JP2021095342A - Polycyclic aromatic compound - Google Patents

Abstract

To provide a novel polycyclic aromatic compound and an organic EL element using the same.SOLUTION: There are provided a polycyclic aromatic compound represented by the formula (1) or a multimer thereof and an organic EL element using the same. (A ring to C ring is an aryl ring or a heteroaryl ring which may be substituted; X1 and X2 are >O or >N-R or the like; the R may be bonded to A- to C-rings by a single bond or a linking group and the compound represented by the formula (1) may be substituted with a halogen or the like.)SELECTED DRAWING: None

Description

The present invention comprises a polycyclic aromatic compound and a multimer thereof (hereinafter, also collectively referred to as "polycyclic aromatic compound"), an organic field emitting device using the polycyclic aromatic compound, an organic field effect transistor, and an organic thin film solar cell. , Display devices and lighting devices. In the present specification, the "organic electroluminescent element" may be referred to as an "organic EL element" or simply an "element".

Conventionally, display devices using an electroluminescent element that emits an electric field have been studied in various ways because they can be reduced in power and thickness. Further, an organic electroluminescent element made of an organic material can be easily reduced in weight and size. Therefore, it has been actively examined. In particular, the development of organic materials having emission characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transporting ability 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 improved by connecting aromatic rings constituting triphenylamine. 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 state of the entire compound is 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. Further, as an electron transporting material or a hole transporting material that sandwiches the light emitting layer, a compound having a novel conjugated structure having a large T1 is required.

The host material for an organic EL device is generally a molecule in which existing aromatic rings such as benzene and carbazole are linked by a single bond or a plurality of phosphorus atoms or silicon atoms. 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 donor or acceptor properties of the aromatic ring and substituents in the molecule by connecting, to localize the SOMO1 and SOMO2 triplet excited state (T1), by reducing the exchange interaction between the two trajectories, it is possible to improve the triplet excitation energy (E _T) Will be. However, the small aromatic ring of the conjugated system does not have sufficient redox stability, and the device using the molecule connecting the existing aromatic ring as the host material does not have a sufficient life. 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.

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 U.S. Patent Application Publication No. 2019/67577

As described above, various materials have been developed as materials used for organic EL devices, but in order to increase the choices of materials for organic EL devices, it is desired to develop a material made of a compound different from the conventional one. There is. In particular, the organic EL properties obtained from materials other than the NO-linking compounds reported in Patent Documents 1 to 4 and the method for producing the same are not yet known.

Further, in Patent Document 6 and Patent Document 7, a polycyclic aromatic compound containing boron and an organic EL device using the same are reported, but in order to further improve the device characteristics, the light emission efficiency and the device life are improved. There is a demand for a material for a light emitting layer that can be used, particularly a dopant material.

As a result of diligent studies to solve the above problems, the present inventors have arranged a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes to form, for example, an organic EL element. We have found that an excellent organic EL element can be obtained, and completed the present invention. That is, the present invention provides materials for organic devices such as the following polycyclic aromatic compounds or multimers thereof, and further materials for organic EL devices containing the following polycyclic aromatic compounds or multimers thereof. ..

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 the 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 having no limitation on the number of carbon atoms" is substituted with "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、
Ａ環、Ｂ環、およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙ^１は、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ−Ｒ、またはＧｅ−Ｒであり、前記Ｓｉ−ＲおよびＧｅ−ＲのＲは、アリール、アルキル、またはシクロアルキルであり、
Ｘ^１は、＞Ｏ、＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、置換されていてもよいアリール、置換されていてもよいヘテロアリール、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シクロアルキルであり、また、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、単結合または連結基により、前記Ａ環およびＢ環の少なくとも１つの環と結合していてもよく、
Ｘ^２は、＞Ｏ、＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、または＞Ｐ−ＲのＲは、置換されていてもよいアリール、置換されていてもよいヘテロアリール、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シクロアルキルであり、また、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、単結合または連結基により、前記Ｂ環およびＣ環の少なくとも１つの環と結合していてもよく（ただし、前記Ｘ^１が、＞Ｏ、＞Ｎ−Ｒ、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅである場合は、Ｘ^２としての＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは前記Ｂ環と結合しない）、そして、
式（１）で表される化合物または単位構造における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 1.
A multimer of a polycyclic aromatic compound represented by the following general formula (1) or a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1).

In the above formula (1),
Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Ge-R. Cycloalkyl,
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-R may be substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. It is a cycloalkyl which may be used, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be formed by a single bond or a linking group. It may be bonded to at least one ring of the A ring and the B ring.
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , or> P-R may be an aryl substituted, a heteroaryl optionally substituted, an alkyl optionally substituted, or a substitution. It is a cycloalkyl which may be used, and R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be formed by a single bond or a linking group. It may be bonded to at least one ring of the B ring and the C ring (provided that X ¹ is>O,>N-R,>P-R,> S, or> Se. > _N-R as _{^{X 2,> C (-R)}} 2,> Si (-R) 2, and> R in P-R does not bind to the B ring), and,
At least one hydrogen in the compound or unit structure represented by the formula (1) may be substituted with halogen, cyano, or deuterium.

Item 2.
In the above formula (1),
Rings A, B, and C are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, respectively. Substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls are bonded via a single bond or a linking group). May be substituted), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl, and these. The ring has a 5-membered ring or a 6-membered ring that shares a bond with the central fused 2-ring structure of the above formula (1) composed of ^{Y 1} , X ¹ , and X ^2.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Ge-R. Cycloalkyl,
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The Rs of (-R) ₂ ,> Si (-R) ₂ , and> PR are aryls optionally substituted with alkyl or cycloalkyl, heteroaryls optionally substituted with alkyl or cycloalkyl, It is alkyl or cycloalkyl, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-, -S. -, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the A ring and the B ring, and the -C (-R) ₂ − and -N (-R)-R is aryl, alkyl, or cycloalkyl,
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , or> P-R may be an aryl substituted with alkyl or cycloalkyl, a heteroaryl optionally substituted with alkyl or cycloalkyl, It is alkyl or cycloalkyl, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-, -S. -, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the B ring and the C ring (provided that X ¹ is> O, >N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P- ^{as X 2} if>N-R,>P-R,> S, or> Se. The R of R does not bind to the B ring), the R of -C (-R) _2- and -N (-R)-is aryl, alkyl, or cycloalkyl, and
At least one hydrogen in the compound or unit structure represented by the formula (1) may be substituted with halogen, cyano, or deuterium.
Item 2. The polycyclic aromatic compound according to Item 1 or a multimer thereof.

上記式（２）中、
ａ環、ｂ環、およびｃ環における、任意の「−Ｃ（−Ｒ）＝」（ここでＲは式（２）中のＲ^１〜Ｒ^１１である）は「−Ｎ＝」に置き換わっていてもよく、任意の「−Ｃ（−Ｒ）＝Ｃ（−Ｒ）−」（ここでＲは式（２）中のＲ^１〜Ｒ^１１である）は、「−Ｎ（−Ｒ）−」、「−Ｏ−」、または「−Ｓ−」に置き換わっていてもよく、前記「−Ｎ（−Ｒ）−」のＲは、アリール、アルキル、またはシクロアルキルであり、
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、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルであり、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、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリル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、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ−Ｒ、またはＧｅ−Ｒであり、前記Ｓｉ−ＲおよびＧｅ−ＲのＲは、炭素数６〜１２のアリール、炭素数１〜６のアルキル、または炭素数３〜１４のシクロアルキルであり、
Ｘ^１は、＞Ｏ、＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−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３〜１４のシクロアルキルであり、また、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、単結合、−Ｏ−、−Ｓ−、−Ｃ（−Ｒ）_２−、または−Ｎ（−Ｒ）−により、前記ａ環およびｂ環の少なくとも１つの環と結合していてもよく、前記−Ｃ（−Ｒ）_２−および−Ｎ（−Ｒ）−のＲは、炭素数６〜１２のアリール、炭素数１〜６のアルキル、または炭素数３〜１４のシクロアルキルであり、
Ｘ^２は、＞Ｏ、＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−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３〜１４のシクロアルキルであり、また、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、単結合、−Ｏ−、−Ｓ−、−Ｃ（−Ｒ）_２−、または−Ｎ（−Ｒ）−により、前記ｃ環と結合していてもよく、前記−Ｃ（−Ｒ）_２−および−Ｎ（−Ｒ）−のＲは、炭素数６〜１２のアリール、炭素数１〜６のアルキル、または炭素数３〜１４のシクロアルキルであり、そして、
式（２）で表される化合物または単位構造における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 3.
Item 2. The polycyclic aromatic compound according to Item 1, or a multimer thereof, wherein the general formula (1) is represented by the following general formula (2).

In the above formula (2),
Any "-C (-R) =" in rings a, b, and c (where R is R ^{1 through} R ¹¹ in equation (2)) has been replaced by "-N =". Any "-C (-R) = C (-R)-" (where R is R ^{1 to} R ¹¹ in equation (2)) may be "-N (-R)-". , "-O-", or "-S-", where the R of "-N (-R)-" is aryl, alkyl, or cycloalkyl.
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, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen is. It may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl ^{, and adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring together with an a ring, a b ring, or a c ring. Alternatively, a heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be bonded via a linking group), substituted with alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R has 6 to 12 carbon atoms. Aryl, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms.
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-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 carbon. It is a cycloalkyl of the number 3 to 14, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-,. It may be bonded to at least one ring of the a ring and the b ring by −S−, −C (−R) _{2− , or −N (−R) −, and the −C (−R) 2} -And -N (-R)-R are aryls having 6 to 12 carbon atoms, alkyls having 1 to 6 carbon atoms, or cycloalkyls having 3 to 14 carbon atoms.
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-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 carbon. It is a cycloalkyl of the number 3 to 14, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-,. It may be bonded to the c ring by −S−, −C (−R) ₂₋ , or −N (−R) −, and the −C (−R) ₂₋ and −N (−R). -R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound or unit structure represented by the formula (2) may be substituted with halogen, cyano, or deuterium.

上記式（２−Ｍ１）および式（２−Ｍ２）中、
ａ環、ｂ環、およびｃ環における、任意の「−Ｃ（−Ｒ）＝」（ここでＲは式（２−Ｍ１）または式（２−Ｍ２）中のＲ^１〜Ｒ^７、Ｒ^１０、およびＲ^１１である）は「−Ｎ＝」に置き換わっていてもよく、任意の「−Ｃ（−Ｒ）＝Ｃ（−Ｒ）−」（ここでＲは式（２−Ｍ１）または式（２−Ｍ２）中のＲ^１〜Ｒ^７、Ｒ^１０、およびＲ^１１である）は、「−Ｎ（−Ｒ）−」、「−Ｏ−」、または「−Ｓ−」に置き換わっていてもよく、前記「−Ｎ（−Ｒ）−」のＲは、アリール、アルキル、またはシクロアルキルであり、
Ｒ^１〜Ｒ^７、Ｒ^１０、および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、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルであり、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^７、Ｒ^１０、および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、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリル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、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ−Ｒ、またはＧｅ−Ｒであり、前記Ｓｉ−ＲおよびＧｅ−ＲのＲは、炭素数６〜１２のアリール、炭素数１〜６のアルキル、または炭素数３〜１４のシクロアルキルであり、
Ｘ^１は、それぞれ独立して、＞Ｏ、＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、＞Ｐ−Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−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３〜１４のシクロアルキルであり、また、前記＞Ｎ−Ｒ、＞Ｃ（−Ｒ）_２、＞Ｓｉ（−Ｒ）_２、および＞Ｐ−ＲのＲは、単結合、−Ｏ−、−Ｓ−、−Ｃ（−Ｒ）_２−、または−Ｎ（−Ｒ）−により、前記ａ環およびｂ環の少なくとも１つの環と結合していてもよく、前記−Ｃ（−Ｒ）_２−および−Ｎ（−Ｒ）−のＲは、炭素数６〜１２のアリール、炭素数１〜６のアルキル、または炭素数３〜１４のシクロアルキルであり、
Ｘ^２は、それぞれ独立して、ＮまたはＰであり、そして、
式（２−Ｍ１）または式（２−Ｍ２）で表される多量体における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 4.
Item 3. A multimer of a polycyclic aromatic compound represented by the following general formula (2-M1) or general formula (2-M2).

In the above formula (2-M1) and formula (2-M2),
Any "-C (-R) =" in rings a, b, and c (where R is R ^{1 to} R ⁷ , R ^{10 in formula (2-M1) or formula (2-M2)).} , And R ¹¹ ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is equation (2-M1) or equation. ^{(2-M2) R 1 ~R} 7, R 10 in, and ^{R 11)} is "- N (-R) -", "- O-', or it has been replaced by the" -S- " Also, the R of the "-N (-R)-" is aryl, alkyl, or cycloalkyl.
R ^{1 to} R ⁷ , R ¹⁰ and R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linked). (May be bonded via a group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, which are these. At least one hydrogen in is optionally substituted with aryl, heteroaryl, alkyl, or cycloalkyl ^{, and adjacent groups of R 1 to} R ⁷ , R ¹⁰ , and R ¹¹ are attached to each other. , A ring, b ring, or c ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, Aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl. , Dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Y ¹ is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is Aryl with 6 to 12 carbon atoms, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms.
X ¹ is independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned> N. -R,> C (-R) ₂ ,> Si (-R) ₂ , and> PR R are aryls with 6 to 12 carbon atoms, heteroaryls with 2 to 15 carbon atoms, and 1 to 6 carbon atoms. Alkyl or cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R R are single bonds. , -O-, -S-, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the a ring and the b ring, and the -C (-R) _2- and -N (-R)-R are aryls having 6 to 12 carbon atoms, alkyls having 1 to 6 carbon atoms, or cycloalkyls having 3 to 14 carbon atoms.
X ² is N or P, respectively, and
At least one hydrogen in the multimer represented by the formula (2-M1) or the formula (2-M2) may be substituted with halogen, cyano, or deuterium.

Item 5.
In the above formula (2), formula (2-M1), and formula (2-M2),
a ring, the b ring, and c rings, any "-C (-R) =" (where R is the formula (2), ^{R 1} in the formula (2-M1), or Formula (2-M2) ~ R ¹¹ ) may be replaced with "-N =", and any "-C (-R) = C (-R)-" (where R is equation (2), equation (2-) M1), or ^R 1 ^{to R 11} in the formula (2-M2)) is "- N (-R) -" - it may be replaced to "O-", or "-S-" The R of "-N (-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, diarylamino (where aryl is aryl with 6 to 12 carbon atoms), and diarylboryl (provided that the aryl is aryl with 6 to 12 carbon atoms). The 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, a cycloalkyl having 3 to 24 carbon atoms, and carbon. It is an alkoxy having a number of 1 to 24 or an aryloxy having 6 to 30 carbon atoms, and at least one hydrogen in these is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and an aryloxy having 1 to 6 carbon atoms. It may be substituted with an alkyl or a cycloalkyl having 3 to 14 carbon atoms ^{, and adjacent groups of R 1 to} R ¹¹ are bonded to each other to form a carbon together with an a ring, a b ring, or a c ring. An aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one hydrogen in the formed ring is an aryl ring having 6 to 30 carbon atoms and having 2 to 30 carbon atoms. Heteroaryl, diarylamino (where aryl is an aryl with 6 to 12 carbons), diarylboryl (where aryl is an aryl with 6 to 12 carbons, and the two aryls are attached via a single bond or a linking group. It may be substituted with an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, and at least one of these. One hydrogen may be substituted with 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 14 carbon atoms.
Y ¹ is independently B, P, P = O, P = S, or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms and 1 to 5 carbon atoms. Alkyl, or cycloalkyl with 5 to 10 carbon atoms,
X ¹ is independently>O,> N-R, or> S, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or carbon. It is a cycloalkyl of the number 5 to 10.
^{X 2} in the formula (2) is>O,> N-R, or> S, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or carbon. It is a cycloalkyl of the number 5 to 10.
^{X 2} in formula (2-M1) or formula (2-M2) is N, and
At least one hydrogen in the compound or unit structure represented by the formula (2) or the multimer represented by the formula (2-M1) or the formula (2-M2) is replaced with a halogen, cyano, or deuterium. May be
Item 3. The polycyclic aromatic compound according to Item 3 or 4, or a multimer thereof.

Item 6.
In the above formula (2), formula (2-M1), and formula (2-M2),
a ring, the b ring, and c rings, any "-C (-R) =" (where R is the formula (2), ^{R 1} in the formula (2-M1), or Formula (2-M2) ~ R ¹¹ ) may be replaced with "-N =", and any "-C (-R) = C (-R)-" (where R is equation (2), equation (2-) M1), or ^R 1 ^{to R 11} in the formula (2-M2)) is "- N (-R) -" - it may be replaced to "O-", or "-S-" The R of "-N (-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diallyl amino (where aryl is aryl with 6 to 10 carbon atoms), and diallyl boryl (provided that aryl is aryl with 6 to 10 carbon atoms). 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 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. Yes, even if at least one hydrogen in these is substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. Often,
Y ¹ is independently B, P, P = O, or P = S, respectively.
X ¹ is independently> O or> N-R, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl,
^{X 2} in the formula (2) is> O or> N-R, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl, and
^{X 2} in formula (2-M1) or formula (2-M2) is N,
Item 3. The polycyclic aromatic compound according to Item 3 or 4, or a multimer thereof.

Item 7.
In the above formula (2), formula (2-M1), and formula (2-M2),
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diallyl amino (where aryl is aryl with 6 to 10 carbon atoms), and diarylboryl (provided that aryl is 6 to 10 carbon atoms). 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 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. Yes,
Y ¹ is B,
X ¹ is independently> O or> N-R, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl,
^{X 2} in the formula (2) is> O or> N-R, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl, and
^{X 2} in formula (2-M1) or formula (2-M2) is N,
Item 3. The polycyclic aromatic compound according to Item 3 or 4, or a multimer thereof.

Item 8.
Item 2. The polycyclic aromatic compound or a multimer thereof, which is represented by any of the following structural formulas.

Item 9.
Item 2. A reactive compound in which a polycyclic aromatic compound according to any one of Items 1 to 8 or a multimer thereof is substituted with a reactive substituent.

Item 10.
A polymer compound obtained by polymerizing the reactive compound according to Item 9 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound.

Item 11.
A pendant type polymer compound in which a main chain type polymer is substituted with the reactive compound according to Item 9, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked.

Item 12.
Substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetra A term comprising, as a repeating unit, at least one selected from phenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran. Item 10. The polymer compound or polymer crosslinked product according to Item 10, or the pendant type polymer compound or polymer crosslinked product according to Item 11.

Item 13.
A material for an organic device containing the polycyclic aromatic compound according to any one of Items 1 to 8 or a multimer thereof.

Item 14.
A material for an organic device containing the reactive compound according to Item 9.

Item 15.
Item 2. A material for an organic device containing the polymer compound or polymer crosslinked product according to Item 10.

Item 16.
A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to Item 11.

Item 17.
Item 2. The material for an organic device according to any one of Items 13 to 16, which is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

Item 18.
Item 2. The material for an organic device according to Item 17, which is a material for a light emitting layer of an organic electroluminescent element.

Item 19.
An ink composition containing the polycyclic aromatic compound according to any one of Items 1 to 8 or a multimer thereof, and an organic solvent.

Item 20.
An ink composition containing the reactive compound according to Item 9 and an organic solvent.

Item 21.
An ink composition containing a main chain polymer, the reactive compound according to Item 9, and an organic solvent.

Item 22.
An ink composition containing the polymer compound or polymer crosslinked product according to Item 10 and an organic solvent.

Item 23.
An ink composition containing the pendant-type polymer compound or the pendant-type polymer crosslinked product according to Item 11 and an organic solvent.

Item 24.
Item 10. A polycyclic aromatic compound or a polymer thereof according to any one of Items 1 to 8, a reactive compound according to Item 9, which is arranged between a pair of electrodes composed of an anode and a cathode and the pair of electrodes. An organic electroluminescent element having an organic layer containing the polymer compound or polymer crosslinked body according to Item 11 or the pendant type polymer compound or pendant type polymer crosslinked body according to Item 11.

Item 25.
An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode, and an organic layer arranged between the pair of electrodes and formed from the ink composition according to any one of Items 19 to 23.

Item 26.
Item 2. The organic electroluminescent device according to Item 24 or 25, wherein the organic layer is a light emitting layer.

Item 27.
The light emitting layer is a host of the polycyclic aromatic compound or its multimer, a reactive compound, a polymer compound, a polymer crosslinked product, a pendant type polymer compound, or a pendant type polymer crosslinked product, and a dopant. 26. The organic field light emitting element according to Item 26.

Item 28.
Item 27. The organic electroluminescent device according to Item 27, wherein the host further comprises an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

Item 29.
It has at least one layer 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, and the like. At least one selected from the group consisting of 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 metal complexes. Item 2. The organic electric field light emitting element according to any one of Items 24 to 28.

Item 30.
At least one layer 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 soil. Contains at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. Item 29. The organic electroluminescent element according to Item 29.

Item 31.
A polymer compound in which 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 polymerized using a low molecular compound capable of forming each layer as a monomer. Alternatively, a polymer crosslinked product obtained by further cross-linking the polymer compound, 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 is further added. Item 6. The organic electric field light emitting element according to any one of Items 24 to 30, which comprises 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 24 to 31.

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for an organic device such as a material for an organic EL element, and the polycyclic aromatic compound can be provided. It is possible to provide an excellent organic device such as an organic EL element by using the above.

Specifically, we have found that polycyclic aromatic compounds in which aromatic rings are linked with heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur create a large HOMO-LUMO gap (bandgap Eg in thin films). Found to have. It is considered that this is because the 6-membered ring containing a hetero element has low aromaticity, so that the decrease in the HOMO-LUMO gap due to the expansion of the conjugated system is suppressed. Since these polycyclic aromatic compounds can arbitrarily move the energies of HOMO and LUMO by introducing a substituent, the ionization potential and electron affinity can be optimized according to the peripheral material. However, the present invention is not particularly limited to these principles.

It is the schematic sectional drawing which shows the organic EL element which concerns on this embodiment.

なお、上記の各構造式中の符号の定義は上述した定義と同じであり、さらに、この段落以降で示すすべての構造式中の符号の定義も上述した定義と同じである。 1. 1. Polycyclic aromatic compounds and multimers thereof The present invention is a polycyclic aromatic compound represented by the following general formula (1) or a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1). Is preferably a polycyclic aromatic compound represented by the following general formula (2), or a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (2). is there.

The definition of the code in each of the above structural formulas is the same as the above-mentioned definition, and the definition of the code in all the structural formulas shown in the following paragraphs is also the same as the above-mentioned definition.

The A ring, B ring, and C ring in the formula (1) are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted with a substituent. The substituents are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino (with aryl). Amino groups with heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl. , Substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl is preferable. When these groups have a substituent, the substituent includes aryl, heteroaryl, alkyl, or cycloalkyl. The details of the rings and substituents listed here will be described later.

^{R 1 to} R ¹¹ in the formula (2) are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryls have a single bond or a linking group). (May be bonded via), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, at least in these. One hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. The details of the substituents listed here will be described later.

The aryl ring or heteroaryl ring in the formula (1) is a 5-membered ring or a 6-membered ring that shares a bond with the central condensed two-ring structure of the formula (1) composed of ^{Y 1} , X ¹ , and X ^2. It is preferable to have.
Here, the "condensed two-ring structure" means a structure in which two saturated hydrocarbon rings ^{including Y 1} , X ¹ , and X ^{2 shown in the center of the formula (1) are condensed.} .. Further, the "6-membered ring sharing a bond with the condensed 2-ring structure" means, for example, an a ring (benzene ring (6-membered ring)) condensed with the condensed 2-ring structure as shown in the formula (2). .. Further, "the aryl ring (which is the A ring) or the heteroaryl ring has the 6-membered ring" means that the A-ring is formed only by the 6-membered ring or includes the 6-membered ring. This means that another ring or the like is further condensed with this 6-membered ring to form an A ring. In other words, the "aryl ring having a 6-membered ring (which is an A ring) or a heteroaryl ring" as used herein means that a 6-membered ring constituting all or a part of the A ring is condensed into the condensed two-ring structure. It means that you are doing it. The same description applies to "B ring (b ring)", "C ring (c ring)", and "5-membered ring".

Equation (1) A ring in (or B ring or C ring), the substituent with a ring in the formula (2) ^R 1 to R ³ (or b ring and substituents thereof ^R 4 to R ^7, or c ring, And its substituents R ^{8 to} R ¹¹ ). That is, the formula (2) corresponds to a structure in which "A to C rings having a 6-membered ring" is selected as the A to C rings of the formula (1). In that sense, each ring of the formula (2) is represented by lowercase letters a to c.

In equation (2), a ring, b ring, and adjacent groups are bonded of the substituents ^R 1 ^{to R 11} of the c ring, a ring, b ring or with c ring, aryl or heteroaryl An aryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linked). It may be attached via a group), substituted with alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. The details of the rings and substituents listed here will be described later.
Therefore, the polycyclic aromatic compounds represented by the formula (2) have the following formulas (2-a) to (2-abc) depending on the mutual bonding form of the substituents in the a ring, the b ring, and the 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 A ring, B ring, and C ring in the formula (1), respectively.

The formula (2-a) A 'ring, B' in ~ formula (2-abc) ring, and C 'ring, will be described by the formula (2), adjoining of the substituents ^R 1 ^{to R 11} The groups are bonded to each other to represent an aryl ring or a heteroaryl ring formed together with the a ring, the b ring, and the c ring (the a ring, the b ring, or the c ring is condensed with another ring structure). It can also be called a fused ring). Further, as can be seen from the above equations (2-a) to (2-abc), for example, R ³ of a ring and R ⁴ of b ring, R ⁷ of b ring and R ⁸ of c ring, and c 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 compound represented by any of the above formulas (2-a) to (2-abc) is, for example, a benzene ring (or b-ring or c-ring), which is a benzene ring, an indole ring, or a pyrrole. A compound having an A'ring (or B'or C'ring) formed by condensing a ring, a benzofuran ring, a benzothiophene ring, or the like, and the formed fused ring A'(or fused ring B'or The fused ring C') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, respectively.

上記式（２−ａ−ｅｘ）は、式（２−ａ）の具体例であり、式（２）のａ環におけるＲ^２とＲ^３が結合して、ａ環（ベンゼン環）と共に、Ａ’で示すアリール環（ナフタレン環）が形成された例である。形成されたアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ａ）を有している。なお、アリール環Ａ’（式（１）のＡ環）への任意の置換基をＲ^１の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
上記式（２−ｂ−ｅｘ）は、式（２−ｂ）の具体例であり、式（２）のｂ環におけるＲ^５とＲ^６が結合して、ｂ環（ベンゼン環）と共に、Ｂ’で示すヘテロアリール環（カルバゾール環）が形成された例である。形成されたヘテロアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ｂ）を有している。なお、ヘテロアリール環Ｂ’（式（１）のＢ環）への任意の置換基をＲ^４およびＲ^７の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
上記式（２−ｃ−ｅｘ）は、式（２−ｃ）の具体例であり、式（２）のｃ環におけるＲ^８とＲ^９が結合して、ｃ環（ベンゼン環）と共に、Ｃ’で示すヘテロアリール環（ジベンゾフラン環）が形成された例である。形成されたヘテロアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ｃ）を有している。なお、ヘテロアリール環Ｃ’（式（１）のＣ環）への任意の置換基をＲ^１０およびＲ^１１の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
これらの具体例の説明は、上述した具体例以外のあらゆる形態にも同様に適用できる。 For example, more specific examples of the formulas (2-a), (2-b), and formula (2-c) are shown below.

The above formula (2-a-ex) is a specific example of the formula (2-a), and R ² and R ³ in the a ring of the formula (2) are bonded to each other together with the a ring (benzene ring) and A. This is an example in which the aryl ring (naphthalene ring) indicated by'is formed. The formed aryl ring has a 6-membered ring (benzene ring a) that shares a bond with the above-mentioned "condensed two-ring structure". Arbitrary substituents on the aryl ring A'(A ring of the formula (1)) are ^{indicated by n R in addition to R 1} , and the upper limit of n is the maximum number of substituents that can be substituted.
The formula (2-b-ex) is a specific example of the formula (2-b), attached ^{R 5} and ^{R 6} in the b ring of formula (2), with b ring (benzene ring), B This is an example in which the heteroaryl ring (carbazole ring) shown by'is formed. The formed heteroaryl ring has a 6-membered ring (benzene ring b) that shares a bond with the above-mentioned "condensed bicyclic structure". Arbitrary substituents on the heteroaryl ring B'(B ring of formula (1)) are ^{indicated by n R in addition to R 4} and R ⁷ , and the upper limit of n is the maximum number of substituents that can be substituted. is there.
The above formula (2-c-ex) is a specific example of the formula (2-c), and R ⁸ and R ⁹ in the c ring of the formula (2) are bonded to each other together with the c ring (benzene ring) and C. This is an example in which the heteroaryl ring (dibenzofuran ring) indicated by'is formed. The formed heteroaryl ring has a 6-membered ring (benzene ring c) that shares a bond with the above-mentioned "condensed bicyclic structure". Arbitrary substituents on the heteroaryl ring C'(C ring of formula (1)) are ^{indicated by n R in addition to R 10} and R ¹¹ , and the upper limit of n is the maximum number of substituents that can be substituted. is there.
The description of these specific examples can be similarly applied to any form other than the above-mentioned specific examples.

^{Y 1} in the formula (1) is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is It is aryl, alkyl, or cycloalkyl. In the case of P = O, P = S, Si-R or Ge-R, ^{the atom bonded to the A ring, B ring, or X 2} is P, Si, or Ge. For Y ¹ , B, P, P = O, P = S, or Si—R is preferable, B, P, P = O, or P = S is more preferable, and B is particularly preferable. This explanation is the same for ^{Y 1} in the equation (2). The details of the substituents listed here will be described later.

^{X 1} and X ² in the formula (1) are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or > Se, and R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be substituted aryl, optionally substituted. Heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.
Here, R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be bonded to a nearby ring by a single bond or a linking group. .. Specifically, R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ ^{, or> P-R as X 1} is associated with at least one ring of A ring and B ring. It may be combined. Further, R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ ^{, or> P-R as X 2} is bonded to at least one ring of B ring and C ring. However, if X ¹ is>O,>N-R,>P-R,> S, or> Se, then>N-R,> C (-R) as ^{X 2.} ₂ ,> Si (-R) ₂ , or> P-R R does not bind to the B ring.
^{X 1} and X ² that may be involved in the binding include>N-R,> C (-R) ₂ ,> Si (-R) ₂ , or>P-R,>N-R,> C ( -R) ₂ , or> P-R is preferable,> N-R or> P-R is more preferable, and> N-R is particularly preferable.
>N-R,> C (-R) ₂ ,> Si (-R) ₂ , or> PR R and ring-bonding groups include -O-, -S-, -C ( -R) _2- or -N (-R)-is preferable. The R of "-C (-R) _2- " and "-N (-R)-" is aryl, alkyl, or cycloalkyl.
The above description is the same for ^{X 1} and X ² in the equation (2).
The details of the substituents listed here will be described later.

In the formula (1), "R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is the A ring and the B ring by a single bond or a linking group. (Or, it is bonded to at least one of the B ring and the C ring) "is defined in the formula (2) as" the above>N-R,> C (-R) ₂ ,> Si (-R). ₂ and> P-R R are single-bonded, -O-, -S-, -C (-R) _2- , or -N (-R)-, and are the a-ring and b-ring (or ring). It is bound to at least one of the b-ring and c-ring). "

This specification can be expressed, for example, by the structure of the following formula (2-aX1), formula (2-bX1), formula (2-bX2Y1), or formula (2-cX2). ¹ or X ² , and in some cases Y ¹ , has a ring structure incorporated into fused ring A', fused ring B', or fused ring C'. The formed fused ring A', fused ring B', and fused ring C are, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, and the like.

上記式（２−ａＸ１）は、Ｘ^１の選択肢におけるＲがａ環と結合した例であり、式（２）におけるａ環（ベンゼン環）に対してＸ^１を取り込むようにして他の環が縮合して形成されるＡ’環を有する化合物を表している。上記式（２−ａＸ１−ｅｘ）は、より具体的な例を表しており、Ｘ^１である＞Ｎ−ＲのＲ（フェニル基）が、連結基である−Ｏ−により、ａ環（ベンゼン環）と結合しており、形成された縮合環Ａ’はフェノキサジン環である。なお、縮合環Ａ’への任意の置換基をＲ^１およびＲ^２の他にｎ個のＲで示しており、ＲはＡ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The formula (2-aX1) is an example in which R is bonded to a ring in choice of X ^1, the other ring so as to capture the X ¹ with respect to a ring in the formula (2) (a benzene ring) It represents a compound having an A'ring formed by condensation. The formula (2-aX1-ex) represents the more specific example, a ^{X 1>} N-R and R (phenyl group), by a certain -O- a linking radical, a ring (benzene The fused ring A'bonded to the ring) is a phenoxazine ring. Any substituent on the fused ring A'is ^{indicated by n R in addition to R 1} and R ² , R is the same as the substituent on the A ring, and the upper limit of n can be substituted. The maximum number.

上記式（２−ｂＸ１）は、Ｘ^１の選択肢におけるＲがｂ環と結合した例であり、式（２）におけるｂ環（ベンゼン環）に対してＸ^１を取り込むようにして他の環が縮合して形成されるＢ’環を有する化合物を表している。上記式（２−ｂＸ１−ｅｘ）は、より具体的な例を表しており、Ｘ^１である＞Ｎ−ＲのＲ（フェニル基）が、連結基である−Ｓ−により、ｂ環（ベンゼン環）と結合しており、形成された縮合環Ｂ’はフェノチアジン環である。なお、縮合環Ｂ’への任意の置換基をＲ^５〜Ｒ^７の他にｎ個のＲで示しており、ＲはＢ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The formula (2-BX1) is an example in which R is bonded to b ring in choice of X ^1, the other ring so as to capture the X ¹ with respect to b ring in formula (2) (a benzene ring) It represents a compound having a B'ring formed by condensation. The above formula (2-bX1-ex) represents a more specific example, in which ^{the R (phenyl group) of X 1} > N-R is the linking group -S-, and the b ring (benzene). The fused ring B'bonded to the ring) is a phenothiazine ring. Any substituent on the fused ring B'is indicated by n R ^{in addition to R 5 to R 7} , R is the same as the substituent on the B ring, and the upper limit of n can be substituted. The maximum number.

上記式（２−ｂＸ２Ｙ１）は、Ｘ^２の選択肢におけるＲがｂ環と結合した例であり、式（２）におけるｂ環（ベンゼン環）に対してＸ^２およびＹ^１を取り込むようにして他の環が縮合して形成されるＢ’環を有する化合物を表している。上記式（２−ｂＸ２Ｙ１−ｅｘ）は、より具体的な例を表しており、Ｘ^２である＞Ｎ−ＲのＲ（フェニル基）が、単結合により、ｂ環（ベンゼン環）と結合しており、形成された縮合環Ｂ’はＮとＹ^１を含む縮合三環系ヘテロアリール環である。なお、縮合環Ｂ’への任意の置換基をＲ^４〜Ｒ^６の他にｎ個のＲで示しており、ＲはＢ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The formula (2-BX2Y1) is an example in which R is bonded to b ring in choice of ^{X 2,} so as to capture the ^{X 2} and ^{Y 1} relative to b ring (benzene ring) in Formula (2) Other Represents a compound having a B'ring formed by condensing the rings of. The formula (2-bX2Y1-ex) represents the more specific example, a ^{X 2>} N-R and R (phenyl group), by a single bond, bonded to the b ring (benzene ring) and, formed condensed ring B 'is a fused tricyclic heteroaryl ring containing N and Y ^1. Arbitrary substituents on the fused ring B'are indicated by n R ^{in addition to R 4 to R 6} , R is the same as the substituent on the B ring, and the upper limit of n can be substituted. The maximum number.

上記式（２−ｃＸ２）は、Ｘ^２の選択肢におけるＲがｃ環と結合した例であり、式（２）におけるｃ環（ベンゼン環）に対してＸ^２を取り込むようにして他の環が縮合して形成されるＣ’環を有する化合物を表している。上記式（２−ｃＸ２−ｅｘ）は、より具体的な例を表しており、Ｘ^２である＞Ｎ−ＲのＲ（フェニル基）が、連結基である−Ｏ−により、ｃ環（ベンゼン環）と結合しており、形成された縮合環Ｃ’はフェノキサジン環である。なお、縮合環Ｃ’への任意の置換基をＲ^９〜Ｒ^１１の他にｎ個のＲで示しており、ＲはＣ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The formula (2-Cx2) is an example in which R is bonded to c ring in choice of X ^2, other ring so as to capture the X ² with respect to the c-ring in Formula (2) (a benzene ring) It represents a compound having a C'ring formed by condensation. The formula (2-cX2-ex) represents the more specific example, a ^{X 2>} N-R and R (phenyl group), by a certain -O- linking group, c ring (benzene The fused ring C'bonded to the ring) is a phenoxazine ring. Any substituent on the fused ring C'is indicated by n R ^{in addition to R 9 to R 11} , R is the same as the substituent on the C ring, and the upper limit of n can be substituted. The maximum number.

In addition to the structures of the above-mentioned formula (2-aX1), formula (2-bX1), formula (2-bX2Y1), or formula (2-cX2), the above-mentioned formula (2-aX1) and the above-mentioned formula (2) -BX1) and are combined structure, i.e., may be a structure so as to capture the X ¹ have the ring a 'and ring B', in a similar manner, may have a structure of the following combinations.
Equation (2-aX1) and Equation (2-bX2Y1)
Equation (2-aX1) and Equation (2-cX2)
Equation (2-bX1) and Equation (2-bX2Y1)
Equation (2-bX1) and Equation (2-cX2)
Equation (2-bX2Y1) and Equation (2-cX2)
Equation (2-aX1), Equation (2-bX1), and Equation (2-bX2Y1)
Equation (2-aX1), Equation (2-bX1), and Equation (2-cX2)
Equation (2-aX1), Equation (2-bX2Y1), and Equation (2-cX2)
Equation (2-bX1), Equation (2-bX2Y1), and Equation (2-cX2)
Equation (2-aX1), Equation (2-bX1), Equation (2-bX2Y1) and Equation (2-cX2)
Further, the description of specific examples of the above-mentioned formula (2-aX1-ex), formula (2-bX1-ex), formula (2-bX2Y1-ex), or formula (2-cX2-ex) is described in these specific examples. The same applies to all forms other than the examples.

以上に示すように、例えばｂ環における「−Ｃ（−Ｒ^５）＝」の箇所が「−Ｎ＝」に置き換わってもよく、このようにして、式（２）でベンゼン環として表示されるｂ環は、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、その他の含窒素ヘテロアリール環に変化してもよい。また、ｂ環上に隣接する基が存在する場合（上記式中ではＲ^６およびＲ^７）には、これらが結合してｂ環と共にヘテロアリール環（上記式中ではキノリン環）を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。
その他、以下のような変形例もある。

その他の箇所が「−Ｎ＝」に置き換わった場合や、ａ環またはｃ環が変化した場合についても同じである。 In equation (2), any "-C (-R) =" in rings a, b, and c (where R is R ^{1 through} R ¹¹ in equation (2)) is "-". It may be replaced with "N =".

As shown above, for example, ^{the portion of "-C (-R 5} ) =" in the b ring may be replaced with "-N =", and in this way, it is displayed as a benzene ring in the formula (2). Ring b may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. When adjacent groups are present on the b ring (R ⁶ and R ^{7 in the} above formula), they are combined to form a heteroaryl ring (quinoline ring in the above formula) together with the b ring. As described above, the formed ring may be further substituted (indicated by n R's).
In addition, there are the following modified examples.

The same applies when other parts are replaced with "-N =" or when the a-ring or c-ring is changed.

Further, as an example, the structure in which all "-C (-R) =" is replaced with "-N =" is shown below.

以上に示すように、例えばｂ環における「−Ｃ（−Ｒ^７）＝Ｃ（−Ｒ^６）−」の箇所が「−Ｎ（−Ｒ）−」、「−Ｏ−」、または「−Ｓ−」に置き換わってもよく、このようにして、式（２）でベンゼン環として表示されるｂ環は、Ｒ置換のピロール環、フラン環、チオフェン環、その他の含窒素・酸素・硫黄ヘテロアリール環に変化してもよい。また、ｂ環上に隣接する基が存在する場合（上記式中ではＲ^４およびＲ^５）には、これらが結合してｂ環と共にヘテロアリール環（上記式中ではＲ置換のインドール環、ベンゾフラン環、またはベンゾチオフェン環）を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。
その他、以下のような変形例もある。

その他の箇所が「−Ｎ（−Ｒ）−」、「−Ｏ−」、または「−Ｓ−」に置き換わった場合や、ａ環またはｃ環が変化した場合についても同じである。 In the formula (2), any "-C (-R) = C (-R)-" in the a ring, the b ring, and the c ring (where R is R ^{1 to} R ^{11 in the formula (2)).} Is replaced with "-N (-R)-", "-O-", or "-S-", and the R of the "-N (-R)-" is aryl, It is alkyl or cycloalkyl. The details of the substituents listed here will be described later.

As shown above, for example, the place of "-C (-R ⁷ ) = C (-R ⁶ )-" in the b ring is "-N (-R)-", "-O-", or "-S". -”Can be replaced, and thus, the b ring represented as the benzene ring in the formula (2) is an R-substituted pyrrole ring, a furan ring, a thiophene ring, or other nitrogen-containing / oxygen / sulfur heteroaryl. It may change into a ring. When adjacent groups are present on the b ring (R ⁴ and R ^{5 in the} above formula), they are bonded to the heteroaryl ring together with the b ring (in the above formula, the R-substituted indole ring and benzofuran). It is as described above that a ring, or a benzothiophene ring) is formed, and the formed ring may be further substituted (indicated by n R's).
In addition, there are the following modified examples.

The same applies when other parts are replaced with "-N (-R)-", "-O-", or "-S-", or when the a-ring or c-ring is changed.

The above formulas (2-a) to (2-abc), the above formulas (2-a-ex) to (2-c-ex), and the above formulas (2-aX1) to (2-cX2). , And the above formulas (2-aX1-ex) to (2-cX2-ex), the a ring, b ring, and c ring are described as benzene rings, but the a ring to c ring contain nitrogen. The same applies when the ring is changed to a heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing / sulfur heteroaryl ring (5-membered ring).

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

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or carbon. It is an aryl ring of the number 6 to 10.
The "aryl ring" as the A to C rings in the formula (1) is the a ring and the b ring in which adjacent groups of ^{"R 1 to} R ^{11" defined in the formula (2) are bonded to each other.} , Or an aryl ring formed with a c ring, because the a ring, b ring, or c ring is already composed of a benzene ring having 6 carbon atoms. , The total carbon number 9 of the fused ring in which the smallest 5-membered ring is condensed with this benzene ring is the lower limit carbon number.

Specific "aryl rings" include, for example, a benzene ring which is a monocyclic system, a naphthalene ring which is a fused dicyclic system, an acenaphthylene ring, a fluorene ring, a phenalene ring which is a condensed tricyclic system, or a phenanthrene ring and a fused tetra. A ring system such as a triphenylene ring, a pyrene ring, or a naphthalene ring, or a fused pentacyclic system such as a perylene ring or a pentacene ring.

The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, and a heteroaryl ring having 2 to 15 carbon atoms. An aryl ring, a heteroaryl ring having 2 to 10 carbon atoms, or the like. The "heteroaryl ring" is, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.
The "heteroaryl ring" as the A to C rings in the formula (1) is the a ring and the b ring in which adjacent groups of the ^{"R 1 to} R ^{11" defined in the formula (2) are bonded to each other.} Corresponds to the "heteroaryl ring formed with the ring or c ring", but for this "formed aryl ring", the a ring, b ring, or c ring is already composed of a benzene ring having 6 carbon atoms. Therefore, the total number of carbon atoms of the fused ring in which the smallest 5-membered ring is condensed with this benzene ring is the lower limit of the number of carbon atoms. However, even if the benzene rings a to c are changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing / sulfur-containing heteroaryl ring (5-membered ring) as described above. Therefore, in this case, the lower limit carbon number changes accordingly.

Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isooxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxaziazole ring, thiazizol ring, triazole ring, tetrazole ring, pyrazole ring, pyridine. Ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, Cinnoline ring, quinazoline ring, quinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysin ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indridin ring, furan Ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole It is an oxide ring, a dibenzophosphole oxide ring, a flazan ring, a thiantolene ring, an indolocarbazole ring, a benzoindolobazole ring, or a benzobenzoindolobazole ring.

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

Specific "aryl" includes, for example, phenyl which is a monocyclic system, biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) which is a bicyclic system, and naphthyl (1-naphthyl or 1-naphthyl or which is a condensed bicyclic system. 2-naphthyl), tricyclic terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'- Il, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o -Terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl- 4-yl), fused tricyclic, acenaphthylene- (1-, 3-, 4-, or 5-) yl, fluorene- (1-, 2-, 3-, 4-, or 9-) yl. , Phenarene- (1- or 2-) yl, or phenanthren- (1-, 2-, 3-, 4-, or 9-) yl, quaterphenylyl (5'-phenyl-m), which is a tetracyclic system. -Terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), fused tetracyclic system. , Triphenylene- (1- or 2-) yl, pyrene- (1-, 2-, or 4-) yl, or naphthacene- (1-, 2-, or 5-) yl, or in a fused pentacyclic system. There are perylene- (1-, 2-, or 3-) yl, or pentasen- (1-, 2-, 5-, or 6-) yl, and the like.

In addition, in the aryl as a second substituent, that is, the aryl as a substituent (second substituent) further substituting for a substituent (first substituent), at least one hydrogen in the aryl is an aryl such as phenyl. A structure substituted with an alkyl (specific example is a group described later), an alkyl such as methyl (a specific example will be described later), or a cycloalkyl (specific example is a group described later) such as cyclohexyl or adamantyl is also used as the second substituent. Included in the aryl of.
As an example, when the second substituent is a fluorenyl group, at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. It is a group or the like, and such a group is also included in aryl as a second substituent.

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

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl Phenazinyl, phenazacillinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphole, dibenzophosphoryl, The monovalent group of the benzophosphole oxide ring, the monovalent group of the dibenzophosphole oxide ring, frazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, or benzobenzoindrocarbazolyl.

In addition, in the heteroaryl as the second substituent, that is, the heteroaryl as the substituent (second substituent) further substituting for the substituent (first substituent), at least one hydrogen in the heteroaryl is phenyl. A structure substituted with aryl (specific examples are the groups described above), alkyl such as methyl (specific examples are groups described below), or cycloalkyls such as cyclohexyl or adamantyl (specific examples are groups described below) is also second. Included in heteroaryl as a substituent.
As an example, when the second substituent is a carbazolyl group, at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. It is a group or the like, and such a group is also included in the heteroaryl as a second substituent.

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

"Diarylboryl" is a boron group substituted with two aryls, and the description of "aryl" described above can be cited for details of this aryl. 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 is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in these groups is. Further, it may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. For more information on the substituents listed here, the description of "aryl", "heteroaryl", and "diarylamino" described above, as well as the "alkyl", "cycloalkyl", "alkoxy", and "aryl" described below. The explanation of "Oxy" can be quoted.

The "alkyl" may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, preferably an alkyl having 1 to 18 carbon atoms (carbon). Branched chain alkyl with 3 to 18 carbon atoms), alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms), alkyl with 1 to 6 carbon atoms (branched chain alkyl with 3 to 6 carbon atoms), carbon number It is an alkyl of 1 to 5 (branched chain alkyl having 3 to 5 carbon atoms), an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms), and the like.

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

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

Specific "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, norbornenyl, bicyclo. [1.0.1] Butyl, Bicyclo [1.1.1] Pentyl, Bicyclo [2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexil, Bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

The "alkoxy" may be either a straight chain or a branched chain, for example, a linear alkoxy having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms, preferably an alkoxy having 1 to 18 carbon atoms (carbon). Branched chain alkoxy with 3 to 18 carbon atoms), alkoxy with 1 to 12 carbon atoms (branched chain alkoxy with 3 to 12 carbon atoms), alkoxy with 1 to 6 carbon atoms (branched chain alkoxy with 3 to 6 carbon atoms), carbon number An alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 5 carbon atoms), an alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms), and the like.

Specific "alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1, 2,2-Tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3 -Dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n -Pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyl Oxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1, 1-Dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexyl Heptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethyl) Butyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n -Pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-eicosyloxy and the like.

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

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

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

"Trialkylsilyl" is a silyl group substituted with three alkyls, and the description of "alkyl" described above can be cited for details of this alkyl.
Specific "trialkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tris-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethyl Cyril, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi n-propylsilyl, ethyldi n-propylsilyl, n-butyldi n-propylsilyl, s-butyldi n-propylsilyl, t-butyldi n-propylsilyl, Methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, t-butyldiisopropylsilyl and the like.

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

The "dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the description of "alkyl" and "cycloalkyl" described above can be cited for details of the alkyl and the cycloalkyl.

The "alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyls, and the details of the alkyl and the cycloalkyl can be cited from the description of "alkyl" and "cycloalkyl" described above. ..

Substituents (including first and second substituents) affect the emission wavelength of polycyclic aromatic compounds due to the steric hindrance, electron donating property, and electron attracting property of the structure. The emission wavelength can be adjusted by selecting the group. Preferred substituents are groups represented by the following structural formulas. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the binding position.

Among these substituents, methyl, t-butyl, t-amyl, t-octyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xsilyl, 2,6-xsilyl , 2,4,6-methethyl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t- Butylcarbazolyl, trimethylsilyl, t-butyldimethylsilyl, triphenylsilyl, and phenoxy are more preferred, methyl, t-butyl, t-amyl, t-octyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl. , 2,4,6-methethyl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t -Butylcarbazolyl is more preferred.
From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis, for example, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2, 4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, diphenylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3, 6-Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred, t-butyl, t-amyl, adamantyl, diphenylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl. , 3,6-di-t-butylcarbazolyl is more preferred.

Further, the present invention is a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), preferably a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (2). It is a multimer of a compound. The multimer is preferably a 2-hexamer, more preferably a 2-3mer, and particularly preferably a dimer. The multimer may be in the form of having a plurality of the unit structures in one compound. For example, the unit structure is a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. In addition to a plurality of bonded forms (connected multimers), any ring (A ring, B ring, or C ring, a ring, b ring, or c ring) included in the unit structure can be used as a plurality of units. It may be in the form of being bonded so as to be shared by a structure (ring-shared multimer), and any ring (A ring, B ring, or C ring, a ring, b ring, or ring) included in the unit structure. It may be a form in which c-rings) are bonded to each other so as to condense (ring-condensation type multimer), or a form in which some rings are shared and some rings are condensed (ring-shared type and ring-condensation). Although it may be a complex type multimer of the type), a ring sharing type multimer, a ring condensation type multimer, and a complex type multimer are preferable, and a ring sharing type multimer and a complex type multimer are more preferable.

上記式（２−Ｍ１）で表される多量体化合物は、式（２）の単位構造におけるｃ環であるベンゼン環を共有し、かつ式（２）の単位構造におけるｂ環であるベンゼン環同士が縮合するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（複合型多量体）である。また、上記式（２−Ｍ２）で表される多量体化合物は、式（２）の単位構造におけるｃ環であるベンゼン環を共有するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環共有型多量体）である。 Examples of such a multimer include a multimer compound represented by the following formula (2-M1) or formula (2-M2).

The multimeric compound represented by the above formula (2-M1) shares the benzene ring which is the c ring in the unit structure of the formula (2), and the benzene rings which are the b ring in the unit structure of the formula (2) are used. Is a multimer compound (composite type multimer) having a unit structure represented by the two formulas (2) in one compound so as to condense. Further, the multimeric compound represented by the above formula (2-M2) shares the benzene ring which is the c ring in the unit structure of the formula (2), and the unit represented by the two formulas (2) is shared. It is a multimer compound (ring-shared multimer) having a structure in one compound.

上記式（２−Ｍ３）で表される多量体化合物は、二つの式（２）で表される単位構造が単結合により連結された多量体化合物（連結型多量体）である。上記式（２−Ｍ４）で表される多量体化合物は、二つの式（２）で表される単位構造がエーテル結合（連結基「−Ｏ−」）により連結された多量体化合物（連結型多量体）である。上記式（２−Ｍ５）で表される多量体化合物は、式（２）の単位構造におけるｂ環であるベンゼン環を共有するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環共有型多量体）である。上記式（２−Ｍ６）で表される多量体化合物は、式（２）の単位構造におけるａ環であるベンゼン環同士が縮合するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環縮合型多量体）である。 Further, for example, a multimeric compound represented by any of the following formulas (2-M3) to (2-M6) can be mentioned.

The multimer compound represented by the above formula (2-M3) is a multimer compound (linked multimer) in which the unit structures represented by the two formulas (2) are linked by a single bond. The multimeric compound represented by the above formula (2-M4) is a multimer compound (linkage type) in which the unit structures represented by the two formulas (2) are linked by an ether bond (linking group "-O-"). Multimer). The multimeric compound represented by the above formula (2-M5) has a unit structure represented by the two formulas (2) so as to share the benzene ring which is the b ring in the unit structure of the formula (2). It is a multimer compound (ring-shared multimer) contained in one compound. The multimeric compound represented by the above formula (2-M6) has a unit structure represented by the two formulas (2) so that the benzene rings, which are the a rings in the unit structure of the formula (2), are condensed with each other. Is a multimer compound (ring-condensation type multimer) having the above in one compound.

Since the multimers represented by the formulas (2-M1) to (2-M6) are composed of the unit structures represented by a plurality of formulas (2), the formulas (2-M1) to (2-M6) are formed. For the definition of each code in M6) and the change in the ring structure, the explanation in the equation (2) can be referred to as it is. ^{However, X 2} in the formula (2-M1) and the formula (2-M2) is limited to N or P, and N is preferable.

At least one hydrogen in the polycyclic aromatic compound represented by the formula (1) or the formula (2) and its multimer may be substituted with halogen, cyano, or deuterium. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine.

As a more specific example of the polycyclic aromatic compound of the present invention, a compound represented by the following structural formula can be mentioned. In the following structural formula, "Me" indicates a methyl group and "tBu" indicates a t-butyl group.

The polycyclic aromatic compound represented by the general formula (1) and its multimer are polymer compounds obtained by polymerizing a reactive compound in which a reactive substituent is substituted therein as a monomer (this polymer compound). The monomer for obtaining 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 pendant type polymer compound obtained by reacting a main chain 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. A material for an organic device, for example, can be used as a pendant type polymer crosslinked product obtained by further cross-linking a type polymer compound (the pendant type polymer compound for obtaining this pendant type polymer crosslinked product has a crosslinkable substituent). , Materials for organic field light emitting elements, materials for organic field effect transistors, or materials 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"). , Substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further cross-linking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain type polymer. Although not particularly limited, 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.

Such a polymer compound, a polymer crosslinked product, a pendant type polymer compound, and a pendant type polymer crosslinked product are used in addition to the repeating unit of the polycyclic aromatic compound represented by the formula (1) and its multimer. , Substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted carbazole. It may contain at least one selected from tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran as a repeating unit. Good.
Substituents in these repeating units include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (even if the two aryls are attached via a single bond or a linking group). Good), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl and the like. For details of the "aryl" of triarylamines and their substituents, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.

Details of the uses of such polymer compounds, polymer crosslinked products, pendant type polymer compounds and pendant type polymer crosslinked products (hereinafter, also simply referred to as “polymer compounds and polymer crosslinked products”) will be described later.

2. Method for Producing Polycyclic Aromatic Compound and Its Multimer The polycyclic aromatic compound represented by the general formula (1) or (2) and its multimer basically first have A ring (a ring) B. An intermediate is produced by binding to a ring (b ring) and a C ring (c ring) with a binding group ( ^{a group containing X 1} and X ² ) (first reaction), and then the A ring (a ring). , it can be produced ring B (b ring), and the final product by binding the C ring (c ring) a linking group (group including Y ¹⁾ (second reaction).

In the first reaction, for example, if it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used, and if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an 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.

まず、Ｘ^１とＸ^２の間の水素原子（Ａ環またはａ環上の「Ｈ」）をｎ−ブチルリチウム、ｓ−ブチルリチウムまたはｔ−ブチルリチウム等でオルトメタル化する。次いで、三塩化ホウ素や三臭化ホウ素等を加え、リチウム−ホウ素の金属交換を行った後、Ｎ，Ｎ−ジイソプロピルエチルアミン等のブレンステッド塩基を加えることで、タンデムボラフリーデルクラフツ反応させ、目的物を得ることができる。第２反応においては反応を促進させるために三塩化アルミニウム等のルイス酸を加えてもよい。 The second reaction, as shown in the following scheme (1) and (2), A ring (a ring), B ring (b ring), and ring C (c rings) in a reaction for introducing the ^{Y 1} to bind Yes, as an example, the case where Y ¹ is a boron atom and X ¹ and X ² are> N-R is shown below. The definitions of the symbols in the structural formulas in the following schemes (1) and (2) are the same as the above-mentioned definitions, and the definitions of the symbols in the structural formulas in all the schemes shown in the following paragraphs are also the above-mentioned definitions. Is the same as.

First, ^{the hydrogen atom between X 1} and X ² (“H” on the A ring or a ring) is orthometalated with n-butyllithium, s-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.

The above schemes (1) and (2) mainly show a method for producing a polycyclic aromatic compound represented by the general formula (1) or (2), but there are a plurality of multimers thereof. It can be produced by using an intermediate having an A ring (a ring), a B ring (b ring) and a C ring (c ring). Details will be described in the following schemes (3) and (4). In this case, the desired dimer or trimer can be obtained by doubling or trebling the amount of the reagent such as n-butyllithium to be used.

In the above schemes (1) to (4), lithium was introduced to a desired position by orthometalation, but a bromine atom or the like was introduced at a position where lithium was to be introduced, and lithium was also introduced to a desired position by halogen-metal exchange. Can be introduced. According to this method, the target product can be synthesized even in a case where orthometalation cannot be performed due to the influence of the substituent, which is useful.

By appropriately selecting the above-mentioned synthesis method and appropriately selecting the raw material to be used ^{, a polycyclic aromatic having a substituent at a desired position, Y 1} being a boron atom, and X ¹ and X ² being> N-R. Group compounds and their multimers can be synthesized. In addition, when synthesizing intermediates, X ¹ and X ² are groups other than>N-R,>O,> C (-R) ₂ ,> Si (-R) ₂ ,>PR,> S. , Or> Se, these polycyclic aromatic compounds can also be synthesized.

スキーム（１）〜（４）と同様に、まずＸ^１とＸ^２の間の水素原子（Ａ環上の「Ｈ」）をｎ−ブチルリチウム等でオルトメタル化する。次いで、三塩化リン、硫黄の順に添加し、最後に三塩化アルミニウム等のルイス酸およびＮ，Ｎ−ジイソプロピルエチルアミン等のブレンステッド塩基を加えることで、タンデムホスファフリーデルクラフツ反応させ、Ｙ^１がリンスルフィド（Ｐ＝Ｓ）である化合物を得ることができる。また、得られたリンスルフィド化合物をｍ−クロロ過安息香酸（ｍ−ＣＰＢＡ）で処理することでＹ^１がリンオキサイド（Ｐ＝Ｏ）である化合物を得ることができ、トリエチルホスフィンで処理することでＹ^１がリン原子である化合物を得ることができる。 Next, when Y ¹ is a phosphorus sulfide (P = S), a phosphorus oxide (P = O), or a phosphorus atom, and X ¹ and X ² are> N-R, the following schemes (5) to ( 7).

Similar to Scheme (1) to (4), first ortho-metalated with n- butyl lithium or the like ( "H" on the A-ring) a hydrogen atom between ^{X 1} and ^{X 2.} Then, phosphorus trichloride were added in the order of sulfur, finally by adding three Lewis acid such as aluminum chloride and N, Bronsted base such as N- diisopropylethylamine, tandem phosphorylase Fafu Riedel is Crafts reaction, Y ¹ is phosphorus A compound that is sulfide (P = S) can be obtained. Further, the Y ¹ by treatment with a resulting Rinsurufido compound m- chloroperbenzoic acid (m-CPBA) is able to obtain the compound is a phosphorus oxide (P = O), treated with triethyl phosphine A compound in which Y ¹ is a phosphorus atom can be obtained.

In the above scheme, an example in which Y ¹ is B, P, P = O, or P = S and X ¹ and X ² are> N-R has been described, but by appropriately changing the raw materials, Y ¹ is Al, Ga, As, Si-R, or Ge-R, and X ¹ and X ² are>O,> C (-R) ₂ ,> Si (-R) ₂ ,> P-. Compounds of R,> S, or> Se can also be synthesized.

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

Further, in the synthesis of the above scheme (1) to (5), the three before adding boron chloride and boron tribromide, hydrogen atom (or a halogen atom) with n- butyllithium between X ¹ and X ² An example of tandem hetero-Friedel-Crafts reaction was shown by orthometalation with orthometalization, but addition of boron trichloride, boron tribromide, etc. without orthometalation using n-butyllithium or the like was shown. The reaction can also be advanced by.

When Y ¹ is phosphorus-based, as shown in the following scheme (8), a hydrogen atom (“H” on the A ring) between ^{X 1} and X ^{2 (> N—R in the following formula).} Is orthometalized with n-butyllithium, s-butyllithium, t-butyllithium, etc., then bisdiethylaminochlorophosphine is added, and after metal exchange of lithium-phosphorus, Lewis acid such as aluminum trichloride is added. By adding it, the tandem phosphafriedelcrafts reaction can be carried out to obtain the desired product. This reaction method is also described in International Publication No. 2010/104047 (for example, page 27).

Also in the above scheme (8), a multimer compound is synthesized by using an orthometalation reagent such as n-butyllithium in a molar amount twice or three times the molar amount of the intermediate 1. Can be done. Further, a halogen such as a bromine atom or a chlorine atom is introduced in advance at a position where a metal such as lithium is to be introduced, and the metal can be introduced at a desired position by exchanging the halogen-metal.

The orthometallation reagents used in the above schemes (1) to (8) include alkyllithium such as methyllithium, n-butyllithium, s-butyllithium, and t-butyllithium, lithium diisopropylamide, and lithium tetramethyl. Examples thereof include organic alkaline compounds such as piperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

As the metal exchange reagent metal -Y ¹ used in the above Scheme (1) to (8), the three fluoride ^{Y 1,} trichloride of ^{Y 1,} tribromide of ^{Y 1,} triiodide of ^{Y 1} halides of ^{Y 1} such as halide, CIPN _{(NEt 2)} 2 amination halide ^{Y 1,} such as, alkoxides of ^{Y 1,} an aryloxy compound of ^{Y 1} are mentioned.

The blended bases used in the above schemes (1) to (8) include N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidin, 1,2,2,6,6. -Pentamethylpiperidin, N, N-dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar _{4 BK, Ar 3 B, Ar} 4 Si ( Incidentally, Ar is aryl, such as phenyl) and the like.

Lewis acids used in the above schemes (1) to (8) include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ , OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , and so on. In (OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc (OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn (OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg (OTf) ₂ , LiOTf, Na _{, KOTf, Me 3 SiOTf, Cu} (OTf) such as _{2, CuCl 2, YCl 3,} Y (OTf) 3, TiCl 4, TiBr 4, ZrCl 4, ZrBr 4, FeCl 3, FeBr 3, CoCl 3, CoBr 3 is Can be mentioned.

In the above schemes (1) to (8), Bronsted bases or Lewis acids may be used to promote the tandem hetero-Friedel-Crafts reaction. However, when Y ¹ halides such as Y ¹ trifluoride, Y ¹ trichloride, Y ¹ tribromide, and Y ¹ triiodide are used, as the aromatic electrophobic substitution reaction progresses, Since acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, it is effective to use a blended base that captures the acid. On the other hand, when ^{an aminated halide of Y 1} and an alkoxyylated product of Y ¹ are used, a blended base is often used because amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds. Although it is not necessary, the use of a Lewis acid that promotes the elimination of amino groups and alkoxy groups is effective because of its low ability to eliminate them.

The polycyclic aromatic compound and its multimer of the present invention also include a structure in which at least one hydrogen is substituted with a halogen such as fluorine, chlorine, bromine, and iodine, cyano, or dehydrogenation. , These can be obtained by using a raw material in which the desired position is halogenated, cyanated, or dehydrogenated, or by halogenating, cyanating, or dehydrogenating in the intermediate or final stages of synthesis. It can be synthesized in the same way.

3. 3. Organic Devices The polycyclic aromatic compounds and their multimers according to the present invention can be used as materials for organic devices. Examples of the organic device include an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, and the like.

3-1. 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.

<Structure of organic electroluminescent device>
The organic EL element 100 shown in FIG. 1 is placed on a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103. The hole transport layer 104 is provided, the light emitting layer 105 is provided on the hole transport layer 104, the electron transport layer 106 is provided on the light emitting layer 105, and the electron transport layer 106 is provided. It has an electron injection layer 107 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 / Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode "," substrate / Anode / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole transport layer / light emitting layer / electron injection layer / cathode "," substrate / anode / hole transport layer / light emitting layer / electron "Transport layer / Anode", "Substrate / Anode / Hole injection layer / Light emitting layer / Electron injection layer / Cathode", "Substrate / Anode / Hole injection layer / Light emitting layer / Electron transport layer / Cone", "Substrate / Anode" The configuration may be "/ light emitting layer / electron transporting layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

<Substrate in organic electroluminescent device>
The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. 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. As for the material of the glass, non-alkali glass is preferable because it is better that there are few elution ions from the glass, but _{soda lime glass with a barrier coat such as SiO 2} is also commercially available, so this can be used. it 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.

<Anode in organic electroluminescent device>
The anode 102 serves to inject holes into the light emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these. ..

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.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, nesa glass, and the like. 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.

<Hole injection layer and hole transport layer in 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. 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 formed by laminating and mixing one or more of the hole injection / transport materials or a mixture of the hole injection / transport material and the polymer binder, respectively. Will be done. 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.

As the material for forming the hole injection layer 103 and the hole transport layer 104, a polycyclic aromatic compound represented by the above general formula (1) and a multimer thereof can be used. Further, in the photoconductive material, among the compounds conventionally used as the hole charge transport material, the p-type semiconductor, the hole injection layer of the organic EL element, and the known compounds used in the hole transport layer. Any compound can be selected and used. 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-hexaazatriphenylene-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. Known matrix materials having hole transport properties include, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly zinc phthalocyanines (ZnPc), etc.) (such as zinc phthalocyanines). Japanese Unexamined Patent Publication No. 2005-167175).

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.

<Light emitting layer in organic electroluminescent device>
The light emitting layer 105 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. As the material for forming the light emitting layer 105, a polycyclic aromatic compound represented by the above general formula (1) and a multimer thereof can be used. Further, any compound (luminescent compound) that is excited by recombination of holes and electrons to emit light can be used, and a stable thin film shape can be formed, and strong light emission (fluorescence) efficiency can be obtained in a solid state. It is preferably the compound shown.

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 two or more. The dopant material may be included in the entire host material, partially, or in any part. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be mixed with the host material in advance and then vapor-deposited at the same time.

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 80 to 99.95% by weight, and further preferably 90 to 99.9% by weight of the entire material for the light emitting layer. Is.

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 0.05 to 20% by weight, still more preferably 0.1 to 10% by weight of the entire light emitting layer material. is there. The above range is preferable in that, for example, the density quenching phenomenon can be prevented.

Host materials include fused ring derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, which have long been known as luminescent materials, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. And so on. In particular, anthracene-based compounds, fluorene-based compounds or dibenzochrysene-based compounds are preferable.

<Anthracene compounds>
The anthracene-based compound as a host is, for example, a compound represented by the following general formula (3).

In equation (3),
X and Ar ⁴ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, respectively. Aryl heteroarylamino which may be substituted, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted, alkoxy which may be substituted, which may be substituted. Aryloxy, optionally substituted arylthio or optionally substituted silyl, all X and Ar ⁴ are not hydrogenated at the same time.
At least one hydrogen in the compound represented by the formula (3) may be substituted with a halogen, cyano, deuterium or a heteroaryl which may be substituted.

Further, a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3) are bonded to each other via X can be mentioned, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine ring, etc.). A group in which a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc. have a divalent bond value) and the like can be mentioned.

Details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl will be described in the section of preferred embodiments below. Examples of the substituents thereof include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, silyl, and the like. Details will also be described in the section of preferred embodiments below.

Preferred embodiments of the anthracene-based compound will be described below. The definition of the code in the structure below is the same as the definition described above.

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

Further, a multimer (preferably a dimer) may be formed by using the structure represented by the formula (3) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3) are bonded to each other via X can be mentioned, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine ring, etc.). A group in which a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc. have a divalent bond value) and the like can be mentioned.

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

Ar ¹ and Ar ² are independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or in the above formula (A). The group represented (including carbazolyl group, benzocarbazolyl group and phenyl-substituted carbazolyl group). When Ar ¹ or Ar ² is a group represented by the formula (A), the group represented by the formula (A) is in the formula (3-X1) or the formula (3-X2) in the *. It binds to the naphthalene ring.

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (carbazolyl group, benzocarba). It also includes a zolyl group and a phenyl-substituted carbazolyl group). When Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to the single bond represented by the straight line in the formula (3-X3) in the *. .. That is, the anthracene ring of the formula (3) and the group represented by the formula (A) are directly bonded.

Further, Ar ³ may have a substituent, and ^{at least one hydrogen in Ar 3} is further an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl and phenanthryl. , Fluolenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group) may be substituted. When the ^{substituent contained in Ar 3} is a group represented by the formula (A), the group represented by the formula (A) is bonded to ^{Ar 3 in the formula (3-X3) in the *.}

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

Examples of alkyl having 1 to 4 carbon atoms to be substituted with silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are independent of each other. , Substituted with these alkyls.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, and ethyl. Dimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyl Diethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldii-propylsilyl, ethyldii-propylsilyl, Examples thereof include butyl di-propyl silyl, sec-butyl di-propyl silyl and t-butyl di-propyl silyl.

Cycloalkyls having 5 to 10 carbon atoms to be substituted with silyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, Bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthalenyl, decahydro Azulenyl and the like are mentioned, and the three hydrogens in silyl are independently substituted with these cycloalkyls.

Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentyl silyl and tricyclohexyl silyl.

Substituted silyls include dialkylcycloalkylsilyls substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls, which are substituted alkyls and cycloalkyls. Specific examples of the above-mentioned group include the above-mentioned groups.

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

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

In the above formula (A), Y is -O-, -S- or> N-R ²⁹ , and R ^{21 to} R ²⁸ are independently hydrogen, optionally substituted alkyl, and optionally substituted, respectively. Good cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, the ^{adjacent groups of R 21-} R ²⁸ are bonded to each other to form a hydrocarbon ring. , may form an aryl or heteroaryl ring, R ²⁹ is aryl which may be hydrogen or substituted.

The "alkyl" of the "optionally substituted alkyl" in R ^21- R ²⁸ may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a linear alkyl having 3 to 24 carbon atoms. Branched chain alkyl can be mentioned. An alkyl having 1 to 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 is more preferable. (Branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable.

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.

The "cycloalkyl" of the "optionally substituted cycloalkyl" in R ^{21 to} R ²⁸ includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, and cycloalkyl having 3 to 16 carbon atoms. , Cycloalkyl having 3 to 14 carbon atoms, 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 the like.

Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (particularly methyl) substituents having 1 to 4 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 [2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like can be mentioned.

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

Specific examples of "aryl" include phenyl, which is a monocyclic system, biphenylyl, which is a bicyclic system, naphthyl, which is a condensed bicyclic system, and terfenylyl, which is a tricyclic system (m-terphenylyl, o-terphenylyl, p-terphenylyl). , Condensed tricyclics such as acenaftyrenyl, fluorenyl, phenylenyl, phenylentrenyl, condensed tetracyclics triphenylenyl, pyrenyl, naphthacenyl, condensed pentacyclics perylenyl, pentasenyl and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" in R ^{21 to} R ²⁸ include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and carbon. Heteroaryls having a number of 2 to 20 are more preferable, heteroaryls having 2 to 15 carbon atoms are further preferable, and heteroaryls having 2 to 10 carbon atoms are 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 "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl Phenazinyl, phenazacillinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoyl, dibenzophosphoryl, benzo Examples thereof include a monovalent group of the phosphor oxide ring, a monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantranyl, indolocarbazolyl, benzoindrocarbazolyl and benzobenzoindrocarbazolyl.

Examples of the “alkoxy” of the “optionally substituted alkoxy” in R ^{21 to} R ²⁸ include a straight-chain alkoxy having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (alkoxy of branched chains having 3 to 18 carbon atoms) is preferable, and 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 is more preferable. Alkoxy (alkoxy of a branched chain having 3 to 6 carbon atoms) is more preferable, and alkoxy having 1 to 4 carbon atoms (alkoxy of a branched chain having 3 to 4 carbon atoms) is particularly preferable.

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

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

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

Examples of the "trialkylsilyl" in R ^{21 to R 28} include groups in which the three hydrogens in the silyl group are independently substituted with alkyl, and this alkyl is referred to as the "alkyl" in ^{R 21 to} R ^{28 described above.} The groups described can be quoted. Preferred alkyls for substitution are alkyls having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl and the like.

Specific "trialkylsilyl" includes trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl. Dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyl Dipropyl silyl, ethyl dipropyl silyl, butyl dipropyl silyl, sec-butyl dipropyl silyl, t-butyl dipropyl silyl, methyl di-propyl silyl, ethyl di-propyl silyl, butyl di-propyl silyl, sec-butyl di i -Propylsilyl, t-butyldii-propylsilyl and the like can be mentioned.

Examples of the "tricycloalkylsilyl" in R ^{21 to R 28} include groups in which the three hydrogens in the silyl group are independently substituted with cycloalkyl, and this cycloalkyl is the above-mentioned "tricycloalkylsilyl" in R ^{21 to} R ²⁸ . The group described as "cycloalkyl" can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [. 2.0.1] Pentyl, Bicyclo [1.2.1] Hexyl, Bicyclo [3.0.1] Hexil, Bicyclo [2.1.2] Heptyl, Bicyclo [2.2.2] Octyl, Adamantyl, Examples thereof include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of the "tricycloalkyl silyl" include tricyclopentyl silyl and tricyclohexyl silyl.

Specific examples of the dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and the alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls are selected from the specific alkyls and cycloalkyls described above. Examples thereof include silyls in which the group to be substituted is substituted.

Examples of the "substituted amino" of the "optionally substituted amino" in R ^{21 to} R ^{28 include an amino group in which two hydrogens are substituted with aryl or heteroaryl.} Aminos in which two hydrogens are substituted with aryls are diaryl substituted aminos, aminos in which two hydrogens are substituted with heteroaryls are diheteroaryl substituted aminos, and aminos in which two hydrogens are substituted with aryls and heteroaryls. Is an aryl heteroaryl substituted amino. As the aryl or heteroaryl, the groups described as "aryl" or "heteroaryl" in ^{R 21 to} R ^{28 described above can be cited.}

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

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

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

R ²⁹ in the "> N-R ^29" as Y is hydrogen or aryl which may be substituted, be cited a group described as the "aryl" in R ²¹ to R ²⁸ described above as the aryl As the substituent, the group described as the substituent for ^{R 21 to} R ^{28 can be cited.}

Adjacent groups of R ^{21 to} R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where a ring is not formed is a group represented by the following formula (A-1), and the case where a ring is formed is, for example, a group represented by the following formulas (A-2) to (A-14). Be done. In addition, at least one hydrogen in the group represented by any of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl. , Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, aryl heteroaryl substituted amino, halogen, hydroxy or cyano. * In each structural formula represents the bond position, and Y has the same definition as above.

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

Examples of the group represented by the formula (A) include groups represented by any of the above formulas (A-1) to (A-14), and the above formulas (A-1) to (A-14). −5) and the group represented by any of the formulas (A-12) to (A-14) are preferable, and the group represented by any of the above formulas (A-1) to (A-4) is preferable. Is more preferable, a group represented by any one of the above formula (A-1), (A-3) and (A-4) is further preferable, and a group represented by the above formula (A-1) is more preferable. Especially preferable.

The group represented by the formula (A) is a naphthalene ring in the formula (3-X1) or the formula (3-X2), a single bond in the formula (3-X3), and a formula in * in the formula (A). ^{As described above, it binds to Ar 3} in (3-X3) and replaces it with at least one hydrogen in the compound represented by the formula (3), but among these binding forms, the formula (3-X1) Alternatively, a form in which the naphthalene ring in the formula (3-X2), the single bond in the formula (3-X3) and / or the Ar ³ in the formula (3-X3) is bonded is preferable.

Further, in the structure of the group represented by the formula (A), the naphthalene ring in the formula (3-X1) or the formula (3-X2), the single bond in the formula (3-X3), and the formula (3-X3). ) Ar ³ is bonded position in, also, the formula (in the structure of groups in represented by a), substituted position with at least one hydrogen in the compound represented by formula (3) has the formula (a) It may be at any position in the structure of, for example, any of the two benzene rings in the structure of formula (A) or adjacent groups ^{of R 21 to} R ^{28 in the structure of formula (A).} It can be bonded at any ring formed by bonding with each other or at any position in R ^{29 in "> N-R 29" as Y in the structure of the formula (A).}

Examples of the group represented by the formula (A) include the following groups. Y and * in the formula have the same definition as above.

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

Specific examples of the anthracene-based compound include compounds represented by the following formulas (3-1) to (3-72). In the following structural formula, "Me" indicates a methyl group, "D" indicates a deuterium, and "tBu" indicates a t-butyl group.

The anthracene-based compound represented by the formula (3) includes a compound having a reactive group at a desired position in the anthracene skeleton and a compound having a reactive group in a partial structure such as the structure of ^{X, Ar 4 and the formula (A).} Can be produced by applying Suzuki coupling, Negishi coupling, and other known coupling reactions using the above as a starting material. Examples of the reactive group of these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to.

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

In the above formula (4),
R ¹ to R ¹⁰ are independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the above formula (4) via a linking group), diarylamino, and dihetero. Arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ are independently combined. It may form a fused ring or a spiro ring, and at least one hydrogen in the formed ring may be aryl or heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group). ), Diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or cycloalkyl. May be replaced with, and
At least one hydrogen in the compound represented by the formula (4) may be substituted with halogen, cyano or deuterium.

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

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

式（４−Ａｒ１）から式（４−Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ−Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（４−Ａｒ１）から式（４−Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 As a specific example of the heteroaryl, any one from the compounds of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) A monovalent group represented by excluding one hydrogen atom can also be mentioned.

Wherein (4-Ar5) from equation (4-Ar1), ^{Y 1} are each independently, O, S or N-R, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structure of the above formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bound to the fluorene skeleton in the above formula (4) via a linking group. That is, not only the fluorene skeleton in the formula (4) and the heteroaryl may be directly bonded, but also they may be bonded via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

^{Further, R 1} and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ in the equation (4) are independently combined. The fused ring may ^{be bonded to R 9} and R ¹⁰ to form a spiro ring. The ^{condensed ring formed by R 1} to R ⁸ is a ring condensed with the benzene ring in the formula (4), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of the structure including the benzene ring in the formula (4) include a naphthalene ring and a phenanthrene ring. The ^{spiro ring formed by R 9} and R ¹⁰ is a ring spiro-bonded to the 5-membered ring in the formula (4), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples thereof include a fluorene ring.

The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), and each of them is represented by the general formula (4). ), The compound in which the benzene ring formed by combining ^{R 1} and R ^{2 is condensed, the compound in which the benzene ring formed by combining R 3} and R ⁴ in the general formula (4) is condensed, and the general formula (4). a compound either is not bound from R ¹ R ⁸ is in).

^{The definitions of R 1} to R ¹⁰ in Eqs. (4-1), Eq. (4-2) and Eq. (4-3) are the same as the ^{corresponding R 1} to R ¹⁰ in Eq. (4), and Eq. (4-4). ^{The definitions of R 11} to R ¹⁴ in 1) and equation (4-2) are the same as those ^{of R 1} to R ¹⁰ in equation (4).

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

^{The definitions of R 2} to R ^{7 in} the formula (4-1A), the formula (4-2A) and the formula (4-3A) are in the formula (4-1), the formula (4-2) and the formula (4-3). corresponding the same from ^{R 2} and ^{R 7, R} in the formula also defined formula (4-1) of the ^{R 14} from ^{R 11} in (4-1A) and (4-2A) and (4-2) ¹¹ from is the same as ^{R 14.}

Further, the hydrogen in the compound represented by the formula (4) may be entirely or partially substituted with halogen, cyano or deuterium.

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

In the above formula (5),
R ¹ to R ¹⁶ are independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzoglycene skeleton in the above formula (5) via a linking group), diarylamino, and di. Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.
Further, ^{adjacent groups of R 1} to R ¹⁶ may be bonded to each other to form a fused ring, and at least one hydrogen in the formed ring is aryl or heteroaryl (the heteroaryl is via a linking group). It may be attached to the formed ring), and may be substituted with diallylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least in these. One hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and
At least one hydrogen in the compound represented by the formula (5) may be substituted with halogen, cyano or deuterium.

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

Examples of the alkenyl in the definition of the above formula (5) include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and 2 to 2 carbon atoms. The alkenyl of 6 is more preferable, and the alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

式（５−Ａｒ１）から式（５−Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ−Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（５−Ａｒ１）から式（５−Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 As a specific example of the heteroaryl, any one from the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) A monovalent group represented by excluding one hydrogen atom can also be mentioned.

Wherein (5-Ar5) from equation (5-Ar1), ^{Y 1} are each independently, O, S or N-R, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structure of the above formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bound to the dibenzochrysene skeleton in the above formula (5) via a linking group. That is, not only the dibenzochrysene skeleton in the formula (5) and the heteroaryl may be directly bonded, but also they may be bonded via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

The compound represented by the general formula (5) is preferably R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are hydrogen. ^{In this case, R 2} , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in the formula (5) are independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl and phenanthrenyl, respectively. , A monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (1 having the structure). The valence group is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- via the above formula (5). (May be bound to the dibenzoglycene skeleton in), methyl, ethyl, propyl, or butyl is preferred.

The compounds represented by the general formula (5) are more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and R. ¹⁶ is hydrogen. In this case, at least one (preferably one or two, more preferably one) ^{of R 3} , R ⁶ , R ¹¹ and R ^{14 in the formula (5) is a single bond, phenylene, biphenylene, naphthylene,.} The above formulas (5-Ar1), formulas (5-Ar2), and formulas via anthrasenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH _{2 O-.} (5-Ar3), a monovalent group having the structure of formula (5-Ar4) or formula (5-Ar5).
Other than the at least one (that is, other than the position where the monovalent group having the structure is substituted) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one of these. Hydrogen may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

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

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.

<Example of polymer host material>

In the formula (SPH-1)
MU is a divalent group that is independently represented by removing any two hydrogen atoms from an aromatic compound, and EC is a divalent group that is independently represented by removing any one hydrogen atom from an aromatic compound. A valence group, two hydrogens in the MU are replaced by EC or MU, where k is an integer of 2-50000.

More specifically
The MUs are arylene, heteroarylene, dialylene arylamino, dialylene arylboryl, oxaborin-diyl, and azaborin-diyl, respectively.
ECs are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, respectively.
At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl.
k is an integer of 2 to 50,000.
k is preferably an integer of 20,000 to 50,000, and more preferably an integer of 100 to 50,000.

At least one hydrogen in MU and EC in the formula (SPH-1) may be substituted with an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a halogen or a heavy hydrogen, and further described above. arbitrary -CH ₂ in the alkyl - is -O- or -Si _{(CH 3) 2} - may be substituted with the formula in the alkyl (SPH-1) -CH connected directly to the EC of ₂ - Any −CH ₂ − except for may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

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

More specifically, a divalent group represented by any of the following structures can be mentioned. In these, the MU binds to another MU or EC at *.

Further, as the EC, for example, a monovalent group represented by any of the following structures can be mentioned. In these, EC binds to MU at *.

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

Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting 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 high 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 a layer function that can efficiently block the movement of holes.

As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, a polycyclic aromatic compound represented by the above general formula (1) and a multimer thereof can be used. Further, it can be arbitrarily selected and used from a compound conventionally used as an electron transfer compound in a photoconducting material, a known compound used in an electron injection layer and an electron transport layer of an organic EL element.

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 is preferable to contain 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, benzoquinolins 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. For example, hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes can 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 derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, and quinolinol 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、シクロアルキル、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１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、置換されていてもよいシクロ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 each independently contain hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, and optionally substituted nitrogen. Heterocycle, or at least one of cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, respectively. , X are optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boron, or optionally substituted carbazolyl, and n. Are independently integers from 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.

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、シクロアルキル、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１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、置換されていてもよいシクロ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、シクロアルキル、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１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、シクロアルキル、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１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、置換されていてもよいシクロ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, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. Containing heterocycles, or at least one of the cyanos ^{, R 13 to R 16} are independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, respectively. Yes, R ²¹ and R ²² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or at least cyano. One, X ¹ is an arylene having 20 or less carbon atoms which may be substituted, n is an integer of 0 to 3 independently, and m is an integer of 0 to 4 independently. It is an integer. 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, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the containing heterocycles, or cyano, R ^{13 to} R ¹⁶ are independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, respectively. Yes, X ¹ is an arylene having 20 or less carbon atoms which may be substituted, 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、シクロ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 structural formula represents the bonding position.

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

Specific examples of this borane derivative include the following compounds.

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. is there.

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 substituents are independently alkyl or carbon having 1 to 4 carbon atoms. It may be substituted with the number 5 to 10 of cycloalkyl. 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. * In each structural formula represents the bonding position.

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. * In each structural formula represents the bonding position.

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

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 compounds.

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 compounds.

<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, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). It may be alkyl, cycloalkyl, alkoxy or aryloxy, 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.

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). A description of the compound can be cited.

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

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. * In each structural formula represents the bonding position.

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. The groups to be formed are more preferable. 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 the "aryl 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 terphenyl (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- Terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracene- (1-, 2-, 9-) yl, acenaphthylene- (1-, 3-, 4-, 5-) yl, fluoren- (1-, 2-, 3-, 4-, 9-) yl, phenalen- (1-, 2-) yl, (1-, 2-) 2-, 3-, 4-, 9-) phenanthryl, fused tetracyclic aryl triphenylene- (1-, 2-) yl, pyrene- (1-, 2-, 4-) yl, tetracene- (1) Examples thereof include −,2-,5-) yl and perylene- (1-,2-,3-) yl, which is a fused pentacyclic aryl.

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, acenaphthylenyl, 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 compounds.

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, acenaphthylenyl, 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 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 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 preferable "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} , 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, 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 compounds.

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３〜２０のシクロアルキル、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３〜２０のシクロアルキル、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 cycloalkyl, aryl, or 5 to 20 carbon atoms of 6 to 20 carbon atoms having 3 to 20 carbon atoms,
R ⁶ is CN, substituted or unsubstituted, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, and 5 to 5 carbon atoms. 20 heteroaryl, alkoxy with 1 to 20 carbons or aryloxy with 6 to 20 carbons.
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, cycloalkylthio 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 in the fused ring formed between adjacent substituents. Is selected from.

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.

Further, the cycloalkenyl group indicates, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexene group, which may be substituted 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.

The cycloalkylthio group is a group in which the oxygen atom of the ether bond of the cycloalkoxy 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 groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and 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 compounds.

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 examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic 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) , Condensed tricyclic aryl, 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-) il and the like.

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, isoindyl, 1H-indazolyl, and the like. Benzoimidazolyl, 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, benzophosphoryl, 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 compounds.

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 an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1, respectively.

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 examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic 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) , Condensed tricyclic aryl, 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-) il and the like.

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, isoindyl, 1H-indazolyl, and the like. Benzoimidazolyl, 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, benzophosphoryl, 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 compounds.

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 examples of "aryl" include phenyl, which is a monocyclic aryl, biphenylyl (2-, 3-, 4-) biphenylyl, and (1-, 2-) naphthyl, which is a fused bicyclic 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) , Condensed tricyclic aryl, 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-) il and the like.

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, isoindyl, 1H-indazolyl, and the like. Benzoimidazolyl, 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, benzophosphoryl, 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 compounds.

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 substituent that replaces the imidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with dehydrogen. * In the following structural formula represents the bonding position.

^{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 above formula (ETM-2-1) or the above formula (ETM-2-2). For R ^{11 to} R ¹⁸ in the formula, the description in the above formula (ETM-2-1) or the 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 of No. 1 may be replaced with a benzoimidazole-based Substituent (that is, n = 2), or any one of the pyridine-based Substituents may be replaced with a benzoimidazole-based Substituent and the other pyridine-based Substituent shall 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 benzoimidazole 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-benzo [d] imidazole, 1- (4) -(10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)) Anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 1- (4- (9,10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -2- Examples thereof include phenyl-1H-benzo [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. is there.

^{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). Further, in addition to the above-mentioned example, φ can be given, 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. In addition, * in each structural formula represents the bonding position.

Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 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' -Difluoro-bi (1,10-phenanthroline-5-yl), vasocproin, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene, compounds represented by the following structural formulas, etc. Can be mentioned.

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、シクロアルキル、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, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, Ga, Be or Zn. n is an integer of 1-3.

Specific examples of the quinolinol-based metal complex include 8-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-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) Latte) 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] quinolinate) 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 substituent in which the following thiazole group or benzothiazole group is replaced, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with dehydrogen. * In the following structural formula represents the bonding position.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be quoted from the above formula (ETM-2-1) or the above formula (ETM-2-2). For R ^{11 to} R ¹⁸ in the formula, the description in the above formula (ETM-2-1) or the 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 element can be extended.

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 electronic 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.

<Cathode in organic electroluminescent device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injecting layer 107 and the electron transporting 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 deposition, sputtering, ion plating and coating.

<Binder that may be used in each layer>
The materials used for the above-mentioned hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer independently, but as a polymer binder, polyvinyl chloride, polycarbonate, etc. Polystyrene, poly (N-vinylcarbazole), polymethylmethacrylate, polybutylmethacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It is also possible to disperse and use it in solvent-soluble resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and curable resin such as silicone resin. is there.

<Method of manufacturing organic electroluminescent device>
Each layer constituting the organic EL element is made of a thin film by a method such as a vapor deposition method, a resistance heating vapor deposition, an electron beam vapor deposition, a sputtering, a molecular lamination method, a printing method, a spin coating method or a casting method, or a coating method. By setting, it can be formed. 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 waveform of the alternating current 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 / a hole injection layer / a hole transport layer / a light emitting layer composed of a host material and a dopant material / an electron transport layer / an electron injection layer / a cathode. The manufacturing method of the above will be described.

<Thin-film deposition method>
A thin film of an anode material is formed on an appropriate substrate by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. 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 the cathode 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.

<Wet film formation method>
The wet film forming method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL device 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 deposition method, the wet film deposition method does not require the use of an expensive vacuum deposition apparatus and can form a film under atmospheric pressure. In addition, the wet film formation method enables a large area and continuous production, which leads 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 having controlled solubility, the cross-linking of the lower layer and the orthogonal solvent (Orthogonal solvent, which 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 an organic EL device is produced by using a wet film forming method for only a few layers and a vacuum vapor deposition method for the rest.

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 including 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.

<Other film formation methods>
A laser heating drawing method (LITI) can be used to form 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.

<Arbitrary process>
Appropriate treatment steps, cleaning steps, and drying steps may be appropriately added before and after each step of film formation. 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. Furthermore, a series of steps for producing a bank can also be mentioned.

Photolithography technology can be used to create the bank. As the bank material that can be used for photolithography, a positive resist material and a negative resist material can be used. 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 polymers, fluorocarbon polymers, etc. However, it is not limited to that.

<Composition for forming an organic layer used in a wet film formation method>
The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL element or a high molecular weight compound obtained by polymerizing the low molecular weight compound in an organic solvent. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or a polymer compound thereof) which is at least one type of dopant material as a first component, at least one kind of host material as a second component, and a third component. It contains at least one organic solvent as a component. The first component functions as a dopant component of the light emitting layer obtained from the composition, and the second component functions as a host component of the light emitting layer. The third component functions as a solvent that dissolves the first 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.

<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 ° C. to 300 ° C., more preferably 140 ° C. to 270 ° C., and even more preferably 150 ° C. to 250 ° C. When the boiling point is higher than 130 ° C., it is preferable from the viewpoint of inkjet ejection property. Further, when the boiling point is lower than 300 ° C., it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent and smoothness. The organic solvent 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 solutes, and the boiling point (BP _GS ) of the good solvent (GS) is higher than _{the boiling point (BP PS} ) of the poor solvent (PS). Also low, configuration is particularly preferred.
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, and the like. 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) benzene benzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether and the like, but are not limited thereto. Further, the solvent may be used alone or may be mixed.

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

(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.), Futagent 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, manufactured by Mitsubishi Materials 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, Fluoroalkyl ammonium 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 composition for forming a light emitting layer, the first component is 0.0001% by weight to 2.0% by weight based on the total weight of the composition for forming a light emitting layer, and the second component is for forming a light emitting layer. 0.0999% by weight to 8.0% by weight based on the total weight of the composition, and 90.0% by weight to 99.9% by weight of the third component based on the total weight of the composition for forming a light emitting layer. preferable.

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

The composition for forming an organic layer can be 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重量％である。 <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 weight in the molecule.

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

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.

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

<Manufacturing method of polymer compound and crosslinkable polymer compound>
The method for producing the polymer compound and the crosslinkable polymer compound will be described by taking the compound represented by the above formula (SPH-1) and the compound represented by (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents and the like, and examples thereof include dimethoxyethane, 2- (2-methoxyethoxy) ethane, and 2- (2). −ethoxyethoxy) ethane and the like can be mentioned.

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, it is possible to prepare a polymer having a concentration gradient in the structure of the monomer units. Further, 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, hyperbranched polymers and dendrimers 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.

<Application example of organic electroluminescent device>
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.). Moreover, as a display system of a display, for example, a matrix and / or a segment system and the like 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. Examples thereof include time and temperature displays on digital clocks and thermometers, operating status displays of audio equipment and electromagnetic cookers, and panel displays of automobiles.

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, as a backlight for a liquid crystal display device, especially for a personal computer for which thinning is an issue, considering that it is difficult to thin the backlight because the conventional method consists of a fluorescent lamp and a light guide plate, the present embodiment The backlight using the light emitting element according to the above is characterized by being thin and lightweight.

3-2. Other Organic Devices The polycyclic aromatic compounds according to the present invention can be used for producing organic electroluminescent transistors, organic thin-film solar cells, and the like, in addition to the above-mentioned organic electroluminescent devices.

The organic field effect transistor is a transistor that controls a current by an electric field generated by a voltage input, and is provided with a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. The field effect transistor is easier to miniaturize than a simple transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.

The structure of the organic field effect transistor is usually provided with a source electrode and a drain electrode in contact with the organic semiconductor active layer formed by using the polycyclic aromatic compound according to the present invention, and further in contact with the organic semiconductor active layer. It suffices if the gate electrode is provided so as to sandwich the insulating layer (dielectric layer). Examples of the element structure include the following structures.
(1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic Semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode It can be applied as a pixel-driven switching element of an active matrix-driven liquid crystal display or an organic electroluminescence display.

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

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto. First, an example of synthesizing a polycyclic aromatic compound will be described below.

Synthesis example (1)
Compound (1-1): Synthesis of 8,13-diphenyl-8H, 13H'-8,13-diaza-12b-borabenzo [gh] tetraphen

2,3-Dichloroaniline (25 g), iodobenzene (70 g), sodium 2-methyl-2-butoxide (34 g), dichlorobis [di-t-butyl (para-dimethylaminophenyl) phosphino] palladium (II) (1) A flask containing (1 g) and toluene (250 ml) was heated under reflux for 4 hours in a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure is dissolved in heptane and passed through a silica gel short pass column (eluent: heptane) to obtain 2,3-dichloro-N, N-diphenylaniline (30 g) as a colorless oil. ) Was obtained.

2,3-Dichloro-N, N-diphenylaniline (6.8 g), 2- (4,5,5-1,3,2-dioxaborolan-2-yl) aniline (5 g), potassium carbonate (6 g) ), Tetrabutylammonium bromide (2.1 g), palladium (II) acetate (0.05 g), dicyclohexyl (2', 6'-dimethoxy- [1,1'-biphenyl] -2-yl) phosphine (0. A flask containing 18 g), toluene (70 ml), Solmix A-11 (manufactured by Japan Alcohol Trading Co., Ltd., solmix, 35 ml) and water (15 ml) was heated and refluxed for 2 hours under a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure is dissolved in toluene, passed through a silica gel short pass column (eluent: toluene), and the solvent of the fraction containing the target substance is distilled off under reduced pressure to form a pale yellow solid. 2'-chloro -N ^{3 ',} N ^3' - diphenyl - obtain [1,1'-biphenyl] -2,3'-diamine (8.6 g).

2'-Chloro-N ^3' , N ^3' -diphenyl- [1,1'-biphenyl] -2,3'-diamine (8.6 g), iodobenzene (4.7 g), sodium 2-methyl-2 A flask containing -butoxide (5 g), dichlorobis [di-t-butyl (para-dimethylaminophenyl) phosphino] palladium (II) (0.16 g) and toluene (90 ml) is heated in a nitrogen atmosphere for 2 hours. It circulated. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure is dissolved in heptane and passed through a silica gel short pass column (eluent: heptane) to obtain 2'-chloro-N ² , N ^3' , N as a light brown oil. ^3' -Triphenyl- [1,1'-biphenyl] -2,3'-diamine (9.4 g) was obtained.

Nitrogen atmosphere in a flask containing 2'-chloro-N ² , N ^3' , N ^3' -triphenyl- [1,1'-biphenyl] -2,3'-diamine (1 g) and toluene (10 ml). Under an ice bath, 1.0 M of sec-butyllithium cyclohexane and n-hexane mixed solution (5 ml) was added dropwise. After completion of the dropping, the mixture was heated and stirred at 50 ° C. for 1 hour. The reaction mixture was cooled to 0 ° C. in the chamber again, and boron tribromide and N, N-diisopropylethylamine were added. After stirring at 0 ° C. for 30 minutes, the mixture was heated and stirred at 120 ° C. for 1 hour. After completion of the reaction, the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the organic layer was separated. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). After distilling off the solvent of the fraction containing the desired product under reduced pressure, the compound (1-1) was recrystallized from cyclopentyl methyl ether and Solmix A-11 (manufactured by Japan Alcohol Trading Co., Ltd., solmix) to form a pale yellow solid. ) (0.2 g) was obtained.

The structure of the obtained compound was confirmed by a liquid chromatograph mass spectrometer (LC-MS).
MS (ACPI): m / z = 421 (M +)

Synthesis example (2)
Synthesis of compound (1-101): 13-phenyl-13H-8-oxa-13-aza-12b-borabenzo [gh] tetraphen

1-Bromo-3-phenoxybenzene (14.8 g), bis (pinacolato) diboron (18.1 g), potassium acetate (11.7 g), potassium carbonate (8.2 g), [1,1'-bis (diphenyl) A flask containing a dichloromethane adduct (1.5 g) of phosphino) ferrocene] palladium (II) dichloride and cyclopentyl methyl ether (150 ml) was heated to reflux in a nitrogen atmosphere for 2 hours. After completion of the reaction, the insoluble material was filtered off, and the solvent of the filtrate was distilled off under reduced pressure. The obtained crude material is dissolved in heptane, passed through a silica gel short pass column (eluent: heptane), and the solvent of the fraction containing the target substance is distilled off under reduced pressure to obtain 4,4,5,5- as a colorless oil. Tetramethyl-2- (3-phenoxyphenyl) -1,3,2-dioxaborolane (14.2 g) was obtained.

2-Bromo-N-phenylaniline (10 g), 4,4,5,5-tetramethyl-2- (3-phenoxyphenyl) -1,3,2-dioxaborolane (13.1 g), potassium carbonate (11. 1 g), tetrabutylammonium bromide (3.9 g), dichlorobis [di-t-butyl (para-dimethylaminophenyl) phosphino] palladium (II) (0.3 g), toluene (100 ml), Solmix A-11 ( A flask containing solmix (50 ml) and water (25 ml) manufactured by Japan Alcohol Trading Co., Ltd. was heated and refluxed for 2 hours in a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). By distilling off the solvent of the fraction containing the desired product under reduced pressure, 3'-phenoxy-N-phenyl-1,1'-biphenyl-2-amine (13.3 g) was obtained as a colorless oil.

A flask containing 3'-phenoxy-N-phenyl-1,1'-biphenyl-2-amine (13.3 g), boron triiodide (25 g) and dichlorobenzene (130 ml) was placed in a nitrogen atmosphere at 200 ° C. Was heated and stirred for 8 hours. After completion of the reaction, ethyl acetate and water were added to the reaction mixture cooled to room temperature, and the organic layer was extracted. The solvent of the organic layer was distilled off under reduced pressure to dissolve the obtained solid in toluene (100 ml), acetic acid (10 ml) was added, and the mixture was heated and stirred at 95 ° C. for 8 hours under a nitrogen atmosphere. After the acetic acid treatment was completed, water was added to the reaction mixture cooled to room temperature to extract the organic layer. The solid obtained by distilling off the solvent of the organic layer under reduced pressure was passed through an amino silica gel pass column (eluent: ethyl acetate, heptane). The solvent of the fraction containing the desired product was distilled off under reduced pressure to obtain compound (1-101) (3.2 g) as a white solid.

The structure of the obtained compound was confirmed by a liquid chromatograph mass spectrometer (LC-MS).
MS (ACPI): m / z = 346 (M +)

Synthesis example (3)
Compound (1-231): Synthesis of 5,15-diphenyl-5,15-dihydro-5,15,19c-triaza-19b, 19d-dibora anthra [9,1-ab] benzo [o] perylene

1-Bromo-3-iodobenzene (50 g), diphenylamine (31.4 g), sodium 2-methyl-2-butoxide (38.9 g), dichlorobis [di-t-butyl (para-dimethylaminophenyl) phosphino] palladium A flask containing (II) (2.5 g) and toluene (500 ml) was heated under reflux for 2 hours in a nitrogen atmosphere. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in heptane and passed through a silica gel short pass column (eluent: heptane). The solvent of the fraction containing the desired product was distilled off under reduced pressure and then recrystallized from heptane to obtain 3-bromo-N, N-diphenylaniline (50 g) as a white solid.

3-Bromo-N, N-diphenylaniline (50 g), bis (pinacolato) diboron (43 g), potassium acetate (30.3 g), potassium carbonate (10.7 g), [1,1'-bis (diphenylphosphino) ) Ferrocene] A flask containing a dichloromethane adduct (1.3 g) of palladium (II) dichloride and cyclopentyl methyl ether (500 ml) was heated under reflux in a nitrogen atmosphere for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature to separate the organic layer. The crude product obtained by concentrating the organic layer under reduced pressure was dissolved in heptane and passed through a silica gel short pass column (eluent: heptane). After distilling off the solvent of the fraction containing the desired product under reduced pressure, it was recrystallized from heptane and Solmix A-11 (manufactured by Japan Alcohol Trading Co., Ltd.) to form N, N-diphenyl-3- (4) as a white solid. , 4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (36 g) was obtained.

2,6-dibromoaniline (8.5 g), N, N-diphenyl-3- (4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (27.7 g) , Potassium carbonate (18.7 g), Tetrabutylammonium bromide (3.3 g), Palladium acetate (II) (0.15 g), Dicyclohexyl (2', 6'-dimethoxy- [1,1'-biphenyl] -2 -Il) A flask containing phosphine (0.56 g), toluene (85 ml), Solmix A-11 (manufactured by Japan Alcohol Trading Co., Ltd., solmix, 40 ml) and water (20 ml) is heated in a nitrogen atmosphere for 2 hours. Circulated. After completion of the reaction, the mixture was cooled to room temperature, the solvent of the organic layer was distilled off under reduced pressure, the obtained solid was dissolved in toluene, and the mixture was passed through a silica gel pass column (eluent: toluene, heptane). The solvent of the fraction containing the desired product was distilled off under reduced pressure and then recrystallized from toluene and heptane to form a white solid of N ³ , N ³ , N ^{3 "} , N ^3" -tetraphenyl- [1,1'. : 3', 1 "-terphenyl] -2'3,3" -triamine (17.5 g) was obtained.

N ³ , N ³ , N ^{3 "} , N ^3" -tetraphenyl- [1,1': 3', 1 "-terphenyl] -2'3,3" -triamine (6 g), boron triiodide ( A flask containing 25 g) and dichlorobenzene (60 ml) was heated and stirred at 160 ° C. for 8 hours under a nitrogen atmosphere. After completion of the reaction, ethyl acetate and water were added to the reaction mixture cooled to room temperature, and the organic layer was extracted. The solvent of the organic layer was distilled off under reduced pressure to dissolve the obtained solid in toluene (60 ml), acetic acid (6 ml) was added, and the mixture was heated and stirred at 95 ° C. for 8 hours under a nitrogen atmosphere. After the acetic acid treatment was completed, water was added to the reaction mixture cooled to room temperature to extract the organic layer. The solid obtained by distilling off the solvent of the organic layer under reduced pressure was passed through an amino silica gel pass column (eluent: ethyl acetate, heptane). The solvent of the fraction containing the desired product was distilled off under reduced pressure to obtain compound (1-231) (0.8 g) as a pale yellow solid.

The structure of the obtained compound was confirmed by a liquid chromatograph mass spectrometer (LC-MS).
MS (ACPI): m / z = 596 (M +)

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

Next, in order to explain the present invention in more detail, examples of an organic EL device using the compound of the present invention will be shown, but the present invention is not limited thereto.

<Evaluation of thin-film deposition type organic EL element>
The organic EL devices of Examples 1-1 to 1-3 and Comparative Example 1 were produced, and the drive voltage (V) and the external quantum efficiency (%), which are the characteristics at the time of ^{100 cd / m 2 emission, were measured, respectively.}

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. The ratio is shown. 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 method for measuring the external quantum efficiency is as follows. A voltage / current generator R6144 manufactured by Advantest Co., Ltd. was used ^{to apply a voltage at which the brightness of the element became 1000 cd / m 2} to cause the element to emit light. 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 over 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 device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

<Examples 1-1 to 1-3 and Comparative Example 1-1>
Table 1 shows the layer configurations of the organic EL devices produced in Examples 1-1 to 1-3 and Comparative Example 1-1.

The chemical structure of each material shown by abbreviation in Table 1 is as follows.

A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science, Inc.) obtained by polishing ITO formed to a thickness of 180 nm by sputtering to 50 nm was 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 a molybdenum vapor deposition boat containing NPD, TcTa, mCP, compound (1-1), and TSPO1 respectively, and LiF. And a tungsten vapor deposition boat containing Al was installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is ^{depressurized to 5.0 × 10 -4} Pa, first, the NPD is heated and vapor-deposited to a film thickness of 50 nm, and TcTa is heated to be vapor-deposited to a film thickness of 15 nm, and the mCP is heated. Then, a hole layer composed of three layers was formed by vapor deposition so as to have a film thickness of 15 nm. Next, compound (1-1) and 4Cz-IPN 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 (1-1) to 4Cz-IPN was approximately 98: 2. Next, the electron transport layer was formed by heating TSPO1 and depositing it so as to have a film thickness of 50 nm. The deposition rate of each layer was 0.01 to 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 at a vapor deposition rate of 0.1 nm to 2 nm / sec so as to have a film thickness of 100 nm to form a cathode. In this way, the organic EL device of Example 1-1 was obtained.

Further, by changing compound (1-1) to compound (1-101), compound (1-231) or Comparative Example compound (mCBP), Examples 1-2, 1-3 and Comparative Example 1-1 The organic EL element of the above was obtained.

Table 2 shows the EL characteristics obtained from each element. It can be confirmed that the organic EL device using the compound according to the present invention has a lower drive voltage and higher external quantum efficiency than the device of the comparative example compound.

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

<Polymer host compound: Synthesis of SPH-101>
SPH-101 was synthesized according to the method described in WO 2015/008851. A copolymer in which M2 or M3 is bonded is obtained next to M1, and it is estimated from the charging ratio that each unit has a ratio of 50:26:24 (molar ratio).

<Polymer hole transport compound: Synthesis of XLP-101>
XLP-101 was synthesized 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).

<Examples 2-1 to 2-8>
A coating solution of the material forming each layer is prepared to prepare a coating type organic EL device.

<Manufacturing of Organic EL Element of Examples 2-1 to 2-3>
Table 3 shows the material composition of each layer in the organic EL device.

The structure of "ET1" in Table 2 is shown below.

<Preparation of composition (1) for forming a light emitting layer>
The composition for forming a light emitting layer (1) is prepared by stirring the following components until a uniform solution is obtained. The prepared composition for forming a light emitting layer is spin-coated on a glass substrate and dried by heating under reduced pressure to obtain a coating film having no film defects and excellent smoothness.
Compound (A) 0.04% by weight
SPH-101 1.96% by weight
Xylene 69.00% by weight
Decalin 29.00% by weight

The compound (A) is a polycyclic aromatic compound represented by the general formula (1), a multimer thereof, the polycyclic aromatic compound or a multimer thereof, and a monomer (that is, the monomer has a reactive substituent). A polymer compound polymerized as (having), a crosslinked polymer obtained by further cross-linking the polymer compound, a pendant type polymer compound in which the monomer is substituted with a main chain type polymer, or the pendant type polymer. It is a pendant type polymer crosslinked product in which a compound is further crosslinked. A polymer compound or a pendant type polymer compound for obtaining a polymer crosslinked body or a pendant type polymer crosslinked body has a crosslinkable substituent.

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

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

<Preparation of XLP-101 solution>
XLP-101 is dissolved in xylene at a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

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

<Example 2-1>
A PEDOT: PSS film having a film thickness of 40 nm is formed by spin-coating a PEDOT: PSS solution on a glass substrate on which ITO is deposited to a thickness of 150 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 the solution, is formed (hole transport layer). Next, the composition for forming a light emitting layer (1) is 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 ET1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, ET1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is 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 is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

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

<Example 2-3>
An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is 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.

<Manufacturing of Organic EL Devices of Examples 2-4 to 2-6>
Table 4 shows the material composition of each layer in the organic EL device.

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

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

The composition for forming a light emitting layer (4) is prepared by stirring the following components until a uniform solution is obtained.
Compound (A) 0.02% by weight
DOBNA 1.98% by weight
Toluene 98.00% by weight

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

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

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 TSPO1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is 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 is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-5 and 2-6>
Using the light emitting layer forming composition (3) or (4), an organic EL device is obtained in the same manner as in Example 2-4.

<Manufacturing of Organic EL Devices of Examples 2-7 to 2-9>
Table 5 shows the material composition of each layer in the organic EL device.

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

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

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

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

<Example 2-7>
An ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution is spin-coated on a glass substrate on which ITO is formed to a thickness of 45 nm, and then heated at 50 ° C. for 3 minutes in an air atmosphere, and further at 230 ° C., 15 By heating for a minute, an ND-3202 film having a film thickness of 50 nm is formed (hole injection layer). Next, the XLP-101 solution is spin-coated and heated on a hot plate at 200 ° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film having a film thickness of 20 nm (hole transport layer). Next, the light emitting layer forming composition (5) is spin-coated and heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm light emitting layer.

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 TSPO1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is 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 is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-8 and 2-9>
Using the light emitting layer forming composition (6) or (7), an organic EL device is obtained in the same manner as in Example 2-7.

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

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for an organic device such as a material for an organic EL element, and the polycyclic aromatic compound can be provided. It is possible to provide an excellent organic device such as an organic EL element by using the above.

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)

A multimer of a polycyclic aromatic compound represented by the following general formula (1) or a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1).

In the above formula (1),
Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Ge-R. Cycloalkyl,
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-R may be substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or substituted. It is a cycloalkyl which may be used, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be formed by a single bond or a linking group. It may be bonded to at least one ring of the A ring and the B ring.
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , or> P-R may be an aryl substituted, a heteroaryl optionally substituted, an alkyl optionally substituted, or a substitution. It is a cycloalkyl which may be used, and R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R may be formed by a single bond or a linking group. It may be bonded to at least one ring of the B ring and the C ring (provided that X ¹ is>O,>N-R,>P-R,> S, or> Se. > _N-R as _{^{X 2,> C (-R)}} 2,> Si (-R) 2, and> R in P-R does not bind to the B ring), and,
At least one hydrogen in the compound or unit structure represented by the formula (1) may be substituted with halogen, cyano, or deuterium. In the above formula (1),
Rings A, B, and C are independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, respectively. Substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted aryl heteroarylamino, substituted or unsubstituted diarylboryl (two aryls are bonded via a single bond or a linking group). May be substituted), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl, and these. The ring has a 5-membered ring or a 6-membered ring that shares a bond with the central fused 2-ring structure of the above formula (1) composed of ^{Y 1} , X ¹ , and X ^2.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl, or Ge-R. Cycloalkyl,
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The Rs of (-R) ₂ ,> Si (-R) ₂ , and> PR are aryls optionally substituted with alkyl or cycloalkyl, heteroaryls optionally substituted with alkyl or cycloalkyl, It is alkyl or cycloalkyl, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-, -S. -, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the A ring and the B ring, and the -C (-R) ₂ − and -N (-R)-R is aryl, alkyl, or cycloalkyl,
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , or> P-R may be an aryl substituted with alkyl or cycloalkyl, a heteroaryl optionally substituted with alkyl or cycloalkyl, It is alkyl or cycloalkyl, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-, -S. -, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the B ring and the C ring (provided that X ¹ is> O, >N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P- ^{as X 2} if>N-R,>P-R,> S, or> Se. The R of R does not bind to the B ring), the R of -C (-R) _2- and -N (-R)-is aryl, alkyl, or cycloalkyl, and
At least one hydrogen in the compound or unit structure represented by the formula (1) may be substituted with halogen, cyano, or deuterium.
The polycyclic aromatic compound according to claim 1 or a multimer thereof. The polycyclic aromatic compound or a multimer thereof according to claim 1, wherein the general formula (1) is represented by the following general formula (2).

In the above formula (2),
Any "-C (-R) =" in rings a, b, and c (where R is R ^{1 through} R ¹¹ in equation (2)) has been replaced by "-N =". Any "-C (-R) = C (-R)-" (where R is R ^{1 to} R ¹¹ in equation (2)) may be "-N (-R)-". , "-O-", or "-S-", where the R of "-N (-R)-" is aryl, alkyl, or cycloalkyl.
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, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen is. It may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl ^{, and adjacent groups of R 1 to} R ¹¹ may be bonded to each other to form an aryl ring together with an a ring, a b ring, or a c ring. Alternatively, a heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be bonded via a linking group), substituted with alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R has 6 to 12 carbon atoms. Aryl, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms.
X ¹ is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-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 carbon. It is a cycloalkyl of the number 3 to 14, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-,. It may be bonded to at least one ring of the a ring and the b ring by −S−, −C (−R) _{2− , or −N (−R) −, and the −C (−R) 2} -And -N (-R)-R are aryls having 6 to 12 carbon atoms, alkyls having 1 to 6 carbon atoms, or cycloalkyls having 3 to 14 carbon atoms.
X ² is>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned>N-R,> C. The R of (-R) ₂ ,> Si (-R) ₂ , and> P-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 carbon. It is a cycloalkyl of the number 3 to 14, and the R of>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R is a single bond, -O-,. It may be bonded to the c ring by −S−, −C (−R) ₂₋ , or −N (−R) −, and the −C (−R) ₂₋ and −N (−R). -R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound or unit structure represented by the formula (2) may be substituted with halogen, cyano, or deuterium. The multimer of the polycyclic aromatic compound according to claim 3, which is represented by the following general formula (2-M1) or general formula (2-M2).

In the above formula (2-M1) and formula (2-M2),
Any "-C (-R) =" in rings a, b, and c (where R is R ^{1 to} R ⁷ , R ^{10 in formula (2-M1) or formula (2-M2)).} , And R ¹¹ ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is equation (2-M1) or equation. ^{(2-M2) R 1 ~R} 7, R 10 in, and ^{R 11)} is "- N (-R) -", "- O-', or it has been replaced by the" -S- " Also, the R of the "-N (-R)-" is aryl, alkyl, or cycloalkyl.
R ^{1 to} R ⁷ , R ¹⁰ and R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded or linked). (May be bonded via a group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, which are these. At least one hydrogen in is optionally substituted with aryl, heteroaryl, alkyl, or cycloalkyl ^{, and adjacent groups of R 1 to} R ⁷ , R ¹⁰ , and R ¹¹ are attached to each other. , A ring, b ring, or c ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, Aryl heteroarylamino, diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl. , Dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Y ¹ is independently B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is Aryl with 6 to 12 carbon atoms, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms.
X ¹ is independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,>P-R,> S, or> Se, and the above-mentioned> N. -R,> C (-R) ₂ ,> Si (-R) ₂ , and> PR R are aryls with 6 to 12 carbon atoms, heteroaryls with 2 to 15 carbon atoms, and 1 to 6 carbon atoms. Alkyl or cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned>N-R,> C (-R) ₂ ,> Si (-R) ₂ , and> P-R R are single bonds. , -O-, -S-, -C (-R) _2- , or -N (-R)-may be bonded to at least one ring of the a ring and the b ring, and the -C (-R) _2- and -N (-R)-R are aryls having 6 to 12 carbon atoms, alkyls having 1 to 6 carbon atoms, or cycloalkyls having 3 to 14 carbon atoms.
X ² is N or P, respectively, and
At least one hydrogen in the multimer represented by the formula (2-M1) or the formula (2-M2) may be substituted with halogen, cyano, or deuterium. In the above formula (2), formula (2-M1), and formula (2-M2),
a ring, the b ring, and c rings, any "-C (-R) =" (where R is the formula (2), ^{R 1} in the formula (2-M1), or Formula (2-M2) ~ R ¹¹ ) may be replaced with "-N =", and any "-C (-R) = C (-R)-" (where R is equation (2), equation (2-) M1), or ^R 1 ^{to R 11} in the formula (2-M2)) is "- N (-R) -" - it may be replaced to "O-", or "-S-" The R of "-N (-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, diarylamino (where aryl is aryl with 6 to 12 carbon atoms), and diarylboryl (provided that the aryl is aryl with 6 to 12 carbon atoms). The 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, a cycloalkyl having 3 to 24 carbon atoms, and carbon. It is an alkoxy having a number of 1 to 24 or an aryloxy having 6 to 30 carbon atoms, and at least one hydrogen in these is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and an aryloxy having 1 to 6 carbon atoms. It may be substituted with an alkyl or a cycloalkyl having 3 to 14 carbon atoms ^{, and adjacent groups of R 1 to} R ¹¹ are bonded to each other to form a carbon together with an a ring, a b ring, or a c ring. An aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one hydrogen in the formed ring is an aryl ring having 6 to 30 carbon atoms and having 2 to 30 carbon atoms. Heteroaryl, diarylamino (where aryl is an aryl with 6 to 12 carbons), diarylboryl (where aryl is an aryl with 6 to 12 carbons, and the two aryls are attached via a single bond or a linking group. It may be substituted with an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, and at least one of these. One hydrogen may be substituted with 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 14 carbon atoms.
Y ¹ is independently B, P, P = O, P = S, or Si-R, and R of the Si-R is an aryl having 6 to 10 carbon atoms and 1 to 5 carbon atoms. Alkyl, or cycloalkyl with 5 to 10 carbon atoms,
X ¹ is independently>O,> N-R, or> S, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or carbon. It is a cycloalkyl of the number 5 to 10.
^{X 2} in the formula (2) is>O,> N-R, or> S, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or carbon. It is a cycloalkyl of the number 5 to 10.
^{X 2} in formula (2-M1) or formula (2-M2) is N, and
At least one hydrogen in the compound or unit structure represented by the formula (2) or the multimer represented by the formula (2-M1) or the formula (2-M2) is replaced with a halogen, cyano, or deuterium. May be
The polycyclic aromatic compound according to claim 3 or 4, or a multimer thereof. In the above formula (2), formula (2-M1), and formula (2-M2),
a ring, the b ring, and c rings, any "-C (-R) =" (where R is the formula (2), ^{R 1} in the formula (2-M1), or Formula (2-M2) ~ R ¹¹ ) may be replaced with "-N =", and any "-C (-R) = C (-R)-" (where R is equation (2), equation (2-) M1), or ^R 1 ^{to R 11} in the formula (2-M2)) is "- N (-R) -" - it may be replaced to "O-", or "-S-" The R of "-N (-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diallyl amino (where aryl is aryl with 6 to 10 carbon atoms), and diallyl boryl (provided that aryl is aryl with 6 to 10 carbon atoms). 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 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. Yes, even if at least one hydrogen in these is substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. Often,
Y ¹ is independently B, P, P = O, or P = S, respectively.
X ¹ is independently> O or> N-R, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl,
^{X 2} in the formula (2) is> O or> N-R, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl, and
^{X 2} in formula (2-M1) or formula (2-M2) is N,
The polycyclic aromatic compound according to claim 3 or 4, or a multimer thereof. In the above formula (2), formula (2-M1), and formula (2-M2),
R ^{1 to} R ¹¹ are independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diallyl amino (where aryl is aryl with 6 to 10 carbon atoms), and diarylboryl (provided that aryl is 6 to 10 carbon atoms). 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 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. Yes,
Y ¹ is B,
X ¹ is independently> O or> N-R, and the R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl,
^{X 2} in the formula (2) is> O or> N-R, and R of> N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10 carbon atoms. Cycloalkyl, and
^{X 2} in formula (2-M1) or formula (2-M2) is N,
The polycyclic aromatic compound according to claim 3 or 4, or a multimer thereof. The polycyclic aromatic compound or a multimer thereof according to claim 1, which is represented by any of the following structural formulas.

A reactive compound in which a polycyclic aromatic compound according to any one of claims 1 to 8 or a multimer thereof is substituted with a reactive substituent. A polymer compound obtained by polymerizing the reactive compound according to claim 9 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound. A pendant type polymer compound in which a main chain type polymer is substituted with the reactive compound according to claim 9, or a pendant type polymer crosslinked product in which the pendant type polymer compound is further crosslinked. Substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetra Claimed to include at least one selected from phenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran as a repeating unit. The polymer compound or polymer crosslinked product according to Item 10, or the pendant type polymer compound or polymer crosslinked product according to claim 11. A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 8 or a multimer thereof. A material for an organic device containing the reactive compound according to claim 9. A material for an organic device containing the polymer compound or polymer crosslinked body according to claim 10. A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to claim 11. The material for an organic device according to any one of claims 13 to 16, which is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell. The material for an organic device according to claim 17, which is a material for a light emitting layer of an organic electroluminescent element. An ink composition containing the polycyclic aromatic compound according to any one of claims 1 to 8 or a multimer thereof, and an organic solvent. An ink composition containing the reactive compound according to claim 9 and an organic solvent. An ink composition containing a main chain polymer, the reactive compound according to claim 9, and an organic solvent. An ink composition containing the polymer compound or the crosslinked polymer according to claim 10 and an organic solvent. An ink composition containing the pendant-type polymer compound or the pendant-type polymer crosslinked product according to claim 11 and an organic solvent. The polycyclic aromatic compound according to any one of claims 1 to 8, or a polymer thereof, which is arranged between the pair of electrodes composed of an anode and a cathode, and the reactive compound according to claim 9. An organic electroluminescent element having an organic layer containing the polymer compound or polymer crosslinked body according to claim 10 or the pendant type polymer compound or pendant type polymer crosslinked body according to claim 11. An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode, and an organic layer arranged between the pair of electrodes and formed from the ink composition according to any one of claims 19 to 23. The organic electroluminescent device according to claim 24 or 25, wherein the organic layer is a light emitting layer. The light emitting layer is a host of the polycyclic aromatic compound or its multimer, a reactive compound, a polymer compound, a polymer crosslinked product, a pendant type polymer compound, or a pendant type polymer crosslinked product, and a dopant. 26. The organic field light emitting element according to claim 26. The organic electroluminescent device according to claim 27, wherein the host further comprises an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound. It has at least one layer 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, and the like. At least one selected from the group consisting of 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 metal complexes. The organic electric field light emitting element according to any one of claims 24 to 28, which is contained. At least one layer 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 soil. Contains at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. 29. The organic electric field light emitting element according to claim 29. A polymer compound in which 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 polymerized using a low molecular compound capable of forming each layer as a monomer. Alternatively, a polymer crosslinked product obtained by further cross-linking the polymer compound, 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 is further added. The organic electroluminescent element according to any one of claims 24 to 30, which comprises 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 24 to 31.

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