescent material that gives blue or green light with high color purity by excitation light, and is also used as a material having such a wavelength conversion function. be able to. Specifically, the polycyclic aromatic compound of the formula (1) converts, for example, light having a wavelength of 300 nm to 449 nm into blue emission having a narrow half width (25 nm or less, further 20 nm or less) having a maximum value at 450 nm to 500 nm. It can be used as a wavelength conversion material. Further, for example, it can be used as a wavelength conversion material for converting light having a wavelength of 300 nm to 499 nm into green light emission having a narrow half width (25 nm or less, further 20 nm or less) having a maximum value of 500 nm to 570 nm.
The composition having a wavelength conversion function may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the formula (1). As the binder resin, for example, the resins described in paragraphs [0173] to [0176] of International Publication No. 2016/190283 can be used. As other additives, the compounds described in paragraphs [0177] to [0181] of International Publication No. 2016/190283 can be used. Further, as the solvent, a solvent capable of appropriately dissolving these materials may be used.
The wavelength conversion film includes a wavelength conversion layer formed by curing a composition having a wavelength conversion function. As a method for producing a wavelength conversion layer from the composition, a known film forming method can be referred to. The wavelength conversion film may consist only of a wavelength conversion layer formed from the composition containing the polycyclic aromatic compound of the formula (1), and other wavelength conversion layers (for example, blue light to green light or red light) may be formed. A wavelength conversion layer for conversion, a wavelength conversion layer for converting blue light or green light into red light) may be included. Further, the wavelength conversion film may include a base material layer and a barrier layer for preventing deterioration of the color conversion layer due to oxygen, moisture and heat.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. That is, the configuration of the organic EL device of the present invention is not limited to the configuration shown in the following examples, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical characteristics of the present invention.

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). The fluorescence spectrum of the sample was measured using a spectrofluorometer (F-7000, manufactured by Hitachi High-Tech Co., Ltd.).

For the measurement of the fluorescence spectrum, photoluminescence was measured by exciting at an appropriate excitation wavelength at room temperature. For the measurement of the phosphorescence spectrum, the sample was measured in a state of being immersed in liquid nitrogen (temperature 77K) using an attached cooling unit. The sample was excited at an appropriate excitation wavelength and photoluminescence was measured.

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

<Evaluation of organic EL elements>
Evaluation items and evaluation methods The evaluation items include drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) of emission spectrum, and full width at half maximum ( nm) and roll-off and so on. For these evaluation items, values at an appropriate emission brightness can be used.

The quantum efficiency of the light emitting element includes the internal quantum efficiency and the external quantum efficiency. In the internal quantum efficiency, the external energy injected as electrons (or holes) into the light emitting layer of the light emitting element is converted into pure photons. Shows the ratio. On the other hand, the external quantum efficiency is calculated based on the amount of these photons emitted to the outside of the light emitting element, and a part of the photons generated in the light emitting layer is continuously absorbed or reflected inside the light emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency because it is not emitted to the outside of the light emitting element.

The methods for measuring the spectral radiance (emission spectrum) and the external quantum efficiency are as follows. Using a voltage / current generator R6144 manufactured by Advantest, the element was made to emit light by applying a voltage. The spectral radiance in the visible light region was measured from 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 diffused surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Next, the number of photons was integrated in the entire observed wavelength region to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the element, and the value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element is the external quantum efficiency. Further, the full width at half maximum of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% centering on the maximum emission wavelength.

Roll-off is a phenomenon in which when a voltage is applied to an element, the efficiency decreases as the voltage is applied, and a smaller value is preferable. In a TADF element, when the tau (delay) of the dopant or assist dopant is large, the roll-off is large, and when the tau (delay) is small, the roll-off is small. As a method for comparing and evaluating the degree of roll-off, it can be evaluated by comparing the efficiencies at any two points in brightness or current density. It is preferable that the efficiency is high and the roll-off is small.

The roll-off indicates the degree of decrease in efficiency between any two luminances, for example, the roll-off (RO) between ^{100 cd / m 2} and 1000 cd / m ^{2 is calculated by the following equation (XXXXX).} Wherein EQE (100cd / ^{m 2)} and EQE (1000cd / ^{m 2)} each represent an external quantum efficiency at 100 cd / ^{m 2} and 1000 cd / ^{m 2.}
RO = 1- (EQE (100cd / m ² ) / EQE (1000cd / m ² ))

(1) Deposited Organic EL Device An organic EL device having an element configuration suitable for a heat-activated delayed fluorescent material and capable of expecting high efficiency, as shown in the literature (Adv. Mater. 2016, 28, 2777-2781). Made.
In the following Examples and Comparative Examples, the materials for forming each layer other than the light emitting layer used in producing the organic EL device of the configuration A are as follows.
The materials for forming each layer of the produced organic EL element in Table 1 are shown.
The hole injection layer material "HI" is N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, and the hole transport layer material "HT" is 4,4'. , 4 "-Tris (N-carbazolyl) triphenylamine, the electron blocking layer material" EB "is 1,3-bis (N-carbazolyl) benzene, and the electron transporting layer material" ET "is It is a diphenyl [4- (triphenylsilyl) phenyl] phosphine oxide.
The chemical structure is shown below.

<Examples 1 to 9, Comparative Examples 1 to 3>
An organic EL device formed by laminating each layer of the forming material and the film thickness shown in Table 1 was produced.

The structure of the compound used as the host and dopant of the light emitting layer is as follows.

<Example 1>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Choshu Industry Co., Ltd.), and is made of tantalum containing HI, HT, EB, compound (BO2-0220), compound (DABNA2), and ET, respectively. A vapor deposition boat and an aluminum nitride vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5 × 10 -4} Pa, and HI is first heated to be vapor-deposited to a film thickness of 40 nm, and then HT is heated to be vapor-deposited to a film thickness of 15 nm. An injection layer and a hole transport layer were formed, respectively. Next, the EB was heated and vapor-deposited to a film thickness of 15 nm to form an electron blocking layer. Next, the compound (BO2-0220) and the compound (DABNA2) were heated at the same time and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of compound (BO2-0220) to compound (DABNA2) was 99: 1. Next, the ET was heated and vapor-deposited to a film thickness of 40 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, LiF is heated and vapor-deposited to a film thickness of 1 nm at a vapor deposition rate of 0.01 to 0.1 nm / sec, and then aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. Then, an organic EL element was obtained. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 467 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 23.7%, and a high quantum efficiency was obtained.

<Example 2>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0511S). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 465 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 15.4%, and a high quantum efficiency was obtained.

<Example 3>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to a compound (BO2-0264 / 0511S). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 465 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 14.2%, and a high quantum efficiency was obtained.

<Comparative example 1>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (EMH1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 465 nm, and deep blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 10.8%, which was lower than that of Examples 1 to 3.

<Example 4>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the dopant was changed to compound (BD1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 462 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 28.6%, and a high quantum efficiency was obtained.

<Example 5>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0220 / 0511S) and the dopant was changed to compound (BD1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 461 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 22.4%, and a high quantum efficiency was obtained.

<Comparative example 2>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the dopant was changed to compound (BD1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 461 nm, and deep blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 12.6%, which was lower than that of Examples 4 and 5.

<Example 6>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0220) and the dopant was changed to compound (BD2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 34.0%, and a high quantum efficiency was obtained.

<Example 7>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0511S) and the dopant was changed to compound (BD2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 28.0%, and a high quantum efficiency was obtained.

<Example 8>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0520S) and the dopant was changed to compound (BD2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 29.2%, and a high quantum efficiency was obtained.

<Example 9>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (BO2-0264 / 0511S) and the dopant was changed to compound (BD2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 470 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 30.3%, and a high quantum efficiency was obtained.

<Comparative example 3>
An organic EL device was obtained by the same procedure and configuration as in Example 1 except that the host was changed to compound (EMH1) and the dopant was changed to compound (BD2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 471 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 19.1%, which was lower than that of Examples 6 to 9.

<Examples 10 to 14, Comparative Examples 4 to 8>
An organic EL device formed by laminating each layer of the forming material and the film thickness shown in Table 2 was produced.

The structure of the compound used as the host and dopant of the light emitting layer is as follows.

<Example 10>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Choshu Industry Co., Ltd.), and is made of tantalum containing HI, HT, EB, compound (BO2-0511S), compound (BD3), and ET, respectively. A vapor deposition boat and an aluminum nitride vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5 × 10 -4} Pa, and HI is first heated to be vapor-deposited to a film thickness of 40 nm, and then HT is heated to be vapor-deposited to a film thickness of 15 nm. An injection layer and a hole transport layer were formed, respectively. Next, the EB was heated and vapor-deposited to a film thickness of 15 nm to form an electron blocking layer. Next, the compound (BO2-0511S) and BD3 were heated at the same time and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of compound (BO2-0511S) to compound (BD3) was 99: 1. Next, the ET was heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, LiF is heated and vapor-deposited to a film thickness of 1 nm at a vapor deposition rate of 0.01 to 0.1 nm / sec, and then aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. Then, an organic EL element was obtained. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 451 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 14.8%, and a high quantum efficiency was obtained.

<Comparative example 4>
An organic EL device was obtained by the same procedure and configuration as in Example 10 except that the host was changed to compound (EMH1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 452 nm, and deep blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 8.1%, which was lower than that of Example 10.

<Example 11>
An organic EL device was obtained by the same procedure and configuration as in Example 10 except that the dopant was changed to compound (BD4). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 461 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 19.5%, and a high quantum efficiency was obtained.

<Comparative example 5>
An organic EL device was obtained by the same procedure and configuration as in Example 11 except that the host was changed to compound (EMH1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 461 nm, and deep blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 11.1%, which was lower than that of Example 11.

<Example 12>
An organic EL device was obtained by the same procedure and configuration as in Example 10 except that the dopant was changed to compound (BD5). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 468 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 17.5%, and a high quantum efficiency was obtained.

<Comparative Example 6>
An organic EL device was obtained by the same procedure and configuration as in Example 12 except that the host was changed to compound (EMH1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 468 nm, and deep blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 11.4%, which was lower than that of Example 12.

<Example 13>
An organic EL device was obtained by the same procedure and configuration as in Example 10 except that the dopant was changed to compound (BD5). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 489 nm, and blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 18.1%, and a high quantum efficiency was obtained.

<Comparative Example 7>
An organic EL device was obtained by the same procedure and configuration as in Example 13 except that the host was changed to compound (EMH1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 490 nm, and blue emission was observed. On the other hand, ^{the external quantum efficiency at the time of 100 cd / m 2} emission was 12.2%, which was lower than that of Example 13.

<Example 14>
An organic EL device was obtained by the same procedure and configuration as in Example 10 except that the dopant was changed to compound (BD7). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 468 nm, and deep blue emission was observed. Further, the external quantum efficiency at the time of 100 cd / m ² emission was 11.6%, and a high quantum efficiency was obtained.

<Comparative Example 8>
An organic EL device was obtained by the same procedure and configuration as in Example 12 except that the host was changed to compound (EMH1). A DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode, and the emission spectrum had a peak wavelength of 468 nm, and deep blue emission was observed, but it did not shine at ^{100 cd / m 2 due to deterioration.}

<Examples 15 to 16, Comparative Example 9>
An organic EL device formed by laminating each layer of the forming material and the film thickness shown in Table 3 was produced.

The structure of the compound used as the host and dopant of the light emitting layer is as follows.

<Example 15>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Choshu Industry Co., Ltd.), and is made of tantalum containing HI, HT, EB, compound (BO2-0231), compound (BD2), and ET, respectively. A vapor deposition boat and an aluminum nitride vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5 × 10 -4} Pa, and HI is first heated to be vapor-deposited to a film thickness of 40 nm, and then HT is heated to be vapor-deposited to a film thickness of 15 nm. An injection layer and a hole transport layer were formed, respectively. Next, the EB was heated and vapor-deposited to a film thickness of 15 nm to form an electron blocking layer. Next, the compound (BO2-0231) and the compound (BD2) were simultaneously heated and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of compound (BO2-0231) to compound (BD2) was 99: 1. Next, the ET was heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, LiF is heated and vapor-deposited to a film thickness of 1 nm at a vapor deposition rate of 0.01 to 0.1 nm / sec, and then aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. Then, an organic EL element was obtained. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 476 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 27.7% and 24.5%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -11.6%.

<Example 16>
An organic EL device was obtained by the same procedure and configuration as in Example 15 except that the host was changed to compound (BO2-0431). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 474 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 29.4% and 25.3%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -14%.

<Comparative Example 9>
An organic EL device was obtained by the same procedure and configuration as in Example 16 except that the host was changed to EMH1. When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 471 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 18.2% and 12.7%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as large as -30%.

<Examples 17 to 25, Comparative Example 10>
An organic EL device formed by laminating each layer of the forming material and the film thickness shown in Table 4 was produced.

The structures of the host and dopant of the light emitting layer and the compound used as the material for forming the electron transport layer are as follows. The structure of the compound used as the forming material for each layer other than the light emitting layer and the electron transporting layer is as described above.

<Example 17>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Choshu Industry Co., Ltd.), and HI, HT, EB, compound (BO2-0431), compound (BD2), 2CzBN and BPy-TP2 are put in, respectively. A tantalum vapor deposition boat and an aluminum nitride vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5 × 10 -4} Pa, and HI is first heated to be vapor-deposited to a film thickness of 40 nm, and then HT is heated to be vapor-deposited to a film thickness of 15 nm. An injection layer and a hole transport layer were formed, respectively. Next, the EB was heated and vapor-deposited to a film thickness of 15 nm to form an electron blocking layer. Next, the compound (BO2-0231) and the compound (BD2) were simultaneously heated and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of compound (BO2-0231) to compound (BD2) was 99: 1. Next, 2 CzBN was heated and vapor-deposited to a film thickness of 10 nm to form an electron transport layer 1. Next, BPy-TP2 was heated and vapor-deposited to a film thickness of 20 nm to form an electron transport layer 1. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, LiF is heated and vapor-deposited to a film thickness of 1 nm at a vapor deposition rate of 0.01 to 0.1 nm / sec, and then aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. Then, an organic EL element was obtained. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 28.0% and 25.1%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -10.4%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 83 hours.

<Example 18>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to compound (BO2-0520). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 28.6% and 25.7%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -9.2%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 90 hours.

<Example 19>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to compound (BO2-0220). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 29.3% and 26.6%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -10.1%. The time until the luminance cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 30 hours.

<Example 20>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to compound (BO2-0220-4). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 24.3% and 20.9%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -14.0%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 100 hours.

<Example 21>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to compound (BO2-0431-1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 26.1% and 23.5%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -10.0%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 90 hours.

<Example 22>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to compound (BO2-0431-2). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 26.3% and 23.5%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -10.6%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 98 hours.

<Example 23>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to a compound (BO2-0220 / 0511S-1). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 473 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 24.7% and 21.1%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -14.6%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 67 hours.

<Example 24>
An organic EL device was obtained by the same procedure and configuration as in Example 18 except that the dopant was changed to compound (BD8). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 470 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 24.6% and 22.5%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -8.5%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 80 hours.

<Example 25>
An organic EL device was obtained by the same procedure and configuration as in Example 18 except that the dopant was changed to compound (BD9). When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 462 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 23.9% and 21.0%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as small as -12.1. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 61 hours.

<Comparative Example 10>
An organic EL device was obtained by the same procedure and configuration as in Example 17 except that the host was changed to EMH1. When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 1000 cd / m 2} emission were measured, the emission spectrum had a peak wavelength of 471 nm, and deep blue emission was observed. Further, the external quantum efficiencies at the time of 100 cd / m ² and 1000 cd / m ² emission were 17.5% and 10.9%, and high quantum efficiencies were obtained. In addition, the roll-off between 100 cd / m ² and 1000 cd / m ² was as large as -38%. The time until the luminance 80 cd / ^{m 2} when is continuously driven at a current value of the luminance 100cd / ^{m 2} _{(LT 80)} was 22 hours.

Next, in order to explain the present invention in more detail, an evaluation of an example of the light emitting layer forming composition of the present invention and an example of an organic EL element using the light emitting layer forming composition of the present invention will be shown. The present invention is not limited to these.

(2) Composition for forming a light emitting layer <Example S-1 to Example S-10 and Comparative Example S-1>
Emission of a solid content concentration of 1% by mass by mixing 0.99% by mass of the host of the first component shown in Table 6, 0.01% by mass of the dopant of the second component and 99% by mass of the solvent of the third component. Each layer-forming composition was prepared.
Among these prepared compositions, when the viscosity and surface tension of the light emitting layer forming composition of Example S-9 were measured, the viscosity was 3.5 mPa · s, and the surface tension was 36.3 mN / m. Met.

The structures of the host and dopant compounds shown in Table 6 used in the preparation of the light emitting layer forming composition are as follows, and the solvents are as shown in Table 5.

The prepared composition for forming a light emitting layer was evaluated as follows. These results are shown in Table 6.

<Evaluation of solubility>
Solubility was evaluated by confirming the presence or absence of turbidity and precipitation of the prepared composition for forming a light emitting layer. The composition without turbidity and precipitation was designated as "A", and the composition with turbidity or precipitation was designated as "F", and the solubility was evaluated.

<Evaluation of film formation>
For the light emitting layer forming composition whose solubility was evaluated as "A", the film obtained after the spin coat film formation or the inkjet printing was observed according to the following operation, and pinholes or precipitations were formed on the film. Alternatively, the uneven film is "C", the pinhole, the precipitation of the compound and the film without unevenness are "B", and the film having high smoothness (Ra <5 nm) without the precipitation and unevenness of the pinhole and the compound is "A". The film-forming property was evaluated.
(Spin coating film formation method)
Thickness 0.5 mm, a clean glass substrate size 28 × 26 mm, was subjected to _{UV-O 3} treatment by irradiating radiation energy 1000 mJ / cm ² (low pressure mercury lamp (254 nm)). Next, 0.3 to 0.6 mL of the light emitting layer forming composition is dropped onto the glass, and spin coating (slope (raise to a predetermined rotation speed in 5 seconds) → apply at 500 to 5000 rpm (at a predetermined rotation speed). (Maintained for 10 seconds) → Slope (decrease the number of revolutions in 5 seconds and set the number of revolutions to 0 rpm)). Further, it was dried on a hot plate at 120 ° C. for 10 minutes to form a film.
(Inkjet film formation method)
Using an inkjet, the composition for forming a light emitting layer was ejected into 100 ppi pixels and dried at 100 ° C. to form a film.

<Evaluation of inkjet ejection stability>
With respect to the light emitting layer forming composition whose solubility was evaluated as "A", the light emitting layer forming composition was started to be ejected into 100 ppi pixels by using an inkjet, and immediately after the start of ejection and after 24 hours of continuous operation. The ejection stability of each inkjet was evaluated. In the evaluation, it was rated as "C" when it could not be discharged, "B" when it could be discharged from less than 90% of the discharge holes, and "A" when it could be discharged from 90% or more of the discharge holes.

(3) Coating Type Organic EL Element Next, an organic EL element obtained by coating and forming an organic layer will be described.

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

<Manufacturing of Organic EL Elements of Examples SD-1 to SD-3>
Table 7 shows the material composition of each layer in the organic EL device.

In Table 7, "PEDOT: PSS", which is a material for forming the hole injection layer, includes a commercially available PEDOT: PSS solution (Clevios (TM) P VP AI4083, an aqueous dispersion of PEDOT: PSS represented by the following formula. Heraeus Holdings Co., Ltd.) was used.

In Table 7, "OTPD" which is a material for forming the hole transport layer includes OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, San-Apro Co., Ltd.) represented by the following formulas. Was dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7% by mass and an IK-2 concentration of 0.007% by mass.

As the material for forming the hole transport layer in Table 7, “XLP-101” was prepared by dissolving the above-mentioned polymer hole transport compound, XLP-101, in xylene at a concentration of 0.6% by mass. It was prepared as an XLP-101 solution.

As “PCz” in Table 7, PCz (polyvinylcarbazole) represented by the following formula was dissolved in dichlorobenzene to prepare a 0.7 mass% PCz solution.

The structures of the compounds of "BO2-0431-2", "BD2", "2CzBN" and "BPy-TP2" in Table 7 are as follows.

<Example SD-1>
A PEDOT: PSS film having a film thickness of 40 nm was formed by spin-coating a PEDOT: PSS solution on a glass substrate on which ITO was vapor-deposited to a thickness of 50 nm and firing it on a hot plate at 200 ° C. for 1 hour. (Hole injection layer). Next, the OTPD solution was spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, exposed to an exposure intensity of 100 mJ / cm ² with an exposure machine, and baked on a hot plate at 100 ° C. for 1 hour to obtain the solution. An OTPD film having a film thickness of 30 nm, which is insoluble in, was formed (hole transport layer). Next, the composition for forming a light emitting layer prepared in Example S-9 was spin-coated and fired on a hot plate at 120 ° C. for 1 hour to form a light emitting layer having a film thickness of 20 nm.

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition equipment (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing 2CzBN and BPy-TP2, a molybdenum vapor deposition boat containing LiF, and aluminum were placed. The put-in tungsten vapor deposition boat was installed. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, 2 CzBN was heated and vapor-deposited to a film thickness of 10 nm to form an electron transport layer 1. Next, BPy-TP2 was heated and vapor-deposited to a film thickness of 20 nm to form an electron transport layer 2. The vapor deposition rate when forming the electron transport layer was 1 nm / sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element was obtained.

A DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode, and the characteristics at the time of ^{100 cd / m 2 emission were measured.} Blue emission was seen. The external quantum efficiency at the time of 100 cd / m ^{2 emission was 10.1%.}

<Example SD-2>
The hole transport layer was spin-coated with an XLP-101 solution and fired on a hot plate at 200 ° C. for 1 hour to form a film having a film thickness of 30 nm. An organic EL element was obtained in the configuration. A DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode, and the characteristics at the time of ^{100 cd / m 2 emission were measured.} Blue emission was seen. The external quantum efficiency at 100 cd / m ^{2 emission was 12.1%.}

<Example SD-3>
The hole transport layer was spin-coated with a PCz solution and fired on a hot plate at 120 ° C. for 1 hour to form a film having a film thickness of 30 nm. Obtained an organic EL element. When a DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode and ^{the characteristics at the time of 100 cd / m 2} emission were measured, the emission surface was uniform, and the emission spectrum was deep with a peak wavelength of 472 nm and a half width of 20 nm. Blue emission was seen. The external quantum efficiency at 100 cd / m ^{2 emission was 11.5%.}

The coated organic EL devices produced in Examples SD-1 to SD-3 had an external quantum efficiency of 10% or more, and showed deep blue color and light emission with a narrow half-value width, and were excellent in color.

(4) Polymer Compound The organic EL element of the present invention may have a structure having a light emitting layer containing a polymer compound or a polymer crosslinked product. Examples of the polymer compound contained in such a light emitting layer include the polymer compound described in Example PS-1.

<Example PS-1>
By the method described in International Patent Publication No. WO2019 / 004248, a polymer compound containing the following structures of the host as the first component and the dopant and the emitting dopant as the second component can be synthesized. The following polymer compounds are polymerized from the first component and the second component, and have structural units derived from each.

As described above, some of the compounds according to the present invention and some of the combinations of the host material and the dopant material have been evaluated as materials for the light emitting layer of the organic EL element, and their usefulness has been shown, but they have not been evaluated. Other compounds and combinations have the same basic skeleton and basic performance, and are compounds having similar structures and similar properties as a whole. Understand that the material is available.

According to a preferred embodiment of the present invention, a polycyclic aromatic compound represented by the formula (1) as a host of the first component and boron as a dopant of the second component, which have not been specifically known in the past. By forming a light emitting layer containing a polycyclic aromatic compound containing the above, the organic EL characteristics such as the light emitting characteristics can be further enhanced.

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 (32)

An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode and a light emitting layer arranged between the pair of electrodes.
The light emitting layer in the organic electroluminescent device is
As the first component, a polycyclic aromatic compound represented by the following general formula (1) is contained as a host.
An organic electroluminescent device containing a boron-containing polycyclic aromatic compound as a dopant as a second component.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. ) In the above general formula (1), R ^{1 to} R ¹¹ are independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, and diallyl amino (where aryl has 6 to 12 carbon atoms). Aryl), diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, and an alkyl having 1 to 24 carbon atoms. 3-12 cycloalkyls, 1-24-carbon alkoxys or 6-30 carbon-carbon aryloxys.
At least one hydrogen in the aryl, the heteroaryl, the diarylamino and the diarylboryl is 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 an alkyl having 3 to 12 carbon atoms. May be substituted with cycloalkyl,
The organic electroluminescent device according to claim 1. In the above general formula (1), R ^{1 to} R ¹¹ are independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and diallyl amino (where aryl has 6 to 10 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms. 6 to 10 cycloalkyl, 1 to 6 carbon alkoxy or 6 to 16 carbon aryloxy.
At least one hydrogen in the aryl, the heteroaryl, the diarylamino and the diarylboryl is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or 6 to 10 carbon atoms. May be substituted with cycloalkyl,
The organic electroluminescent device according to claim 1. In the above general formula (1), ^{at least one of R 1 to} R ¹¹ is any of claims 1 to 3, which is a group represented by any of the following formulas (1-a) to (1-s). The organic electroluminescent device according to claim 1.

(In the above formula, * indicates the bonding position, and
At least one hydrogen in formulas (1-a) to (1-h) and formulas (1-p) to (1-q) is an aryl having 6 to 30 carbon atoms and a heteroaryl having 2 to 30 carbon atoms. , May be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 12 carbon atoms.
R in the formula (1-i), the formula (1-j), the formula (1-k) and the formula (1-r) are independently hydrogen, an aryl having 6 to 30 carbon atoms, and 2 to 2 carbon atoms. It represents 30 heteroaryls, alkyls with 1 to 24 carbon atoms or cycloalkyls with 3 to 12 carbon atoms. ) The organic electroluminescent device according to claim 4, wherein in the general formula (1), ^{at least one of R 1 to} R ¹¹ is a group represented by the above formula (1-d). In the above general formula (1), R ^{1 to} R ¹¹ are independently bonded to hydrogen, aryl, heteroaryl, diarylamino, and diarylboryl (even if the two aryls are bonded via a single bond or a linking group). Good), alkyl, cycloalkyl or alkoxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
The organic electroluminescent device according to any one of claims 1 to 5. In the above general formula (1), ^{at least one of R 4 to} R ¹¹ is a heteroaryl, and at least one hydrogen in the heteroaryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. The organic electroluminescent device according to any one of claims 1 to 6. In the above general formula (1), ^{at least one of R 1 to} R ³ is aryl or dibenzofuranyl, and the aryl and at least one hydrogen in the dibenzofuranyl are aryl, heteroaryl, alkyl or cycloalkyl. The organic electroluminescent device according to any one of claims 1 to 7, which may be substituted. In the above general formula (1), ^{at least one of R 1 to} R ³ is a heteroaryl (at least one hydrogen in the heteroaryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl). And, ^{at least one of R 4 to} R ¹¹ is an aryl (at least one hydrogen in the aryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl), claim 1-6. The organic electric field light emitting element according to any one item. The organic electroluminescent device according to claim 1, wherein the host of the first component is a polycyclic aromatic compound represented by any of the following formulas.

The organic electroluminescent device according to any one of claims 1 to 10, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (2) or a multimer thereof.

(In the above formula (2),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, ^{adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring. Are Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl. It may be substituted with oxy, at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Y ¹ is B (boron) and
X ¹ and X ² are independently>O,>N-R,>S,> Se or -C (-R) _2- (where X ¹ and X ² are> O at the same time. The -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and the above-mentioned> N-R R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, and the R of> N-R is -O. -, -S-, -C (-R') _2- , may be bonded to at least one of the a ring, b ring and c ring by a single bond or condensation (note that "-C (-R')". ') _2- 'R'is hydrogen or an alkyl with 1 to 5 carbons or a cycloalkyl with 5 to 10 carbons), and
At least one hydrogen in the compound represented by the formula (2) may be substituted with cyano, halogen or deuterium. ) In the above general formula (2), R ⁸ is a halogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
The organic electric field according to claim 11, wherein R ⁷ is hydrogen, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms. Light emitting element. The dopant as the second component is a dimer compound composed of two partial structures represented by the above general formula (2) and a linking group L1 connecting the two partial structures.
The linking group L1 is a single bond, an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, and an alkynylene having 1 to 6 carbon atoms. -O-, -S-,> N-R, or a combination thereof, and the R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and 1 to 1 carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms.
The organic electroluminescent device according to claim 11, wherein at least one hydrogen in the dimer compound may be substituted with cyano, halogen or deuterium. The organic electroluminescent device according to any one of claims 1 to 11, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (3).

(In the above formula (3),
R ^{3 to} R ¹² , Z ¹ and Z ² are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. ,
Further, ^{adjacent groups of R 5 to} R ⁷ and R ^{10 to} R ¹² may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the b ring and the d ring. At least one hydrogen in the ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl. , Cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Z ¹ may be bonded to the a ring with a linking group or a single bond, and Z ² may be bonded to the c ring with a linking group or a single bond.
Y is B (boron),
X ¹ , X ² , X ³ and X ⁴ are independently>O,>N-R,>S,> Se or -C (-R) _2- (where X ¹ and X ^2). There never is> O simultaneously, nor that ^{X 3} and ^{X 4} are> O simultaneously), the -C _{(-R) 2} - in which R is an alkyl of 1 to 6 carbon atoms, carbon atoms It is a cycloalkyl of 3 to 14 or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and an alkyl having 1 to 6 carbon atoms. Alternatively, it is a cycloalkyl having 3 to 6 carbon atoms, and the R of the> N-R is -O-, -S-, -C (-R') _2- , the a ring, b by a single bond or condensation. It may be bonded to at least one of the ring, the c ring and the d ring (note that the R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 5 carbon atoms or 5 to 5 carbon atoms. 10 cycloalkyl),
R ¹ and R ² are independently hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 14 carbon atoms, aryl with 6 to 12 carbon atoms, heteroaryl or diarylamino with 2 to 15 carbon atoms, respectively. (However, aryl is an aryl having 6 to 12 carbon atoms), and diarylboryl (however, aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group). ,
At least one hydrogen in the compound represented by the formula (3) may be substituted with cyano, halogen or deuterium. ) The organic electroluminescent device according to any one of claims 1 to 11, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (4) or a multimer thereof.

(In the above formula (4),
R ^{1 to} R ³ and R ^{5 to} R ¹⁵ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryls are single-bonded or linking groups). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. ,
In addition, ^{adjacent groups of R 1 to} R ³ , R ^{5 to} R ⁷ , R ^{8 to} R ¹¹ and R ^{12 to} R ¹⁵ are bonded to each other to form at least one of a ring, b ring, c ring and d ring. They may form an aryl ring or a heteroaryl ring together, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl (two aryls). May be attached via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be aryl, heteroaryl, alkyl or cyclo. May be substituted with alkyl
Y ¹ is B (boron) and
X is>O,>N-R,>S,> Se or -C (-R) _2- , and the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms and a carbon number of carbons. It is a cycloalkyl of 3 to 14 or an aryl having 6 to 12 carbon atoms, and R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or It is a cycloalkyl with 3 to 6 carbon atoms.
L is a single bond, -C (-R) ₂ -,>O,> S or> N-R, and R in -C (-R) _2- and> N-R is independent of each other. , Hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these. One hydrogen may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl,
However, when X is> N-R, L is never> O.
^{R 2} in equation (4) for multimers is hydrogen, and
At least one hydrogen in the compound and structure represented by the general formula (4) may be substituted with cyano, halogen or deuterium. ) The organic electroluminescent device according to any one of claims 1 to 10, wherein the dopant as the second component is a polycyclic aromatic compound represented by the following general formula (5) or a multimer thereof.

(In the above formula (5),
R ^{1 to} R ⁹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy, aryloxy, cyano or halogen, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, ^{adjacent groups of R 1 to} R ⁹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of a ring, b ring and c ring, and the formed ring may be formed. At least one hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl. , Alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Y ¹ is B (boron) and
X ¹ , X ² and X ³ are independently>O,>N-R,>S,> Se or -C (-R) _2- (of X ¹ , X ² and X ³ ). At least two of them are N-R), the -C (-R) _2- R is an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms. R of> N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 6 carbon atoms, and the said> N The R of −R may be bonded to at least one of the a ring, b ring and c ring by a single bond or condensation of −O−, −S−, −C (−R ′) _{2− (note that it should be noted).} The R'of the "-C (-R') _2- " is hydrogen or an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), and
At least one hydrogen in the compound represented by the formula (5) may be substituted with cyano, halogen or deuterium. ) The organic electroluminescent device according to claim 1, wherein the dopant of the second component is a polycyclic aromatic compound represented by any of the following formulas.

It has at least one of an electron transporting layer and an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or a fluorantene derivative. , BO-based derivative, anthracene derivative, benzofluorene derivative, phosphine oxide derivative, pyrimidine derivative, carbazole derivative, triazine derivative, benzoimidazole derivative, phenanthroline derivative and quinolinol-based metal complex. The organic electric field light emitting element according to any one of claims 1 to 17. At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline earth metal. Contains at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes. Item 18. The organic electric field light emitting element according to Item 18. A polycyclic aromatic compound represented by the following general formula (1).

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy, aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At ^{least one of R 1 to} R ¹¹ is a group represented by the following formula (1-d).
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above formula, * indicates a bond position, and at least one hydrogen in the formula (1-d) may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl.) A reactive compound in which a polycyclic aromatic compound represented by the following general formula (1) is substituted with a reactive substituent.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. ) A polymer compound obtained by polymerizing the reactive compound according to claim 21 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound. A pendant type polymer compound in which the main chain type polymer is substituted with the reactive compound according to claim 21, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked. As the first component, the reactive compound according to claim 21, the polymer compound or polymer crosslinked product according to claim 22, or the pendant type polymer compound or pendant type polymer crosslinked product according to claim 23. As a host,
As the second component, a polycyclic aromatic compound containing boron is contained as a dopant.
Contains an organic solvent as the third component,
A composition for forming a light emitting layer. As the first component, a polycyclic aromatic compound represented by the following general formula (1) is contained as a host.
As the second component, a polycyclic aromatic compound containing boron is contained as a dopant.
A composition for forming a light emitting layer, which contains an organic solvent as a third component.

(In the above formula (1),
R ^{1 to} R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, respectively. Alkoxy or aryloxy,
At least one hydrogen in said aryl, said heteroaryl, said diarylamino and said diarylboryl may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
At least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or deuterium. ) The composition for forming a light emitting layer according to claim 24 or 25, wherein the boiling point of at least one organic solvent of the third component is 130 to 350 ° C. The organic solvent of the third component contains a good solvent (GS) and a poor solvent (PS) for at least one of the host of the first component and the dopant of the second component, and the boiling point (BP _GS ) of the good solvent (GS). There below the boiling point _{(BP PS)} of the poor solvent (PS), light-emitting layer forming composition according to any one of claims 24 to 26. The first component is 0.0999% by mass to 8.0% by mass with respect to the total mass of the composition for forming a light emitting layer.
The second component is 0.0001% by mass to 2.0% by mass with respect to the total mass of the composition for forming a light emitting layer.
The third component is 90.0% by mass to 99.9% by mass with respect to the total mass of the composition for forming a light emitting layer.
The composition for forming a light emitting layer according to any one of claims 24 to 27. It has a first structural unit derived from the reactive compound according to claim 21, and a second structural unit derived from a reactive compound in which a reactive substituent is substituted on a boron-containing polycyclic aromatic compound. High molecular compound,
A polymer crosslinked product obtained by further cross-linking the polymer compound,
A pendant type polymer compound in which the reactive compound according to claim 21 and a polycyclic aromatic compound containing boron are substituted with a reactive compound in which a reactive substituent is substituted in the main chain type polymer, and
At least one selected from pendant-type polymer crosslinked products obtained by further cross-linking the pendant-type polymer compound, and
A composition for forming a light emitting layer, which comprises an organic solvent. A pair of electrodes consisting of an anode and a cathode, and arranged between the pair of electrodes,
An organic electroluminescent device having a light emitting layer formed by using the light emitting layer forming composition according to any one of claims 24 to 29. At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or a polymer compound. , A polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type polymer compound. The organic electroluminescent element according to any one of claims 1 to 19 and 30, further comprising a crosslinked pendant type polymer crosslinked body. A display device or a lighting device including the organic electroluminescent element according to any one of claims 1 to 19, 30 and 31.

Images