JP2022090294A - Polycyclic aromatic compound - Google Patents

Abstract

To provide a novel compound suitable as a material for organic devices such as an organic EL device.SOLUTION: The present invention discloses a polycyclic aromatic compound having a structure comprising one or more structural units represented by formula (1) [where, A ring, B ring and C ring each denote a substituted/unsubstituted aryl ring or a substituted/unsubstituted heteroaryl ring; Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R; X1 and X2 each denote >O, >N-R, >C(-R)2, >Si(-R)2, >S, or >Se, where at least one of X1 and X2 is >N-R with R being a group represented by formula (G)].SELECTED DRAWING: None

Description

The present invention relates to polycyclic aromatic compounds. The present invention specifically relates to polycyclic aromatic compounds containing nitrogen and boron. The present invention also relates to materials for organic devices containing the above polycyclic aromatic compounds, organic electroluminescent elements, and display devices and lighting devices.

Conventionally, display devices using electroluminescent elements that emit electric field light have been studied in various ways because they can be reduced in power consumption and thickness, and further, organic electroluminescent elements made of organic materials 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 regardless of whether it is a high molecular weight compound or a low molecular weight compound.

The organic electroluminescent device has a structure composed of a pair of electrodes consisting of an anode and a cathode, and one layer or a plurality of layers including an organic compound, which are 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.

Among them, Patent Document 1 discloses that a polycyclic aromatic compound containing boron is useful as a material for an organic electroluminescent device or the like. It has been reported that the organic electroluminescent device containing this polycyclic aromatic compound has good external quantum efficiency. Patent Documents 2 and 3 disclose polycyclic aromatic compounds having a condensed cycloalkane structure. Since this structure has a low sublimation temperature due to the condensed cycloalkane structure and high stability, it has the effect of obtaining an organic electric field light emitting element having excellent efficiency and long life characteristics, and the condensed cycloalkyl structure provides concentration quenching. The effect of being suppressed can also be expected.

International release 2015/102118 International release 2020/017931 International release 2020/218079

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.
It is an object of the present invention to provide.

The present inventors have diligently studied to solve the above problems, and have been making diligent studies to produce a novel polycyclic aromatic compound having a structure similar to that of the compound described in Patent Document 1 and having more excellent light emission characteristics. Successful. That is, we have succeeded in producing a polycyclic aromatic compound that gives high luminous efficiency by combining a condensed cycloalkyl structure that has the effect of suppressing concentration quenching and a specific substitution structure. Further, they have found that an excellent organic EL element can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL element, and completed the present invention. That is, the present invention provides a polycyclic aromatic compound such as the following, and a material for an organic device containing the following polycyclic aromatic compound.

Specifically, the present invention has the following configurations.

式（１）中、
Ａ環、Ｂ環、およびＣ環はそれぞれ独立して、置換もしくは無置換のアリール環、または置換もしくは無置換のヘテロアリール環であり；
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および前記Ｇｅ－ＲのＲは置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり；
Ｘ^１およびＸ^２は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－ＲのＲは水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキル、または式（Ｇ）で表される１価の基であり、前記＞Ｃ（－Ｒ）_２、および＞Ｓｉ（－Ｒ）_２のＲはそれぞれ独立して水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成してもよく、前記＞Ｎ－ＲのＲ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の少なくとも１つのＲは、前記Ａ環および前記Ｂ環の少なくとも１つ、または前記Ａ環および前記Ｃ環の少なくとも１つと、単結合または連結基を介して結合していてもよく、
ただし、Ｘ^１およびＸ^２の少なくとも１つは、Ｒが式（Ｇ）で表される１価の基である＞Ｎ－Ｒであり、
式（Ｇ）中、
Ｌは単結合、アルキレン、シクロアルキレン、アリーレンまたはヘテロアリーレンであり、これらの少なくとも１つの水素は置換されていてもよく、（Ｇ－Ａ）環および（Ｇ－Ｂ）環はそれぞれ独立して、置換もしくは無置換のアリール環、または置換もしくは無置換のヘテロアリール環であり；
Ｘ^３およびＸ^４はそれぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、前記＞Ｃ（－Ｒ）_２、および前記＞Ｓｉ（－Ｒ）_２のＲはそれぞれ独立して水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成してもよく、前記＞Ｎ－ＲのＲ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の少なくとも１つのＲは前記（Ｇ－Ａ）環および前記（Ｇ－Ｂ）環の少なくとも１つ、または前記（Ｇ－Ａ）環および前記（Ｇ－Ｂ）環の少なくとも１つと単結合、または連結基を介して結合していてもよく、
式（１）で表される構造における前記構造における、アリール環またはヘテロアリール環の少なくとも１つは、少なくとも１つのシクロアルカンで縮合されていてもよく、当該シクロアルカン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、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていてもよく、そして；
式（１）で表される構造における少なくとも１つの水素はシアノ、ハロゲン、または重水素で置換されていてもよい。
＜２＞
式（１）で表される構造単位が、下記式（２）で表される構造単位である、＜１＞に記載の多環芳香族化合物；

式（２）中、
ａ環、ｂ環およびｃ環におけるＺはそれぞれ独立して、ＮまたはＣ－Ｒ^１１であり、前記Ｃ－Ｒ^１１の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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、または置換シリルであり、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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく；
前記ジアリールアミノの２つのアリールは互いに結合していないか、連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、単結合または連結基を介して結合しており；
隣接する２つのＲ^１１は互いに結合して、アリール環またはヘテロリール環を形成してもよく、前記形成されたアリール環およびヘテロリール環はそれぞれ、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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、または置換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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく；
前記ジアリールアミノの２つのアリールは互いに結合していないか、連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、単結合または連結基を介して結合しており；
Ｚ＝Ｚはそれぞれ独立して＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであってもよく、前記＞Ｎ－Ｒ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２のＲはそれぞれ独立して水素、アリール、ヘテロアリール、アルキル、シクロアルキルであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成していてもよく；
Ｙ^１は、Ｂ、またはＰ＝Ｏであり、
Ｘ^１およびＸ^２は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－ＲのＲは水素、アリール、ヘテロアリール、アルキル、シクロアルキル、または式（Ｇ－２）で表される１価の基であり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２、および前記＞Ｓｉ（－Ｒ）_２のＲは水素、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あり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成してもよく、前記＞Ｎ－ＲのＲ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２のＲの少なくとも１つのＲは、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－または単結合により、Ｃ－Ｒ^１１であるＺにおけるＣの１つまたは２つと結合してもよく、ただしＸ^１およびＸ^２の少なくとも１つは、Ｒが式（Ｇ－２）で表される１価の基である＞Ｎ－Ｒであり、
式（Ｇ－２）中、
Ｇ－ａ環およびＧ－ｂ環におけるＺ^Ｇはそれぞれ独立して、ＮまたはＣ－Ｒ^１２であり、前記Ｃ－Ｒ^１２のＲ^１２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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、または置換シリルであり、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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく；
前記ジアリールアミノの２つのアリールは互いに結合していないか、連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、単結合または連結基を介して結合しており；
隣接する２つのＲ^１２は互いに結合して、アリール環またはヘテロリール環を形成してもよく、前記形成されたアリール環およびヘテロリール環、は、それぞれ、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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、または置換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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく；
前記ジアリールアミノの２つのアリールは互いに結合していないか、連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、単結合または連結基を介して結合しており；
Ｚ^Ｇ＝Ｚ^Ｇはそれぞれ独立して＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであってもよく、前記＞Ｎ－Ｒ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２のＲはそれぞれ独立して水素、アリール、ヘテロアリール、置換アルキル、またはシクロアルキルであり、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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成していてもよく；
Ｘ^３およびＸ^４はそれぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、前記＞Ｃ（－Ｒ）_２、および前記＞Ｓｉ（－Ｒ）_２、のＲは、それぞれ独立して、水素、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、ジアリールアミノ、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２の２つのＲは互いに結合して環を形成してもよく、また前記＞Ｎ－Ｒ、前記＞Ｃ（－Ｒ）_２および前記＞Ｓｉ（－Ｒ）_２のＲの少なくとも１つのＲは、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^１４）_２－または単結合により、Ｃ－Ｒ^１２であるＺ^ＧにおけるＣの１つまたは２つと結合してもよく、前記－Ｃ（－Ｒ^１４）_２－のＲ^１４は、水素、アルキル、またはシクロアルキルであり、
Ｌは単結合、アリーレンまたはヘテロアリーレンであり、前記アリーレンおよび前記ヘテロアリーレンの少なくとも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、アルキル、シクロアルキル、または置換シリルで置換されていてもよく、
式（２）で表される構造における、アリール環またはヘテロアリール環の少なくとも１つは、少なくとも１つのシクロアルカンで縮合されていてもよく、当該シクロアルカン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、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていてもよく、そして；
式（２）で表される構造における少なくとも１つの水素はシアノ、ハロゲン、または重水素で置換されていてもよい。
＜３＞
式（２）中、Ｙ^１がＢであり、かつ前記構造における、アリール環またはヘテロアリール環の少なくとも１つは、少なくとも１つのシクロアルカンで縮合されており、当該シクロアルカン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、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていてもよい、＜２＞に記載の多環芳香族化合物。
＜４＞
下記式で表される、＜１＞～＜３＞のいずれかに記載の多環芳香族化合物。

＜５＞
＜１＞～＜４＞のいずれかに記載の多環芳香族化合物を含有する、有機デバイス用材料。
＜６＞
陽極および陰極からなる一対の電極と、該一対の電極間に配置された発光層とを含み、前記発光層が＜１＞～＜４＞のいずれかに記載の多環芳香族化合物を含有する、有機電界発光素子。
＜７＞
前記発光層が、ホストと、ドーパントとしての前記多環芳香族化合物とを含む、＜６＞に記載の有機電界発光素子。
＜８＞
前記ホストが、アントラセン化合物、フルオレン化合物、またはジベンゾクリセン化合物である、＜７＞に記載の有機電界発光素子。
＜９＞
＜６＞～＜８＞のいずれかに記載の有機電界発光素子を備えた表示装置または照明装置。 <1>
A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the following formula (1);

In equation (1),
Rings A, B, and C are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings;
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and the Si-R and the R of the Ge-R are substituted or unsubstituted. Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
X ¹ and X ² are>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and R of> N-R is hydrogen. A substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, or a monovalent group represented by the formula (G), which is the above-mentioned> C. The Rs of (-R) ₂ and> Si (-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted, respectively. The two Rs of> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring. At least one R of C (-R) ₂ and> Si (-R) ₂ is single-bonded or single-bonded to at least one of the A ring and the B ring, or at least one of the A ring and the C ring. It may be bonded via a linking group.
However, at least one of X ¹ and X ² has R> N—R, which is a monovalent group represented by the formula (G).
In formula (G),
L is a single bond, alkylene, cycloalkylene, arylene or heteroarylene, at least one of which may be substituted, with the (GA) and (GB) rings being independent of each other. A substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring;
X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The> C (-R) ₂ and the> Si (-R) ₂ R are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or It is a substituted or unsubstituted cycloalkyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring, and the above> N-R may be formed. R, at least one R of the> C (-R) ₂ and the> Si (-R) ₂ is at least one of the (GA) ring and the (GB) ring, or the (G-). A) It may be attached to at least one of the ring and the (GB) ring via a single bond or a linking group.
At least one of the aryl ring or the heteroaryl ring in the structure in the structure represented by the formula (1) may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is substituted. At least one of -CH _2- in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by the formula (1) may be substituted with cyano, halogen, or deuterium.
<2>
The polycyclic aromatic compound according to <1>, wherein the structural unit represented by the formula (1) is the structural unit represented by the following formula (2);

In equation (2),
Z in the a ring, b ring and c ring is N or CR ^{11 independently, and R 11 of} the CR ¹¹ is independently hydrogen, aryl, heteroaryl, diarylamino, di Heteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen in these is aryl, heteroaryl, diarylamino, alkyl, May be substituted with cycloalkyl or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Two adjacent R ^11s may be coupled to each other to form an aryl ring or a heteroryl ring, wherein the formed aryl ring and heteroryl ring are aryl, heteroaryl, diarylamino, diheteroarylamino, respectively. , Arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyls, wherein at least one hydrogen thereof is aryl, heteroaryl, diarylamino, May be substituted with alkyl, cycloalkyl, or substituted silyls;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Z = Z may be independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The R of> C (-R) ₂ and the above> Si (-R) ₂ are independently hydrogen, aryl, heteroaryl, alkyl, and cycloalkyl, respectively, and at least one hydrogen in these is further aryl and hetero. It may be substituted with aryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other to form a ring. May be;
Y ¹ is B or P = O,
X ¹ and X ² are>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and R of> N-R is hydrogen. Aryl, heteroaryl, alkyl, cycloalkyl, or a monovalent group represented by the formula (G-2), wherein at least one hydrogen in these is further aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, Alternatively, it may be substituted with a substituted silyl, where the R of> C (-R) ₂ and> Si (-R) ₂ is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least in these. One hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two> C (-R) ₂ and> Si (-R) ₂ . The Rs may be coupled to each other to form a ring, and at least one R of the> N-R R, the> C (-R) ₂ and the> Si (-R) ₂ R is -O. -, -S-, -C (-R) ₂ -or may be coupled to one or two of C in Z at CR ¹¹ by single coupling, but at least one of X ¹ and X ² . Is a monovalent group in which R is represented by the formula (G-2)> N-R.
In formula (G-2),
^ZG in the GA ring and Gb ring are independently N or CR ^{12, and R 12 of} the CR ¹² is independently hydrogen, aryl, heteroaryl, and diarylamino. , Diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen in these is aryl, heteroaryl, diarylamino, May be substituted with alkyl, cycloalkyl, or substituted silyls;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Two adjacent ^R12s may be coupled to each other to form an aryl ring or a heteroreel ring, wherein the formed aryl ring and heteroreel ring are aryl, heteroaryl, diarylamino, and dihetero, respectively. It may be substituted with arylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, in which at least one hydrogen is aryl, heteroaryl, diaryl. May be substituted with amino, alkyl, cycloalkyl, or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Z ^G = Z ^G may be independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N- R, said> C (-R) ₂ and said> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, substituted alkyl, or cycloalkyl, wherein at least one hydrogen in these is hydrogen. It may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other. It may form a ring;
X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The R of> C (-R) ₂ and the above> Si (-R) ₂ are independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is hydrogen. , Aryl, Heteroaryl, Diarylamino, Alkyl, Cycloalkyl, or Substituted Cyril, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other. And at least one R of the> N-R, the> C (-R) ₂ and the> Si (-R) ₂ may be -O-, -S-,. -C (-R ¹⁴ ) ₂ -or may be bonded to one or two of ^C in ZG, which is C-R ¹² , by a single bond, and the R ¹⁴ of -C (-R ¹⁴ ) _2- , Hydrogen, alkyl, or cycloalkyl,
L is a single bond, arylene or heteroarylene, and the arylene and at least one hydrogen of the heteroarylene may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl.
At least one of the aryl ring or the heteroaryl ring in the structure represented by the formula (2) may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted. Well, at least one -CH _2- in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by the formula (2) may be substituted with cyano, halogen, or deuterium.
<3>
In formula (2), Y ¹ is B, and at least one of the aryl rings or heteroaryl rings in the structure is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is. The polycyclic aromatic compound according to <2>, which may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
<4>
The polycyclic aromatic compound according to any one of <1> to <3>, which is represented by the following formula.

<5>
A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <4>.
<6>
A pair of electrodes composed of an anode and a cathode and a light emitting layer arranged between the pair of electrodes are included, and the light emitting layer contains the polycyclic aromatic compound according to any one of <1> to <4>. , Organic electroluminescent element.
<7>
The organic electroluminescent device according to <6>, wherein the light emitting layer contains a host and the polycyclic aromatic compound as a dopant.
<8>
The organic electroluminescent device according to <7>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.
<9>
A display device or a lighting device provided with the organic electroluminescent element according to any one of <6> to <8>.

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

It is a schematic sectional drawing which shows an example of an organic electroluminescent element. It is an energy level diagram which shows the energy relation of the host of the TAF element using a general fluorescent dopant, the assisting dopant and the emitting dopant. FIG. 3 is an energy level diagram showing an example of the energy relationship between a host, an assisting dopant, and an emerging dopant in an organic electroluminescent device according to an aspect of the present invention.

Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be based on typical embodiments and specific examples, but the present invention is not limited to such embodiments. In addition, the numerical range represented by using "-" in this specification means the range including the numerical values before and after "-" as the lower limit value and the upper limit value. Further, in the present specification, "hydrogen" in the description of the structural formula means "hydrogen atom (H)". In the present specification, the organic electroluminescent device may be referred to as an organic EL device.

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

Since the chemical structural formula described in the present specification (including the general formula drawn by the Marcus structural formula as in the formula (1) described later) is a planar structural formula, it is actually an enantio isomer, a diah. Various isomer structures such as stereo isomers and rotational isomers may be present. In the present specification, unless otherwise specified, the compound described may have any isomer structure conceivable from its planar structural formula, and a mixture of any ratio composed of possible isomers. It may be.

<1. Polycyclic aromatic compounds>
The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by the formula (1). The polycyclic aromatic compound of the present invention has a high emission quantum yield (PLQY), a narrow emission half width, and is excellent in color purity.

In the formula (1), the A ring, the B ring, and the C ring are independently an aryl ring which may be substituted or a heteroaryl ring which may be substituted.

The aryl ring or heteroaryl ring in the A ring, B ring and C ring is preferably bonded to any one of Y ¹ and X ¹ and X ² by a 5-membered ring or a 6-membered ring. "It is bonded to any one of Y ¹ and X ¹ and X ² by a 5-membered ring or a 6-membered ring" means that the ring is formed only by the 5-membered ring or the 6-membered ring, or this ring is formed. It means that the ring is formed by further condensing another ring so as to include a 5-membered ring or a 6-membered ring. In other words, it means that the 5-membered ring or the 6-membered ring constituting all or a part of the ring is bonded to Y ¹ and any one of X ¹ and X ² . In aryl or heteroaryl rings in rings A, B and C, two or three continuous ring-constituting atoms (carbon atoms) are directly bonded to Y ¹ and any one of X ¹ and X ² . You just have to do it. That is, in the aryl ring or the heteroaryl ring in the B ring, any ^one set of consecutive ring ^- constituting atoms (carbon atoms) are directly bonded to Y1 and X1, and in the aryl ring or the heteroaryl ring in the C ring. ^Two sets of contiguous ring-constituting atoms (carbon atoms) are directly bonded to Y1 and X2, and any ^one set of contiguous ring-constituting atoms (carbon) in the aryl ring or heteroaryl ring in the A ring. Atoms) Three are directly bonded to Y ¹ , X ¹ and X ² .

Examples of the "aryl ring" in the A ring, B ring, or C ring of the formula (1) include an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, and 6 carbon atoms. An aryl ring of ~ 12 is more preferable, and an aryl ring having 6 to 10 carbon atoms is particularly preferable.

Specific examples of the "aryl ring" include a benzene ring, which is a monocyclic system, a biphenyl ring, which is a bicyclic system, a naphthalene ring, an inden ring, which is a fused bicyclic system, and a terphenyl ring (m-tel), which is a tricyclic system. Phenyl, o-terphenyl, p-terphenyl), fused tricyclics, acenaphtylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthalene ring, Examples thereof include a chrysen ring, a perylene ring which is a fused pentacyclic system, and a pentacene ring. Further, the fluorene ring, the benzofluorene ring, and the indene ring also include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, and the like are spiro-bonded, respectively. In the fluorene ring, benzofluorene ring, and indene ring, two of the two hydrogens of methylene are substituted with an alkyl such as methyl as the first substituent described later, respectively, and the dimethylfluorene ring and the dimethylbenzofluorene ring are substituted. And those with a dimethylindene ring are also included.

Examples of the "heteroaryl ring" in the A ring, B ring, or C ring of the formula (1) include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferable. A heteroaryl ring having 2 to 20 carbon atoms is more preferable, a heteroaryl ring having 2 to 15 carbon atoms is further preferable, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferable. Further, examples of the "heteroaryl ring" include a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothazole ring, an imidazole ring, an oxaziazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, and a pyrazole ring. Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring. , Synnoline ring, quinazoline ring, quinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, carboline ring, aclydin ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, India Lydin ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, frazan ring, thiantolen ring, indolocarbazole ring, benzoindrocarbazole ring, benzobenzoindrocarbazole ring, naphtho Examples thereof include a benzofuran ring, a dioxin ring, a dihydroaclydin ring, a xanthene ring, a thioxanthene ring, and a dibenzodioxine ring. Further, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, two of the two hydrogens of methylene are substituted with an alkyl such as methyl as the first substituent described later, respectively, and the dimethyldihydroacridine ring and dimethyl are substituted. Those having a xanthene ring, a dimethylthioxanthene ring, or the like are also preferable. Further, a bicyclic bipyridine ring, a phenylpyridine ring, a pyridylphenyl ring, a tricyclic terpyridyl ring, a bispyridylphenyl ring, and a pyridylbiphenyl ring are also mentioned as "heteroaryl rings". Further, the "heteroaryl ring" shall also include a pyran ring.

The following formula (BO) is also included in the heteroaryl ring.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" is the first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted. "Diarylamino (two aryls are not attached to each other or may be attached via a linking group)", substituted or unsubstituted "diheteroarylamino (two heteroaryls are not attached to each other) , Can be attached via a single bond or a linking group) ”, substituted or unsubstituted“ aryl heteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group). ) ”, Substituted or unsubstituted“ diarylboryl (two aryls may not be attached to each other or may be attached via a single bond or a linking group)”, substituted or unsubstituted “alkyl”, substituted or substituted. Unsubstituted "alkenyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or "substituted silyl" It may be replaced with.

Specifically, the "aryl" is a monovalent group obtained by removing one hydrogen from the above-mentioned "aryl ring", and examples thereof include aryls having 6 to 30 carbon atoms and aryls having 6 to 24 carbon atoms. Preferably, aryls having 6 to 20 carbon atoms are more preferable, aryls having 6 to 16 carbon atoms are more preferable, aryls having 6 to 12 carbon atoms are particularly preferable, and aryls having 6 to 10 carbon atoms are most preferable.

Further, the "heteroaryl" is a monovalent group obtained by removing one hydrogen from the above-mentioned "heteroaryl ring", and examples thereof include heteroaryls having 2 to 30 carbon atoms and having 2 to 25 carbon atoms. Heteroaryl is preferable, heteroaryl having 2 to 20 carbon atoms 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.

As the first substituent, "optionally substituted diarylamino (two aryls may or may not be attached via a linking group)", "may be substituted". Diheteroarylamino (two heteroaryls may or may not be attached via a linking group) "," optionally substituted aryl heteroarylamino (aryl and heteroaryl may be linked) As the aryl and heteroaryl in each of "may be bonded via a group and may not be bonded)", those described as "aryl" and "heteroaryl" described above can be cited.

Diarylamino as the first substituent (two aryls may or may not be attached via a linking group), diheteroarylamino as the first substituent (two heteros). Aryl may or may not be attached via a linking group), and aryl heteroarylamino as a first substituent (aryl and heteroaryl are attached via a linking group. The description "may be bonded via a linking group or may not be bonded" in "may be bonded or not bonded" is, for example, two phenyls of a diphenylamino group as shown below. Represents that a group forms a bond with a linking group. This description also applies to diheteroarylaminos and arylheteroarylaminos formed of aryls and heteroaryls.

Specifically, the linking group is>O,> N- ^RX ,> C ( ^-RX ) ₂ ,> Si ( ^-RX ) ₂ ,>S,>CO,>CS,>SO,> SO. ₂ and> Se, where ^RX is independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl, and> C. ^{RX at (-RX) 2,> Si (-RX) 2, may be single-bonded or bonded via a linking group XY to} _form ^a _ring ^. As ^XY ,>O,> N- ^RY ,> C ( ^-RY ) ₂ ,> Si ( ^-RY ) ₂ ,>S,>CO,>CS,>SO,> SO ₂ , and> Se. ^RY is independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. However, when ^XY is> C ( ^-RY ) ₂ and> Si ( ^-RY ) ₂ , the two ^RYs do not combine to form a further ring. Further, as a linking group, alkenylene can also be mentioned. Any hydrogen of the ^alkenylene may be independently substituted with RX, where ^RX is independently alkyl, cycloalkyl, substituted silyl, aryl and heteroaryl, which are alkyl, cycloalkyl, respectively. Substitution It may be substituted with silyl or aryl.

In addition, when it is simply described as "diarylamino", "diheteroarylamino" or "arylheteroarylamino" in this specification, "two aryls are via a linking group" unless otherwise specified. They may or may not be bonded together, "" the two heteroaryls may or may not be bonded via a linking group, "and" aryls and heteroaryls may or may not be bonded. " It may or may not be bonded via a linking group. "

The "alkyl" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a linear alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. 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 8 carbon atoms is more preferable. (Branch chain alkyl having 3 to 8 carbon atoms) is more preferable, and an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is particularly preferable, and an alkyl having 1 to 5 carbon atoms (3 to 5 carbon atoms) is particularly preferable. Branched chain alkyl) is most preferred.

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

As the above-mentioned substituent containing "alkyl", tertiary-alkyl represented by the following formula (tR) is particularly preferable as a substituent to an aryl ring or a heteroaryl ring in the A ring, B ring and C ring. It is one. This is because such a bulky substituent increases the intramolecular distance and thus the emission quantum yield (PLQY) is improved. Further, a substituent in which the tertiary-alkyl represented by the formula (tR) is substituted with another substituent as the second substituent is also preferable. Specifically, the tertiary-alkyl substituted diarylamino represented by (tR) (the two aryls may not be attached to each other or may be attached via a linking group), and is represented by (tR). Carbazolyl substituted with tertiary-alkyl (preferably N-carbazolyl) or benzocarbazolyl substituted with tertiary-alkyl represented by (tR) (preferably N-benzocarbazolyl). Be done. As for "diarylamino (two aryls may not be bonded to each other or may be bonded via a linking group)", the group described below as "first substituent" can be mentioned. Diarylamino (two aryls may not be attached to each other or may be attached via a linking group), carbazolyl and benzocarbazolyl as substitution forms of the group of formula (tR) in these groups. Examples thereof include a partial or all hydrogen of an aryl ring or a benzene ring substituted with a group of the formula (tR).

In the formula (tR ^{), Ra, R b, and R c are independently} alkyls having 1 to 24 carbon atoms, and any _—CH2 − in the alkyl may be substituted with —O—. , The group represented by the formula (tR) is replaced with at least one hydrogen in the structure containing the structural unit represented by the formula (1) in *.

The "alkyl having 1 to 24 carbon atoms" of R ^a , R ^b and R ^c may be either a straight chain or a branched chain, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. Chain alkyl, alkyl with 1 to 18 carbon atoms (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 (carbon) Examples thereof include a branched chain alkyl having 3 to 6 carbon atoms and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

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

Specific alkyls of R ^a , R ^b , and R ^c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t. -Pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, Examples thereof include 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl and n-eicocil.

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

The "cycloalkyl" as the first substituent includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and cycloalkyl having 3 to 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. As listed below, cyclohexyl in the present specification includes monocyclic cyclohexyl and polycyclic ones such as adamantyl.

Specific cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo. [2.0.1] Pentyl, Bicyclo [1.2.1] Hexil, Bicyclo [3.0.1] Hexil, Bicyclo [2.1.2] Heptyl, Bicyclo [2.2.2] Octyl, Adamantyl , Diamantyl, decahydronaphthalenyl, decahydroazurenyl, and alkyl (particularly methyl) substituents thereof having 1 to 5 carbon atoms.

Examples of the "alkenyl" as the first substituent include straight chain alkenyl of 2 to 24 or branched chain alkenyl having 4 to 24 carbon atoms. An alkenyl having 2 to 18 carbon atoms is preferable, an alkenyl having 2 to 12 carbon atoms is more preferable, an alkenyl having 2 to 6 carbon atoms is further preferable, and an alkenyl having 2 to 4 carbon atoms is particularly preferable.
Specific examples of the "alkenyl" include vinyl, allyl, butadienyl and the like.

Further, as the "alkoxy" as the first substituent, for example, an alkoxy having a linear chain having 1 to 24 carbon atoms or a branched chain having 3 to 24 carbon atoms can be mentioned. Aalkoxy having 1 to 18 carbon atoms (alkoxy of a branched chain having 3 to 18 carbon atoms) is preferable, and an alkoxy having 1 to 12 carbon atoms (alkoxy of a branched chain 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 5 carbon atoms (alkoxy of a branched chain having 3 to 5 carbon atoms) is particularly preferable.

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

As the "arylthio" as the first substituent, the hydrogen of the -SH group is substituted with an aryl, and this aryl can be quoted as described above.

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

The "trialkylsilyl" includes a group in which each of the three hydrogens in the silyl is independently substituted with an alkyl, and this alkyl refers to the group described as "alkyl" in the first substituent described above. Can be done. Preferred alkyls for substitution are alkyls having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl and t-amyl.

Specific examples of the trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, and propyldimethylsilyl. i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethyl Cyril, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, Examples thereof include methyldi i-propyl silyl, ethyl di-propyl silyl, butyl di-propyl silyl, sec-butyl di-propyl silyl, t-butyl di-propyl silyl, and t-amyldi i-propyl silyl.

Examples of the "tricycloalkylsilyl" include groups in which the three hydrogens in the silyl group are independently substituted with cycloalkyl, and this cycloalkyl has been described as "cycloalkyl" in the first substituent described above. The group can be quoted. 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. Examples include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of the tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of the dialkyl cycloalkylsilyl 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 Cyril in which the group to be substituted is substituted.

Specific examples of the dialkylarylsilyl substituted with two alkyls and one aryl, the alkyldiarylsilyl substituted with one alkyl and two aryls, and the triarylsilyl substituted with three aryls are the specific alkyls described above. And silyl substituted with a group selected from aryl. Specific examples of triarylsilyl include triphenylsilyl.

Further, as the "aryl" in the first substituent "diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group)", the above-mentioned description of the aryl is used. Can be quoted. Further, the two aryls may be bonded via a single bond or a linking group (for example,> C (—R) ₂ ,>O,> S or> N—R). Here, R of> C (-R) ₂ and> N-R are aryl, heteroaryl, diarylamino (the two aryls may not be bonded to each other or may be bonded via a linking group),. It is alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and the first substituent is further substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent). Also, specific examples of these groups include aryls, heteroaryls, and diarylaminos as the first substituents described above (the two aryls may not be attached to each other or may be attached via a linking group). , Alkyl, cycloalkyl, alkoxy, or aryloxy can be cited.

The first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino (two aryls are not bonded to each other or have a linking group). ”, Substituted or unsubstituted“ diheteroarylamino (two heteroaryls are not attached to each other or are attached via a single bond or a linking group) ”, substituted. Alternatively, unsubstituted "aryl heteroarylamino (aryl and heteroaryl are not attached to each other or are attached via a single bond or a linking group)", substituted or unsubstituted "diarylboryl (two aryls)". Are not attached to each other or are attached via a single or linking group) ", substituted or unsubstituted" alkyl ", substituted or unsubstituted" cycloalkyl ", substituted or unsubstituted" alkenyl ". , Substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or substituted "silyl" as described as substituted or unsubstituted. At least one hydrogen in them may be substituted with a second substituent. Preferred examples of the second substituent include aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and specific examples thereof include "aryl" and "aryl" as the first substituent. References can be made to the description of "heteroaryl", "diarylamino", "alkyl", "cycloalkyl" or "substituted silyl". Further, in aryls and heteroaryls as the second substituent, at least one hydrogen in them is aryl such as phenyl (specific examples are the groups described above), methyl, t-butyl and the like (specific examples are described above). Aryl or heteroaryl as a second substituent is also included in the structure substituted with a cycloalkyl (specific example is the group described above) such as (the group described above) or cyclohexyl. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9-position is substituted with aryl such as phenyl, alkyl such as methyl or cycloalkyl such as cyclohexyl is also the second. Included in heteroaryl as a substituent. This description is also applicable to the description of other primary and secondary substituents herein.

The emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent. It is preferably a group represented by the following structural formula, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-. Xyryl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6- Dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl,. 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6 -Di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, the one with a large steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, and p-tolyl. , 2,4-Xylylyl, 2,5-Xylylyl, 2,6-xylyl, 2,4,6-methityl, di-p-tolylamino, bis (p- (t-butyl) phenyl) amino, 3,6- Dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

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

The polycyclic aromatic compound having a structure consisting of one or more of the structural units represented by the formula (1) is a tertiary-alkyl (t-butyl or t-amyl) represented by the above formula (tR). , Etc.), preferably having a structure containing at least one neopentyl or adamantyl, and preferably containing a tertiary-alkyl represented by the formula (tR) (such as t-butyl or t-amyl). This is because such a bulky substituent increases the intramolecular distance and thus the emission quantum yield (PLQY) is improved. Further, as the substituent, diarylamino (two aryls may not be bonded to each other or may be bonded via a linking group) is also preferable. In addition, diarylamino substituted with a group of formula (tR) (two aryls may not be attached to each other or may be attached via a linking group), carbazolyl substituted with a group of formula (tR) (tR). Preferably, N-carbazolyl) or benzocarbazolyl substituted with a group of formula (tR) (preferably N-benzocarbazolyl) is also preferred. Diarylamino (two aryls may not be attached to each other or may be attached via a linking group), carbazolyl and benzocarbazolyl as substitution forms of the group of formula (tR) in these groups. Examples thereof include a partial or all hydrogen of an aryl ring or a benzene ring substituted with a group of the formula (tR).

In the formula (1), Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si—R, or Ge—R, respectively, and B or P = O is B is most preferred, and B is most preferred. The R of Si-R and Ge-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. The R of Si—R and Ge—R in Y1 of the formula ( ¹ ) is aryl, alkyl or cycloalkyl, and examples of the aryl, alkyl or cycloalkyl include the above-mentioned groups. In particular, aryls having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), alkyls having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferable.

X ¹ and X ² in the formula (1) have>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,>S,> Se, or R, respectively. It is a monovalent group represented by the formula (G)> NR. In the formula (2) described later, including the case where R is a monovalent group represented by the formula (G-2)> N-R, in the present specification, such a form> N-R. Is expressed as> NG. However, at least one of X ¹ and X ² is> NG. When one of X ¹ and X ² is> NG, the other X ¹ or X ² is>NG,>NR,> C (-R) ₂ , or> O. , And more preferably> NG or> NR.

The R of> N—R, which is X ¹ or X ² , is hydrogen, optionally substituted aryl (except amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl. Alternatively, it is a cycloalkyl which may be substituted. The Rs of> Si (-R) ₂ which are X ¹ and X ² are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or It is a cycloalkyl which may be substituted.

The Rs of> Si (-R) ₂ and> C (-R) ₂ which are X ¹ or X ² are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, respectively. It is an alkyl that may be substituted, or a cycloalkyl that may be substituted, preferably the two Rs are identical, and the two Rs may be bonded to form a ring.

For aryl, heteroaryl, alkyl, cycloalkyl in R of>N-R,> Si (-R) ₂ , or> C (-R) ₂ which is X ¹ or X ² , the first substituent above. You can refer to their description as.

The R of> N—R which is X ¹ or X ² is preferably substituted aryl, optionally substituted heteroaryl, or optionally substituted cycloalkyl, preferably substituted. More preferably, it may be a good aryl or a heteroaryl which may be substituted. Examples of cycloalkyl include the examples described below. Here, the aryl is preferably phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl), and the heteroaryl is benzothienyl (2-benzothienyl, 6-benzo). Thienyl, etc.), benzofuranyl (2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl, etc.), dibenzofuranyl (2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 5-dibenzofuranyl, etc.), etc. Is preferable. As the substituent, tertiary-alkyl (particularly t-butyl) represented by the above formula (tR) or cycloalkyl (particularly adamantyl) is preferable. The number of substituents in aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the above aryl is condensed with a cycloalkane which may be substituted as described later. As the specific cycloalkane, those described later can be referred to.

Particularly preferred examples of R> N- ¹ or X2 are condensed with optionally substituted ² -biphenylyl, optionally substituted terphenyl-2'-yl, and cycloalkane. Aryl (which may be substituted) is mentioned. As the 2-biphenylyl which may be substituted, 2-biphenylyl substituted with 1 to 3 t-butyl is particularly preferable. As the optionally substituted terphenyl-2'-yl, unsubstituted [1,1': 3', 1'''-terphenyl] -2'-yl is particularly preferable. The following are particularly preferable as the aryl condensed with cycloalkane.

（Ｍｅはメチル、ｔＢｕはｔ－ブチル、＊は結合位置を示す。）

(Me indicates methyl, tBu indicates t-butyl, * indicates the binding position.)

When any of X ¹ and X ² is> N-R, it is also preferred that the R of> N-R is an aryl (which may be substituted) condensed with a cycloalkane.

R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ which is X ¹ or X ² is either one of A ring and B ring by a linking group or a single bond. , Or may be bonded to any one of the A ring and the C ring. That is, R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ which is X ¹ is bonded to any one of A ring and B ring by a linking group or a single bond. R in at least one of> N _- R,> Si (-R) ₂ and> C (-R) ² which is X2 can be either an A ring or a C ring by a linking group or a single bond. It may be combined with one or the other. The linking group is preferably —O—, —S—, or —C (—R ¹³ ) _2- . R ¹³ of the above-mentioned "-C (-R ¹³ ) _2- " is hydrogen, alkyl or cycloalkyl, and examples of the alkyl or cycloalkyl include the above-mentioned groups as the first substituents, respectively. In particular, an alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

This regulation can be expressed by a compound having a ring structure in which X ¹ and X ² are incorporated into the fused ring B'and the condensed ring C', which are represented by the following formula (1-3-1). That is, it has a B'ring (or C'ring) formed by condensing another ring so as to incorporate X ¹ (or X ² ) into, for example, a B ring (or C ring) which is a benzene ring. It is a compound. The formed fused ring B'(or fused ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

Further, the above regulation defines a ring structure in which any one of X ¹ and X ² represented by the following formula (1-3-2) or formula (1-3-3) is incorporated into the fused ring A'. It can also be expressed by a compound having it. That is, for example, it is a compound having an A'ring formed by condensing the other ring so as to incorporate any one of X ¹ and X ² with respect to the A ring which is a benzene ring. The formed fused ring A'is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

As an example, a cycloalkyl in which R of> NR may be substituted and is bonded to the A ring, the B ring, or the C ring by a single bond is also preferable. As the cycloalkyl, cyclopentyl which may be substituted or cyclohexyl which may be substituted is preferable.

As a particularly preferable example of the fused ring formed as described above, the structure represented by the formula (A11) can be given. As described above, in this case, the two carbons substituted with the methyl group are asymmetric carbons, and diastereomers and enantiomers may exist as the compounds represented by the formula (1), but the formula (1). The compound represented by may be any of these isomers, or may be in a form in which possible isomers are mixed at an arbitrary ratio.

In formula (A11), Me is methyl and is attached to one ring of the two rings to which X ¹ or X ² is attached at the two * positions and to the other ring at the ** position. As an example of such a structure, the structure of the compound represented by any of the formula (1-17), the formula (1-32), the formula (1-56), and the formula (1-72) described later can be used. can give.

By using the compound of the present invention having> N—R as X ¹ or X ² in the above-mentioned preferable range as a light-emitting material in the manufacture of a device, the luminous efficiency and the device life can be further improved.

X ¹ or X ² of formula (1)> R of Si (-R) ₂ is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or It is a cycloalkyl which may be substituted. Here, as the substituent when substituted, the above-mentioned second substituent can be mentioned. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the above-mentioned groups as the first substituents. In particular, aryls with 6 to 10 carbon atoms (eg, phenyl, naphthyl, etc.), heteroaryls with 2 to 15 carbon atoms (eg, carbazolyl, etc.), alkyls with 1 to 5 carbon atoms (eg, methyl, ethyl, etc.) or 5 to 10 carbon atoms. Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred.

X ¹ or X ² of formula (1)> C (-R) ₂ R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or It is a cycloalkyl which may be substituted. Here, as the substituent when substituted, the above-mentioned second substituent can be mentioned. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the above-mentioned groups as the first substituents. In particular, aryls with 6 to 10 carbon atoms (eg, phenyl, naphthyl, etc.), heteroaryls with 2 to 15 carbon atoms (eg, carbazolyl, etc.), alkyls with 1 to 5 carbon atoms (eg, methyl, ethyl, etc.) or 5 to 10 carbon atoms. Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred.

Next, the group represented by the formula (G) in the formula (1) will be described.

In formula (G), L is a single bond, alkylene, cycloalkylene, arylene or heteroarylene. As "alkylene", "cycloalkylene", "arylene" and "heteroarylene", one hydrogen is removed from "alkyl", "cycloalkyl", "aryl" and "heteroaryl" in the present specification. The basis of the price can be raised. As L, a single bond, an arylene or a heteroarylene is preferable, a single bond or an arylene is preferable, and a single bond is most preferable. Further, at least one hydrogen of "alkylene", "cycloalkylene", "arylene" and "heteroarylene" may be substituted, but the substituent at this time is a substituted or unsubstituted aryl, substituted or unsubstituted. Heteroaryl, substituted or unsubstituted diarylamino (two aryls may not be attached to each other or may be attached via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may be attached). Aryl heteroarylaminos that are not attached to each other or may be attached via a single bond or a linking group), substituted or unsubstituted aryl heteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group). ), Substituted or unsubstituted diarylboryl (two aryls may not be attached to each other or may be attached via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or absent. Substituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl can be mentioned. Is also preferred in an undamaged form. The above description can be referred to with respect to the second substituent for these first substituents.

In formula (G), the (GA) ring and the (GB) ring are substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings. Regarding the preferable range and substituents, the description regarding the A ring, the B ring and the C ring in the above formula (1) can be referred to, but a substituted or unsubstituted benzene ring is preferable.

In formula (G), X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se. ,> R of N-R are hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,> C (-R) ₂ , And> R of Si (-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, respectively. ,> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring.

Further, in the formula (G), at least one R of>N-R,> C (-R) ₂ and> Si (-R) ₂ as X ³ and X ⁴ is formed by a linking group or a single bond (GA). ) And at least one of (GB) may be attached via a linking group or a single bond. The linking group is preferably —O—, —S—, or —C (—R ¹⁴ ) _2- . In addition, R ¹⁴ of the said "-C (-R ¹⁴ ) _2- " is hydrogen, alkyl or cycloalkyl, and examples of this alkyl or cycloalkyl include the above-mentioned groups as the first substituents, respectively. In particular, an alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by the formula (1) and the formula (2) described later. Examples of the polycyclic aromatic compound having a structure consisting of one of the structural units include the polycyclic aromatic compound represented by the formula described above as the structural unit represented by the formula (1). The polycyclic aromatic compound having a structure consisting of two or more structural units represented by the formula (1) is a polycyclic aromatic compound represented by the formula described above as the structural unit represented by the formula (1). Examples thereof include compounds corresponding to multimers of group compounds. The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the unit structures in one compound, and any ring (A ring, B ring or C ring) contained in the structural unit may be shared by the plurality of unit structures. It may be a form in which the rings (A ring, B ring or C ring) included in the unit structure are fused so as to be bonded to each other. Further, the unit structure may be in the form of a single bond or a plurality of bonds having a linking group such as an alkylene having 1 to 3 carbon atoms, phenylene and naphthylene. Of these, the form bonded so as to share a ring is preferable.

At least one selected from the group consisting of aryl rings and heteroaryl rings in a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the formula (1) is at least one cyclo. Condensed with alkanes. The same applies to the polycyclic aromatic compound represented by the formula (2) described later, and the following description also applies to the polycyclic aromatic compound represented by the formula (2).

The cycloalkane may be any cycloalkane having 3 to 24 carbon atoms. At least one hydrogen in the cycloalkane at this time is substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms. Also, at least one -CH _2- in the cycloalkane may be substituted with -O-, but cycloalkanes in which all are -CH _2- are preferred.

At least one selected from the group consisting of an aryl ring and a heteroaryl ring in a structure consisting of one or two or more structural units represented by the formula (1) is condensed with at least one cycloalkane. One cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, and 1 to 12 carbon atoms. It is preferably a cycloalkane that may be substituted with an alkyl of the above or a cycloalkane having 3 to 16 carbon atoms.

The "cycloalkane" includes cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, and cycloalkanes having 5 to 10 carbon atoms. Examples thereof include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 6 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptan, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, and so on. Bicyclo [2.0.1] pentane, bicyclo [1.2.1] hexane, bicyclo [3.0.1] hexane, bicyclo [2.1.2] heptane, bicyclo [2.2.2] octane, Examples thereof include adamantane, diamantan, decahydronaphthalene and decahydroazulene, as well as alkyl (particularly methyl) substituents, halogen (particularly fluorine) substitutes and dehydrohydrogen substitutes having 1 to 5 carbon atoms thereof.

Among these, for example, as shown in the following structural formula, the carbon at the α-position of the cycloalkane (in the cycloalkyl condensed on the aryl ring or the heteroaryl ring, corresponds to the carbon at the position adjacent to the carbon at the condensation site, the benzyl position. ), The structure in which at least one hydrogen is substituted is preferable, the structure in which two hydrogens are substituted in the carbon at the α-position is more preferable, and the structure in which a total of four hydrogens are substituted in the two carbons at the α-position is further preferable. .. This is to protect chemically active sites and improve the durability of the compound. Examples of this substituent include an alkyl (particularly methyl) substituted product having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituted product, and a deuterium substituted product. In particular, it is preferable that the aryl ring or the heteroaryl ring has a structure in which a partial structure represented by the following formula (Z-11) is bonded to an adjacent carbon atom.

式（Ｚ－１１）中、Ｍｅはメチルを示し、＊は結合位置を示す。

In formula (Z-11), Me indicates methyl and * indicates the binding position.

The number of cycloalkanes condensed on one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed on one benzene ring (phenyl) is shown below. * Indicates a bond position, and the position may be any of carbons constituting a benzene ring and not a cycloalkane. Cycloalkanes condensed as in the formulas (Cy-1-4) and (Cy-2-4) may be condensed with each other. Even if the ring (group) to be condensed is an aryl ring or a heteroaryl ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Is the same.

At least one -CH _2- in the cycloalkane may be substituted with -O-. For example, an example in which one or more -CH _2- are replaced with -O- in a cycloalkane condensed on one benzene ring (phenyl) is shown below. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even if there is, it is the same.

At least one hydrogen in the cycloalkane may be substituted, and the substituents include, for example, aryl, heteroaryl, diarylamino (the two aryls are not bonded to each other or are bonded via a linking group). ), Diheteroarylamino (two heteroaryls are not attached to each other or are attached via a single bond or a linking group), aryl heteroarylamino (aryl and heteroaryl are attached to each other). No or bonded via a single bond or linking group), diarylboryl ((the two aryls are not bonded to each other or bonded via a single bond or linking group), alkyl, Cycloalkyl, alkoxy, aryloxy, substituted silyl, dehydrogen, cyano or halogen can be mentioned, and the details thereof can be cited from the description of the first substituent described above. Among these substituents, alkyl. (For example, an alkyl having 1 to 6 carbon atoms), a cycloalkyl (for example, a cycloalkyl having 3 to 14 carbon atoms), a halogen (for example, fluorine) and a heavy hydrogen are preferable, and when the cycloalkyl is substituted, a spiro structure is formed. This may be a replacement form, and an example of this is shown below.

As a form of cycloalkane condensation, first, an aryl ring in each of the A ring, B ring, and C ring in a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the formula (1). And a heteroaryl ring, an aryl ring and a heteroaryl ring which are described later (a ring, b ring, and c ring in the formula (2)), and an aryl ring and a heteroaryl ring in a fused ring are condensed with a cycloalkane. can give.

Other forms of cycloalkane condensation include a polycyclic aromatic compound having a structure consisting of one or more structural units represented by the formula (1), and a polycycle represented by the formula (2) described later. The aromatic compound is, for example, R is a cycloalkane-condensed aryl> NR, cycloalkane-condensed diarylamino (the two aryls are not bound to each other or are bound via a linking group). Examples include carbazolyl condensed with cycloalkane (condensed to this benzene ring moiety) or benzocarbazolyl condensed with cycloalkane (condensed to this benzene ring moiety). Be done. As for "diarylamino (two aryls may not be bonded to each other or may be bonded via a linking group)", the group described as the above "first substituent" can be mentioned.

In the polycyclic aromatic compound having a structure consisting of one or more of the structural units represented by the formula (1) and the polycyclic aromatic compound represented by the formula (2) described later, the above cyclo The alkane condensation is preferably in the form of being fused to the A (a) ring, the B (b) ring, or the C (c) ring, and more preferably in the form of being condensed to the A (a) ring or the B (b) ring. preferable. Further, a form in which both the A (a) ring and the B (b) ring are condensed is also preferable.

By introducing a cycloalkane structure into the polycyclic aromatic compound of the present invention, it is expected that the melting point and the sublimation temperature will be lowered. This means that in sublimation purification, which is almost indispensable as a method for purifying materials for organic devices such as organic EL devices that require high purity, it can be purified at a relatively low temperature, so that thermal decomposition of the material can be avoided. means. This also applies to the vacuum deposition process, which is a powerful means for manufacturing organic devices such as organic EL devices, and since the process can be carried out at a relatively low temperature, thermal decomposition of the material can be avoided. As a result, a high-performance organic device can be obtained. In addition, since the introduction of the cycloalkane structure improves the solubility in an organic solvent, it can be applied to device fabrication using a coating process. However, the present invention is not particularly limited to these principles. Therefore, in the polycyclic aromatic compound having a structure consisting of one or more of the structural units represented by the formula (1) and the polycyclic aromatic compound represented by the formula (2) described later, the polycyclic aromatic compound is described. It is preferable that the above cycloalkane condensation is introduced.

The hydrogen in the structure consisting of one or more of the structural units represented by the formula (1) may be all or part of deuterium, cyano, or halogen. The same applies to the polycyclic aromatic compound represented by the formula (2) described later, and the following description also applies to the polycyclic aromatic compound represented by the formula (2).

For example, in a structure consisting of one or more structural units represented by the formula (1), A ring, B ring, C ring (A to C rings are aryl rings or heteroaryl rings), A to C. Substituents to the ring, R (= alkyl, cycloalkyl, aryl) when Y ¹ is Si-R or Ge-R, and>N-R,> C (-R) for X ¹ and X ² . Hydrogen in R (= alkyl, cycloalkyl, aryl) when ₂ or> Si (-R) ₂ can be replaced with dehydrogen, cyano or halogen, among which all or one in aryl or heteroaryl. Examples thereof include an embodiment in which hydrogen in the portion is replaced with heavy hydrogen, cyano, or halogen. The halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, even more preferably fluorine. Further, from the viewpoint of durability, it is preferable that all or part of the hydrogen in the structure consisting of one or more of the structural units represented by the formula (1) is deuterium, and all of them are heavy. It is also preferable that it is hydrogenated.

A preferable example of a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the formula (1) is a polycyclic aromatic compound represented by the following formula (2). For the substituents in the formula (2), the structure of the ring contained therein, and the preferable range, each description of the corresponding formula (1) can be referred to.

In equation (2), Y ¹ is synonymous with Y ¹ in equation (1).

In formula (2), Z is independently N or CR ¹¹ , and ^{11 of the CR 11 is} independently hydrogen, aryl, heteroaryl, and diarylamino (two aryls are mutually exclusive). Unbound or bonded via a linking group), diheteroarylamino (two heteroaryls are not bound to each other or bonded via a linking group), aryl heteroaryl Amino (aryls and heteroaryls are not attached to each other or are attached via a linking group), diarylboryl (two aryls are not attached to each other or are attached via a single bond or a linking group). ), Alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyls, at least one hydrogen in which is substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyls. May be. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

Two adjacent R ^11s may be coupled to each other to form an aryl ring or a heteroryl ring, wherein the formed aryl ring and heteroreel ring are aryl, heteroaryl, and diarylamino, respectively. Not bound to each other or bonded via a linking group), diheteroarylamino (two heteroaryls are not bound to each other or bonded via a linking group), aryl hetero Arylamino (aryls and heteroaryls are not attached to each other or are attached via a linking group), diarylboryl (two aryls are not attached to each other, or are attached via a single bond or a linking group). , Alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyls, in which at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cyclo. It may be substituted with alkyl or substituted silyl. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

In the formula (2), Z = Z may be independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se. >O,>N-R,> C (-R) ₂ , or> S is more preferable. The> N-R, the> C (-R) ₂ and the> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one of them. Hydrogen may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyls. Further, the two Rs of> C (-R) ₂ and the above> Si (-R) ₂ may be bonded to each other to form a ring. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

In the b-ring, c-ring, etc., the place where "Z = Z" is replaced with>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se. Examples of the ring to be used include a cyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring and the like. Further, when the remaining Zs are adjacent and they are CR ¹¹ and the R ¹¹ is bonded to form a benzene ring, an indene ring, an indole ring, a benzofuran ring, or a benzothiophene ring is formed. Can form. The formed ring may have a substituent. An example in which one Z = Z is>NR,>O,>S,> C (-R) ₂ and the remaining Z is CH in the b ring or the like, and one Z = Z is>NR,>O,>S,> C (-R) ₂ , the remaining Zs are adjacent, and they are all CR ¹¹ , and these R ^11s are combined with each other. An example of forming a benzene ring is shown below. However, the forms that the b-ring, c-ring, and the like can take are not limited to the following examples.

In addition, R ¹¹ of CR ¹¹ is bonded to an aryl ring such as a bencyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring, an indene ring, an indole ring, a benzofuran ring, or a benzothiophene ring, and a heteroaryl ring. An example of forming is shown below.

In the above example, the example regarding the b ring bonded to Y ¹ and X ¹ in the formula (1) is given, but this description is similarly applied to the a ring or the c ring in the formula (2). be able to.

X ¹ and X ² in the formula (2) have>O,>N-R,> Si (-R) ₂ ,> C (-R) ₂ ,>S,> Se, or R, respectively. It is> NR (> NG) which is a monovalent group represented by the formula (G-2). However, at least one of X ¹ and X ² is> NG. Regarding the specific range of>N-R,> Si (-R) ₂ , and> C (-R) ₂ , the description regarding X ¹ and X ² in the above formula (1) can be referred to. When either X ¹ or X ² is> NG, the other X ¹ or X ² is>NG,>NR,> C (-R) ₂ , or>. O, is preferable, and> NG or> NR is more preferable.

R in at least one of>N-R,> Si (-R) ₂ and> C (-R) ₂ in X ¹ and X ² in formula (1) is an A ring and a B ring by a linking group or a single bond. The above statement that it may be attached to at least one of the rings A and at least one of the rings A and C via a linking group or a single bond is described in the formula (2) as "also> N-. R in at least one of R of R, said> C (-R) ₂ and said> Si (-R) ₂ , is -O-, -S-, -C (-R ¹³ ) _2- or single. By binding, it is bound to one or two of C in Z, which is ^CR11 . " Specifically, the above R may be bonded to C (carbon atom) in Z, which is the spatially closest CR ¹¹ in each ring shown below, and is designated as X ¹ in the formula (2). >N-R,> Si (-R) ₂ or> C (-R) ₂ R is at least one spatially closest C- of ring a and ring b via a linking group or single bond. It may be bonded to C (carbon atom) in Z which is R11, and R of>N-R,> Si (-R) ² or> _{C (-R) 2} ^as X1 is a linking group. Alternatively, it may be bonded to C (carbon atom) in Z, which is the spatially closest CR ¹¹ , at least one of the a ring and the c ring via a single bond. Regarding R13 of "-C ⁽ -R ¹³ ) _2- " among these, the above description can be referred to.

In the formula (2), the number of rings (single ring) containing Z, which is N, is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and 0 to 1. Is particularly preferable. In each of the above equations, it is also preferable that Z is all CR ¹¹ .

In the ring (single ring) containing Z which is N in the formula (2), it is preferable that one or two of the plurality of Zs are N, and when two are N, the two Ns are adjacent to each other. It is preferable not to do so. When the 6-membered ring is a ring containing Z, which is N, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When the 5-membered ring is a ring containing Z which is N, a thiazole ring and an oxazole ring are preferable.

The group represented by the formula (G-2) in the formula (2) will be described. In formula (G-2), Z ^G is N or CR ^{12, and R 12 of} the CR ¹² is independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are bonded to each other). Aryl heteroarylamino (two heteroaryls are not attached to each other or are attached via a linking group), aryl heteroarylamino (Aryl and heteroaryl are not attached to each other or are attached via a linking group), Diarylboryl (two aryls are not attached to each other or are attached via a single bond or a linking group). ), Alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyls, at least one hydrogen in which is substituted with aryl, heteroaryl, arylamino, alkyl, cycloalkyl, or substituted silyls. May be. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

Two adjacent ^R12s may be coupled to each other to form an aryl ring or a heteroryl ring, wherein the formed aryl ring and heteroreel ring are aryl, heteroaryl, and diarylamino, respectively. Not bound to each other or bonded via a linking group), diheteroarylamino (two heteroaryls are not bound to each other or bonded via a linking group), aryl hetero Arylamino (aryls and heteroaryls are not attached to each other or are attached via a linking group), diarylboryl (two aryls are not attached to each other, or are attached via a single bond or a linking group). , Alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyls, in which at least one hydrogen is aryl, heteroaryl, arylamino, alkyl, cyclo. It may be substituted with alkyl or substituted silyl. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

In the formula (G-2), Z ^G = Z ^G are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se. It may be>O,>N-R,> C (-R) ₂ , or> S, more preferably. The> R, the> C (-R) ₂ and the> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, and at least one hydrogen in these. May be substituted with aryl, heteroaryl, arylamino, alkyl, cycloalkyl, or substituted silyl. The two Rs of> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring. For the details of the substituents listed here, the description of the first substituent and the second substituent can be referred to.

In the formula ( ^G -2), the places of "Z ^G = ZZ" of the ring (GA) and the ring (G-b) are>O,>N-R,> C (-R) ₂ ,> Si. (-R) For the ring obtained by substituting ₂ ,> S, or> Se, the description regarding "Z = Z" in the a ring and the b ring in the above formula (1) can be referred to. Further, regarding the specific form thereof, the above description can be referred to by replacing Y ¹ and X ¹ with X ³ and X ⁴ .

-O-, -S-, -C (-R ¹⁴ ) 2 of>N-R,> Si (-R) ₂ and> C (-R) ₂ in X ³ and X ⁴ in the formula (G-2) ₂ ^-Or by a single bond, it may be bonded to one or two of C in ZG, which is CR ¹² . This means that in the formula (G) in the formula (1), at least one R of ">N-R,> C (-R) ₂ and> Si (-R) ₂ is a linking group or a single bond (G). -A) It may be attached to at least one of the ring and (GB) via a linking group or a single bond. " Specifically, the above R in the formula ( ^G -2) is -O-, -S-,-to the C (carbon atom) of ZG, which is the spatially closest CR ¹² in each ring. It may be bonded by C (-R ¹³ ) _2- or a single bond. Among these, R ¹⁴ of "-C (-R ¹⁴ ) _2- " is hydrogen, alkyl, or cycloalkyl, and the above-mentioned group is mentioned as the first substituent of this alkyl or cycloalkyl, respectively. Be done. In particular, an alkyl having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

In formula ( ^G -2), one bond of L, which is a divalent group, is any ZZ in the (GA) ring ( ^C (carbon atom) of CR ¹² which is ZZ). ), And the other bond is bonded to N (nitrogen atom) of> NG.

In the formula (G-2), the number of rings (single ring) containing Z, which is N, is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and 0 to 0 to 2. It is particularly preferable to have one. In each of the above equations, it is also preferable that Z is all CR ^Z.

In the ring (single ring) containing Z which is N in the formula (G-2), it is preferable that one or two of the plurality of Zs are N, and when two are N, the two Ns are. It is preferable that they are not adjacent to each other. When the 6-membered ring is a ring containing Z, which is N, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When the 5-membered ring is a ring containing Z which is N, a thiazole ring and an oxazole ring are preferable.

Specific examples of the group represented by the formula (G-2) include the following forms described by the formulas (G-2-1) to (G-2-16). However, it is not limited to these examples.

In formulas (G-2-1) to (G-2-16), R is the R of>N-R,> Si (-R) ² and> C _{(-R) 2} ⁱⁿ X3 and _X4 . You can refer to what is defined as. At least one hydrogen of these groups may be substituted with a substituent, and the above description of the first substituent and the second substituent can be referred to for the form of substitution.

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

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

<Method for producing polycyclic aromatic compounds>
Having a structure consisting of one or more of the structural units represented by the formula (1) or the formula (2), basically, first, the A ring (a ring), the B ring (b ring), and the C ring. An intermediate is produced by binding a ring (c ring) with a binding group (a group containing X ¹ and X ² ) (first reaction), and then A ring (a ring) and B ring (b ring). ) And C ring (c ring) are bonded with a binding group (group containing Y ¹ ) to produce the final product (second reaction). In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. At least one ring selected from the group consisting of A ring, B ring and C ring by using a raw material having a desired fused ring or adding a step of condensing the ring somewhere in the reaction step. The compound can be produced from a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

<Manufacturing method via Intermediate-1>
The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each step below, the description of International Publication No. 2015/102118 can be referred to.

A reaction step of metallizing a halogen atom (Hal) between X1 and X2 in the following intermediate ^{- 1} using ^an organic alkaline compound, ^a halide of Y1, ^an amination halide of Y1, and Y1. The above is carried out by a reaction step of exchanging the metal with Y1 using ^{a reagent selected from the group consisting of an alkoxy substance and an aryl oxy compound of Y 1 ,} and a continuous aromatic electrophobic substitution reaction using a Bronsted base. The reaction including the reaction step of binding the B ring and the ^C ring at Y1 is described below.

The metallizing reagents used in the halogen-metal exchange reaction in the schemes described so far include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium and t-butyllithium, isopropylmagnesium chloride, and bromide. Examples thereof include isopropylmagnesium, phenylmagnesium chloride, phenylmagnesium bromide and a lithium chloride complex of isopropylmagnesium chloride known as a turbo Grignard reagent.

In addition to the above reagents, the metalation reagents used in the orthometal exchange reaction in the schemes described so far include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexa. Examples thereof include organic alkaline compounds such as methyldisilazide, lithium tetramethylpiperidinylmagnesium chloride / lithium chloride complex, and lithium tri-n-butylmagnate.

Further, examples of the additive that accelerates the reaction when alkyllithium is used as the metalation reagent include N, N, N', N'-tetramethylethylenediamine, 1,4-diazabicyclo [2.2.2] octane, and the like. Examples thereof include N, N-dimethylpropylene urea and the like.

The Lewis acids used in the schemes described so far include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ , OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , and In. (OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc (OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn (OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg (OTf) ₂ , LiOTf, NaOTf KOTf, Me ₃ SiOTf, Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y (OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , CoCl ₃ , etc. Be done. Further, those in which these Lewis acids are supported on a solid can also be used in the same manner.

The blended acids used in the schemes described so far include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carbolanic acid, trifluoroacetic acid, and (trifluoromethanesulfonyl) imide. Tris (trifluoromethanesulfonyl) methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride and the like can be mentioned. Examples of the solid Bronsted acid include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), Zeolite, and Tayca Cure (trade name: TAYCA Corporation).

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

The solvents used in the schemes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4. -Methylbenzene, xylene, diphenyl ether, anisole, cyclopentylmethyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether and the like can be mentioned.

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

In the above scheme, Bronsted bases or Lewis acids may be used to facilitate the tandem hetero-Friedel-Crafts reaction. However, when Y ¹ halides such as Y ^{1 trifluoride, Y 1 trichloride} , Y ¹ triodoride, 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 Bronsted base that captures the acid. On the other hand, when an aminated halide of Y ¹ and an alkoxylate of Y ¹ are used, a Bronsted base is often used because amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds. Although not necessary, the low desorption ability of aminos and alkoxys makes the use of Lewis acid, which promotes their desorption, effective.

Further, the polycyclic aromatic compound of the present invention also includes a compound in which at least a part of hydrogen atoms is substituted with heavy hydrogen or cyano, or a compound in which a halogen such as fluorine or chlorine is substituted. Compounds and the like can be synthesized in the same manner as described above by using a raw material in which the desired position is dehydrogenated, cyanated, fluorinated or chlorinated.

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

The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, and the like, and an organic electroluminescent element is preferable. The polycyclic aromatic compound and its multimer according to the present invention are preferably an organic electroluminescent element material, more preferably a light emitting layer material (light emitting material), and preferably a light emitting layer dopant material. Most preferred. In particular, in an organic electric field light emitting element, the dopant material of the light emitting layer has a structure consisting of one or two or more structural units represented by the formula (1) of the present invention or the formula (2) described later. Among the ring aromatic compounds, compounds in which one of Y ¹ is B, X ¹ and X ² is> N-G and the other is>N-G,> N-R or> O are preferred. ,> NG, or> NR are more preferred, and as the host material for the light emitting layer, Y ¹ is> NG for either B, X ¹ or X ² , and the other is> NG. A compound having NR or> O is preferable, a compound in which Y ¹ is B, X ¹ and X ² is> NG, and the other is> O, more preferably, as an electron transporting material. A compound in which Y ¹ is B or P = O is preferably used.

<2-1. Organic electroluminescent device>
<2-1-1. Structure of organic electroluminescent device>
FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
The organic EL element 100 shown in FIG. 1 is formed 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. May have a configuration having a hole injection layer 103 provided in the hole injection layer 103 and an anode 102 provided on the hole injection layer 103.

Not all of the above layers are indispensable, 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" configuration mode, " 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 / Anodic / 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 / "Anodic / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer / electron" Transport layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron injection layer / cathode ”,“ substrate / anode / hole injection layer / light emitting layer / electron transport layer / cathode ”,“ substrate / anode ” The configuration may be "/ light emitting layer / electron transport layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

<2-1-2. Light emitting layer in organic electroluminescent device>
The polycyclic aromatic compound of the present invention is preferably used as a material for forming any one or more organic layers in an organic electroluminescent device, and more preferably used as a material for forming a light emitting layer. 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. The material for forming the light emitting layer 105 may be a compound (luminescent compound) that is excited by the recombination of holes and electrons to emit light, and can form a stable thin film shape and is in a solid state. It is preferably a compound that exhibits strong emission (fluorescence) efficiency. The polycyclic aromatic compound of the present invention can be used as a material for a light emitting layer, may be used as a dopant material, or may be used as a host material, but is preferably used as a material for a light emitting layer, and is preferably a dopant material. It is more preferable to use as.

As the dopant, there is an example in which the assisting dopant and the emitting dopant are used in combination, but in the present specification, when the term "dopant" is simply used, it means a light emitting dopant used alone. ..

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 either one type or a plurality of combinations. The dopant material may be included in the entire host material, partially, or partially. As a doping method, it can be formed by a co-deposited 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 mass, more preferably 80 to 99.95% by mass, and further preferably 90 to 99.9% by mass of the entire light emitting layer material. 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 mass, more preferably 0.05 to 20% by mass, and further preferably 0.1 to 10% by mass of the entire light emitting layer material. be. Within the above range, for example, it is preferable in that the density quenching phenomenon can be prevented.

<Host material>
Host materials include fused ring derivatives such as anthracene, pyrene, dibenzoclycene or fluorene, which have long been known as illuminants, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. , Fluorene derivatives, benzofluorene derivatives and the like.

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

In the formulas (H1), (H2) and (H3), L1 has an arylene having 6 to 24 carbon atoms, ^a heteroarylene having 2 to 24 carbon atoms, a heteroarylene arylene having 6 to 24 carbon atoms and an arylene having 6 to 24 carbon atoms. Aliren Heteroarylene An arylene, an arylene having 6 to 16 carbon atoms is preferable, an arylene having 6 to 12 carbon atoms is more preferable, and an arylene having 6 to 10 carbon atoms is particularly preferable, specifically, a benzene ring, a biphenyl ring, and the like. Divalent groups such as the terphenyl ring and the fluorene ring can be mentioned. As the heteroarylene, a heteroarylene having 2 to 24 carbon atoms is preferable, a heteroarylene having 2 to 20 carbon atoms is more preferable, a heteroarylene having 2 to 15 carbon atoms is further preferable, and a heteroarylene having 2 to 10 carbon atoms is particularly preferable. Preferably, specifically, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothazole ring, an imidazole ring, an oxazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, and the like. 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. , Kinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indridin ring, furan ring, benzofuran ring, isobenzofuran ring. , Dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, frazan ring, oxazole ring and thiantolene ring and the like. At least one hydrogen in the compound represented by each of the above formulas may be substituted with an alkyl, cyano, halogen or deuterium having 1 to 6 carbon atoms.

Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, an alkyl having 1 to 4 carbon atoms (for example, methyl or t-butyl), phenyl or naphthyl.

(mCP)

(mCP)

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

In formula (3-H),
X and Ar ⁴ are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted diarylamino (the two aryls are not bonded to each other or are not bonded to each other. Diheteroarylamino may be substituted (the two heteroaryls may not be attached to each other, or may be single-linked or attached via a linking group), Aryl Heteroarylamino May Be Substituted (Aryl and Heteroaryl may not be attached to each other or may be attached via a single bond or a linking group), Alkyl may be substituted, Already substituted. All of them are cycloalkyl, which may be substituted, alkenyl, which may be substituted, alkoxy, which may be substituted, aryloxy, which may be substituted, arylthio, which may be substituted, or silyl, which may be substituted. X and Ar ⁴ do not become hydrogen at the same time,
At least one hydrogen in the compound represented by the formula (3-H) may be substituted with a halogen, cyano, deuterium or a optionally substituted heteroaryl.

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

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

Preferred embodiments of the anthracene compound will be described below. The definition of the sign in the following structure is the same as the above definition.

In the formula (3-H), X is a group independently represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3), and the formula (3-X1) and the formula (3-X1) are used. The group represented by (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) in *. Preferably, the two Xs cannot be the basis of the formula (3-X3) at the same time. More preferably, 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-H) as a unit structure. In this case, for example, the unit structures represented by the formula (3-H) may be bonded to each other via X, and the X includes a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.) and a heteroarylene (pyridine). A group in which a ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, or the like has a divalent bond value) and the like can be mentioned.

The naphthylene moiety in the formula (3-X1) and the formula (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 represented by hydrogen, phenyl, biphenylyl, terfenyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or formula (A). Groups to be (including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). 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 formula (A) (carbazolyl, benzocarbazolyl). And phenyl-substituted carbazolyl). 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-H) 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, terfenylyl, naphthyl and phenanthryl. , Fluolenyl, chrysenyl, triphenylenyl, pyrenylyl, or may be substituted with a group represented by the formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 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, turfenyl, 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 the 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. , These are substituted with alkyl.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, 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 butyldi i-propylsilyl, sec-butyldii-propylsilyl, and t-butyldii-propylsilyl.

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 tricyclopentylsilyl and tricyclohexylsilyl.

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. As a specific example of, the above-mentioned group can be mentioned.

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

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

In 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. Cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tri. Cycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, the adjacent groups of R ²¹ to R ²⁸ are bonded to each other to form a hydrocarbon ring. An aryl ring or a heteroaryl ring may be formed, and R ²⁹ is a hydrogen or an aryl which may be substituted.
It is preferable that Y in the formula (A) is —O—.

The "alkyl" of the "optionally substituted alkyl" in R ²¹ to 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, decahydroazurenyl 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 preferably 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-terfenylyl, o-terfenylyl, p-terphenylyl). , Acenafutyrenyl, fluorenyl, phenylenyl, phenanthrenyl which is a condensed tricyclic system, triphenylenyl, pyrenyl, naphthalenyl which is a condensed tetracyclic system, perylenyl, pentasenyl which is a condensed pentacyclic system, and the like.

Examples of the "heteroaryl" of the "optionally substituted heteroaryl" in R ²¹ to R ²⁸ include heteroaryl having 2 to 30 carbon atoms, and heteroaryl having 2 to 25 carbon atoms is preferable. Heteroaryls having 2 to 20 carbon atoms 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, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. Examples thereof include phenazinyl, indolidinyl, frill, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo [b] thienyl, dibenzothienyl, frazanyl, thiantrenyl, naphthobenzofuranyl, naphthobenzothienyl and the like.

Examples of the “alkoxy” of the “optionally substituted alkoxy” in R ²¹ to R ²⁸ include a straight chain having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. Aalkoxy having 1 to 18 carbon atoms (alkoxy of a branched chain having 3 to 18 carbon atoms) is preferable, and an alkoxy having 1 to 12 carbon atoms (alkoxy of a branched chain 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 the above-mentioned R ²¹ to R ²⁸ . 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. You can cite the groups described. 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 and cyclobutyl.

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-butyldi i-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 "tricycloalkyl silyl" 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. Examples include decahydronaphthalenyl and decahydroazurenyl.

Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of the dialkyl cycloalkylsilyl 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 Cyril 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 aminos in which two hydrogens are substituted with aryl or heteroaryl. The amino in which the two hydrogens were substituted with aryl was the diaryl (the two aryls may not be attached to each other or may be attached via a linking group) substituted amino, and the two hydrogens were substituted with heteroaryl. Aminos are diheteroaryl substituted aminos, and aminos in which two hydrogens are substituted with aryls and heteroaryls are aryl heteroaryl substituted aminos. 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.

Some of the groups described as R ²¹ to R ²⁸ 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 "> N-R ²⁹ " as Y is an aryl that may be hydrogen or substituted, and as this aryl, the group described as "aryl" in R ²¹ to R ²⁸ described above can be cited. 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 the ring is not formed is the group represented by the following formula (A-1), and the case where the ring is formed is, for example, the group represented by the following formulas (A-2) to (A-14). Will be. The at least one hydrogen in the group represented by any of the formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, and the like. Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryls may not be attached to each other or may be attached via a linking group) substituted amino, diheteroaryl substituted amino, aryl Heteroaryl Substitution May be substituted with amino, halogen, hydroxy or cyano.

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

The group represented by the formula (A) is a group obtained by removing one hydrogen at any position of the formula (A), and * indicates the position. That is, the group represented by the formula (A) may have any position as the bonding position. For example, any carbon atom on two benzene rings in the structure of formula (A), or any of R ²¹ to R ²⁸ in the structure of formula (A) formed by bonding adjacent groups to each other. An atom on the ring of, or any position in R ²⁹ at "> N-R ²⁹ " as Y in the structure of formula (A), or N (R ²⁹ is bonded) at "> N-R ²⁹ ". It can be a base that directly binds to (becomes a hand). The same applies to the group represented by any of the formulas (A-1) to (A-14).

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

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

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

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

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

In formula (3-H2), Ar ^c is an aryl that may be substituted or a heteroaryl that may be substituted, and R ^c is hydrogen, alkyl, or cycloalkyl, which is Ar ¹¹ , Ar ¹² . , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ , respectively, are hydrogen, optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted, respectively. Good diarylamino (two aryls are not attached to each other or may be attached via a linking group), diheteroarylamino which may be substituted (two heteroaryls are not attached to each other or attached to each other). Aryl heteroarylamino may be substituted (which may be attached via a single bond or a linking group), or the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group. May be), alkyl optionally substituted, cycloalkyl optionally substituted, alkenyl optionally substituted, alkoxy optionally substituted, aryloxy optionally substituted, aryloxy optionally substituted A good arylthio, or a optionally substituted silyl, at least one hydrogen in the compound of formula (1) may be substituted with a halogen, cyano, or dehydrogen.

"Aryls that may be substituted", "heteroaryls that may be substituted", and diarylaminos that may be substituted (whether the two aryls are bonded to each other) in the formula (3-H2). , May be attached via a linking group) ”,“ May be substituted diheteroarylamino (two heteroaryls are not bound to each other, or are single-bonded or bonded via a linking group). May) "," optionally substituted aryl heteroarylamino (two heteroaryls may not be attached to each other, or may be attached via a single bond or a linking group) "," may be substituted. Good alkyl, "may be substituted cycloalkyl", "may be substituted alkenyl", "may be substituted alkoxy", "may be substituted aryloxy", "may be substituted" The definition of "may be arylthio" or "may be substituted silyl" is the same as that given in the above formula (3-H), and the explanation in the formula (1) can be quoted.

The "may be substituted aryl" is preferably a group represented by any of the following formulas (3-H2-X1) to (3-H2-X8).

In the formulas (3-H2-X1) to (3-H2-X8), * indicates the binding position. In the formulas (3-H2-X1) to (3-H2-X3), Ar ²¹ , Ar ²² and Ar ²³ are independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, respectively. Phenyltril, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthrasenyl, or a group represented by the formula (A). In the description of the formula (3-H2), the group represented by the formula (A) is the same as that described for the anthracene compound represented by the formula (3-H).

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

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

Examples of the "optionally substituted heteroaryl" include a group represented by the formula (A). In addition, specific examples of the "optionally substituted aryl" and the "optionally substituted heteroaryl" include dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl and the like.

At least one hydrogen in the compound represented by the formula (1) may be substituted with halogen, cyano, or deuterium. Examples of the "halogen" in this case include fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogen in the compound represented by the formula (3-H2) is replaced with deuterium is preferable.

In formula (3-H2), R ^c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, more preferably hydrogen.
In formula (3-H2), at least two of Ar ¹¹ to Ar ¹⁸ are preferably substituted aryls or substituted heteroaryls. That is, in the anthracene compound represented by the formula (3-H2), at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring. It is preferable to have the above-mentioned structure.

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

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

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

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

In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ^18'are independent of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthril, fluorenyl, benzofluorenyl. , Chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A), and at least one hydrogen in these groups is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofur. It may be substituted with olenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A). Here, when the hydrogen of methylene in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other in a single bond. Instead of hydrogen, the carbon atom of the anthracene ring to which Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ^18'are not bonded is methyl or t-Butyl may be bonded.

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ^18'are substituted or unsubstituted phenyls or substituted or unsubstituted naphthyls, respectively. In some cases, it is preferable that the group is represented by any of the above formulas (3-H2-X1) to (3-H2-X7).

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ^18'are independent of phenyl, biphenylyl (particularly biphenyl-2-yl or biphenyl), respectively. -4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or represented by any of the above formulas (A-1) to (A-4). The groups are more preferably phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formulas (A-1) to (A-4). It may be substituted with a group represented by either.

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

As a particularly preferable anthracene compound represented by the formula (3-H2), an anthracene compound represented by the following formula (3-H2-Aa) can be mentioned.

In formula (3-H2-Aa), Ar ^c ', Ar ¹⁴ ', and Ar ^15'are independent of each other, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl. , Or a group represented by any of the above formulas (A-1) to (A-11), and at least one hydrogen in these groups is phenyl, biphenylyl, terfenylyl, naphthyl, phenanthryl, fluorenyl, benzo. It may be substituted with fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of the formulas (A-1) to (A-11). Here, when the hydrogen of methylene in fluorenyl and benzofluorenyl are both substituted with phenyl, these phenyls may be bonded to each other in a single bond. Further, the carbon atom on the anthracene ring to which Ar ^c ', Ar ¹⁴ ', and Ar ^15'are not bonded may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by the formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (3-H2-Aa) may be substituted. It has been replaced by deuterium.

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

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

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

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

The above-mentioned anthracene compound is a compound having a reactive group at a desired position in the anthracene skeleton, and if it is an anthracene compound represented by the formula (3-H), X, Ar ⁴ and the structure of the formula (A) and the like. It can be produced by applying a Suzuki coupling, a Negishi coupling, or another known coupling reaction using a compound having a reactive group in its structure 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 [089] to [0175] of International Publication No. 2014/141725 can be referred to.

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

In equation (4-H),
R ¹ to R ¹⁰ are independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4-H) via a linking group), and diarylamino (2). The two aryls are not attached to each other or may be attached via a linking group), diheteroarylamino (the two heteroaryls are not attached to each other, or are attached through a single bond or a linking group). Aryl heteroarylamino (aryls and heteroaryls may not be attached to each other or may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ may be independently bonded to form a fused ring or a spiro ring, and at least one hydrogen in the formed ring is aryl. Heteroaryl (the heteroaryl may be attached to the formed ring via a linking group), diarylamino (the two aryls may not be attached to each other or may be attached via a linking group). ), Diheteroarylamino (two heteroaryls are not attached to each other, or may be attached via a single bond or a linking group), aryl heteroarylamino (aryl and heteroaryl are not attached to each other). , Can be attached via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, in which at least one hydrogen is aryl, heteroaryl, alkyl or cyclo. It may be substituted with an alkyl, or at least one hydrogen in the compound represented by the formula (4-H) may be substituted with a halogen, cyano or a heavy hydrogen.

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

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 alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, It is 3-hexenyl, 4-hexenyl, or 5-hexenyl.

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.

From formula (4- ^Ar1 ) to formula (4-Ar5), Y1 is independently O, S or N-R, and R is phenyl, biphenylyl, naphthyl, anthrasenyl or hydrogen, respectively, and formula (4-Ar1). At least one hydrogen in the structure of formula (4-Ar5) from 4-Ar1) may be substituted with phenyl, biphenylyl, naphthyl, anthrasenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

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

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 or R ⁷ and R ⁸ in the equation (4-H) are independent of each other. They may be bonded to form a fused ring, and R ⁹ and R ¹⁰ may be bonded to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring fused to the benzene ring in the formula (4-H), 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-H) 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-H), 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 formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3). , A compound in which a benzene ring formed by bonding R ¹ and R ² in the formula (4-H) is condensed, and a benzene ring formed by bonding R ³ and R ⁴ in the formula (4-H), respectively. Is a condensed compound, and is a compound to which none of ^R1 to R8 is bound ⁱⁿ the formula (4-H).

The definitions of R ¹ to R ¹⁰ in equations (4-H-1), (4-H-2) and (4-H-3) are the corresponding R ¹ to R ¹⁰ in equation (4-H). It is the same, and the definitions of R ¹¹ to R ¹⁴ in the formula (4-H-1) and the formula (4-H-2) are the same as those of R ¹ to R ¹⁰ in the formula (4-H).

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

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). Same as the corresponding R ² to R ⁷ , and the definitions of R ¹¹ to R ¹⁴ in equations (4-1A) and (4-2A) are also R ¹¹ in equations (4-1) and (4-2). ^Is the same as R14.

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

As a more specific example of the fluorene compound as the host of the present invention, there is a compound represented by the following structural formula. In addition, "Me" indicates methyl.

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

In formula (5-H), R ¹ to R ¹⁶ are independently bonded to hydrogen, aryl, and heteroaryl (the heteroaryl is bound to the dibenzocrisen skeleton in formula (5-H) via a linking group, respectively. (May be), diarylamino (two aryls are not attached to each other or may be attached via a linking group), diheteroarylamino (two heteroaryls are not attached to each other or are single bonded). Alternatively, they may be attached via a linking group), aryl heteroarylamino (aryl and heteroaryl may not be bonded to each other, or may be single-bonded or bonded via a linking group), alkyl, cycloalkyl, It is alkenyl, alkoxy or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and adjacent groups of R ¹ to R ¹⁶ are bonded to each other. A fused ring may be formed, and at least one hydrogen in the formed ring may be aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), or diarylamino. (Two aryls may not be attached to each other or may be attached via a linking group), diheteroarylamino (two heteroaryls may not be attached to each other, or may be attached via a single bond or a linking group). (May be), aryl heteroarylamino (aryl, heteroaryl may not be attached to each other, or may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy. It may be substituted, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the compound represented by the formula (5-H) is halogen. It may be substituted with cyano or heavy hydrogen.

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

Examples of the alkenyl in the definition of the formula (5-H) 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 carbon atoms. Alkenyl of -6 is more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, It is 3-hexenyl, 4-hexenyl, or 5-hexenyl.

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.

From formula (5- ^Ar1 ) to formula (5-Ar5), Y1 is independently O, S or N-R, and R is phenyl, biphenylyl, naphthyl, anthrasenyl or hydrogen, respectively, and formula (5-Ar1). At least one hydrogen in the structure of formula (5-Ar5) from 5-Ar1) may be substituted with phenyl, biphenylyl, naphthyl, anthrasenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

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

The compound represented by the formula (5-H) 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-H) are independently hydrogen, phenyl, biphenylyl, naphthyl and anthrasenyl, respectively. , Phenentrenyl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (having the structure). The monovalent group is via phenylene, biphenylene, naphthylene, anthrasenylene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- via formula (5-). It may be bonded to the dibenzoclysen skeleton in H)), and is preferably methyl, ethyl, propyl, or butyl.

The compounds represented by the formula ^{( 5 -} H) are more preferably ^R1 , ^R2 , ^R4 , ^R5 , ^R7 , R8, R9, R10, ^R12 , ^R13 , ^R15 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 formula (5-H) is a single bond, phenylene, biphenylene, Equation (5-Ar1), Equation (5-Ar2), via -OCH _{2 CH 2-, -CH 2 CH 2 O-, or -OCH 2 CH 2 O- , naphthylene ,} anthrasenylene, methylene, ethylene, A monovalent group having a structure of formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5), wherein a monovalent group having a structure other than the at least one (that is, having the structure) is substituted. (Other than position) is hydrogen, phenyl, biphenylyl, naphthyl, anthrasenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these is phenyl, biphenylyl, naphthyl, anthrasenyl, methyl, ethyl, propyl, or, It may be substituted with butyl.

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

A more specific example of the dibenzochrysene compound as the host of the present invention is a compound represented by the following structural formula. In addition, "tBu" indicates t-butyl.

The above-mentioned materials for the light emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound 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.

<Light emitting layer containing an assisting dopant and an eliminating dopant>
The light emitting layer in the organic electroluminescent device may include a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. It is also preferable to use the polycyclic aromatic compound of the present invention as an emtituting dopant. As the assisting dopant (compound), a thermally active delayed phosphor can be used.

In the following description, an organic electroluminescent device that uses a thermally activated delayed fluorescent substance as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). The "host compound" in the TAF element means that the excitation singlet energy level obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum is a thermally active delayed phosphor as the second component and Emi as the third component. It means a compound that is higher than the ting dopant.

A "thermally activated delayed fluorescent substance" absorbs thermal energy, causes an inverse intersystem crossing from an excited triplet state to an excited singlet state, and radiates delayed fluorescence from the excited singlet state. It means a possible compound. However, "thermally activated delayed fluorescence" includes those that undergo higher-order triplets in the excitation process from the excited triplet state to the excited singlet state. For example, a paper by Durham University Monkman et al. (NATURE COMMUNICATIONS, 7: 13680, DOI: 10.1038 / ncomms13680), a paper by AIST Hosogai et al. (Hosokai et al., Sci. Adv. 2017; 3: e1603282), Kyoto. Paper by Sato et al. (Scientific Reports, 7: 4820, DOI: 10.1038 / s41598-017-05007-7) and presentation by Sato et al., Kyoto University (98th Annual Meeting of the Chemical Society of Japan, presentation number: 2I4- 15. Mechanism of high-efficiency light emission in organic electric field light emission using DABNA as a light-emitting molecule, Graduate School of Engineering, Kyoto University). In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300 K, it is determined that the target compound is a "thermoactive delayed phosphor" when a slow fluorescence component is observed. Here, the slow fluorescence component means a fluorescence component having a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.).

The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermoactive delayed phosphor" functions as an assisting dopant that assists the emission of the polycyclic aromatic compound of the present invention. Can be done.

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF element using a general fluorescent dopant as an emtituting dopant (ED). In the figure, the energy level in the base state of the host is E (1, G), the excitation single-term energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the host is E (1, S, Sh), and the host. The excitation triplet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum is E (1, T, Sh), and the energy level of the base state of the assisting dopant, which is the second component, is E (2, G). The excitation single-term energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the assisting dopant, which is the second component, is E (2, S, Sh), and the phosphorescence spectrum of the assisting dopant, which is the second component. The excited triple-term energy level obtained from the shoulder on the short wavelength side is E (2, T, Sh), and the basic energy level of the emitting dopant, which is the third component, is E (3, G), the third component. The excitation single-term energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant is E (3, S, Sh), and the phosphorus light spectrum of the emitting dopant, which is the third component, is on the short wavelength side. Let E (3, T, Sh) be the excited triple-term energy level obtained from the shoulder. When a general fluorescent dopant is used as the emtituting dopant (ED) in the TAF element, the energy up-converted by the assisting dopant becomes the excited singlet energy level E (3, S, Sh) of the emtiting dopant. It emits light in transition. However, some of the excited triplet energies E (2, T, Sh) on the assisting dopant may be transferred to the excited triplet energy level E (3, T, Sh) of the emerging dopant or on the emerging dopant. Intersystem crossing from the excited single-term energy level E (3, S, Sh) to the excited triple-term energy level E (3, T, Sh) occurs at, and subsequently heats to the ground state E (3, G). Inactive. Due to this path, some energy is not used for light emission, resulting in wasted energy.

On the other hand, in the organic electroluminescent device of this embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, whereby high light emission efficiency can be realized. This is presumed to be due to the following light emission mechanism.

FIG. 3 shows a preferable energy relationship in the organic electroluminescent device of this embodiment. In the organic electroluminescent device of this embodiment, the compound having a boron atom as an emtiting dopant has a high excited triplet energy level E (3, T, Sh). Therefore, even when the excited singlet energy up-converted by the assisting dopant crosses intersystem crossing to the excited triplet energy level E (3, T, Sh) by the emerging dopant, it is on the eliminating dopant. It is up-converted or recovered to the excited triplet energy level E (2, T, Sh) on the assisting dopant (thermoactive delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. In addition, by dividing the functions of up-conversion and luminescence into two types of molecules, which are good at each, it is expected that the residence time of high energy will be reduced and the burden on the compound will be reduced.

In this embodiment, known host compounds can be used, and examples thereof include compounds having at least one of a carbazole ring and a furan ring, among which at least one of furanyl and carbazolyl, and arylene and heteroarylene. It is preferable to use a compound in which at least one of the above is bound. Specific examples include mCP and mCBP.

The excited triple-term energy level E (1, T, Sh) obtained from the shoulder on the peak short wavelength side of the phosphorous spectrum of the host compound is a light emitting layer from the viewpoint of promoting the generation of TADF in the light emitting layer without inhibiting it. It is preferable that it is higher than the excited triple-term energy levels E (2, T, Sh) and E (3, T, Sh) of the emitting dopant or the assisting dopant having the highest excited triple-term energy level. Specifically, the excited triple-term energy level E (1, T, Sh) of the host compound is 0.01 eV or more as compared with E (2, T, Sh) and E (3, T, Sh). Preferably, 0.03 eV or more is more preferable, and 0.1 eV or more is further preferable. Further, a TADF active compound may be used as the host compound.

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

<Thermal active delayed phosphor (assisting dopant)>
Thermally activated delayed fluorescent substances (TADF compounds) used in TAF elements use intramolecular HOMO (Highest Occupied Molecular Orbital) and LUMO using electron-donating substituents called donors and electron-accepting substituents called acceptors. Donor-Acceptor Thermally Activated Delayed Fluorescence (DA-A TADF Compound) designed to localize (Lowest Unoccupied Molecular Orbital) and cause efficient reverse intersystem crossing. ) Is preferable. Here, the "electron-donating substituent" (donor) in the present specification means a substituent and a partial structure in which the HOMO orbital is localized in the thermally active delayed phosphor molecule, and "electrons". The "acceptor" (acceptor) is meant to mean a substituent and a partial structure in which the LUMO orbital is localized in a thermally active delayed phosphor molecule.

In general, a thermally activated delayed fluorescent substance using a donor or an acceptor has a large spin-orbit coupling (SOC) due to its structure and a small exchange interaction between HOMO and LUMO (ST). ) Is small, so a very fast intersystem crossing speed can be obtained. On the other hand, the thermally active delayed fluorophore using a donor or acceptor has a large structural relaxation in the excited state (for some molecules, the stable structure differs between the ground state and the excited state, so it is excited from the ground state by an external stimulus. When the conversion to the state occurs, the structure then changes to a stable structure in the excited state), and since it gives a wide emission spectrum, it may reduce the color purity when used as a light emitting material.

As the heat-activated delayed fluorophore in the TAF device, for example, a compound to which the donor and the acceptor are bound directly or via a spacer can be used. Examples of the electron-donating group (donor-like structure) and electron-accepting group (acceptor-like structure) used in the heat-active delayed phosphor of the present invention include Chemistry of Materials, 2017, 29, 1946-1963. The described structure can be used. As donor structures, carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindrocarbazole, phenylbicarbazole, bicarbazole, turcarbazole , Diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butyl) phenyl) amine, (diphenylamino) phenyl) diphenylbenzenediamine, dimethyltetraphenyl Examples thereof include dihydroacridindiamine, tetramethyl-dihydro-indenoaclydin and diphenyl-dihydrodibenzoazacillin. Acceptable structures include sulfonyldibenzene, benzophenone, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazol. , Benzenethiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzoimidazole, dibenzoquinoxalin, heptaazaphenalene, thioxanthonedioxide, dimethylanthrasenone, anthracendione, cycloheptabipyridine, full orange carbonitrile, Triephenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis (phenylsulfonyl) benzene, dimethylthioxanthendioxide, thianthrenetetraoxide and tris (dimethylphenyl) ) Benzene can be given. In particular, compounds having thermally activated delayed fluorescence in TAF elements have carbazole, phenoxazine, aclysine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, as partial structures. It is preferably a compound having at least one selected from oxadiazole, thiadiazole and benzophenone.

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

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

In the above formulas (AD1), (AD2) and (AD3), M is a single bond, —O—,> N—Ar or> CAR ₂ , respectively, and the depth of HOMO of the partial structure to be formed. And in terms of the height of the excited singlet energy level and the excited triplet energy level, it is preferably singlet, —O— or> N—Ar. J is a spacer structure that separates the donor substructure and the acceptor substructure, each of which is an arylene having 6 to 18 carbon atoms, and is a conjugate that exudes from the donor substructure and the acceptor substructure. From the viewpoint of the size of the alloyene, an arylene having 6 to 12 carbon atoms is preferable. More specifically, phenylene, methylphenylene and dimethylphenylene can be mentioned. Q is independently = C (-H)-or = N-, and is a viewpoint of the shallowness of LUMO and the height of the excited singlet energy level and the excited triplet energy level of the forming partial structure. Therefore, preferably = N−. Ar is a partial structure formed independently of hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 18 carbon atoms. From the viewpoint of the depth of HOMO and the height of the excited single-term energy level and the excited triple-term energy level, hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, and a carbon number of carbon atoms are preferable. It is an alkyl of 1 to 4 or a cycloalkyl of 6 to 10 carbon atoms, more preferably hydrogen, phenyl, trill, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazil, carbazolyl, dimethylcarbazolyl, di tert-butyl. Carbazolyl, benzoimidazole or phenylbenzoimidazole, more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2. n is an integer of (6-m) or less, and is preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance. Further, at least one hydrogen in the compound represented by each of the above formulas may be substituted with halogen or deuterium.

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

The compound used as the second component of this embodiment may be a donor acceptor type TADF compound represented by DA in which one donor D and one acceptor A are directly bound or bound via a linking group. The organic field light emitting element has more excellent characteristics when it has a structure represented by the following formula (DAD1) in which a plurality of donors D are directly bonded to one acceptor A or bonded via a linking group. It is preferable because it becomes a thing.

(D1-L ¹ ) n- ^{A 1 (} DAD1)

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

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In formula (DAD1) and ^formula (DAD2), D1 ^, D2 and D3 ^each independently represent a donor group. As the donor group, the above-mentioned donor structure can be adopted. A ¹ and A ² each independently represent an acceptor group. As the acceptor group, the above-mentioned acceptor structure can be adopted. L ¹ , L ² and L ³ independently represent a single bond or conjugated linking group, respectively. The conjugated linking group has a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, and more preferably an acceptor group having 6 to 12 carbon atoms. It is more preferable that L ¹ , L ² and L ³ are independently phenylene, methylphenylene or dimethylphenylene, respectively. In the formula (DAD1), n is 2 or more and represents an integer equal to or less than the maximum ^number that A1 can replace. For example, n may be selected within the range of 2 to 10 or may be selected within the range of 2 to 6. When n is 2, it becomes a compound represented by the formula (DAD2). The n D ^1s may be the same or different, and the n L ^1s may be the same or different. Preferred specific examples of the compounds represented by the formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, and the second component that can be adopted in the present invention is these compounds. Not limited.

In this embodiment, the light emitting layer may be either a single layer or a plurality of layers. Further, the host compound, the thermally active delayed fluorescent substance and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component may be contained in each of a plurality of layers. The host compound, the thermally active delayed fluorescent substance, and the polycyclic aromatic compound of the present invention contained in the light emitting layer may be one kind or a plurality of combinations, respectively. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as a matrix. The light emitting layer doped with the assisting dopant and the emitting dopant is a method of forming a film of the host compound, the assisting dopant and the emitting dopant by a ternary co-deposition method, and the host compound, the assisting dopant and the emitting dopant are mixed in advance. Then, it can be formed by a method of vapor deposition at the same time, a wet film forming method, etc., in which a composition (paint) for forming a light emitting layer prepared by dissolving a host compound, an assisting dopant, and an emitting dopant in an organic solvent is applied. can.

The amount of the host compound used varies depending on the type of the host compound, and may be determined according to the characteristics of the host compound. The guideline for the amount of the host compound used is preferably 40 to 99.99% by mass, more preferably 50 to 99.99% by mass, and further preferably 60 to 99.9% by mass of the entire material for the light emitting layer. Is. The above range is preferred, for example, in terms of efficient charge transport and efficient energy transfer to the dopant.

The amount of the assisting dopant (thermoactive delayed phosphor) used varies depending on the type of the assisting dopant and may be determined according to the characteristics of the assisting dopant. The guideline for the amount of the assisting dopant used is preferably 1 to 60% by mass, more preferably 2 to 50% by mass, and further preferably 5 to 30% by mass of the entire material for the light emitting layer. Within the above range, for example, energy can be efficiently transferred to the emerging dopant.

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

It is preferable that the amount of the emitting dopant used is low because the concentration quenching phenomenon can be prevented. A high concentration of the assisting dopant is preferable from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the emitting dopant used is lower than the amount of the assisting dopant used.

<2-1-3. 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 to have less elution ions from the glass, but soda lime glass with a barrier coat such as SiO ₂ is also commercially available, so it is possible to use this. 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 surface, and a synthetic resin plate, film or sheet having a particularly low gas barrier property may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<2-1-4. Anode in organic electroluminescent device>
The anode 102 serves to inject holes into the light emitting layer 105. If any one of the hole injection layer 103 and the transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 via these. ..

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, etc. Examples of the organic compound include polythiophene such as poly (3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from the substances used as the anode of the organic EL element.

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

<2-1-5. Hole injection layer, 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 serves to efficiently transport the holes injected from the anode 102 or the 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 forming the hole injection layer 103 and the hole transport layer 104, the hole injection layer of a compound, a p-type semiconductor, or an organic EL element conventionally used as a hole charge transport material in a photoconductive material. And any compound can be selected and used from the known compounds used for the hole transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis (N-arylcarbazole) or bis (N-alkylcarbazole), and triarylamine derivatives (4,4', 4 "-Tris (N-carbazolyl) triphenylamine, polymer with aromatic tertiary 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, N4, ^{N4' -} diphenyl-N4, ^{N4' -} bis (9-phenyl-9H-carbazole-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 (triphenylamine derivatives such as 3-methylphenyl (phenyl) amino) triphenylamine, starburstamine derivatives, etc.), stylben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.) , Pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxalin derivatives (eg 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10, 11-Hexacarbonitrile and the like), heterocyclic compounds such as porphyrin derivatives, polysilane and the like. In the polymer system, polycarbonate or styrene derivative having the monomer in the side chain, polyvinylcarbazole, polysilane, etc. are preferable, but a thin film necessary for manufacturing a light emitting device can be formed, holes can be injected from the anode, and holes can be further injected. Is not particularly limited as long as it is a compound capable of transporting.

It is also known that the conductivity of organic semiconductors is strongly affected by its doping. Such an organic semiconductor matrix material 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 tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (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." .Pfeiffer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (6), 729-731 (1998) "). They generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material changes considerably. As the matrix substance having the hole transport property, for example, a benzidine derivative (such as TPD) or a starburst amine derivative (such as TDATA), or a specific metal phthalocyanine (particularly, zinc phthalocyanine (ZnPc)) is known (such as zinc phthalocyanine (ZnPc)). Japanese Unexamined Patent Publication No. 2005-167175). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

<2-1-6. Electroluminescent layer in organic electroluminescent device>
An electron blocking layer may be provided between the hole injection / transport layer and the light emitting layer to prevent the diffusion of electrons from the light emitting layer. For the formation of the electron blocking layer, a compound represented by any of the above formulas (H1), (H2) and (H3) can be used. The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

<2-1-7. Electron injection layer, electron transport layer in organic electroluminescent device>
The electron injection layer 107 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 serves to efficiently transport 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 that controls the electron injection from the cathode and further transports the 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, the effect of improving the luminous efficiency is equivalent to that of a material having a 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, it is used for a compound conventionally used as an electron transfer compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic EL element. It can be arbitrarily selected and used from known known compounds.

The material used for the electron transport layer or the electron injection layer is a compound composed of an aromatic ring or a complex aromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus. It preferably contains at least one selected from a pyrrole derivative, a fused 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. , Quinone derivatives such as anthraquinone and diphenoquinone, phosphoroxide derivatives, arylnitrile 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, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, and diphenylquinone derivatives. , Perylene derivative, oxadiazole derivative (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene, etc.), thiophene derivative, triazole derivative (N-naphthyl-2,5-diphenyl) -1,3,4-triazole, etc.), thiadiazole derivative, metal complex of oxine derivative, quinolinol metal complex, quinoxalin derivative, polymer of quinoxalin derivative, benzazole compound, gallium complex, pyrazole derivative, perfluorophenylene derivative, triazine Derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis (benzo [h] quinoline-2-yl) -9,9'-spirobifluorene, etc.), imidazole pyridine derivatives, borane derivatives, benzoimidazole derivatives (triss) (N-phenylbenzoimidazole-2-yl) benzene, etc.), benzoxazole derivative, thiazole derivative, benzothiazole derivative, quinoline derivative, oligopyridine derivative such as telpyridine, bipyridine derivative, telpyridine derivative (1,3-bis (4') -(2,2': 6', 2 "-telpyridinyl)) benzene, etc.), naphthylidine derivatives (bis (1-naphthyl) -4- (1,8-naphthylidine-2-yl) phenylphosphine oxide, etc.), aldazine Examples thereof include derivatives, pyrimidine derivatives, arylnitrile derivatives, indol derivatives, phosphoroxide derivatives, bisstyryl derivatives, silol derivatives and azoline derivatives.

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, azomethin complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes can be used. can give.

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

Among the above-mentioned materials, borane derivative, pyridine derivative, fluorentene derivative, BO derivative, anthracene derivative, benzofluorene derivative, phosphinoxide derivative, pyrimidine derivative, arylnitrile derivative, triazine derivative, benzoimidazole derivative, phenanthroline derivative, quinolinol metal. Complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives are preferred.

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

The electron transport layer or 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 (2.15 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 improved. Further, as a reducing substance having a work function of 2.9 eV or less, a combination of these two or more kinds of alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By containing Cs, the reducing ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, the emission brightness and the life of the organic EL device can be improved.

<2-1-8. 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 the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium or their alloys (magnesium-silver alloy, magnesium). -Indium alloy, aluminum such as lithium fluoride / aluminum-lithium alloy, etc.) are preferable. 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.

<2-1-9. Bundling agent that may be used in each layer>
The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer 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 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. be.

<2-1-10. Manufacturing method of organic electroluminescent device>
Each layer constituting the organic EL element is made of a material to be formed of each layer, such as thin film deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, inkjet method, spin coating method or casting method, coating method, etc. It can be formed by forming a thin film by the method. The film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured by a crystal oscillation type film thickness measuring device or the like. When thinning using a thin film method, the thin film 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.

Next, as an example of a method for manufacturing an organic EL element, an organic EL element 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. 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 device, it is also possible to reverse the production order and manufacture 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 in this order. Is.

When a DC voltage is applied to the organic EL element thus obtained, the anode may be applied as a + and the cathode as a negative polarity, and when a voltage of about 2 to 40 V is applied, a transparent or translucent electrode may be applied. Light 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.

<2-1-11. Application example of organic electroluminescent device>
The organic EL element can also be applied to a display device, a lighting device, or 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 and a known drive device, and a known drive method such as DC drive, pulse drive, or AC drive can be used. It can be driven by using it 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 and JP-A-2003-321546. See Japanese Patent Publication No. 2004-281806, etc.). Further, as the display method of the display, for example, any one of the matrix method and the segment method can be mentioned. The matrix display and the segment display may coexist in the same panel.

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

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

Examples of the lighting device include a lighting device such as an indoor lighting device, a backlight of a liquid crystal display device, and the like (for example, JP-A-2003-257621, JP-A-2003-277471, 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 liquid crystal display devices, especially for personal computers, where thinning is an issue, it is difficult to make the backlight thinner because the conventional method consists of fluorescent lamps and light guide plates. The backlight using the is thin and lightweight.

<2-2. Other organic devices>
The polycyclic aromatic compound according to the present invention can be used for manufacturing an organic field effect transistor, an organic thin film solar cell, or the like, in addition to the above-mentioned organic field light emitting device.

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 dammed 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. As the organic thin-film solar cell, known materials used for the organic thin-film solar cell can be appropriately selected and used in combination.

<3. Wavelength conversion material>
The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.
At present, application of multicoloring technology by a color conversion method to liquid crystal displays, organic EL displays, lighting, and the like is being actively studied. The color conversion means converting the light emitted from the light emitter into light having a longer wavelength, for example, converting ultraviolet light or blue light into green light or red light. By forming a wavelength conversion material having this color conversion function into a film and combining it with, for example, a blue light source, it is possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. A white light source that combines such a blue light source and a wavelength conversion film having a color conversion function is used as a light source unit, and a full-color display can be manufactured by combining the liquid crystal drive portion and a color filter. Further, if there is no liquid crystal drive portion, it can be used as it is as a white light source, and can be applied as a white light source such as LED lighting. Further, by using a blue organic EL element as a light source and using it in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to manufacture a full-color organic EL display without using a metal mask. Further, by using a blue micro LED as a light source and using it in combination with a wavelength conversion film that converts blue light into green light and red light, it is possible to manufacture a low-cost full-color micro LED display.

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

The composition for wavelength conversion may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Effect 2016/190283 can be used. As other additives, the compounds described in paragraphs 0177 to 0181 of International Effect 2016/190283 can be used. As the solvent, the description of the solvent contained in the above-mentioned composition for forming a light emitting layer can be referred to.

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

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

Synthesis example (1):
Synthesis of compound (1-1)

Under a nitrogen atmosphere, intermediate (X-1) (50.0 g), 1-t-butyl-3,4,5-trichlorobenzene (32.0 g), dichlorobis (di-t-butyl (4-t-butyl) (4-t-butyl) as a palladium catalyst Dimethylaminophenyl) phosphino) palladium (Pd-132) (0.909 g), sodium-t-butoxide (NaOtBu, 18.5 g) and toluene (500 ml) were placed in a flask and heated at 120 ° C. for 5 hours. After completion of the reaction, water and ethyl acetate were added to the reaction solution, and the mixture was stirred, and then the organic layer was separated and washed with water. Then, the crude product obtained by concentrating the organic layer was purified by a silica gel short pass column (eluent: heptane) to obtain 49.3 g of an intermediate (X-2).

Intermediate (X-2) (30.0 g), Intermediate (X-3) (26.6 g), Pd-132 (0.719 g) as palladium catalyst, NaOtBu (7.32 g) and toluene under nitrogen atmosphere. (300 ml) was placed in a flask and heated at 120 ° C. for 3 hours. After completion of the reaction, water and ethyl acetate were added to the reaction solution, and the mixture was stirred, and then the organic layer was separated and washed with water. Then, the crude product obtained by concentrating the organic layer was purified by a silica gel short pass column (eluent: toluene / heptane = 1/9 (volume ratio)) to obtain 43. I got 8g.

In a flask containing the intermediate (X-4) (21.5 g) and tert-butylbenzene (tBu-benzene, 215 ml), a 1.60 M tert-butyllithium pentane solution (tBuLi) at 0 ° C. under a nitrogen atmosphere. , 25.0 ml) was added. After completion of the dropping, the temperature was raised to 70 ° C. and the mixture was stirred for 0.5 hours, and then components having a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to −50 ° C., boron tribromide (10.0 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Then, the mixture was cooled to 0 ° C. again, N, N-diisopropylethylamine (EtNiPr ₂ , 5.15 g) was added, and the mixture was stirred at room temperature until the exotherm subsided, then the temperature was raised to 100 ° C. and the mixture was heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath, and then ethyl acetate were added to separate the layers. After concentrating the organic layer, it was purified with a silica gel short pass column (eluent: chlorobenzene). The obtained crude product was recrystallized from toluene to obtain 2.05 g of compound (1-1).

The structure of the compound obtained by NMR measurement was confirmed.
^{1 1} H-NMR (CDCl ₃ ): δ = 8.96-8.86 (m, 2H), 7.66-7.55 (m, 2H), 7.40-7.24 (m, 3H), 7.16-7.06 (m, 1H), 6.95 (d, 1H), 6.72-6.64 (m, 2H), 6.42 (d, 1H), 6.20-6. 12 (m, 2H), 1.82-1.61 (m, 18H), 1.56-1.38 (m, 18H), 1.34 (s, 9H), 1.29-1.22 ( m, 15H), 1.14-1.04 (m, 9H), 0.93-0.87 (m, 12H).

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

<Evaluation method of basic physical properties>
<Preparation of sample>
When evaluating the absorption characteristics and emission characteristics (fluorescence and phosphorescence) of the compound to be evaluated, the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or may be evaluated in a thin film state. Further, in the case of evaluation in a thin film state, depending on the mode of use of the compound to be evaluated in the organic EL element, only the compound to be evaluated is thinned and evaluated, and the compound to be evaluated is dispersed in an appropriate matrix material. It may be thinned and evaluated. Here, a thin film obtained by depositing only the compound to be evaluated is referred to as a "single film", and a thin film obtained by applying a coating liquid containing the compound to be evaluated and a matrix material and drying the film is referred to as a "coating film".

As the matrix material, commercially available PMMA (polymethylmethacrylate) or the like can be used. In this example, PMMA and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent support substrate (10 mm × 10 mm) made of quartz by a spin coating method to prepare a sample.

Further, when the matrix material is a host compound, a thin film sample is prepared as follows. A transparent support substrate made of quartz (10 mm x 10 mm x 1.0 mm) is fixed to a substrate holder of a commercially available vapor deposition equipment (manufactured by Choshu Industry Co., Ltd.), and a molybdenum vapor deposition boat containing a host compound and a dopant material are inserted. After installing the molybdenum vapor deposition boat, reduce the pressure of the vacuum chamber to 5 × 10 ^-4 Pa. Next, the vapor deposition boat containing the host compound and the vapor deposition boat containing the dopant material are heated at the same time, and the host compound and the dopant material are co-deposited to an appropriate thickness to obtain the host compound and the dopant material. A mixed thin film (sample) was formed. Here, the vapor deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.

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

For the measurement of the fluorescence spectrum, the photoluminescence is measured by exciting at an appropriate excitation wavelength at room temperature. For the measurement of the phosphorescence spectrum, the sample is measured in a state of being immersed in liquid nitrogen (temperature 77K) using an attached cooling unit. In order to observe the phosphorescence spectrum, the delay time from the excitation light irradiation to the start of measurement was adjusted using an optical chopper. The sample is excited at an appropriate excitation wavelength and photoluminescence is measured.

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

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

<Evaluation of fluorescent lifetime (delayed fluorescence)>
The fluorescence lifetime was measured at 300 K using a fluorescence lifetime measuring device (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.). Specifically, the emission component having a fast fluorescence lifetime and the emission component having a slow fluorescence lifetime were observed at the maximum emission wavelength measured at an appropriate excitation wavelength. In the fluorescence lifetime measurement of a general organic EL material that emits fluorescence at room temperature, it is almost always the case that a slow emission component involving a triplet component derived from phosphorescence is observed due to the deactivation of the triplet component due to heat. do not have. When a slow emission component is observed in the compound to be evaluated, it indicates that the triplet energy having a long excitation lifetime is transferred to the singlet energy by thermal activation and observed as delayed fluorescence.

<Calculation of energy gap (Eg)>
It is calculated from the long wavelength terminal A (nm) of the absorption spectrum obtained by the above method at Eg = 1240 / A.

<Measurement of ionization potential (Ip)>
A transparent support substrate (28 mm x 26 mm x 0.7 mm) with ITO (indium tin oxide) vapor deposition fixed to a substrate holder of a commercially available vapor deposition equipment (manufactured by Choshu Industry Co., Ltd.), and molybdenum containing the target compound. After installing the vapor deposition boat, reduce the pressure of the vacuum chamber to 5 × 10 ^-4 Pa. Next, the vapor deposition boat is heated to evaporate the target compound to form a single film (Neat film) of the target compound.

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

<Calculation of electron affinity (Ea)>
The electron affinity can be estimated from the difference between the ionization potential measured by the above method and the energy gap calculated by the above method.

<Measurement of excited singlet energy level E (S, Sh) and excited triplet energy level E (T, Sh)>
For the single film of the target compound formed on the glass substrate, the fluorescence spectrum was observed at 77K with the peak on the long wavelength side as the excitation light so that the fluorescence peaks of the absorption spectrum did not overlap, and the peak on the short wavelength side of the fluorescence spectrum was observed. The excited single-term energy level E (S, Sh) is obtained from the shoulder. Further, on a single film of the target compound formed on the glass substrate, a phosphorescence spectrum was observed at 77K with a peak on the long wavelength side as nm excitation light so that the fluorescence peak of the absorption spectrum did not overlap, and the peak of the phosphorescence spectrum was short. The excited triple-term energy level E (T, Sh) is obtained from the shoulder on the wavelength side.

<Evaluation of organic EL element>
As described above, the compounds of the present invention are characterized by an appropriate energy gap (Eg), high triplet excitation energy (ET) and small _ΔEST , and thus can be applied to, for example, a light emitting layer and a charge transport layer. Can be expected, and in particular, it can be expected to be applied to the light emitting layer.

<Evaluation items and evaluation methods>
Evaluation items include drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) of emission spectrum, and full width at half maximum (nm). .. For these evaluation items, values at appropriate emission luminance can be used.

The quantum efficiency of the light emitting element includes the internal quantum efficiency and the external quantum efficiency. In the internal quantum efficiency, the external energy injected as electrons (or holes) into the light emitting layer of the light emitting element is converted into pure photons. 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 spectral radiance (emission spectrum) and the external quantum efficiency is as follows. A voltage / current generator R6144 manufactured by Advantest Co., Ltd. was used to make the element emit light by applying a voltage. The spectral radiance in the visible light region was measured from the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a perfect diffusion surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Next, the number of photons was integrated in the entire observed wavelength region to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency. Further, the full width at half maximum of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% centering on the maximum emission wavelength.

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

<Structure of organic EL element>
An organic EL device was manufactured using the polycyclic aromatic compound of the present invention.

[Element configuration A]
The material composition of each layer in the organic EL elements of Example 1 and Comparative Examples 1 to 4 is shown in Table 1 below.

In Table 1, "HI" is N ⁴ , N ^4' -diphenyl-N ⁴ , N ^4' -bis (9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl] -4, 4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexazatriphenylene hexacarbonitrile, "HT-1" is N- ([1,1'-biphenyl". ] -4-yl-9,9-dimethyl-N- [4- (9-phenyl-9H-carbazole-3-yl) phenyl] -9H-fluoren-2-amine, where "HT-2" is N , N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl)-[1,1': 4', 1 "-terphenyl] -4-amine, where "BH" is 2- (10-Phenylanthracene-9-yl) dibenzo [b, d] furan, "ET-1" is 9,9'-[(5- (6- (1,1'-biphenyl)- 4-yl) -2-phenylpyrimidine-4-yl) -1,3-phenylene] bis (9H-carbazole), and "ET-2" is 4- (6- (10-phenylanthracene-9-yl) ) Naphthalene-2-yl) pyridine. "Liq", Comparative Compound (1) (Compound described in International Publication No. 2015/102118), Comparative Compound (2) (International Publication No. 2019/132028). The chemical structure is shown below together with the comparative compound (3) (compound according to International Publication No. 2020/017931) and the comparative compound (4) (compound according to International Publication No. 2020/218079).

(Example 1)
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 180 nm by sputtering to 150 nm is used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available thin-film deposition device (manufactured by Showa Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1. A molybdenum vapor deposition boat containing ET-2 and an aluminum nitride vapor deposition boat containing Liq, LiF and aluminum were installed.

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

(Comparative Examples 1 to 4)
Comparative Example 1 in the same manner as in Example 1 except that the comparative compound (1), the comparative compound (2), the comparative compound (3), and the comparative compound (4) were used instead of the compound (1-1). To 4 organic EL elements were obtained.

<Evaluation items and evaluation methods>
Evaluation items include drive voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) of emission spectrum, half width (nm), and the like. .. For these evaluation items, for example, a value at the time of 1000 cd / m ² emission can be used.

The quantum efficiency of the light emitting element includes the internal quantum efficiency and the external quantum efficiency. In the internal quantum efficiency, the external energy injected as electrons (or holes) into the light emitting layer of the light emitting element is converted into pure photons. 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 spectral radiance (emission spectrum) and the external quantum efficiency is as follows. Using a voltage / current generator R6144 manufactured by Advantest, a voltage at which the brightness of the element becomes 1000 cd / m ² is applied to cause the element to emit light. A spectral radiance meter SR-3AR manufactured by TOPCON is used to measure the spectral radiance in the visible light region from the direction perpendicular to the light emitting surface. Assuming that the light emitting surface is a perfect diffusion 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 is integrated in the entire observed wavelength region to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency. Further, the full width at half maximum of the emission spectrum is obtained as the width between the upper and lower wavelengths at which the intensity becomes 50% centering on the maximum emission wavelength.

With respect to the organic EL elements of Examples 1 and Comparative Examples 1 to 4, a DC voltage was applied using the ITO electrode as an anode and the LiF / aluminum electrode as a cathode, and the characteristics at the time of light emission of 1000 cd / m ² were measured.
The results are shown in Table 2.

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

100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (9)

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

In equation (1),
Rings A, B, and C are independently substituted or unsubstituted aryl rings or substituted or unsubstituted heteroaryl rings;
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R, and the Si-R and the R of the Ge-R are substituted or unsubstituted. Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
X ¹ and X ² are>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and R of> N-R is hydrogen. A substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, or a monovalent group represented by the formula (G), which is the above-mentioned> C. The Rs of (-R) ₂ and> Si (-R) ₂ are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted, respectively. The two Rs of> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring. At least one R of C (-R) ₂ and> Si (-R) ₂ is single-bonded or single-bonded to at least one of the A ring and the B ring, or at least one of the A ring and the C ring. It may be bonded via a linking group.
However, at least one of X ¹ and X ² has R> N—R, which is a monovalent group represented by the formula (G).
In formula (G),
L is a single bond, alkylene, cycloalkylene, arylene or heteroarylene, at least one of which may be substituted, with the (GA) and (GB) rings being independent of each other. A substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring;
X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The> C (-R) ₂ and the> Si (-R) ₂ R are independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or It is a substituted or unsubstituted cycloalkyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ may be bonded to each other to form a ring, and the above> N-R may be formed. R, at least one R of the> C (-R) ₂ and the> Si (-R) ₂ is at least one of the (GA) ring and the (GB) ring, or the (G-). A) It may be attached to at least one of the ring and the (GB) ring via a single bond or a linking group.
At least one of the aryl ring or the heteroaryl ring in the structure in the structure represented by the formula (1) may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is substituted. At least one of -CH _2- in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by the formula (1) may be substituted with cyano, halogen, or deuterium. The polycyclic aromatic compound according to claim 1, wherein the structural unit represented by the formula (1) is the structural unit represented by the following formula (2);

In equation (2),
Z in the a ring, b ring and c ring is N or CR ^{11 independently, and R 11 of} the CR ¹¹ is independently hydrogen, aryl, heteroaryl, diarylamino, di Heteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen in these is aryl, heteroaryl, diarylamino, alkyl, May be substituted with cycloalkyl or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Two adjacent R ^11s may be coupled to each other to form an aryl ring or a heteroryl ring, wherein the formed aryl ring and heteroreel ring are aryl, heteroaryl, diarylamino, diheteroarylamino, respectively. , Arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyls, wherein at least one hydrogen thereof is aryl, heteroaryl, diarylamino, May be substituted with alkyl, cycloalkyl, or substituted silyls;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Z = Z may be independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The R of> C (-R) ₂ and the above> Si (-R) ₂ are independently hydrogen, aryl, heteroaryl, alkyl, and cycloalkyl, respectively, and at least one hydrogen in these is further aryl and hetero. It may be substituted with aryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other to form a ring. May be;
Y ¹ is B or P = O,
X ¹ and X ² are>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and R of> N-R is hydrogen. Aryl, heteroaryl, alkyl, cycloalkyl, or monovalent groups represented by the formula (G-2), wherein at least one hydrogen in these is further aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, Alternatively, it may be substituted with a substituted silyl, where the R of> C (-R) ₂ and> Si (-R) ₂ is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least in these. One hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two> C (-R) ₂ and> Si (-R) ₂ . The Rs may be coupled to each other to form a ring, and at least one R of the> N-R R, the> C (-R) ₂ and the> Si (-R) ₂ R is -O. -, -S-, -C (-R) ₂ -or may be coupled to one or two of C in Z at CR ¹¹ by single coupling, but at least one of X ¹ and X ² . Is a monovalent group in which R is represented by the formula (G-2)> N-R.
In formula (G-2),
^ZG in the GA ring and Gb ring are independently N or CR ^{12, and R 12 of} the CR ¹² is independently hydrogen, aryl, heteroaryl, and diarylamino. , Diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen in these is aryl, heteroaryl, diarylamino, May be substituted with alkyl, cycloalkyl, or substituted silyls;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Two adjacent ^R12s may be coupled to each other to form an aryl ring or a heteroreel ring, wherein the formed aryl ring and heteroreel ring are aryl, heteroaryl, diarylamino, and dihetero, respectively. It may be substituted with arylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, in which at least one hydrogen is aryl, heteroaryl, diaryl. May be substituted with amino, alkyl, cycloalkyl, or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group. The aryl of the aryl heteroarylamino and the heteroaryl are not bonded to each other or are bonded via a linking group, and the two aryls of the diallylboryl are not bonded to each other, or are single-bonded or linked. Bonded via a group;
Z ^G = Z ^G may be independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N- R, said> C (-R) ₂ and said> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, substituted alkyl, or cycloalkyl, wherein at least one hydrogen in these is hydrogen. It may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other. It may form a ring;
X ³ and X ⁴ are independently>O,>N-R,> C (-R) ₂ ,> Si (-R) ₂ ,> S, or> Se, and the above-mentioned> N-R, The R of> C (-R) ₂ and the above> Si (-R) ₂ are independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is hydrogen. , Aryl, Heteroaryl, Diarylamino, Alkyl, Cycloalkyl, or Substituted Cyril, and the two Rs of> C (-R) ₂ and> Si (-R) ₂ are bonded to each other. And at least one R of the> N-R, the> C (-R) ₂ and the> Si (-R) ₂ may be -O-, -S-,. -C (-R ¹⁴ ) ₂ -or may be bonded to one or two of ^C in ZG, which is C-R ¹² , by a single bond, and the R ¹⁴ of -C (-R ¹⁴ ) _2- , Hydrogen, alkyl, or cycloalkyl,
L is a single bond, arylene or heteroarylene, and the arylene and at least one hydrogen of the heteroarylene may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl.
At least one of the aryl ring or the heteroaryl ring in the structure represented by the formula (2) may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted. Well, at least one -CH _2- in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by the formula (2) may be substituted with cyano, halogen, or deuterium. In formula (2), Y ¹ is B, and at least one of the aryl rings or heteroaryl rings in the structure is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is. The polycyclic aromatic compound according to claim 2, which may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-. The polycyclic aromatic compound according to any one of claims 1 to 3, which is represented by the following formula.

A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 4. A pair of electrodes composed of an anode and a cathode and a light emitting layer arranged between the pair of electrodes are included, and the light emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 4. , Organic electroluminescent element. The organic electroluminescent device according to claim 6, wherein the light emitting layer contains a host and the polycyclic aromatic compound as a dopant. The organic electroluminescent device according to claim 7, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound. A display device or a lighting device provided with the organic electroluminescent element according to any one of claims 6 to 8.

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