JP2022074041A - Polycyclic aromatic compound - Google Patents

Abstract

To provide a novel polycyclic aromatic compound and an organic EL device including the same, which has a narrow half-width of an emission spectrum, has excellent color purity, and also excels in quantum efficiency and service life.SOLUTION: The present invention discloses an organic EL device that employs polycyclic aromatic compounds represented by formula (1A), (1B) as dopant materials.SELECTED DRAWING: None

Description

There is an application for exception of loss of novelty

The present invention relates to a polycyclic aromatic compound, an organic field light emitting device using the polycyclic aromatic compound, an organic field effect transistor, an organic thin film solar cell, an organic device such as a wavelength conversion filter, and a display device and a lighting device. In the present specification, the "organic electroluminescent element" may be referred to as an "organic EL element" or simply an "element".

Conventionally, display devices using electroluminescent elements that emit electric field light have been studied in various ways because they can be reduced in power consumption and thickness. Furthermore, 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 that have emission characteristics such as blue and green, which are one of the three primary colors of light, and organics that have the ability to transport charges such as holes and electrons (which have the potential to become semiconductors and superconductors). The development of materials has been actively studied regardless of whether they are high molecular weight compounds or low molecular weight compounds.

The organic EL element has a structure composed of a pair of electrodes consisting of an anode and a cathode, and one layer or a plurality of layers arranged between the pair of electrodes and containing an organic compound. 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.

Currently, three types of light emitting layer materials are used: fluorescent materials, phosphorescent materials, and thermal activated delayed fluorescent (TADF) materials. For example, benzofluorene compounds have been developed for fluorescent materials (International Publication No. 2004/061047), and noble metal complexes having polydentate ligands have been developed for phosphorescent materials (Japanese Patent Laid-Open No. 2014-239225). Issue).

In recent years, materials with improved azaborin derivatives have also been reported (International Publication No. 2015/102118). Compounds with a single peak with a narrow emission half-price range and a conjugate structure with a small energy difference (ΔS ¹ T ¹ ) between singlet energy (S ¹ ) and triplet energy (T ¹ ) have high color purity. High efficiency due to Thermally Activated Delayed Fluorescence (TADF) is useful as a material for blue and green light emitting layers. Further, as an electron transporting material or a hole transporting material sandwiching a light emitting layer, a compound having a novel conjugated structure having a large triplet energy (T ¹ ) is required.

However, the fluorescent material has a problem of low luminous efficiency, and the phosphorescent material and TADF material have a problem that the half-value range of the emission spectrum is wide and the color purity of emission is low, although the phosphorescent material and TADF material have high luminous efficiency, and the phosphorescent material is a noble metal. There was a problem that it was expensive to include (Nature Vol.492 13 December 2012, Applied Physics Letters 75, 4 (1999)).

International Publication No. 2004/061047 Japanese Unexamined Patent Publication No. 2014-239225 International Publication No. 2015/102118

Nature Vol.492 13 December 2012 Applied Physics Letters 75, 4 (1999)

As described above, various materials used for organic EL devices have been developed, 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. It is rare. Further, Patent Document 3 reports a polycyclic aromatic compound containing boron and an organic EL device using the same. In order to further improve the device characteristics, the color purity, light emission efficiency and device life should be improved. There is a demand for a material for a light emitting layer capable of producing a light emitting layer, particularly a dopant material. Further, as shown in Non-Patent Documents 1 and 2, in the thermally activated delayed fluorescent material and the phosphorescent light emitting material utilizing the heavy atom effect, the half-value range of the emission spectrum is wide and the color purity is improved. There was a problem with.

Further, as a method for forming an organic layer constituting an organic EL element, a wet film forming method is currently used in addition to the vacuum vapor deposition method, so that a hole injection layer, a hole transport layer and a light emitting layer are particularly formed. Wet film formation ink materials for this purpose are being actively developed, and it is also useful to search for such ink materials.

As a result of diligent studies to solve the above problems, the present inventors have succeeded in producing a novel polycyclic aromatic compound, and the difference between the singlet energy and triplet energy required for thermally activated delayed fluorescence is small. We have found that this compound is effective as a material. Then, for example, by arranging a light emitting layer using such a polycyclic aromatic compound as a dopant material and a compound having a triple term energy larger than that as a host material between the pair of electrodes to form an organic EL element. The present invention has been completed by finding that an excellent thermally activated delayed fluorescent organic EL element can be obtained.

In the present specification, the chemical structure or the 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. It means the carbon number of each of the substituents and substituents, and does not mean the total carbon number of the chemical structure and the substituents or the total carbon number of the substituents and the substituents. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent A of carbon number X" is substituted with "substituent B of carbon number Y". However, the number of carbon atoms Y is not the total number of carbon atoms of the substituent A and the substituent B. Further, for example, "substituent B 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.

上記式（１Ａ）または式（１Ｂ）中、
Ｒ^ａは水素または置換基であり、ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていてもよく、
Ｂ環、Ｃ環、Ｄ環、Ｅ環、Ｆ環、およびＧ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙ^１、Ｙ^２、およびＹ^３は、それぞれ独立して、＞Ｂ－、＞Ｐ－、＞Ｐ（＝Ｏ）－、＞Ｐ（＝Ｓ）－、＞Ａｌ－、＞Ｇａ－、＞Ａｓ－、＞Ｃ（－Ｒ）－、＞Ｓｉ（－Ｒ）－、または＞Ｇｅ（－Ｒ）－であり、前記＞Ｃ（－Ｒ）－のＲ、＞Ｓｉ（－Ｒ）－のＲ、および＞Ｇｅ（－Ｒ）－のＲは、それぞれ独立して、置換されてもよいアリール、置換されてもよいヘテロアリール、置換されてもよいアルキル、または置換されてもよいシクロアルキルであり、
Ｘ^１およびＸ^２は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲは、それぞれ独立して、水素、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキル、または置換されていてもよいシクロアルキルであり、前記＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士の少なくとも１つは、単結合または連結基により結合していてもよく、
Ｘ^１としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびＢ環の少なくとも１つと結合していてもよく、
Ｘ^２としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびＥ環の少なくとも１つと結合していてもよく、
Ｃ環およびＤ環、Ｇ環およびＢ環、ならびにＦ環およびＥ環は、それぞれ独立して、単結合または連結基により結合していてもよく、
ただし、上記式（１Ａ）では、Ｃ環およびＤ環のＣＤ結合と、Ｘ^１としての＞Ｎ－ＲのＲ（このＲは、前記置換されていてもよいアリール、前記置換されていてもよいヘテロアリール、または前記置換されていてもよいシクロアルキルに限る）およびＢ環のＸ^１Ｂ結合と、Ｘ^２としての＞Ｎ－ＲのＲ（このＲは、前記置換されていてもよいアリール、前記置換されていてもよいヘテロアリール、または前記置換されていてもよいシクロアルキルに限る）およびＥ環のＸ^２Ｅ結合との３つの結合のうち、いずれか１つまたは２つの結合が存在しており、
また、上記式（１Ｂ）では、Ｃ環およびＤ環のＣＤ結合と、Ｇ環およびＢ環のＧＢ結合と、Ｆ環およびＥ環のＦＥ結合との３つの結合のうち、いずれか１つまたは２つの結合が存在しており、
上記式（１Ａ）または式（１Ｂ）で表される化合物における、Ｂ環、Ｃ環、Ｄ環、Ｅ環、Ｆ環、Ｇ環、アリール、およびヘテロアリールの少なくとも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、
上記式（１Ａ）または式（１Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 Item 1.
A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B).

In the above formula (1A) or formula (1B),
R ^a is a hydrogen or a substituent, and "-C (-R ^a ) =" in the a ring may be replaced with "-N =".
The B ring, C ring, D ring, E ring, F ring, and G ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-R are independently substituted aryls, substituted heteroaryls, substituted alkyls, or optionally substituted cycloalkyls, respectively.
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted, respectively. It is an alkyl which may be substituted or a cycloalkyl which may be substituted, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is , Can be attached by a single bond or a linking group,
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ¹ can be at least one of the a ring and the B ring by a single bond or a linking group. May be combined,
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is at least one of the a ring and the E ring by a single bond or a linking group. May be combined,
The C and D rings, the G and B rings, and the F and E rings may be independently bonded by a single bond or a linking group, respectively.
However, in the above formula (1A), the CD bond of the C ring and the D ring and the R of> N ^— R as X1 (this R may be the substituted aryl, the substituted may be the case). Heteroaryl, or the optionally substituted cycloalkyl) and the X ¹ B bond of the B ring and> NR R as X ² (where this R is the optionally substituted aryl, said. There is one or two of the three bonds (limited to the substituted heteroaryl or the substituted cycloalkyl) and the ^X2E bond of the E ring. And
Further, in the above formula (1B), any one or one of the three bonds of the CD bond of the C ring and the D ring, the GB bond of the G ring and the B ring, and the FE bond of the F ring and the E ring. There are two bonds,
At least one of the B ring, C ring, D ring, E ring, F ring, G ring, aryl, and heteroaryl in the compound represented by the above formula (1A) or formula (1B) is at least one cyclo. It may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound represented by the above formula (1A) or the formula (1B) may be substituted with deuterium, cyano, or halogen.

Item 2.
In the above formula (1A) or formula (1B),
^Ra is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted aryl. Heteroarylamino, optionally substituted diarylboryl (two aryls may be attached by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, substituted. An alkoxy optionally, an aryloxy optionally substituted, or a substituted silyl,
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
The B ring, C ring, D ring, E ring, F ring, and G ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted. Aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (The two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, substituted. May be substituted with aryloxy, or substituted silyl,
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-Rs are independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. ,
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least 1 in the R. One hydrogen may be substituted with alkyl or cycloalkyl, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is a single bond. , -CH = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) It may be bound by _2- or -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-Si (-). R) ₂ -Rs are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, or a heteroarylene.
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and B ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the E ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) _2- are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, or two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene.
The C and D rings, the G and B rings, and the F and E rings are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, and alkenyl. , Alkinyl, or cycloalkyl, the at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and the two adjacent Rs form a ring with the cycloalkylene, arylene, and It may form a heteroarylene,
However, in the above formula (1A), the CD bond of the C ring and the D ring and the R of> N ^— R as X1 (the R may be substituted with the alkyl or the cycloalkyl, the aryl, The X ¹ B bond of the heteroaryl or the cycloalkyl and the B ring and an R of> N-R as X ² (where R may be substituted with the alkyl or cycloalkyl, said. Any one or two of the three bonds with aryl, said heteroaryl, or said cycloalkyl) and the ^X2E bond of the E ring is present.
Further, in the above formula (1B), any one or one of the three bonds of the CD bond of the C ring and the D ring, the GB bond of the G ring and the B ring, and the FE bond of the F ring and the E ring. There are two bonds,
At least one of the B ring, C ring, D ring, E ring, F ring, G ring, aryl, and heteroaryl in the compound represented by the above formula (1A) or formula (1B) is at least one cyclo. It may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound represented by the above formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen.
Item 2. The polycyclic aromatic compound according to Item 1.

上記式（２Ａ）または式（２Ｂ）中、
Ｒ^ａは、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基により結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルであり、当該Ｒ^ａにおける少なくとも１つの水素は、アリール、ヘテロアリール、アルキル、またはシクロアルキルで置換されていてもよく、
ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていてもよく、
Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、およびＲ^ｇは、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基により結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルであり、当該Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、およびＲ^ｇにおける少なくとも１つの水素は、アリール、ヘテロアリール、アルキル、またはシクロアルキルで置換されていてもよく、また、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、およびＲ^ｇのうちの隣接する基同士が結合して、それぞれｂ環、ｃ環、ｄ環、ｅ環、ｆ環、およびｇ環と共に、アリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基により結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルで置換されていてもよく、これらの置換基における少なくとも１つの水素は、アリール、ヘテロアリール、アルキル、またはシクロアルキルで置換されていてもよく、
ｂ環、ｃ環、ｄ環、ｅ環、ｆ環、およびｇ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲは、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、またはＲ^ｇである）は「－Ｎ＝」に置き換わっていてもよく、任意の「－Ｃ（－Ｒ）＝Ｃ（－Ｒ）－」（ここでＲは、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、またはＲ^ｇである）は、「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｎ（－Ｒ）－」のＲ、「－Ｃ（－Ｒ）_２－」のＲ、および「－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、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、前記「－Ｃ（－Ｒ）_２－」の２つのＲ同士および「－Ｓｉ（－Ｒ）_２－」の２つのＲ同士の少なくとも１つは、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－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、アルケニル、アルキニル、またはシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、また、隣接する２つのＲ同士が環を形成し、シクロアルキレン、アリーレン、またはヘテロアリーレンを形成していてもよく、
Ｙ^１、Ｙ^２、およびＹ^３は、それぞれ独立して、＞Ｂ－、＞Ｐ－、＞Ｐ（＝Ｏ）－、＞Ｐ（＝Ｓ）－、＞Ａｌ－、＞Ｇａ－、＞Ａｓ－、＞Ｃ（－Ｒ）－、＞Ｓｉ（－Ｒ）－、または＞Ｇｅ（－Ｒ）－であり、前記＞Ｃ（－Ｒ）－のＲ、＞Ｓｉ（－Ｒ）－のＲ、および＞Ｇｅ（－Ｒ）－のＲは、それぞれ独立して、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、当該Ｒにおける少なくとも１つの水素は、アルキルもしくはシクロアルキルで置換されていてもよく、
Ｘ^１およびＸ^２は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞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、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、前記＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士の少なくとも１つは、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－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、アルケニル、アルキニル、またはシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、また、隣接する２つのＲ同士が環を形成し、シクロアルキレン、アリーレン、またはヘテロアリーレンを形成していてもよく、
Ｘ^１としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により、ａ環およびｂ環の少なくとも１つと結合していてもよく、Ｘ^２としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により、ａ環およびｅ環の少なくとも１つと結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－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、アルケニル、アルキニル、またはシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、また、隣接する２つのＲ同士が環を形成し、シクロアルキレン、アリーレン、およびヘテロアリーレンを形成していてもよく、
ｃ環およびｄ環、ｇ環およびｂ環、ならびにｆ環およびｅ環は、それぞれ独立して、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－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、アルケニル、アルキニル、またはシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていてもよく、また、隣接する２つのＲ同士が環を形成し、シクロアルキレン、アリーレン、およびヘテロアリーレンを形成していてもよく、
ただし、上記式（２Ａ）では、ｃ環およびｄ環のｃｄ結合と、Ｘ^１としての＞Ｎ－ＲのＲ（このＲは、前記アルキルまたはシクロアルキルで置換されていてもよい、前記アリール、前記ヘテロアリール、または前記シクロアルキルに限る）およびｂ環のＸ^１ｂ結合と、Ｘ^２としての＞Ｎ－ＲのＲ（このＲは、前記アルキルまたはシクロアルキルで置換されていてもよい、前記アリール、前記ヘテロアリール、または前記シクロアルキルに限る）およびｅ環のＸ^２ｅ結合との３つの結合のうち、いずれか１つまたは２つの結合が存在しており、
また、上記式（２Ｂ）では、ｃ環およびｄ環のｃｄ結合と、ｇ環およびｂ環のｇｂ結合と、ｆ環およびｅ環のｆｅ結合との３つの結合のうち、いずれか１つまたは２つの結合が存在しており、
上記式（２Ａ）または式（２Ｂ）で表される化合物における、前記ｂ環、前記ｃ環、前記ｄ環、前記ｅ環、前記ｆ環、前記ｇ環、前記形成された環、前記アリール、および前記ヘテロアリールの少なくとも１つは、炭素数３～２４の少なくとも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、炭素数６～３０のアリール、炭素数２～３０のヘテロアリール、炭素数１～２４のアルキル、または炭素数３～２４のシクロアルキルで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、
上記式（２Ａ）または式（２Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 Item 3.
Item 2. The polycyclic aromatic compound represented by the following general formula (2A) or the following general formula (2B).

In the above formula (2A) or formula (2B),
Ra is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, ^diarylboryl (two aryls may be single-bonded or bonded by a linking group), alkyl, cycloalkyl, An alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or ^{alkyldicycloalkylsilyl} , wherein at least one hydrogen in the Ra is aryl, heteroaryl, alkyl, or. May be substituted with cycloalkyl,
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two). Aryl may be attached by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. And at least one hydrogen in the R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R Adjacent groups of ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are attached to each other together with the b ring, c ring, d ring, e ring, f ring, and g ring, respectively. An aryl ring or a heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls). Substituted with a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Any "-C (-R) =" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f or R ^g ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N (-R)-", "-O-", "-S-", "-C (-R) _2- ", It may be replaced with "-Si (-R) _2- " or "-Se-", and the R of the above-mentioned "-N (-R)-", the R of "-C (-R) _2- ", And the R of "-Si (-R) _2- " is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. , At least one of the two Rs of "-C (-R) _2- " and the two Rs of "-Si (-R) _2- " is a single bond, -CH = CH-, -CR. = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- -CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R, respectively. Independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and two adjacent. R may form a ring with each other to form a cycloalkylene, an arylene, or a heteroarylene.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-Rs are independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. ,
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least 1 in the R. One hydrogen may be substituted with alkyl or cycloalkyl, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is a single bond. , -CH = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) It may be bound by _2- or -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-Si (-). R) ₂ -Rs are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, or a heteroarylene.
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and b ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) _2- are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, or two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene.
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, and alkenyl. , Alkinyl, or cycloalkyl, the at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and the two adjacent Rs form a ring with the cycloalkylene, arylene, and It may form a heteroarylene,
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N ^— R as X1 (this R may be substituted with the alkyl or the cycloalkyl, the aryl, The X ¹ b bond of the heteroaryl or the cycloalkyl and the b ring and an R of> N-R as X ² (where R may be substituted with the alkyl or cycloalkyl, said. Any one or two of the three bonds with aryl, said heteroaryl, or said cycloalkyl) and the X ² e bond of the e-ring is present.
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
The b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, and the aryl in the compound represented by the formula (2A) or the formula (2B). And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms and 2 carbon atoms. It may be substituted with ~ 30 heteroaryl, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane is substituted with -O-. May,
At least one hydrogen in the compound represented by the above formula (2A) or the formula (2B) may be substituted with deuterium, cyano, or halogen.

Item 4.
In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 30 carbon atoms, ^a heteroaryl having 2 to 30 carbon atoms, a diallyl amino (where the aryl is an aryl having 6 to 12 carbon atoms), and a diallyl boryl (where the aryl is an aryl having 6 to 12 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or ^a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diarylamino (however, the aryl is). Aryl with 6 to 12 carbon atoms), diarylboryl (where the aryl is an aryl with 6 to 12 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms. , Or a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g is an aryl having 6 to 12 carbon atoms and 2 carbon atoms. It may be substituted with ~ 15 heteroaryl, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and may be substituted with R ^b , R ^c , R ^d , R ^e , R ^f , and R. Adjacent groups of ^g are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring having 9 to 16 carbon atoms or a hetero having 6 to 15 carbon atoms, respectively. An aryl ring may be formed, and at least one hydrogen in the formed ring is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diarylamino (where the aryl has 6 to 12 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or an alkyl having 3 to 3 carbon atoms. It may be substituted with 24 cycloalkyls, the at least one hydrogen in these substituents being an aryl with 6-12 carbons, a heteroaryl with 2-15 carbons, an alkyl with 1-6 carbons, or carbon. It may be substituted with the number 3 to 14 cycloalkyl.
Any "-C (-R) =" in the b ring, c ring, d ring, e ring, f ring, and g ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f or R ^g ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N (-R)-", "-O-", "-S-", "-C (-R) _2- ", It may be replaced with "-Si (-R) _2- " or "-Se-", and the R of "-N (-R)-", the R of "-C (-R) _2- ", And R of "-Si (-R) _2- " is hydrogen, aryl with 6 to 12 carbon atoms, heteroaryl with 2 to 15 carbon atoms, alkyl with 1 to 6 carbon atoms, or cyclo with 3 to 14 carbon atoms. It is an alkyl, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and the 2 of the above-mentioned "-C (-R) _2- ". At least one of the two Rs of "-Si (-R) _2- " is a single bond, -CH = CH-, -CR = CR-, -C≡C-, -N (-). R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, respectively. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, at least 1 in the R. One hydrogen may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs form a ring with each other to form a ring and a cycloalkylene having 3 to 14 carbon atoms. , An arylene having 6 to 12 carbon atoms or a heteroarylene having 2 to 15 carbon atoms may be formed.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-R are independently aryls with 6 to 12 carbon atoms, heteroaryls with 2 to 15 carbon atoms, alkyls with 1 to 6 carbon atoms, or cyclos with 3 to 14 carbon atoms. It is alkyl, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and carbon. It is an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the R is substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. Often,
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and b ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, and 1 carbon atom. An alkenyl having a number of carbon atoms of 1 to 6, an alkynyl having a carbon content of 1 to 6 or a cycloalkyl having a carbon number of 3 to 14, and at least one hydrogen in the R is an alkyl having a carbon number of 1 to 6 or a cycloalkyl having a carbon number of 3 to 14. It may be substituted with, and two adjacent Rs form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms. You may be
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, respectively. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, at least 1 in the R. One hydrogen may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs form a ring with each other to form a ring and a cycloalkylene having 3 to 14 carbon atoms. , An arylene having 6 to 12 carbon atoms or a heteroarylene having 2 to 15 carbon atoms may be formed.
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N—R as X1 (this R is the alkyl having ¹ to 6 carbon atoms or the cyclo having 3 to 14 carbon atoms). ^With the X1 b bond of the b ring (limited to the aryl having 6 to 12 carbon atoms, the heteroaryl having 2 to 15 carbon atoms, or the cycloalkyl having 3 to 14 carbon atoms, which may be substituted with an alkyl). , R of> NR as X ² (where R may be substituted with the alkyl having 1 to 6 carbon atoms or the cycloalkyl having 3 to 14 carbon atoms, said the aryl having 6 to 12 carbon atoms, There is one or two of the three bonds (limited to the heteroaryl having 2 to 15 carbon atoms or the cycloalkyl having 3 to 14 carbon atoms) and the ^X2e bond of the e-ring. And
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
In the compound represented by the formula (2A) or the formula (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and the like. And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms and 2 carbon atoms. It may be substituted with ~ 15 heteroaryl, an alkyl having 1-12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 3. The polycyclic aromatic compound.

Item 5.
In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 16 carbon atoms, ^a heteroaryl having 2 to 20 carbon atoms, a diallyl amino (however, the aryl is an aryl having 6 to 10 carbon atoms), and a diallyl boryl (however, the aryl has 6 to 10 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or ^a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (however, the aryl is). Aryl having 6 to 10 carbon atoms), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms. , Or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is an aryl having 6 to 10 carbon atoms and 2 carbon atoms. It may be substituted with up to 10 heteroaryls, 1 to 5 carbons of alkyl, or 5 to 10 carbons of cycloalkyl, as well as R ^b , R ^c , R ^d , R ^e , R ^f , and R. Adjacent groups of ^g are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring having 9 to 16 carbon atoms or a hetero having 6 to 15 carbon atoms, respectively. An aryl ring may be formed, and at least one hydrogen in the formed ring is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (where the aryl has 6 to 10 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or an alkyl having 3 to 3 carbon atoms. It may be substituted with 16 cycloalkyls, the at least one hydrogen in these substituents being an aryl 6-10 carbons, a heteroaryl 2-10 carbons, an alkyl 1-5 carbons, or carbon. It may be substituted with the number 5 to 10 cycloalkyl.
Any "-C (-R) =" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f ), or ^Rg ) may be replaced with "-N =".
Y ¹ , Y ² and Y ³ are independently>B-,>P-,> P (= O)-or> P (= S)-, respectively.
X ¹ and X ² are independently>N-R,>O,> S, or> C (-R) ₂ , and of the above-mentioned> N-R R and> C (-R) ₂ . R is independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
The R of> N-R or the R of> C (-R) ₂ as X ¹ is a single bond, -N (-R)-, -O-, -S-, or -C (-R) ₂ . -May be bonded to the b ring, and the R of> N-R or the R of> C (-R) ₂ as X ² is a single bond, -N (-R)-, -O-. , -S-, or -C (-R) ₂ -may be bonded to the e-ring, and the R of -N (-R)-and the R of -C (-R) _2- are respectively. Independently, hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R. May be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -N (-R)-, -O-, -S-, or -C (-R). ) ₂ -R may be bonded by 2-, and the -N (-R)-R and the -C (-R) ₂ -R are independently hydrogen, an aryl having 6 to 10 carbon atoms, and carbon. It is a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R is an alkyl having 1 to 5 carbon atoms or an alkyl having 5 to 10 carbon atoms. May be substituted with cycloalkyl in
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N—R as X1 (this R is the alkyl having ¹ to 5 carbon atoms or the cyclo having 5 to 10 carbon atoms). The X ¹ b bond of the ring (limited to the aryl having 6 to 10 carbon atoms) and the b ring, which may be substituted with an alkyl, and an R of> NR as X ² (this R is the above carbon number 1 to 1 to 10). One of the three bonds (limited to the aryl having 6 to 10 carbon atoms, which may be substituted with an alkyl of 5 or a cycloalkyl having 5 to 10 carbon atoms) and the ^X2e bond of the e-ring. There is one or two bonds,
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
In the compound represented by the above formula (2A) or the above formula (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and the like. And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 10 carbon atoms and 2 carbon atoms. It may be substituted with ~ 10 heteroaryl, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 3. The polycyclic aromatic compound.

Item 6.
In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 16 carbon atoms, ^a heteroaryl having 2 to 20 carbon atoms, a diallyl amino (however, the aryl is an aryl having 6 to 10 carbon atoms), and a diallyl boryl (however, the aryl has 6 to 10 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or ^a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (however, the aryl is). Aryl with 6 to 10 carbon atoms), diarylboryl (where the aryl is an aryl with 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms. , Or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g is an alkyl having 1 to 5 carbon atoms, or an alkyl having 1 to 5 carbon atoms. It may be substituted with 5-10 cycloalkyls.
Y1 ^{, Y2} , and Y3 ^are > B-, and
X ¹ and X ² are> N-R, and the R of> N-R is hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, and an alkyl having 1 to 5 carbon atoms. Alternatively, it is a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 5 carbon atoms.
The R of> N—R as X ¹ may be bonded to the b ring by a single bond, and the R of the> N—R as X ² may be bonded to the e ring by a single bond. May,
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring may be independently bonded by a single bond.
However, in the above formula (2A), the cd bond of the c ring and the d ring and R of> N ^— R as X1 (this R may be substituted with the alkyl having 1 to 5 carbon atoms). The X ¹ b bond of the ring (limited to aryls of number 6 to 10) and the R of> NR as X ² (this R may be substituted with the alkyl having 1 to 5 carbon atoms). One or two of the three bonds (limited to aryls of number 6 to 10) and the ^X2e bond of the e-ring are present.
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
At least of the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl in the compound represented by the formula (2A) or the formula (2B). One may be condensed with at least one cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 5 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 3. The polycyclic aromatic compound.

各式中、
Ｒは、それぞれ独立して、水素、炭素数６～１６のアリール、炭素数２～２０のヘテロアリール、ジアリールアミノ（ただしアリールは炭素数６～１０のアリール）、ジアリールボリル（ただしアリールは炭素数６～１０のアリールであり、２つのアリールは単結合または連結基により結合していてもよい）、炭素数１～１２のアルキル、または炭素数３～１６のシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、炭素数１～５のアルキルまたは炭素数５～１０のシクロアルキルで置換されていてもよく、
ｏはそれぞれ独立して１～３の整数であり、
ｐはそれぞれ独立して１～４の整数であり、
ｑはそれぞれ独立して１～５の整数であり、
上記各式で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 Item 7.
Item 3. The polycyclic aromatic compound represented by any of the following structural formulas.

In each formula,
R is independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diarylamino (where aryl is aryl with 6 to 10 carbon atoms), and diarylboryl (where aryl is carbon number of carbon atoms). It is an aryl of 6 to 10 and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least in the R. One hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
o is an integer of 1 to 3 independently,
p is an integer of 1 to 4 independently of each other.
q is an independent integer of 1 to 5, respectively.
At least one hydrogen in the compound represented by each of the above formulas may be substituted with deuterium, cyano, or halogen.

Item 8.
Item 2. The polycyclic aromatic compound represented by any of the following structural formulas.

Item 9.
A reactive compound in which a reactive substituent is substituted on the polycyclic aromatic compound according to any one of Items 1 to 8.

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

Item 11.
A pendant type polymer compound in which a main chain type polymer is substituted with the reactive compound according to Item 9, or a pendant type polymer crosslinked body obtained by further cross-linking the pendant type polymer compound.

Item 12.
A material for an organic device containing the polycyclic aromatic compound according to any one of Items 1 to 8.

Item 13.
A material for an organic device containing the reactive compound according to Item 9.

Item 14.
Item 2. A material for an organic device containing the polymer compound or polymer crosslinked body according to Item 10.

Item 15.
Item 2. A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to Item 11.

Item 16.
Item 2. The organic device according to any one of Items 12 to 15, wherein the organic device material is a material for an organic field light emitting device, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter. material.

Item 17.
Item 6. The material for an organic device according to Item 16, wherein the material for the organic electroluminescent element is a material for a light emitting layer.

Item 18.
An ink composition containing the polycyclic aromatic compound according to any one of Items 1 to 8 and an organic solvent.

Item 19.
An ink composition containing the reactive compound according to Item 9 and an organic solvent.

Item 20.
An ink composition containing a main chain polymer, the reactive compound according to Item 9, and an organic solvent.

Item 21.
An ink composition containing the polymer compound or polymer crosslinked body according to Item 10 and an organic solvent.

Item 22.
An ink composition containing the pendant type polymer compound or the pendant type polymer crosslinked body according to Item 11 and an organic solvent.

Item 23.
Item 2. A polycyclic aromatic compound according to any one of Items 1 to 8, a reactive compound according to Item 9, and a high molecular weight compound according to Item 10, which are arranged between a pair of electrodes composed of an anode and a cathode and the pair of electrodes. An organic electric field light emitting element having an organic layer containing a molecular compound or a polymer crosslinked body, or the pendant type polymer compound or the pendant type polymer crosslinked body according to Item 11.

Item 24.
Item 2. The organic electroluminescent device according to Item 23, wherein the organic layer is a light emitting layer.

Item 25.
Item 24, wherein the light emitting layer contains a host and the polycyclic aromatic compound, a reactive compound, a polymer compound, a polymer crosslinked body, a pendant type polymer compound or a pendant type polymer crosslinked body as a dopant. The organic field light emitting element to be described.

上記一般式（Ｈ１）中、Ｌ^１は炭素数６～３０のアリーレンまたは炭素数２～３０のヘテロアリーレンであり、
上記一般式（Ｈ２）中、Ｌ^２およびＬ^３は、それぞれ独立して、炭素数６～３０のアリールまたは炭素数２～３０のヘテロアリールであり、
上記一般式（Ｈ３）中、ＭＵはそれぞれ独立して芳香族化合物から任意の２つの水素原子を除いて表される２価の基、ＥＣはそれぞれ独立して芳香族化合物から任意の１つの水素原子を除いて表される１価の基であり、ＭＵ中の２つの水素がＥＣまたはＭＵと置換され、ｋは２～５００００の整数であり、
上記一般式（Ｈ４）中、Ｇはそれぞれ独立して＝Ｃ（－Ｈ）－または＝Ｎ－であり、前記＝Ｃ（－Ｈ）－中のＨは置換基または他の式（Ｈ４）で表される構造で置換されていてもよく、
上記一般式（Ｈ５）中、
Ｒ^１～Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールへテロアリールアミノ、アルキルまたはシクロアルキルであり、当該Ｒ^１～Ｒ^１１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、アルキルまたはシクロアルキルで置換されていてもよく、
Ｒ^１～Ｒ^１１のうちの隣接する基同士が結合してａ環、ｂ環またはｃ環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキルまたはシクロアルキルで置換されていてもよく、これらの置換基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、アルキルまたはシクロアルキルで置換されていてもよく、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲはＲ^１～Ｒ^１１である）は「－Ｎ＝」に置き換わっていてもよく、
上記一般式（Ｈ６）中、
Ｒ^１～Ｒ^１６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、アリールへテロアリールアミノ、アルキルまたはシクロアルキルであり、当該Ｒ^１～Ｒ^１６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、アルキルまたはシクロアルキルで置換されていてもよく、
Ｒ^１～Ｒ^１６のうちの隣接する基同士が結合してａ環、ｂ環、ｃ環またはｄ環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキルまたはシクロアルキルで置換されていてもよく、これらの置換基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、アルキルまたはシクロアルキルで置換されていてもよく、そして、
上記各式で表される化合物または構造における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 Item 26.
The light emitting layer is further represented by a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), and a compound represented by the following general formula (H4). Contains at least one selected from the group consisting of a compound comprising the structure to be, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. 25. The organic electroluminescent element according to 25.

In the above general formula (H1), L1 is ^an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms.
In the above general formula (H2), L ² and L ³ are independently aryls having 6 to 30 carbon atoms or heteroaryls having 2 to 30 carbon atoms.
In the above general formula (H3), MU is a divalent group independently represented by removing any two hydrogen atoms from the aromatic compound, and EC is independently represented by any one hydrogen from the aromatic compound. It is a monovalent group represented by excluding atoms, two hydrogens in MU are replaced with EC or MU, k is an integer of 2 to 50,000, and
In the general formula (H4), G is independently = C (-H)-or = N-, and H in the above = C (-H)-is a substituent or another formula (H4). It may be replaced by the structure represented.
In the above general formula (H5),
R ¹ to R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, ^{diheteroarylamino} , arylhetelloarylamino, alkyl or cycloalkyl, and at least ^one of R1 to R11. Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl.
Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring or a c ring, and at least one hydrogen in the formed ring is a hydrogen. It may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further aryl, heteroaryl, diarylamino, alkyl. Alternatively, it may be substituted with cycloalkyl.
Any "-C (-R) =" (where R is R ¹ to R ¹¹ ) in the a-ring, b-ring, and c-ring may be replaced with "-N =".
In the above general formula (H6),
R ¹ to R ¹⁶ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetelloarylamino, alkyl or cycloalkyl, and at least ^one of R1 to ^R16 . Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl.
Adjacent groups of R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring, a c ring or a d ring, and at least one in the formed ring. Hydrogen may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further aryl, heteroaryl, diaryl. May be substituted with amino, alkyl or cycloalkyl, and
At least one hydrogen in the compound or structure represented by each of the above formulas may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, cyano, a halogen or deuterium.

Item 27.
It has at least one layer of an electron transporting layer and an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or fluoranthene. Derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives Item 6. The organic electric field light emitting element according to any one of Items 23 to 26, which comprises at least one selected from the group consisting of.

Item 28.
At least one layer of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline soil. Contains at least one selected from the group consisting of halides of similar metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals. 27. The organic electric field light emitting element according to Item 27.

Item 29.
At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or a polymer compound. , A polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type polymer compound. Item 6. The organic electric field light emitting element according to any one of Items 23 to 28, which comprises a pendant type polymer crosslinked body further crosslinked.

Item 30.
A display device or a lighting device provided with the organic electroluminescent element according to any one of Items 23 to 29.

Item 31.
Item 16. A wavelength conversion filter including the material for the wavelength conversion filter according to Item 16.

According to a preferred embodiment of the present invention, by manufacturing an organic EL device using, for example, a novel polycyclic aromatic compound as a dopant material, an organic EL device having a narrow half-value width of the emission spectrum and excellent color purity, and further a quantum It is possible to provide an organic EL element having excellent efficiency and element life. Further, since the novel polycyclic aromatic compound of the present invention has a rigid structure, the emission spectrum is sharper, the half width of the emission spectrum is narrow, and the compound which gives light emission with high color purity. There are many.

Specifically, the present inventors have found that a polycyclic aromatic compound in which an aromatic ring is linked with a hetero element such as boron, phosphorus, oxygen, nitrogen, or sulfur has a large HOMO-LUMO gap (band gap Eg in a thin film). And found to have high tricyclic energy. This is because the 6-membered ring containing the hetero element has low aromaticity, so that the decrease in the HOMO-LUMO gap due to the expansion of the conjugated system is suppressed, and the electronic perturbation of the hetero element suppresses the decrease in the HOMO-LUMO gap. And it is considered that the cause is the localization of SOMO2.

Further, the polycyclic aromatic compound containing a hetero element according to the present invention is singlet with the triplet excited state because the exchange interaction between both orbitals becomes smaller due to the localization of SOMO1 and SOMO2 in the triplet excited state. Since the energy difference in the term excited state is small and the thermally activated delayed fluorescence is exhibited, it is also useful as a fluorescent material for organic EL elements. Further, the material having high triplet energy is also useful as an electron transport layer or a hole transport layer of a phosphorescent organic EL device or an organic EL device using thermally activated delayed fluorescence. Furthermore, since these polycyclic aromatic compounds can arbitrarily move the HOMO and LUMO energies by introducing a substituent, the ionization potential and electron affinity can be optimized according to the peripheral material. ..

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

1. 1. Polycyclic aromatic compounds of the present invention
<Explanation of the overall structure of the compound>
The present invention is a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B), and preferably a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). It is a group compound. In each of the above equations, "B" to "G" in the circle are symbols indicating the ring structure represented by the circle, and "a" to "g" in the 6-membered aromatic ring are benzene rings or, in some cases, benzene rings. It is a modified ring (such as a 6- or 5-membered complex aromatic ring), with other reference numerals being the same as defined above. Furthermore, the definitions of the symbols in all the structural formulas shown in the following paragraphs are the same as the definitions described above.

The compounds of the present invention are characterized by having one or two carbazole-like structures in the molecule. As will be described below, in each formula, the carbazole-like structure can be formed at three sites, and the carbazole-like structure is formed at one or two of the three sites.

This carbazole-like structure will be described in detail later, but in the formula (1A), for example, it is formed by binding the C ring and the D ring to include "N", and when X ¹ or X ² is> N-R. Is formed when R is bonded to the B ring or the E ring, respectively. Further, in the formula (2A), for example, it is formed by the bond of the c ring and the d ring (the bond between R ^c and R ^d ) including "N", and when X ¹ or X ² is> N-R. Is formed when R is bonded to ring b or ring ^e , respectively (bonding of R to R ^b or Re). Similarly, in formula (1B), the C ring and the D ring are bonded to each other to contain "N", and the G ring and the B ring are bonded to each other to contain the "N". It is formed to contain "N" by the binding of the E ring. Further, also in the formula (2B), similarly, for example, it is formed by the bond of the c ring and the d ring (the bond between R ^c and R ^d ) including "N", and the bond of the g ring and the b ring (the bond). It is formed by the bond of R ^g and R ^b ) containing "N", and is formed by the bond of the f ring and the ^e ring (the bond between R ^f and Re) including "N".

<Explanation of ring structure and its substituent>
Ra is hydrogen or ^a substituent. The substituents include aryls that may be substituted, heteroaryls that may be substituted, diarylaminos that may be substituted, diheteroarylaminos that may be substituted, and aryls that may be substituted. Heteroarylamino, optionally substituted diarylboryl (two aryls may be attached by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, substituted. Aryloxy which may be present, aryloxy which may be substituted, or substituted silyl is preferable. When these groups have a substituent, the substituent includes aryl, heteroaryl, alkyl, or cycloalkyl. The details of the substituents listed here will be described later.

The B ring, C ring, D ring, E ring, F ring, and G ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is substituted with a substituent. May be good. The substituents include aryls that may be substituted, heteroaryls that may be substituted, diarylaminos that may be substituted, diheteroarylaminos that may be substituted, and aryls that may be substituted. Heteroarylamino, optionally substituted diarylboryl (two aryls may be attached via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, Preferred are optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyls. When these groups have a substituent, the substituent includes aryl, heteroaryl, alkyl, or cycloalkyl. The details of the rings and substituents listed here will be described later.

R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two). Aryl may be attached by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. And at least one hydrogen in the R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. The details of the substituents listed here will be described later.

The aryl ring or heteroaryl ring (that is, the B ring to the G ring) in the formula (1A) and the formula (1B) is a 5-membered ring or a 6-membered ring that shares a bond with the condensed bicyclic structure contained in each formula. It is preferable to have.

Here, the "condensed bicyclic structure" is a structure in which two saturated hydrocarbon rings including Y ¹ , X ¹ , and N are condensed in the formula (1A) (the first on the left side in the formula). (Fused bicyclic structure) and a structure in which ^two saturated hydrocarbon rings containing Y2, X2, and N are fused (the ^second fused bicyclic structure on the right side in the formula). Similarly, in the formula (1B), a structure in which two saturated hydrocarbon rings including Y1 and two N are condensed (the ^first fused bicyclic structure on the left side in the formula) and It is composed of a structure in which two saturated hydrocarbon rings containing Y ² and two N are condensed (the second condensed two-ring structure on the right side in the formula) and a structure containing Y ³ and two N. It means a structure in which two saturated hydrocarbon rings are condensed (the lower third condensed bicyclic structure in the formula). Although not shown in the formulas (2A) and (2B), a condensed bicyclic structure exists at the same location.

Further, the "six-membered ring sharing a bond with the condensed bicyclic structure" is, for example, as shown by the formula (2A) or the formula (2B), the b ring (benzene ring (6-membered ring) fused to the fused bicyclic structure). )) Means. Further, "the aryl ring (which is the B ring) or the heteroaryl ring has the 6-membered ring" means that the B ring is formed only by the 6-membered ring or includes the 6-membered ring. This means that another ring or the like is further condensed with this 6-membered ring to form a B ring. In other words, the "aryl ring having a 6-membered ring (which is a B ring) or a heteroaryl ring" as used herein means that a 6-membered ring constituting all or a part of the B ring is condensed into a condensed bicyclic structure. It means that it is. Similar explanations are given for "C ring (c ring)", "D ring (d ring)", "E ring (e ring)", "F ring (f ring)", and "G ring (g ring)". The same applies to the "5-membered ring".

The B ring, C ring, D ring, and E ring in the formula (1A) are the b ring and its substituent R ^b , the c ring and its substituent R ^c , and the d ring and its substituent, respectively, in the formula (2A). Corresponds to R ^d , and the e-algebra and its substituent R ^e . That is, the formula (2A) corresponds to the structure in which "the B ring to the E ring having a 6-membered ring" is selected as the B ring to the E ring of the formula (1A). As will be described later, "having" a 6-membered ring means that, for example, a ring b, which is a 6-membered ring, is bonded to adjacent groups among its four substituents ^Rb to form a ring. This is because a ring b, which is a 6-membered ring, and another ring condensed therein may correspond to the ring B. In this sense, each ring of the formula (1A) is represented by uppercase letters B to E, whereas each ring of the formula (2A) is represented by lowercase letters b to e.

The B ring, C ring, D ring, E ring, F ring, and G ring in the formula (1B) are the b ring and its substituent R ^b , and the c ring and its substituent R ^c , respectively, in the formula (2B). Corresponds to the d ring and its substituent R ^d , the e ring and its substituent R ^e , the f ring and its substituent R ^f , and the g ring and its substituent R ^g . That is, the formula (2B) corresponds to the structure in which "the B ring to the G ring having a 6-membered ring" is selected as the B ring to the G ring of the formula (1B). As will be described later, "having" a 6-membered ring means that, for example, a ring b, which is a 6-membered ring, is bonded to adjacent groups among its four substituents ^Rb to form a ring. This is because a ring b, which is a 6-membered ring, and another ring condensed therein may correspond to the ring B. In this sense, each ring of the formula (1B) is represented by uppercase letters B to G, whereas each ring of the formula (2B) is represented by lowercase letters b to g.

<Explanation of changes in ring structure due to bonds between substituents>
Adjacent groups of the substituents R ^b , R ^c , R ^d , Re ^e , R ^f , and R ^g of the b ring, c ring, d ring, e ring, f ring, and g ring are bonded to each other. Aryl ring or heteroaryl ring may be formed together with b ring, c ring, d ring, e ring, f ring, and g ring, respectively, and at least one hydrogen in the formed ring is aryl. , Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diallylboryl (two aryls may be single-bonded or bonded by a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triaryl. It may be substituted with silyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents is aryl, heteroaryl, alkyl, or cyclo. It may be substituted with alkyl. The details of the rings and substituents listed here will be described later.

Therefore, the polycyclic aromatic compounds of the formula (2A) or the formula (2B) are, for example, the following formulas (2A-fr) and (2B-fr) depending on the mutual binding form of the substituents in the b ring to the g ring. As shown in, the ring structure constituting the compound changes. The B'ring and C'ring in the following formula correspond to the B ring and the C ring in the formula (1A) and the formula (1B), respectively. The d-ring to g-ring can be changed in the same manner.

The B'ring and C'ring in the above formula (2A-fr) and the formula (2B-fr) are among a plurality of substituents R ^b and R ^c as described by the formulas (2A) and (2B). It shows an aryl ring or a heteroaryl ring formed by bonding adjacent groups of the b ring and the c ring, respectively (it can also be said to be a condensed ring formed by condensing another ring structure with the b ring or the c ring). Further, as can be seen from the above equation, for example, R b of ring ^b and R ^{c of ring c} , that is, substituents in different rings do not correspond to "adjacent groups", and they are basically bonded. There is no such thing. That is, "adjacent groups" means adjacent groups on the same ring.

In the above formula (2A-fr) and formula (2B-fr), for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring is condensed with a benzene ring which is a b ring or a c ring. The fused ring B'or fused ring C'formed by the above is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, respectively. be.

More specific examples of the formula (2A-fr) and the formula (2B-fr) are shown below.

The above formula (2A-fr-ex) and the formula (2B-fr-ex) are specific examples of the formula (2A-fr) and the formula (2B-fr), respectively, of the formula (2A) and the formula (2B). Two adjacent R bs in the ^b ring are bonded to form an aryl ring (naphthalene ring) represented by B'together with the b ring (benzene ring), and two adjacent R cs in the ^c ring are bonded to each other. This is an example in which an aryl ring (dibenzofuran ring) represented by C'is formed together with a c ring (benzene ring). The formed aryl ring has a 6-membered ring (benzene ring b or c) that shares a bond with the condensed bicyclic structure described above. Any substituents on the aryl rings B'and C'(rings B and C of formula (1A) and formula (1B)) are also indicated by n R in addition to R ^b and R ^c , n. The upper limit of is the maximum number that can be replaced. It should be noted that these explanations can be similarly applied to any form other than the above-mentioned specific examples, for example, when the d-ring to g-ring is changed, or when another aryl ring or heteroaryl ring is formed.

<Explanation of central elements ^Y1 to Y3 ⁱⁿ the compound >
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-R are independently substituted aryls, substituted heteroaryls, substituted alkyls, or optionally substituted cycloalkyls, respectively. As Y1 ^{, Y2} , and Y3,> ^B -,>P-,> P (= O)-, or> P (= S)-are preferable, and> B- is more preferable. The details of the substituents listed here will be described later.

<Explanation of changes in ring structure due to bonding between rings>
The C ring and D ring in the formula (1A) and the formula (1B) may be bonded by a single bond or a linking group (collectively referred to as a linking group). Further, the G-ring and the B-ring and the F-ring and the E-ring in the formula (1B) may also be independently bonded by a single bond or a linking group (collectively referred to as a linking group). The C-ring and D-ring bonds are also referred to as CD bonds, the G-ring and B-ring bonds are referred to as GB bonds, and the F-ring and E-ring bonds are also referred to as FE bonds.

The linking groups include -CH ₂ -CH _2- , -CHR-CHR-, -CR ₂ -CR _2- , -CH = CH-, -CR = CR-, -C≡C-, -N (-R). )-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-. The R of -CHR-CHR-, the R of -CR _{2 -} CR2-, the R of -CR = CR-, the R of -N (-R)-, the R of -C (-R) _2- , And -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or cycloalkyl. It may be replaced with. Further, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, and a heteroarylene. The details of the substituents listed here will be described later.

The linking group is a single bond, -CR = CR-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) ₂ as a linking group. -, And -Se- are preferred, and single bonds, -CR = CR-, -N (-R)-, -O-, -S-, and -C (-R) _2- as linking groups are more preferred. , Single bond, -CR = CR- as a linking group, -N (-R)-, -O-, and -S- are more preferable, and single bond is most preferable.

The position where the two rings are bonded by the binding group is not particularly limited as long as it can be bonded, but it is preferable to bond at the most adjacent position, for example, the bond position (1st position) of "N" in each ring. As a reference, it is preferable to bond the positions of the ortho (2nd position) to each other (see the structural formulas of the formulas (1A) and (1B)).

The c-ring and d-ring in the lower formulas (2A) and (2B) may also be bonded by a single bond or a linking group (collectively referred to as a binding group) in the same manner as in the higher formula. Further, the g-ring and b-ring and the f-ring and e-ring in the lower formula (2B) are also independently formed by a single bond or a linking group (collectively referred to as a binding group) in the same manner as in the higher formula. It may be combined. The bond between the c ring and the d ring is also referred to as a cd bond, the bond between the g ring and the b ring is referred to as a gb bond, and the bond between the f ring and the e ring is also referred to as a fe bond. The explanation of the superordinate formula can be quoted for the type of linking group and the bonding position.

<Explanation of carbazole-like structure (1)>
In the compound of the present invention, as described above, C ring and D ring (c ring and d ring), G ring and B ring (g ring and b ring), and F ring and E ring (f ring and e ring). The first carbazole-like structure in formulas (1A) and (2A) and the first, second and third carbazole-like structures in formulas (1B) and (2B). Can be formed. The dotted line in the following structural formula means a bonding group (single bond and linking group). However, the compounds of the present invention are characterized in that one or two of the three carbazole-like structures that can be formed intramolecularly are formed.

The reason for calling it a "carbazole-like structure" is, for example, explained by the formula (2A), that the c-ring and the d-ring are single-bonded between the ortho (2-position) positions with respect to the "N" bond position (1-position). This is because the carbazole structure as the most basic structure is formed in the molecule when it is bound by. Further, as described above, the bonding group is not limited to a single bond, the bonding position between the rings is not limited, and as described elsewhere, each ring such as the c ring is a bond between adjacent substituents. Since the ring structure changes due to such factors, structures other than carbazole are also formed. Therefore, it is called "carbazole-like structure" in the sense that a structure similar to carbazole is also formed.

When a carbazole-like structure is formed, the linking group is a single bond, -CH ₂ -CH _2- as a linking group, -CHR-CHR-, -CR ₂ -CR _2- , -CR = CR-,-. N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , and -Se- are preferable, and single bond, -CR = as a linking group. CR-, -N (-R)-, -O-, -S-, and -C (-R) ₂ -are more preferred, single bond, -CR = CR-, -N (-R) as a linking group. )-, -O-, and -S- are more preferred, and single bonds are most preferred.

When a carbazole-like structure is formed, the position where the two rings are bonded by the binding group is not particularly limited as long as it can be bonded, but it is preferable that the two rings are bonded at the most adjacent positions, for example, "N" in each ring. It is preferable to bond the ortho (2nd position) positions with reference to the bonding position (1st position) (formula (1A), formula (1B), formula (2A), and formula (2B) structural formulas. reference).
When a carbazole-like structure is formed, the two rings to be bonded are preferably benzene rings.

<Explanation of linking elements X ¹ and X ² in the compound >
X ¹ and X ² in the formula (1A) and the formula (2A) are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or. > Se, and the above-mentioned> N-R R,> C (-R) ₂ R, and> Si (-R) ₂ R are independently hydrogen and optionally substituted aryl, respectively. Heteroaryl which may be substituted, alkyl which may be substituted, or cycloalkyl which may be substituted. The details of the substituents listed here will be described later.

As X ¹ and X ² ,>N-R,>O,> S, or> C (-R) ₂ is preferable,> N-R or> O is more preferable, and> N-R is even more preferable. From the viewpoint of good TADF properties,>N-R,> O and> S are preferable, and more specifically,> N-R is preferable from the viewpoint of orbital localization due to the multiple resonance effect, and heavy atoms. From the viewpoint of effect,> S is preferable. From the viewpoint of emission wavelength,> O is preferable for short wavelength emission, and> NR or> S is preferable for long wavelength emission.

At least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ are bound by a single bond or a linking group (collectively referred to as a linking group). May be. The linking groups include -CH ₂ -CH _2- , -CHR-CHR-, -CR ₂ -CR _2- , -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- can be mentioned, and examples thereof include the following structures. The R of -CHR-CHR-, the R of -CR _{2 -} CR2-, the R of -CR = CR-, the R of -N (-R)-, the R of -C (-R) _2- , And -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or cycloalkyl. It may be replaced with. Further, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, and a heteroarylene. The details of the substituents listed here will be described later.

The linking group is a single bond, -CR = CR-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) ₂ as a linking group. -, And -Se- are preferred, and single bonds, -CR = CR-, -N (-R)-, -O-, -S-, and -C (-R) _2- as linking groups are more preferred. , Single bond, -CR = CR- as a linking group, -N (-R)-, -O-, and -S- are more preferable, and single bond is most preferable.

The position where the two Rs are bonded by the binding group is not particularly limited as long as it can be bonded, but it is preferable that the two Rs are bonded at the most adjacent positions. For example, when the two Rs are phenyl groups, the "" in the phenyl group It is preferable to bond the ortho (2nd position) positions with reference to the bonding position (1st position) of "C" or "Si" (see the above structural formula).

<Explanation of changes in ring structure due to the bond between X ¹ or X ² and the ring>
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ¹ in formulas (1A) and (2A) are single bonds or linking groups (these). May be bonded to at least one of the a ring and the B ring (b ring) by means of a binding group).
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² in formulas (1A) and (2A) are single bonds or linking groups (these). May be bonded to at least one of the a ring and the E ring (e ring) by means of a binding group).

The linking groups include -CH ₂ -CH _2- , -CHR-CHR-, -CR ₂ -CR _2- , -CH = CH-, -CR = CR-, -C≡C-, -N (-R). )-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , and -Se-. The R of -CHR-CHR-, the R of -CR _{2 -} CR2-, the R of -CR = CR-, the R of -N (-R)-, the R of -C (-R) _2- , And -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or cycloalkyl. It may be replaced with. Further, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, and a heteroarylene. The details of the substituents listed here will be described later.

As X ¹ or X ² involved in binding,> N-R and> C (-R) ₂ are preferable, and> N-R is more preferable.

The linking group is a single bond, -CR = CR-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) ₂ as a linking group. -, And -Se- are preferred, and single bonds, -CR = CR-, -N (-R)-, -O-, -S-, and -C (-R) _2- as linking groups are more preferred. , Single bond, -CR = CR- as a linking group, -N (-R)-, -O-, and -S- are more preferable, and single bond is most preferable.

As the ring to be bonded, the B ring (b ring) is preferable for X ¹ , and the E ring (e ring) is preferable for X ² .

In the upper formula (1A), "R of> N-R, R of> C (-R) ₂ or R of> Si (-R) ₂ is a ring and B by a single bond or a linking group. The stipulation that "it is bound to at least one of the rings (or E-rings)" is that in the lower equation (2A), "R of> N-R, R of> C (-R) ₂ ", or> R of Si (-R) ₂ is single bond, -CH = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C ( -R) _2- , -Si (-R) _2- , or -Se- is attached to at least one of the a ring and the b ring (or e ring). "

This regulation can be expressed, for example, by the following structural formula. Although the substituents R ^a , R ^b , R ^c , R ^d , and R ^e in the structural formula are hidden, they actually exist.

In the structural formula on the left, in the example where R in the options (>N-R,> C (-R) ₂ , and> Si (-R) ₂ ) of X ¹ and X ² is bonded to the b ring and the e ring, respectively. Represents a compound having a B'ring and an E'ring formed by condensing other rings so as to incorporate X ¹ or X ² with respect to the b ring (benzene ring) and the e ring (benzene ring). ing. The formed fused ring B'and fused ring E'are, for example, a phenoxazine ring, a phenothiazine ring, a carbazole ring, an acridine ring, or the like.

The structural formula in the center represents a more specific example of the structural formula on the left, where R (phenyl group) of> NR of X ¹ and X ² is a b ring (benzene ring) by a single bond, respectively. This is an example in which the carbazole rings B'and E'enclosed by a broken line are formed by bonding with the e-ring (benzene ring).

The structural formula on the right represents a more specific example of the structural formula on the left, where R (phenyl group) of> NR of X ¹ and X ² is the linking group -O-, respectively. A phenoxazine ring B'enclosed by a broken line is formed by being bonded to the b ring (benzene ring), and a phenoxazine ring E'enclosed by a broken line is formed by being bonded to the e ring (benzene ring) by the linking group -S-. It is an example formed.

R in the choices of X ¹ and X ² (>N-R,> C (-R) ₂ , and> Si (-R) ₂ ) is a ring (B ring, E ring, b ring and e ring) due to a linking group. The position to bond with is not particularly limited as long as it can be bonded, but it is preferable to bond at the most adjacent position. For example, when R is a phenyl group, "X ¹ " in the ring to be bonded and the phenyl group. And, it is preferable to bond the ortho (2nd position) positions with reference to the bonding position (1st position) of "X ² " (see the above structural formula).

In the description of the above-mentioned specific examples, all forms other than these specific examples, for example, when any one of X ¹ and X ² is bonded to the ring, when it is bonded to the a ring, it is bonded to the other linking group. It can be applied in the same way.

<Explanation of carbazole-like structure (2)>
In the compound of the present invention, as described above, R of X1 and X2 in the ^formula ( ^1A ) and the formula (2A) can be bonded to the adjacent ring, and ^among these bonding forms, "X1" is used as "X1". > N-R "(this R is limited to the substituted aryl, the substituted heteroaryl, or the substituted cycloalkyl) and the" B ring "or" Due to the bond formed with the "b ring" (also referred to as the X ¹ B bond or the X ¹ b bond), the second carbazole-like structure is further "> N-R R" as X ² (this R). Is limited to the substituted aryl, the substituted heteroaryl, or the substituted cycloalkyl) and the bond formed by the "E-ring" or "e-ring". A third carbazole-like structure may be present (also referred to as an ^X2E bond or an ^X2e bond).

As the R of> NR that can form a carbazole-like structure, an aryl that may be substituted is preferable.
Further, as the bonding group between R and the ring, a single bond is preferable.

<Explanation of the number of carbazole-like structures>
As mentioned above, in formulas (1A) and (2A), the first carbazole-like structure is formed from a CD or cd bond and the second structure is an X ¹ B bond or an X ¹ b. It is formed from a bond, and a third structure is formed from an ^X2E or ^X2e bond. Further, in the formulas (1B) and (2B), the first carbazole-like structure is formed from a CD bond or a cd bond, and the second structure is formed from a GB bond or a gb bond. A third structure is formed from an FE bond or a fe bond. The compounds of the present invention are characterized in that one or two of these three carbazole-like structures that can be formed within the molecule are formed.

In formulas (1A) and (2A), when only the first carbazole-like structure is present (1Cz form), when only the second carbazole-like structure is present (2Cz form), the first and 2 There are cases where the second carbazole-like structure is present (12 Cz body) and the second and third carbazole-like structures are present (23 Cz body), but 1 Cz body, 12 Cz body, and 23 Cz body are preferable. The 1Cz form and the 12Cz form are more preferable, and the 1Cz form is further preferable.

In formulas (1B) and (2B), there are cases where only the first carbazole-like structure is present (1 Cz form) and cases where the first and second carbazole-like structures are present (12 Cz form). A 1 Cz form is preferable.

<Explanation of structural changes in rings a and b to g>
In the explanation so far, the a ring, b ring, c ring, d ring, e ring, f ring, and g ring have been illustrated and described as benzene rings, but hereinafter, the a ring, b ring to g ring are benzene rings. An example of structural change to a 5-membered or 6-membered aryl ring or a heteroaryl ring will be described. The above description will be similarly understood even when these rings undergo the following structural changes.

<Structural change of a ring>
The "-C (-R ^a ) =" in the a ring in the formulas (1A) and (2A) may be replaced with "-N =" to form a pyridine ring. The following structural diagram is a diagram in which only a part of the a ring and its peripheral structure is extracted.

以上に示すように、例えばｄ環における「－Ｃ（－Ｒ^ｄ）＝」の箇所が「－Ｎ＝」に置き換わってもよく、このようにして、各式中でベンゼン環として表示されるｄ環は、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、その他の含窒素ヘテロアリール環に変化してもよい。また、ｄ環上に隣接する基が存在する場合（上記式中では残りの２つの隣接するＲ^ｄ）には、これらが結合してｄ環と共にヘテロアリール環（上記式中ではキノリン環）を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。 <Structural change of b to g ring>
Any "-C (-R) =" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring in formulas (2A) and (2B) (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be replaced with "-N =".

As shown above, for example, the place of "-C (-R ^d ) =" in the d ring may be replaced with "-N =", and in this way, d displayed as a benzene ring in each equation. The ring may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. When adjacent groups are present on the d-ring (the remaining two adjacent R ^ds in the above formula), they are bonded to form a heteroaryl ring (quinoline ring in the above formula) together with the d-ring. It is as described above that the rings formed and formed may be further substituted (indicated by n R's).

In addition, there are the following modification examples.

It is preferable that "-C (-R ^d ) =" at the ortho-position or para-position is replaced with "-N =" with respect to the carbon to which X ¹ , X ² , or> N- is bonded.

The same applies when other parts are replaced with "-N =" or when the b ring, c ring, e ring, f ring, and g ring other than the d ring are changed.

以上に示すように、例えばｄ環における「－Ｃ（－Ｒ^ｄ）＝Ｃ（－Ｒ^ｄ）－」の箇所が「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わってもよく、このようにして、各式中でベンゼン環として表示されるｄ環は、Ｒ置換のピロール環、フラン環、チオフェン環、その他の含窒素・酸素・硫黄ヘテロアリール環（５員環）やアリール環（５員環）に変化してもよい。また、ｄ環上に隣接する基が存在する場合（上記式中では残りの２つの隣接するＲ^ｄ）には、これらが結合してｄ環と共にヘテロアリール環（上記式中ではＲ置換のインドール環、ベンゾフラン環、またはベンゾチオフェン環などの環）やアリール環を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。 Any "-C (-R) = C (-R)-" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring in formulas (2A) and (2B) (here. R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N (-R)-", "-O-", "-S-", "-". It may be replaced with C (-R) _2- "," -Si (-R) _2- ", or" -Se- ", and R," -C (-C ( -R) _2- "R and" -Si (-R) _2- "R are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl. The details of the substituents listed here will be described later.

As shown above, for example, the place of "-C (-R ^d ) = C (-R ^d )-" in the d ring is "-N (-R)-", "-O-", "-S-". , "-C (-R) _2- ", "-Si (-R) _2- ", or "-Se-", thus displayed as a benzene ring in each equation. The d-ring may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-containing / oxygen / sulfur heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). When adjacent groups are present on the d-ring (the remaining two adjacent R ^ds in the above formula), they are combined to form a heteroaryl ring together with the d-ring (R-substituted indole in the above formula). As described above, a ring (a ring such as a ring, a benzofuran ring, or a benzothiophene ring) or an aryl ring may be formed, and the formed ring may be further substituted (indicated by n R).

In addition, there are the following modification examples.

Other parts are "-N (-R)-", "-O-", "-S-", "-C (-R) _2- ", "-Si (-R) _2- ", or " The same applies to the case where it is replaced with "-Se-" or when the b ring, c ring, e ring, f ring, and g ring other than the d ring are changed.

At least one of the two Rs of "-C (-R) _2- " and the two Rs of "-Si (-R) _2- " is a single bond or a linking group (these are collectively a bonding group). It may be bonded by (also referred to as). The linking groups include -CH ₂ -CH _2- , -CHR-CHR-, -CR ₂ -CR _2- , -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- can be mentioned, and examples thereof include the following structures. The R of -CHR-CHR-, the R of -CR _{2 -} CR2-, the R of -CR = CR-, the R of -N (-R)-, the R of -C (-R) _2- , And -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or cycloalkyl. It may be replaced with. Further, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, and a heteroarylene. The details of the substituents listed here will be described later.

The linking group is a single bond, -CR = CR-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) ₂ as a linking group. -, And -Se- are preferred, and single bonds, -CR = CR-, -N (-R)-, -O-, -S-, and -C (-R) _2- as linking groups are more preferred. , Single bond, -CR = CR- as a linking group, -N (-R)-, -O-, and -S- are more preferable, and single bond is most preferable.

The position where the two Rs are bonded by the binding group is not particularly limited as long as it can be bonded, but it is preferable that the two Rs are bonded at the most adjacent positions. For example, when the two Rs are phenyl groups, the "" in the phenyl group It is preferable to bond the ortho (2nd position) positions with reference to the bonding position (1st position) of "C" or "Si" (see the above structural formula).

<Specific explanation of rings and substituents>
Next, the details of the rings and substituents (including the second substituent further substituted with the first substituent) listed in the above description will be described collectively.

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or carbon. It is an aryl ring of the number 6 to 10.
The "aryl ring" as the B ring to the G ring in the formula (1A) and the formula (1B) is "R ^b , R ^c , R ^d , R ^e " defined by the formula (2A) and the formula (2B). , R ^f , and R ^g , which are bonded to each other to correspond to an aryl ring formed with a b ring, a c ring, a d ring, an e ring, an f ring, and a g ring, respectively. As for this "formed aryl ring", since the b ring to the g ring are already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the fused ring in which the smallest 5-membered ring is condensed with this benzene ring is 9 carbon atoms. Is the lower limit of carbon number.
However, the b-ring to g-ring, which are the benzene rings, are changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing / sulfur-containing heteroaryl ring (5-membered ring) as described above. In this case, the lower limit of the number of carbon atoms changes accordingly.

The specific "aryl ring" is, for example, a benzene ring which is a monocyclic system, a naphthalene ring which is a fused bicyclic system, an acenaphtylene ring, a fluorene ring, a phenalene ring, or a phenanthrene ring or an anthracene ring which is a fused tricyclic system. , A triphenylene ring, a pyrene ring, or a naphthalene ring, which is a fused tetracyclic system, or a perylene ring or a pentacene ring, which is a fused pentacyclic system.

The “heteroaryl ring” is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, and a heterocycle having 2 to 15 carbon atoms. An aryl ring, a heteroaryl ring having 2 to 10 carbon atoms, or the like. The "heteroaryl ring" is, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.
The "heteroaryl ring" as the B ring to the G ring in the formula (1A) and the formula (1B) is "R ^b , R ^c , R ^d , R" defined by the formula (2A) and the formula (2B). Corresponds to "heteroaryl ring formed with b-ring, c-ring, d-ring, e-ring, f-ring, and ^g -ring, respectively, by bonding adjacent groups of ^e , ^Rf , and Rg". However, regarding this "formed heteroaryl ring", since the b ring to the g ring are already composed of a benzene ring having 6 carbon atoms, the total number of fused rings in which the smallest 5-membered ring is condensed with this benzene ring. The carbon number 6 is the lower limit carbon number.
However, the b-ring to g-ring, which are the benzene rings, are changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing / sulfur-containing heteroaryl ring (5-membered ring) as described above. In this case, the lower limit of the number of carbon atoms changes accordingly.

Specific "heteroaryl rings" include, for example, a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxaziazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, and a 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, phenanthrolin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclydin ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indridin ring. Ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphor ring, dibenzophosphore ring, A benzophosphor oxide ring, a dibenzophosphol oxide ring, a frazan ring, a thiantolene ring, an indolocarbazole ring, a benzoindorocarbazole ring, a benzobenzoindolocazole ring, an imidazoline ring, an oxazoline ring, and the like.

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

Specific "aryl" is, for example, phenyl which is a monocyclic system, biphenylyl (2-biphenylyl, 3-biphenyryl, or 4-biphenylyl) which is a bicyclic system, and naphthyl (1-naphthyl or which is a fused bicyclic system). 2-naphthyl), terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-, which is a tricyclic system. Il, o-terphenyl-4'-il, p-terphenyl-2'-il, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o -Terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl- 4-yl), fused tricyclics, acenaphtylene- (1-, 3-, 4-, or 5-) yl, fluorene- (1-, 2-, 3-, 4-, or 9-) yl. , Phenanthrene- (1- or 2-) ill, phenanthrene- (1-, 2-, 3-, 4-, or 9-) il, or anthracene- (1-, 2-, or 9-) il, 4 The ring system quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl) , Or m-quaterphenyl), a fused tetracyclic system, triphenylene- (1- or 2-) yl, pyrene- (1-, 2-, or 4-) yl, or naphthacene- (1-, 2) -Or 5-) yl, or perylene- (1-, 2-, or 3-) yl, or pentasen- (1-, 2-, 5-, or 6-) yl, which is a fused pentacyclic system. And so on.

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

The "allylen" is, for example, an arylene having 6 to 30 carbon atoms, preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms. Arilen and so on.
Specific examples of the "arylene" include a structure in which one hydrogen is removed from the above-mentioned "aryl" (monovalent group) to form a divalent group.

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

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-. Indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, Phenoxadinyl, Phenothiadinyl, Phenazinyl, Phenazasilinyl, Indridinyl, Franyl, Benzofuranyl, Isobenzofuranyl, Dibenzofuranyl, Naftbenzofuranyl, Thiophenyl, Benzothiophenyl, Isobenzothiophenyl, Dibenzothiophenyl, Naftbenzothiophenyl, Benzo Phenyl, dibenzophosphoryl, monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphol oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocrabazolyl, benzobenzoindorocarbazolyl, For example, imidazolinyl or oxazolinyl.

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

The "heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or carbon. Heteroarylene of the number 2 to 10 and the like. Further, the "heteroarylene" is a divalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.
Specific examples of the "heteroarylene" include a structure in which one hydrogen is removed from the above-mentioned "heteroaryl" (monovalent group) to form a divalent group.

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

A "diarylboryl" is a boron group substituted with two aryls, and the description of "aryl" described above can be cited for details of this aryl. Further, these two aryls may be a single bond or a linking group (for example, -CH = CH-, -CR = CR-, -C≡C-,>N-R,>O,>S,> C (-R). ) ₂ ,> Si (-R) ₂ , or> Se) may be bonded. Here, the R of -CR = CR-, the R of> N-R, the R of> C (-R) ₂ , and the R of> Si (-R) ₂ are aryl, heteroaryl, diarylamino, and alkyl. , Alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, the at least one hydrogen in said R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Further, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, and a heteroarylene. For details of the substituents listed here, the description of "aryl", "arylene", "heteroaryl", "heteroallylene", and "diarylamino" described above, and "alkyl", "alkoxy" described later. , "Alkinyl", "Cycloalkyl", "Cycloalkylene", "Alkoxy", and "aryloxy" can be cited.

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

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

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

For "alkynyl", the above description of "alkyl" can be referred to, and it is a group in which the CC single bond in the structure of "alkyl" is replaced with a C≡C triple bond, and only one is used. It also includes groups in which two or more single bonds are replaced with triple bonds (also called alkaziin-yl or alcantriin-yl).

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

Specific "cycloalkyl" is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyls having 1 to 5 carbon atoms or 1 to 4 carbon atoms (particularly methyl). Substitutes, norbornenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1] .0] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazurenyl.

The "cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, and a carbon number of carbon atoms. It is a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms.
Specific examples of the "cycloalkylene" include a structure in which one hydrogen is removed from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

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

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

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

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

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

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

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

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

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

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron attracting property of the structure of the first substituent or the second substituent, and the group represented by the following structural formula is preferable. Yes, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6- Xyryl, 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" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "toct" represents t-octyl, and * represents the binding position.

<Explanation of cycloalkane condensation>
Further, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

For example, in the compound represented by the formula (1A) or the formula (1B), the B ring, the C ring, the D ring, the E ring, the F ring, the G ring, the aryl, and the heteroaryl, the formula (2A) or the formula (2B). ), At least one of the b ring, c ring, d ring, e ring, f ring, g ring, the "formed ring", aryl, and heteroaryl is at least one cycloalkane. It may be condensed with.

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 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo [1.1.0] butane, bicyclo [1.1.1] pentane, and so on. Bicyclo [2.1.0] pentane, bicyclo [2.1.1] hexane, bicyclo [3.1.0] hexane, bicyclo [2.2.1] heptane, bicyclo [2.2.2] octane, Examples thereof include adamantane, diamantane, decahydronaphthalene and decahydroazulene, as well as alkyl (particularly methyl) substituents, halogen (particularly fluorine) substitutes and dehydrogenated substitutes having 1 to 5 carbon atoms thereof.

Among these, at least 1 in the carbon at the α-position of the cycloalkane (the carbon at the position adjacent to the carbon at the condensation site in the cycloalkyl condensed to the aromatic ring or the heteroaromatic ring) as shown in the following structural formula, for example. A structure in which one hydrogen is substituted is preferable, a structure in which two hydrogens are substituted in the carbon at the α-position is more preferable, and a structure in which a total of four hydrogens are substituted in the carbon at the two α-positions is further preferable. 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.

The number of cycloalkanes condensed on one aromatic ring or complex aromatic 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 group) is shown below. When it is a benzene ring, * in each structural formula means that it is a benzene ring contained in the skeleton structure of the compound, and when it is a phenyl group, it means a bond that replaces it with the skeleton structure of the compound. 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 aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl group), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even so, the same is true.

At least one -CH _2- in the cycloalkane may be substituted with -O-. However, when a plurality of -CH _2- are replaced by -O-, the adjacent -CH _2- is not replaced by -O-. For example, an example in which one or more -CH _2- are substituted with -O- in a cycloalkane condensed on one benzene ring (phenyl group) is shown below. When it is a benzene ring, * in each structural formula means that it is a benzene ring contained in the skeleton structure of the compound, and when it is a phenyl group, it means a bond that replaces it with the skeleton structure of the compound. Even if the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl group), the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. Even so, the same is true.

At least one hydrogen in the cycloalkane may be substituted, and the substituents include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are single-bonded). (Or may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, dehydrogen, cyano or halogen, the details of which are described above for the first substituent. Can be quoted. Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine), deuterium and the like are preferable. Further, when cycloalkyl is substituted, a substituted form forming a spiro structure may be used. For example, an example in which a spiro structure is formed on a cycloalkane condensed on one benzene ring (phenyl group) is shown below. When it is a benzene ring, * in each structural formula means that it is a benzene ring contained in the skeleton structure of the compound, and when it is a phenyl group, it means a bond that replaces it with the skeleton structure of the compound.

As another form of cycloalkane condensation, the polycyclic aromatic compound of the present invention is, for example, a diarylamino group condensed with cycloalkane (condensed to this aryl group portion), a carbazolyl group condensed with cycloalkane (this). Examples thereof include substitution with a benzocarbazolyl group (condensed on the benzene ring portion) or cycloalkane condensed (condensed on the benzene ring portion). The above description can be cited for the "diarylamino group".

Further, as a more specific example, ^Ra in the polycyclic aromatic compound represented by the formula (1A) or the formula (2A) is a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion). Alternatively, there is an example of a carbazolyl group condensed with a cycloalkane (condensed on this benzene ring portion).

<Explanation of substitution with deuterium, cyano, or halogen>
At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine.

各式中、
Ｒは、それぞれ独立して、水素、炭素数６～１６のアリール、炭素数２～２０のヘテロアリール、ジアリールアミノ（ただしアリールは炭素数６～１０のアリール）、ジアリールボリル（ただしアリールは炭素数６～１０のアリールであり、２つのアリールは単結合または連結基により結合していてもよい）、炭素数１～１２のアルキル、または炭素数３～１６のシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は、炭素数１～５のアルキルまたは炭素数５～１０のシクロアルキルで置換されていてもよく、
ｏはそれぞれ独立して１～３の整数であり、
ｐはそれぞれ独立して１～４の整数であり、
ｑはそれぞれ独立して１～５の整数であり、
上記各式で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 <Explanation of Specific Examples of Polycyclic Aromatic Compounds of the Present Invention>
For example, a compound represented by any of the following structural formulas is preferable.

In each formula,
R is independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diarylamino (where aryl is aryl with 6 to 10 carbon atoms), and diarylboryl (where aryl is carbon number of carbon atoms). It is an aryl of 6 to 10 and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least in the R. One hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
o is an integer of 1 to 3 independently,
p is an integer of 1 to 4 independently of each other.
q is an independent integer of 1 to 5, respectively.
At least one hydrogen in the compound represented by each of the above formulas may be substituted with deuterium, cyano, or halogen.

For a more specific explanation of R, the above-mentioned explanation of aryl and the like can be quoted. Further, as o, p, and q, 1 or 2 is preferable, 1 is more preferable, and 0 is further preferable.

<Use as Thermally Activated Delayed Fluorescence (TADF) Material>
The compound of the present invention can also be used as a TADF material. In particular, the compounds represented by the formulas (1A) and (2A) are preferable to the compounds represented by the formulas (1B) and (2B), and the B ring to G ring and the b ring to g are preferable. The ring that shares a bond with the condensed bicyclic structure in the ring is preferably a 6-membered ring, and more preferably a 6-membered aryl ring including the a ring.
Further, as a binding group for forming a carbazole-like structure, a single bond is preferable (as an example, the following structural formula), and a case where only the first carbazole-like structure is present (1Cz form) is preferable (1A-111, 1A). (Structural formulas other than -112, 1A-214), among carbazole-like structures, in particular, an aryl ring such as a phenyl group at the para position (particularly the para position in the c ring or d ring) based on the bond position of "N" in the carbazole structure. Is preferably substituted (structural formulas other than 1A-214, 1A-331, 1A-702), and diaryl to the meta position (particularly the meta position in the b ring and e ring) with respect to the bond position of X ¹ and X ² . It is preferable to substitute a nitrogen-containing group such as an amino group or a carbazolyl group (structural formula of 1A-31, 1A-32, 1A-38, 1A-407).

<Explanation of Specific Examples of Polycyclic Aromatic Compounds of the Present Invention>
As a more specific example of the polycyclic aromatic compound, a compound represented by the following structural formula can be mentioned. In the following structural formula, "Me" indicates a methyl group, "tBu" indicates a t-butyl group, and "D" indicates deuterium.

The polycyclic aromatic compound according to the present invention is a polymer compound obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer (the monomer for obtaining this polymer compound is a polymerizable substituent). (Having), or a polymer crosslinked product obtained by further cross-linking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent), or a main chain type polymer and the above. A pendant type polymer compound reacted with a reactive compound (the reactive compound for obtaining this pendant type polymer compound has a reactive substituent) or a pendant further crosslinked with the pendant type polymer compound. As a type polymer crosslinker (the pendant type polymer compound for obtaining this pendant type polymer crosslinker has a crosslinkable substituent), a material for an organic device, for example, a material for an organic electric field light emitting element, an organic electric field Effect It can be used as a material for a transistor, a material for an organic thin film solar cell, or a wavelength conversion filter.

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

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

Such a polymer compound, a polymer crosslinker, a pendant type polymer compound, and a pendant type polymer crosslinker are not only the repeating unit of the polycyclic aromatic compound according to the present invention, but also substituted or unsubstituted triaryl. Amine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetrasen, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted tetraphenylsilane. It may contain at least one selected from the group of compounds consisting of spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran as a repeating unit.

Substituents in these repeating units include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (even if the two aryls are attached via a single bond or a linking group). Good), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. For details of the "aryl" of triarylamines and their substituents, the description of the polycyclic aromatic compounds according to the present invention can be cited.

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

2. 2. Method for Producing Polycyclic Aromatic Compound According to the Present Invention The polycyclic aromatic compound of the present invention basically first has a ring a and a ring B to G or a ring b to g ring (“N”). , Or a group containing X ¹ or X ² ) to produce an intermediate (first reaction), followed by a ring a and a ring B to G or a ring b to g. The final product can be produced by binding with (a group containing Y ¹ to Y ³ ) (second reaction). The manufacturing method described in International Publication No. 2015/102118 can be referred to.

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-Heartwig 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.

The ^second reaction is ^a reaction for introducing Y1 to Y3 that binds the a ring to the B ring to the G ring or the b ring to the g ring, as shown in the following schemes (1) and (2). First, the hydrogen atom between "N" and X ¹ and X ² and the hydrogen atom between "N" are orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Next ^{, a} halide of Y1 to Y3 such as boron trichloride and boron tribromide is added, metal exchange of lithium-boron is performed, and then a Bronsted base such as N, N-diisopropylethylamine is added. Tandem Bora Friedel Crafts can be reacted to obtain the desired product. In the second reaction, Lewis acid such as aluminum trichloride may be added to accelerate the reaction. In addition, the definition of the code in each structural formula in the following schemes (1) and (2), and further in the subsequent schemes is the same as the above-mentioned definition.

In the above scheme, lithium was introduced to the desired position by orthometalation, but as in scheme (3) below, a bromine atom or the like was introduced at the position where lithium was to be introduced, and the desired position was also achieved by halogen-metal exchange. Lithium can be introduced. According to this method, a target product can be produced even in a case where orthometalation cannot be performed due to the influence of a substituent, which is useful.

In the above schemes (1) to (3), Y ¹ to Y ³ are typical manufacturing methods such as boron (B).

Next, as ^an example, the cases where Y1 to Y3 ^are phosphorus sulfides, phosphoroxides or phosphorus atoms are shown in the following schemes (4) and (5). As in the past, first, the hydrogen atom between "N" and X ¹ and X ² and the hydrogen atom between "N" are orthometalated with n-butyllithium or the like. Then, phosphorus trichloride and sulfur are added in this order, and finally Lewis acid such as aluminum trichloride and Bronsted base such as N, N-diisopropylethylamine are added to cause a tandem phospha Friedel ^- Crafts reaction, Y1 to Y. A compound in which ³ is a phosphorous sulfide can be obtained. Further, the obtained phosphorous sulfide compound can be treated with m-chloroperbenzoic acid (m-CPBA) to obtain ^a compound in which Y1 to Y3 ^are phosphates, and the obtained compound can be treated with triethylphosphine to obtain Y. Compounds in which ¹ to Y ³ are phosphorus atoms can be obtained.

In the above scheme, examples of B, P, P = O or P = S are mainly described for Y1 to Y3 ^, but ^other compounds can also be produced by appropriately changing the raw materials.

^In the above scheme, before adding Y1 to Y3 halides such as boron trichloride and boron tribromide, the hydrogen atom (or halogen atom) between "^{N" and X 1 and X 2 or "} An example of tandem heterofree delcrafts reaction by orthometalizing hydrogen atoms (or halogen atoms) between "N" with butyllithium or the like was shown, but orthometalation using butyllithium or the like was performed. Instead ^, the reaction can be allowed to proceed by adding Y1 to ^Y3 halides such as boron trichloride and boron tribromide.

Examples of the solvent used in the above scheme include t-butylbenzene and xylene.

Examples of the orthometallation reagent used in the above scheme include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, lithium diisopropylamide, lithium tetramethylpiperidide, and lithium hexamethyldisila. Examples thereof include organic alkaline compounds such as dido and potassium hexamethyldisilazide, and dispersed alkali metals such as organic solvent-dispersed Na.

Metal exchange reagents for the metals used in the above scheme include Y1 to ^Y3 trifluorides ^{, Y1} to ^Y3 trichlorides ^, and ^Y1 to ^{Y3 triiodides} . Y ¹ to Y ³ halides such as Y ¹ to Y ³ triiodides, Y ¹ to Y ³ amination halides such as CIPN (NET ₂ ) ₂ , Y ¹ to Y ³ alkoxys, Y ¹ Examples thereof include aryl ^oxidates of ~ Y3.

Bronsted bases used in the above scheme include N, N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N, N-. Dimethylaniline, N, N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylboran, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Examples thereof include Si (where Ar is aryl such as phenyl).

Lewis acids used in the above scheme include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ , OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In (OTf) ₃ , SnCl. ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc (OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn (OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg (OTf) ₂ , LiOTf, NaOTf, KOTf, Me ₃ Examples thereof include Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y (OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , and CoBr ₃ .

In the above scheme, Bronsted bases or Lewis acids may be used to facilitate the tandem hetero-Friedel-Crafts reaction. However ^, Y1 to ^Y3 halides such as Y1 to ^Y3 trifluoride ^, Y1 to ^Y3 trichloride ^, Y1 to ^{Y3 triodoride ,} and Y1 to ^Y3 triiodide. When is used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophobic substitution reaction progresses, so it is effective to use a Bronsted base that captures the acid. be. ^On the ^other hand ^, when the amination halides of Y1 to Y3 and the ^alkoxydoates of Y1 to Y3 are used, amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds, so that in many cases, they are produced. Although it is not necessary to use a Bronsted base, the use of Lewis acid, which promotes the elimination of amino and alkoxy groups, is effective because of its low ability to desorb.

Further, the polycyclic aromatic compound of the present invention also includes a compound in which at least a part of hydrogen is substituted with dehydrogen, cyano, or halogen, but such a compound or the like is dehydrogenated at a desired position. By using a halogenated raw material such as cyanation, fluorination or chlorination, it can be produced in the same manner as described above.

3. 3. Organic device In the chemical structural formulas exemplified below, "Me" represents a methyl group and "tBu" represents a t-butyl group.
The polycyclic aromatic compound according to the present invention can be used as a material for organic devices. Examples of the organic device include an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, and the like.

3-1. Organic electroluminescent device The organic EL device according to this embodiment will be described in detail below with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.

<Structure of organic electroluminescent device>
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 an aspect of the layer constituting the organic EL element, in addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", " Substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode "," substrate / 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 / cathode " The configuration may be "/ light emitting layer / electron transport layer / cathode" or "substrate / anode / light emitting layer / electron injection layer / cathode".

<Substrate in organic electroluminescent device>
The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Of these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. As for the glass substrate, soda lime glass, non-alkali glass, or the like is used, and the thickness may be sufficient to maintain the mechanical strength. Therefore, for example, 0.2 mm or more may be used. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, non-alkali glass is preferable because it is better to have less elution ions from the glass, but soda lime glass having 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.

<Anode in organic electroluminescent device>
The anode 102 serves to inject holes into the light emitting layer 105. When at least one layer of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 via these layers. It will be.

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.

<Hole injection layer and hole transport layer in organic electroluminescent device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 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. In the present invention, as the material for the hole injection layer and the hole transport layer, a polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) can be used.

The material forming the hole injection layer 103 and the hole transport layer 104 is a compound, a p-type semiconductor, or a hole injection layer of an organic EL element that has been 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 (aromatic tertiary). Polymers with amino in the main or side chains, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , 4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-di (3-methylphenyl) -4 , ^4' -diphenyl-1,1'-diamine, N, N'-dinaphthyl-N, N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4, ^N4' -diphenyl- N ⁴ , N ^4' -bis (9-phenyl-9H-carbazole- ³ -yl)-[1,1'-biphenyl] -4,4'-diamine, ^N4 , N4, N4 ^' , ^{N4 '} -Tetra ([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4,4'-diamine, 4,4', 4 "-tris (3-methylphenyl (phenyl) ) Amino) Triphenylamine derivatives such as triphenylamine, starburstamine derivatives, etc.), stylben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole Derivatives, quinoxalin derivatives (eg, 1,4,5,8,9,12-hexazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes. 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 producing a light emitting element can be formed and holes can be injected from the anode. Further, the compound is not particularly limited as long as it can transport holes.

It is also known that the conductivity of organic semiconductors is strongly affected by its doping. Such an organic semiconductor matrix substance is composed of a compound having a good electron donating property or a compound having a good electron accepting property. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron donors. (For example, the document "M.Pfeiffer, A.Beyer, T.Fritz, K.Leo, Appl.Phys.Lett., 73 (22), 3202-3204 (1998)" and the document "J.Blochwitz, M." .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 varies considerably. Known matrix materials having hole transport properties include, for example, benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or specific metallic phthalocyanines (particularly zinc phthalocyanines (ZnPc)) (such as zinc phthalocyanines). Japanese Unexamined Patent Publication No. 2005-167175).

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

<Light emitting layer in organic electroluminescent device>
The light emitting layer 105 is a layer that emits light by recombining the holes injected from the anode 102 and the electrons injected from the cathode 108 between the electrodes to which an electric field is applied. 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 preferable that the compound exhibits a strong emission (fluorescence) efficiency. In the present invention, as the material for the light emitting layer, a host material and, for example, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) as a dopant material can be used.

The light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting layer material (host material, dopant material). The host material and the dopant material may be one kind or a 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 can be manufactured by a wet film forming method after being mixed with a host material in advance and then vapor-deposited at the same time, or mixed with an organic solvent in advance with a host material. It may be filmed.

The amount of the host material used depends on the type of host material and may be determined according to the characteristics of the host material. The guideline for the amount of the host material used is preferably 50 to 99.99% by weight, more preferably 80 to 99.95% by weight, and further preferably 90 to 99.9% by weight of the entire 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 material used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, still more preferably 0.1 to 10% by weight, based on the total amount of the light emitting layer material. Is. Within the above range, for example, it is preferable in that the density quenching phenomenon can be prevented. Further, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

On the other hand, in an organic electroluminescent device using a thermally activated delayed fluorescent dopant material, it is preferable that the amount of the dopant material used is low because the concentration dimming phenomenon can be prevented, but the amount of the dopant material used is high. The concentration is preferable from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic electroluminescent device using a thermally activated delayed fluorescence assisted dopant material, the dopant material is more efficient than the amount of the assisted dopant material used in terms of the efficiency of the thermal activated delayed fluorescent mechanism of the assisted dopant material. It is preferable that the amount used is low.

When the assist dopant material is used, the guideline for the amount of the host material, the assist dopant material, and the dopant material to be used is 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 20 to the total weight of the light emitting layer material, respectively. 0.001% by weight, preferably 60-99.99% by weight, 39-5% by weight and 10-0.01% by weight, more preferably 70-99.95% by weight, 29. It is ~ 10% by weight and 5 ~ 0.05% by weight. The compound represented by the general formula (1A) or the general formula (1B) and its polymer compound can also be used as an assist dopant material.

Host materials include fused ring derivatives such as anthracene and pyrene, which have long been known as illuminants, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzos. Examples include fluorene derivatives.

The triplet energy of the host material should be higher than the triplet energy of the dopant or assist dopant having the highest triplet energy in the light emitting layer from the viewpoint of promoting the generation of TADF in the light emitting layer without inhibiting it. Preferably, specifically, the triplet energy of the host material is preferably 0.01 eV or more, more preferably 0.03 eV or more, still more preferably 0.1 eV or more. Further, a TADF active compound may be used as the host material.

Examples of the host material include a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), and the following general formula (H4). Examples thereof include a compound having a structure represented by the following, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. It is preferably a compound represented by the general formula (H1).

上記式（Ｈ１）中、Ｌ^１は炭素数６～３０のアリーレンまたは炭素数２～３０のヘテロアリーレンであり、炭素数６～２４のアリーレンが好ましく、炭素数６～１６のアリーレンがより好ましく、炭素数６～１２のアリーレンがさらに好ましく、炭素数６～１０のアリーレンが特に好ましく、また、炭素数２～２５のヘテロアリーレンが好ましく、炭素数２～２０のヘテロアリーレンがより好ましく、炭素数２～１５のヘテロアリーレンがさらに好ましく、炭素数２～１０のヘテロアリーレンが特に好ましい。アリーレンとして具体的には、ベンゼン環、ビフェニル環、ナフタレン環、テルフェニル環、アセナフチレン環、フルオレン環、フェナレン環、フェナントレン環、トリフェニレン環、ピレン環、ナフタセン環、ペリレン環およびペンタセン環などの二価の基が挙げられる。また、ヘテロアリーレンとして具体的には、ピロール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、イミダゾール環、オキサジアゾール環、チアジアゾール環、トリアゾール環、テトラゾール環、ピラゾール環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、トリアジン環、インドール環、イソインドール環、１Ｈ－インダゾール環、ベンゾイミダゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、１Ｈ－ベンゾトリアゾール環、キノリン環、イソキノリン環、シンノリン環、キナゾリン環、キノキサリン環、フタラジン環、ナフチリジン環、プリン環、プテリジン環、カルバゾール環、アクリジン環、フェノキサチイン環、フェノキサジン環、フェノチアジン環、フェナジン環、フェナザシリン環、インドリジン環、フラン環、ベンゾフラン環、イソベンゾフラン環、ジベンゾフラン環、チオフェン環、ベンゾチオフェン環、ジベンゾチオフェン環、フラザン環、チアントレン環、インドロカルバゾール環、ベンゾインドロカルバゾール環、ベンゾベンゾインドロカルバゾール環およびナフトベンゾフラン環などの二価の基が挙げられる。
式（Ｈ１）で表される化合物における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 <Compound represented by the general formula (H1)>

In the above formula (H1), L1 is ^an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, preferably an arylene having 6 to 24 carbon atoms, and more preferably an arylene having 6 to 16 carbon atoms. An arylene having 6 to 12 carbon atoms is more preferable, an arylene having 6 to 10 carbon atoms is particularly preferable, a heteroarylene having 2 to 25 carbon atoms is preferable, a heteroarylene having 2 to 20 carbon atoms is more preferable, and an arylene having 2 to 20 carbon atoms is more preferable. Heteroarylene of ~ 15 is more preferred, and heteroarylene of 2-10 carbon atoms is particularly preferred. Specifically, the arylene is a divalent ring such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthalene ring, a perylene ring and a pentacene ring. The basis of. Specific examples of the heteroarylene include a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiazazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, and a pyridine ring. Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring , Kinazoline ring, quinoxalin ring, phthalazine ring, naphthylidine ring, purine ring, pteridine ring, carbazole ring, aclysine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indridin ring, furan ring, Bivalent such as benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, frazan ring, thiantrene ring, indolocarbazole ring, benzoindorocarbazole ring, benzobenzoindorocarbazole ring and naphthobenzofuran ring. The basis of.
At least one hydrogen in the compound represented by the formula (H1) may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, cyano, a halogen or deuterium.

上記式（Ｈ２）中、Ｌ^２およびＬ^３は、それぞれ独立して、炭素数６～３０のアリールまたは炭素数２～３０のヘテロアリールである。アリールとしては、炭素数６～２４のアリールが好ましく、炭素数６～１６のアリールがより好ましく、炭素数６～１２のアリールがさらに好ましく、炭素数６～１０のアリールが特に好ましく、具体的には、ベンゼン環、ビフェニル環、ナフタレン環、テルフェニル環、アセナフチレン環、フルオレン環、フェナレン環、フェナントレン環、トリフェニレン環、ピレン環、ナフタセン環、ペリレン環およびペンタセン環などの一価の基が挙げられる。ヘテロアリールとしては、炭素数２～２５のヘテロアリールが好ましく、炭素数２～２０のヘテロアリールがより好ましく、炭素数２～１５のヘテロアリールがさらに好ましく、炭素数２～１０のヘテロアリールが特に好ましく、具体的には、ピロール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、イミダゾール環、オキサジアゾール環、チアジアゾール環、トリアゾール環、テトラゾール環、ピラゾール環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、トリアジン環、インドール環、イソインドール環、１Ｈ－インダゾール環、ベンゾイミダゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、１Ｈ－ベンゾトリアゾール環、キノリン環、イソキノリン環、シンノリン環、キナゾリン環、キノキサリン環、フタラジン環、ナフチリジン環、プリン環、プテリジン環、カルバゾール環、アクリジン環、フェノキサチイン環、フェノキサジン環、フェノチアジン環、フェナジン環、フェナザシリン環、インドリジン環、フラン環、ベンゾフラン環、イソベンゾフラン環、ジベンゾフラン環、チオフェン環、ベンゾチオフェン環、ジベンゾチオフェン環、フラザン環、チアントレン環、インドロカルバゾール環、ベンゾインドロカルバゾール環、ベンゾベンゾインドロカルバゾール環およびナフトベンゾフラン環などの一価の基が挙げられる。
式（Ｈ２）で表される化合物における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 <Compound represented by the general formula (H2)>

In the above formula (H2), L ² and L ³ are independently aryls having 6 to 30 carbon atoms or heteroaryls having 2 to 30 carbon atoms. As the aryl, an aryl having 6 to 24 carbon atoms is preferable, an aryl having 6 to 16 carbon atoms is more preferable, an aryl having 6 to 12 carbon atoms is further preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable, specifically. Examples include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthalene ring, a perylene ring and a pentasen ring. .. As the heteroaryl, a heteroaryl having 2 to 25 carbon atoms is preferable, a heteroaryl having 2 to 20 carbon atoms is more preferable, a heteroaryl having 2 to 15 carbon atoms is further preferable, and a heteroaryl having 2 to 10 carbon atoms is particularly preferable. Preferably, specifically, a pyrrole ring, an oxazole ring, an isooxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxazazole 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, phenazacillin ring, indoleidine ring, furan ring, benzofuran ring, Monovalent groups such as isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, frazane ring, thiantolen ring, indolecarbazole ring, benzoindrocarbazole ring, benzobenzoindrocarbazole ring and naphthobenzofuran ring Can be mentioned.
At least one hydrogen in the compound represented by the formula (H2) may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, cyano, a halogen or deuterium.

<Compound represented by the general formula (H3) (example of polymer host material)>

In formula (H3)
MU is a divalent group independently represented by removing any two hydrogen atoms from an aromatic compound, and EC is independently represented by removing any one hydrogen atom from an aromatic compound1 It is the basis of the valence, where two hydrogens in the MU are replaced with EC or MU, where k is an integer of 2-50000.

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

At least one hydrogen in MU and EC in the formula (H3) may be substituted with an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a halogen or a heavy hydrogen, and further in the alkyl. Any -CH _2- may be substituted with -O- or -Si (CH ₃ ) _2- , and any other than -CH _2- directly linked to EC in the formula (H3) in the above alkyl. -CH _2- may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

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

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

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

From the viewpoint of solubility and coating film-forming property, the compound represented by the formula (H3) preferably has an alkyl having 1 to 24 carbon atoms in which 10 to 100% of the total number of MUs (k) in the molecule has an alkyl having 1 to 24 carbon atoms. It is more preferable that 30 to 100% of the total number of MUs (k) in the molecule has an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and the total number of MUs in the molecule (k). It is more preferable that 50 to 100% of the MU has an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that MU of 10 to 100% of the total number of MUs (k) in the molecule has an alkyl having 7 to 24 carbon atoms, and the total number of MUs in the molecule (k). ), It is more preferable that 30 to 100% of the MU has an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

<Compound containing a structure represented by the general formula (H4)>
The compound is a compound containing a structure represented by the following formula (H4), and has a plurality of the structures, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2, most preferably. Is included, and when a plurality of the structures are contained, the structures are directly bonded to each other by a single bond or bonded by a specific linking group.

In the above general formula (H4), G is independently "= C (-H)-" or "= N-", and H in the above "= C (-H)-" is a substituent or another. It may be substituted with the structure represented by the formula (H4) of.

As the compound containing the structure represented by the general formula (H4), for example, the compounds described in International Publication No. 2012/153780 and International Publication No. 2013/038650 can be used, and the methods described in the above-mentioned documents can be used. Can be manufactured according to.

Examples of substituents in the case where H in "= C (-H)-" which is G is substituted are as follows, but are not limited to these.

Specific examples of the "aryl group" as a substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo [c] phenanthryl, benzo [g] chrysenyl, benzoanthril, triphenylenyl, fluorenyl, 9. Examples thereof include 9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl and the like, preferably phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl and the like. And fluorenyl and the like. Examples of the aryl group having a substituent include tolyl, xylyl and 9,9-dimethylfluorenyl. As specific examples show, aryl groups include both condensed aryl groups and non-condensed aryl groups.

Specific examples of the "heteroaryl group" as a substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridadinyl, pyridyl, triazinyl, indolyl, isoindryl, imidazolyl, benzimidazolyl, indazolyl, imidazole [1,2-a] pyridinyl, Frill, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthyldinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl , Phenanthrolinyl, phenazinyl, phenothiazine, phenoxadinyl, oxazolyl, oxadiazolyl, frazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl and the like, preferably dibenzofuranyl, dibenzothienyl, etc. Examples thereof include carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl and azadibenzothienyl. Further preferred are dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl.

The substituent "substituted silyl group" is a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group. It is also preferable to have.

Specific examples of the substituted or unsubstituted trialkylsilyl group include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl group include diphenylmethylsilyl, ditrilmethylsilyl, phenyldimethylsilyl and the like. Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl and tritrylsilyl.

The "substituted phosphine oxide group" which is a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditrilphosphine oxide.

Examples of the "substituted carboxy group" which is a substituent include benzoyloxy and the like.

Examples of the linking group that binds a plurality of structures represented by the formula (H4) include the above-mentioned divalent to tetravalent to tetravalent, divalent to trivalent, or divalent derivatives of aryls and heteroaryls.

Specific examples of the compound containing the structure represented by the general formula (H4) are shown below.

上記式（Ｈ５）において、
Ｒ^１～Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールへテロアリールアミノ、アルキルまたはシクロアルキル（以上、第１置換基）であり、当該Ｒ^１～Ｒ^１１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、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
Ｒ^１～Ｒ^１１のうちの隣接する基同士が結合してａ環、ｂ環またはｃ環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキルまたはシクロアルキル（以上、第１置換基）で置換されていてもよく、これらの置換基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、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲはＲ^１～Ｒ^１１である）は「－Ｎ＝」に置き換わっていてもよく、
式（Ｈ５）で表される化合物における少なくとも１つの水素は、それぞれ独立して、ハロゲンまたは重水素で置換されてもよい。 <Compound represented by the general formula (H5)>

In the above formula (H5)
R ¹ to R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetelloarylamino, alkyl or cycloalkyl (these are the first substituents), and the R1 to R11 are the same. At least one hydrogen in ¹ to R ¹¹ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent).
Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring or a c ring, and at least one hydrogen in the formed ring is a hydrogen. It may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, first substituent), and at least one hydrogen in these substituents is further aryl. , Heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent).
Any "-C (-R) =" (where R is R ¹ to R ¹¹ ) in the a-ring, b-ring, and c-ring may be replaced with "-N =".
At least one hydrogen in the compound represented by the formula (H5) may be independently substituted with a halogen or deuterium.

Any "-C (-R) =" in the a-ring, b-ring, and c-ring in formula (H5) (where R is R ¹ to R ¹¹ ) is replaced with "-N =" and pyridine. It may be changed to a ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. For the details of this explanation, the explanations in the above general formulas (2A) and (2B) can be quoted.

Preferably, in the above formula (H5),
R ¹ to R ¹¹ are independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (however, the aryl is an aryl having 6 to 12 carbon atoms), and 1 to 1 carbon atoms. It is an alkyl of 12 or a cycloalkyl of 3 to 16 carbon atoms, and at least one hydrogen in the R ¹ to R ¹¹ is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diaryl amino (provided to be aryl). Is an aryl with 6 to 12 carbon atoms), may be substituted with an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.
Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring or c ring. , At least one hydrogen in the formed ring is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (where the aryl is an aryl having 6 to 12 carbon atoms), and 1 to 12 carbon atoms. It may be substituted with an alkyl or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in these substituents is further an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diarylamino (provided to be diarylamino). The aryl may be substituted with an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

More preferably, in the above formula (H5),
R ¹ to R ¹¹ are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (however, the aryl is an aryl having 6 to 10 carbon atoms), and 1 to 1 carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in the R ¹ to R ¹¹ is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and a diaryl amino (provided to be aryl). Is an aryl with 6 to 10 carbon atoms), may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a ring, b ring or c ring. , At least one hydrogen in the formed ring is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (where the aryl is an aryl having 6 to 10 carbon atoms), and an aryl having 1 to 6 carbon atoms. It may be substituted with an alkyl or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in these substituents is further an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and a diarylamino (provided to be diarylamino). The aryl may be substituted with an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.

Examples of the "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylhetelloarylamino in the first and second substituents include the following examples.

Specific examples of the "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and aryls having 6 to 16 carbon atoms. Is more preferable, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a fused dicyclic aryl, and tricyclic aryl. Terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'- Il, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o- Telphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl Yes, acenaphtylene- (1-, 3-, 4-, 5-) yl, fluoren- (1-, 2-, 3-, 4-, 9-) yl, phenylen- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) Phenantril, quaterphenylyl, a tetracyclic aryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-) Terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-) 1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, fused pentacyclic aryl perylene- (1-, 2-, 3-) yl, pentasen- (1) -, 2-, 5-, 6-) Il and the like.

Specific examples of the "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, and 2 carbon atoms. Heteroaryl of to 15 is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. For example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indrill, isoindryl, 1H-indazolyl, benzoimidazolyl, benzoidazolyl , 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenylazacillinyl Monovalent group of isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphole oxide ring , The monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocarbazolyl and benzobenzoindorocarbazolyl and the like.

In the first substituent and the second substituent, the "alkyl" may be either a straight chain or a branched chain, and for example, a linear alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms may be used. Alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 12 carbon atoms is more preferable. Alkyl of 6 (branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) and alkyl having 1 to 4 carbon atoms (3 to 4 carbon atoms) are more preferable. Branched chain alkyl) is particularly preferred, and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methyl. 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-eicocil and the like can be mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2- Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3- Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1 -Propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can also be mentioned.

In the first substituent and the second substituent, the "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and 3 to 16 carbon atoms. Examples thereof include 14 cycloalkyls, cycloalkyls having 5 to 10 carbon atoms, cycloalkyls having 5 to 8 carbon atoms, cycloalkyls having 5 to 6 carbon atoms, and cycloalkyls having 5 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents thereof having 1 to 4 carbon atoms, bicyclo [1.1.0] butyl, bicyclo. [1.1.1] Pentyl, Bicyclo [2.1.0] Pentyl, Bicyclo [2.1.1] Hexil, Bicyclo [3.1.0] Hexil, Bicyclo [2.2.1] Heptyl, Bicyclo [2.2.2] Examples thereof include octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazurenyl.

When the first substituent is aryl, the substitution positions are preferably R ¹ , R ³ , R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ , for example, substitution with R ¹ and R ³ , to R ⁵ and R ¹⁰ . , Substitution with ^R4 and ^R11 is more preferred, and aryl is preferably a phenyl group.

When the first substituent is heteroaryl, the substitution positions are preferably R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ and R ¹¹ , for example, substitution with R ¹ . , R ² substitution, R ³ substitution, R ¹ and R ³ substitution, R ⁴ and R ¹¹ substitution, R ⁵ and R ¹⁰ substitution, R ⁶ and R ⁹ substitution. Preferably, the heteroaryl is preferably a carbazolyl group. This heteroaryl (eg, carbazolyl) may be substituted at the above position via a phenylene group.

Specific examples of the compound represented by the formula (H5) include a compound represented by the following structural formula. In addition, "Me" in the formula is a methyl group.

For the compound represented by the formula (H5), an intermediate is first produced by binding the a to c rings with a binding group (—O—) (first reaction), and then the a to c rings are B (1). The final product can be produced by binding with boron) (second reaction). In the first reaction, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used. Further, in the second reaction, a tandem hetero-Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction) can be used. For details of the first and second reactions, the explanation described in International Publication No. 2015/102118 can be referred to.

上記式（Ｈ６）において、
Ｒ^１～Ｒ^１６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、アリールへテロアリールアミノ、アルキルまたはシクロアルキル（以上、第１置換基）であり、当該Ｒ^１～Ｒ^１６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、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
Ｒ^１～Ｒ^１６のうちの隣接する基同士が結合してａ環、ｂ環、ｃ環、またはｄ環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキルまたはシクロアルキル（以上、第１置換基）で置換されていてもよく、これらの置換基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、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
式（Ｈ６）で表される化合物における少なくとも１つの水素は、それぞれ独立して、ハロゲンまたは重水素で置換されてもよい。 <Compound represented by the general formula (H6)>

In the above formula (H6)
R ¹ to R ¹⁶ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetelloarylamino, alkyl or cycloalkyl (these are the first substituents), and the R1 to R16 are the same. At least one hydrogen in ¹ to R ¹⁶ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent).
Adjacent groups of R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring, a c ring, or a d ring, and at least one in the formed ring. The hydrogen may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, first substituent), and at least one of these substituents. Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent).
At least one hydrogen in the compound represented by the formula (H6) may be independently substituted with a halogen or deuterium.

Preferably, in the above formula (H6),
R ¹ to R ¹⁶ are independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (however, the aryl is an aryl having 6 to 12 carbon atoms), and 1 to 1 carbon atoms. It is an alkyl of 12 or a cycloalkyl of 3 to 16 carbon atoms, and at least one hydrogen in the R ¹ to R ¹⁶ is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diaryl amino (provided to be aryl). Is an aryl with 6 to 12 carbon atoms), may be substituted with an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.
Adjacent groups of R ¹ to R ¹⁶ are bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring, c ring, or d ring. At least one hydrogen in the formed ring may be an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (where the aryl is an aryl having 6 to 12 carbon atoms), and a carbon number of carbon atoms. It may be substituted with an alkyl of 1 to 12 or a cycloalkyl of 3 to 16 carbons, and at least one hydrogen in these substituents is an aryl having 6 to 30 carbon atoms and a heteroaryl having 2 to 30 carbon atoms. It may be substituted with diarylamino (where aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

More preferably, in the above formula (H6),
R ¹ to R ¹⁶ are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (however, the aryl is an aryl having 6 to 10 carbon atoms), and 1 to 1 carbon atoms. It is an alkyl of 6 or a cycloalkyl of 3 to 14 carbon atoms, and at least one hydrogen in the R ¹ to R ¹⁶ is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and a diaryl amino (provided to be aryl). Is an aryl with 6 to 10 carbon atoms), may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
Adjacent groups of R ¹ to R ¹⁶ are bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a ring, b ring, c ring, or d ring. At least one hydrogen in the formed ring may be an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (where the aryl is an aryl having 6 to 10 carbon atoms), and a carbon number of carbon atoms. It may be substituted with an alkyl of 1 to 6 or a cycloalkyl of 3 to 14 carbons, and at least one hydrogen in these substituents is further an aryl of 6 to 16 carbons, a heteroaryl of 2 to 15 carbons, It may be substituted with diarylamino (where aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.

Examples of the "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylhetelloarylamino in the first and second substituents include the following examples.

Specific examples of the "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and aryls having 6 to 16 carbon atoms. Is more preferable, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a fused dicyclic aryl, and tricyclic aryl. Terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'- Il, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o- Telphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl Yes, acenaphtylene- (1-, 3-, 4-, 5-) yl, fluoren- (1-, 2-, 3-, 4-, 9-) yl, phenylen- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) Phenantril, quaterphenylyl, a tetracyclic aryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-) Terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene- (1-, 2-) yl, which is a fused tetracyclic aryl, pyrene- (1-, 2-) 1-, 2-, 4-) yl, naphthacene- (1-, 2-, 5-) yl, fused pentacyclic aryl perylene- (1-, 2-, 3-) yl, pentasen- (1) -, 2-, 5-, 6-) Il and the like.

Specific examples of the "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, and 2 carbon atoms. Heteroaryl of to 15 is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. For example, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indrill, isoindryl, 1H-indazolyl, benzoimidazolyl, benzoidazolyl , 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenothiazinyl, phenazinyl, phenazacilinyl Monovalent group of isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphole oxide ring , The monovalent group of the dibenzophosphole oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocarbazolyl and benzobenzoindorocarbazolyl and the like.

In the first substituent and the second substituent, the "alkyl" may be either a straight chain or a branched chain, and for example, a linear alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms may be used. Alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 12 carbon atoms is more preferable. Alkyl of 6 (branched chain alkyl having 3 to 6 carbon atoms) is more preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) and alkyl having 1 to 4 carbon atoms (3 to 4 carbon atoms) are more preferable. Branched chain alkyl) is particularly preferred, and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methyl. 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-eicocil and the like can be mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2- Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3- Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1 -Propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can also be mentioned.

In the first substituent and the second substituent, the "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and 3 to 16 carbon atoms. Examples thereof include 14 cycloalkyls, cycloalkyls having 5 to 10 carbon atoms, cycloalkyls having 5 to 8 carbon atoms, cycloalkyls having 5 to 6 carbon atoms, and cycloalkyls having 5 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents thereof having 1 to 4 carbon atoms, bicyclo [1.1.0] butyl, bicyclo. [1.1.1] Pentyl, Bicyclo [2.1.0] Pentyl, Bicyclo [2.1.1] Hexil, Bicyclo [3.1.0] Hexil, Bicyclo [2.2.1] Heptyl, Bicyclo [2.2.2] Examples thereof include octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazurenyl.

The compound represented by the formula (H6) can be produced with reference to the description described in International Publication No. 2014/042197.

<TADF material>
By reducing the energy difference between the excited singlet state and the excited triplet state, reverse energy transfer from the excited triplet state, which normally has a low transition probability, to the excited singlet state can be generated with high efficiency from the singlet. Luminescence (thermally activated delayed fluorescence, TADF) is expressed. In normal fluorescence emission, 75% of triplet excitons generated by current excitation cannot be taken as fluorescence because they pass through the heat deactivation path. On the other hand, in TADF, all excitons can be used for fluorescent emission, and a highly efficient organic EL device can be realized.

式（Ｈ７）において、ＥＤは電子供与性基であり、Ｌｎは結合基であり、ＥＡは電子受容性基であり、式（Ｈ７）で表される化合物の一重項エネルギー（Ｓ^１）と三重項エネルギー（Ｔ^１）のエネルギー差（ΔＳ^１Ｔ^１）は０．２ｅＶ以下である（Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)）。エネルギー差（ΔＳ^１Ｔ^１）は、好ましくは０．１５ｅＶ以下であり、より好ましくは０．１０ｅＶ以下であり、さらに好ましくは０．０８ｅＶ以下である。 Examples of the TADF material that can be used for such a purpose include a compound represented by the following general formula (H7) and a compound having the following general formula (H7) as a partial structure.

In formula (H7), ED is an electron-donating group, Ln is a binding group, and EA is an electron-accepting group, which is triplet with the singlet energy (S ¹ ) of the compound represented by the formula (H7). The energy difference (ΔS ¹ T ¹ ) of the term energy (T ¹ ) is 0.2 eV or less (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS ¹ T ¹ ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

TADF materials use electron-donating substituents called donors and electron-accepting substituents called acceptors to localize intramolecular HOMOs and LUMOs for efficient reverse intersystem crossing. ) Is preferably a donor-acceptor type TADF compound (DA type TADF compound) designed to cause this.

Here, the term "electron-donating substituent" (donor) as used herein means a substituent and a partial structure in which the LUMO orbital is localized in the TADF compound molecule, and "electron acceptor substitution". The "group" (acceptor) is meant to mean a substituent and a partial structure in which the HOMO orbital is localized in the TADF compound molecule.

In general, TADF compounds using donors and acceptors have a large spin-orbit coupling (SOC) due to their structure, a small exchange interaction between HOMO and LUMO, and a small ΔE (ST). In addition, a very fast intersystem crossing speed is obtained. On the other hand, TADF compounds using donors and acceptors have greater structural relaxation in the excited state (for some molecules, the stable structure differs between the ground state and the excited state, so conversion from the ground state to the excited state by an external stimulus is performed. When this occurs, the structure 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.

If the TADF material reduces color purity, a fluorescent compound may be added to the light emitting layer or a layer adjacent to the light emitting layer as another component. The TADF material acts as an assisting dopand and the other components act as an emerging dopant. The other component may be a compound in which the absorption spectrum of the compound at least partially overlaps with the emission peak of the assisting dopant.

As the donor and acceptor structures used for TADF materials, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of the ED include functional groups containing sp ³ nitrogen, and more specifically, carbazole, dimethylcarbazole, di-tbutylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, and benzothienocarbazole. , Phenyldihydroindrocarbazole, phenylbicarbazole, bicarbazole, turcarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, (bis (tbutyl) phenyl ) Amine, ((diphenylamino) phenyl) diphenylbenzenediamine, dimethyltetraphenyldihydroacridindiamine, tetramethyl-dihydro-indenoaclydin, diphenyl-dihydrodibenzoazacillin and the like. Examples of EA include sp ² nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings having ketones and cyano groups, and more specifically, sulfonyldibenzene, benzophenone, and phenylenebis (phenylmethanone). Benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazol, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzoimidazole, dibenzoquinoxalin, hepta Azaphenalene, thioxanthonedioxide, dimethylanthrasenone, anthracendione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fullorangecarbonitrile, pyrazinedicarbonitrile, pyridinedicarbonitrile, dibenzoquinoxalin dicarbonitrile, pyrimidine, phenyl Examples thereof include groups derived from pyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis (phenylsulfonyl) benzene, dimethylthioxanthendioxide, thianthrenetetraoxide and tris (dimethylphenyl) borane. Examples of Ln include single bond and arylene, and more specifically, phenylene, biphenylene, naphthylene and the like. Further, hydrogen may be substituted with alkyl, cycloalkyl and aryl in any structure. In particular, at least one selected from carbazole, phenoxazine, aclysine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone as partial structures. It is preferably a compound having one.

The compound represented by the general formula (H7) is more specifically a compound represented by any of the following general formulas (H7-1), formula (H7-2) and formula (H7-3). ..

In the above general formula (H7-1), formula (H7-2) and formula (H7-3),
M are independently single-bonded, -O-,> N-Ar or> C (-Ar) ₂ , respectively, and the HOMO depth and excited singlet energy level and excited triplet of the substructure to be formed. From the standpoint of high 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 above, an arylene having 6 to 12 carbon atoms is preferable, and more specific examples thereof include phenylene, methylphenylene and dimethylphenylene.
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, triazineyl, carbazolyl, dimethylcarbazolyl, di-tbutyl. Carbazolyl, benzoimidazole or phenylbenzoimidazole, more preferably hydrogen, phenyl or carbazolyl.
m is 1 or 2 and
n is an integer of 2 to (6-m), 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.

Examples of the compound represented by the formula (H7) include a compound represented by the following structure. In the structural formula, * indicates a bond position, “Me” indicates a methyl group, and “tBu” indicates a t-butyl group.

Among the above-mentioned specific compounds, the compound represented by the general formula (H7) is particularly 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA. -TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz are preferable.

Further, as the dopant material, a known compound can be used in addition to the polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B), and various compounds can be used depending on the desired emission color. You can choose from the materials. Specifically, for example, fused ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopylene, dibenzopyrene, rubrene and chrysen, benzoxazole derivatives, benzothiazole derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxasols. Bistylyl derivatives such as derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazol derivatives, triazole derivatives, pyrazoline derivatives, stilben derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives. (Japanese Patent Laid-Open No. 1-245087), bisstyrylallylene derivative (Japanese Patent Laid-Open No. 2-247278), diazaindacene derivative, furan derivative, benzofuran derivative, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl) Isobenzofuran, di (2-trifluoromethylphenyl) isobenzofuran, phenylisobenzofuran and other isobenzofuran derivatives, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7- Cmarin derivatives such as methoxycoumarin derivative, 7-acetoxycmarin derivative, 3-benzothiazolyl coumarin derivative, 3-benzoimidazolyl coumarin derivative, 3-benzoxazolyl coumarin derivative, dicyanomethylenepyrine derivative, dicyanomethylenethiopyran derivative, polymethine Derivatives, cyanine derivatives, oxobenzoanthrasene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostylyl derivatives, acridin derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrolopyridine derivatives, flopyridine derivatives, Examples thereof include 1,2,5-thiadiazolopylene derivatives, pyromethene derivatives, perinone derivatives, pyrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

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

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

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

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

Among the above-mentioned dopant materials, amines, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyrane derivatives or pyrene derivatives having a stillben structure are particularly preferable.

当該式中、Ａｒ^１は炭素数６～３０のアリールに由来するｍ価の基であり、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６～３０のアリールであるが、Ａｒ^１～Ａｒ^３の少なくとも１つはスチルベン構造を有し、Ａｒ^１～Ａｒ^３は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよく、そして、ｍは１～４の整数である。 The amine having a stilbene structure is represented by, for example, the following formula.

In the formula, Ar ¹ is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ are independently aryls having 6 to 30 carbon atoms, but Ar ¹ to Ar are respectively. At least one of ³ has a stilben structure, and Ar ¹ to Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl substituted with at least one of aryl, alkyl and cycloalkyl). Alternatively, it may be substituted with cyano, and m is an integer of 1 to 4.

当該式中、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６～３０のアリールであり、Ａｒ^２およびＡｒ^３は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよい。 As the amine having a stilbene structure, diaminostilbene represented by the following formula is more preferable.

In the formula, Ar ² and Ar ³ are independently aryls having 6 to 30 carbon atoms, and Ar ² and Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, and trisubstituted silyls (aryl, alkyl and tri-substituted silyls). It may be tri-substituted with at least one of cycloalkyl) or cyano.

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthalsenyl, perylenyl, stillbenyl, distyrylphenyl, distyrylbiphenylyl. , Distylyl fluorenyl, etc.

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

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

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

当該式中、Ａｒ^４は炭素数６～３０のアリールに由来するｎ価の基であり、Ａｒ^５およびＡｒ^６はそれぞれ独立して炭素数６～３０のアリールであり、Ａｒ^４～Ａｒ^６は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよく、そして、ｎは１～４の整数である。 The aromatic amine derivative is represented by, for example, the following formula.

In the formula, Ar ⁴ is an n-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are independently aryls having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are independent aryls having 6 to 30 carbon atoms. , Aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl substituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 1-4. It is an integer.

In particular, Ar ⁴ is a divalent group derived from anthracene, chrysen, fluorene, benzofluorene or pyrene, Ar ⁵ and Ar ⁶ are independently aryls having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are respectively. May be aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl substituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 2. , Aromatic amine derivatives are more preferred.

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthalenyl, perylenyl, pentasenyl and the like.

As the aromatic amine derivative, as a chrysen system, for example, N, N, N', N'-tetraphenylcrisen-6,12-diamine, N, N, N', N'-tetra (p-tolyl) Chrysen-6,12-diamine, N, N, N', N'-tetra (m-tolyl) chrysen-6,12-diamine, N, N, N', N'-tetrakis (4-isopropylphenyl) chrysen -6,12-diamine, N, N, N', N'-tetra (naphthalen-2-yl) chrysen-6,12-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) ) Chrysen-6,12-diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) Chrysen-6,12-diamine, N, N'-diphenyl-N, N'-bis ( 4-isopropylphenyl) lysene-6,12-diamine, N, N'-diphenyl-N, N'-bis (4-t-butylphenyl) lysene-6,12-diamine, N, N'-bis (4) -Isopropylphenyl) -N, N'-di (p-tolyl) chrysen-6,12-diamine and the like can be mentioned.

The pyrene system includes, for example, N, N, N', N'-tetraphenylpyrene-1,6-diamine, N, N, N', N'-tetra (p-tolyl) pyrene-1,6. -Diamine, N, N, N', N'-tetra (m-tolyl) pyrene-1,6-diamine, N, N, N', N'-tetrakis (4-isopropylphenyl) pyrene-1,6- Diamine, N, N, N', N'-tetrakis (3,4-dimethylphenyl) pyrene-1,6-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) pyrene-1 , 6-Diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) pyrene-1,6-diamine, N, N'-diphenyl-N, N'-bis (4-isopropylphenyl) ) Pyrene-1,6-diamine, N, N'-diphenyl-N, N'-bis (4-t-butylphenyl) Pyrene-1,6-diamine, N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) pyrene-1,6-diamine, N, N, N', N'-tetrakis (3,4-dimethylphenyl) -3,8-diphenylpyrene-1,6 -Diamine, N, N, N, N-Tetraphenylpyrene-1,8-diamine, N, N'-bis (biphenyl-4-yl) -N, N'-diphenylpyrene-1,8-diamine, N ¹ , N ⁶ -diphenyl-N ¹ , N ⁶ -bis- (4-trimethylsilanyl-phenyl) -1H, 8H-pyrene-1, 6-diamine and the like can be mentioned.

The anthracene system includes, for example, N, N, N, N-tetraphenylanthracene-9,10-diamine, N, N, N', N'-tetra (p-tolyl) anthracene-9,10-diamine. , N, N, N', N'-tetra (m-tolyl) anthracene-9,10-diamine, N, N, N', N'-tetrakis (4-isopropylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-di (p-tolyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-di (m-tolyl) anthracene-9,10- Diamine, N, N'-diphenyl-N, N'-bis (4-ethylphenyl) anthracene-9,10-diamine, N, N'-diphenyl-N, N'-bis (4-isopropylphenyl) anthracene- 9,10-Diamine, N, N'-diphenyl-N, N'-bis (4-t-butylphenyl) anthracene-9,10-diamine, N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene-9,10-diamine, 2,6-di-t-butyl-N, N, N', N'-tetra (p-tolyl) anthracene-9,10-diamine , 2,6-di-t-butyl-N, N'-diphenyl-N, N'-bis (4-isopropylphenyl) anthracene-9,10-diamine, 2,6-di-t-butyl-N, N'-bis (4-isopropylphenyl) -N, N'-di (p-tolyl) anthracene-9,10-diamine, 2,6-dicyclohexyl-N, N'-bis (4-isopropylphenyl) -N , N'-di (p-tolyl) anthracene-9,10-diamine, 2,6-dicyclohexyl-N, N'-bis (4-isopropylphenyl) -N, N'-bis (4-t-butylphenyl) ) Anthracene-9,10-diamine, 9,10-bis (4-diphenylamino-phenyl) anthracene, 9,10-bis (4-di (1-naphthylamino) phenyl) anthracene, 9,10-bis (4) -Di (2-naphthylamino) phenyl) anthracene, 10-di-p-tolylamino-9- (4-di-p-tolylamino-1-naphthyl) anthracene, 10-diphenylamino-9- (4-diphenylamino-) 1-naphthyl) anthracene, 10-diphenylamino-9- (6-diphenylamino-2-naphthyl) anthracene and the like can be mentioned.

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

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

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

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

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

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 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. In the present invention, the polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) can be used as the electron transport material.

The material used for the electron transport layer or the electron injection layer is a compound composed of an aromatic ring or a heteroaromatic 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. , Kinone derivatives such as anthraquinone and diphenoquinone, phosphoroxide derivatives, carbazole derivatives and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex and benzoquinoline metal complex. These materials may be used alone, but may be mixed with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, and oxadiazole. Derivatives (1,3-bis [(4-t-butylphenyl) 1,3,4-oxadiazolyl] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- Triazole, etc.), thiazazole derivatives, oxine derivative metal complexes, quinolinol-based metal complexes, quinoxalin derivatives, quinoxalin derivative polymers, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline Derivatives (2,2'-bis (benzo [h] quinoline-2-yl) -9,9'-spirobifluorene, etc.), imidazole pyridine derivatives, borane derivatives, benzoimidazole derivatives (tris (N-phenylbenzoimidazole-) 2-yl) benzene, etc.), benzoxazole derivative, benzothiazole derivative, quinoline derivative, oligopyridine derivative such as telpyridine, bipyridine derivative, telpyridine derivative (1,3-bis (2,2': 6', 2 "-telpyridine" -4'-yl) benzene, etc.), naphthylidine derivatives (bis (1-naphthyl) -4- (1,8-naphthylidine-2-yl) phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indol derivatives, phosphin oxides, etc. Derivatives, bisstyryl derivatives and the like can be mentioned.

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 derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphinoxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, and quinolinol-based metals Complexes are preferred.

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

In the above formula (ETM-1), R ¹¹ and R ¹² each independently contain hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, and optionally substituted nitrogen. At least one of a heterocycle or a cyano, R ¹³ to R ¹⁶ are independently substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, respectively. , X are optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boron, or optionally substituted carbazolyl, and n. Are independently integers from 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

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

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

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

In formula (ETM-1-2), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen, respectively. At least one of the contained heterocycles, or cyano, R ¹³ to R ¹⁶ are independently substituted alkyl, substituted cycloalkyl or optionally substituted aryl, respectively. Yes, X ¹ is an arylene having 20 or less carbon atoms which may be substituted, and n is an independently integer of 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

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

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

Specific examples of this borane derivative include the following compounds.

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

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

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

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

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

In each formula, the "pyridine-based substituent" is any of the following formulas (Py-1) to (Py-15), and the pyridine-based substituents are independently alkyl or carbon having 1 to 4 carbon atoms. It may be substituted with the number 5 to 10 cycloalkyl. Further, the pyridine-based substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or a naphthylene group. * In each structural formula represents the bonding position.

The pyridine-based substituent is any of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44). Is preferable. * In each structural formula represents the bonding position.

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

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

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

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

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

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

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

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

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

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

Specific examples of this pyridine derivative include the following compounds.

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

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

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

Specific examples of this fluoranthene derivative include the following compounds.

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

R ¹ to R ¹¹ are independently bonded to hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diallylboryl (two aryls are bonded via a single bond or a linking group). , Alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, and at least one hydrogen in the R ¹ to R ¹¹ may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Further, adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring or a c ring, and at least one hydrogen in the formed ring. Are Aryl, Heteroaryl, Diarylamino, Diheteroarylamino, Arylheteroarylamino, Diarylboryl (two aryls may be attached via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryl. It may be substituted with oxy or substituted silyls, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

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

The description of the substituent and the form of ring formation in the formula (ETM-4) and the multimer formed by combining a plurality of structures of the formula (ETM-4) is shown in the above general formula (1A) or general formula (1B). The description of the polycyclic aromatic compound to be used can be quoted.

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

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

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

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

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

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

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

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

As for the aryls having 6 to 20 carbon atoms in ^R1 to ^R4 , the aryls having 6 to 16 carbon atoms are preferable, the aryls having 6 to 12 carbon atoms are more preferable, and the aryls having 6 to 10 carbon atoms are particularly preferable.

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

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

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

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

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

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

Specific examples of these anthracene derivatives include the following compounds.

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

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

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

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

The "alkyl" in Ar ² may be either a straight chain or a branched chain, and examples thereof include a linear alkyl having 1 to 24 carbon atoms and a branched chain alkyl having 3 to 24 carbon atoms. The preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). A more preferable "alkyl" is an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms). A particularly preferable "alkyl" is an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms). Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), and the like. Examples thereof include n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl and 1-methylhexyl.

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

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

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

The two Ar ^2s may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene are spiro-bonded to the 5-membered ring of the fluorene skeleton. You may.

Specific examples of this benzofluorene derivative include the following compounds.

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

Ｒ^５は、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^６は、ＣＮ、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数１～２０のヘテロアルキル、炭素数６～２０のアリール、炭素数５～２０のヘテロアリール、炭素数１～２０のアルコキシまたは炭素数６～２０のアリールオキシであり、
Ｒ^７およびＲ^８は、それぞれ独立して、置換または無置換の、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^９は酸素または硫黄であり、
ｊは０または１であり、ｋは０または１であり、ｒは０～４の整数であり、ｑは１～３の整数である。
ここで、置換されている場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどがあげられる。 <Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/079217.

R5 is a substituted or unsubstituted alkyl having ¹ to 20 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms.
R ⁶ is CN, substituted or unsubstituted, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, and 5 to 5 carbon atoms. 20 heteroaryl, 1 to 20 carbon alkoxy or 6 to 20 carbon aryloxy.
R ⁷ and R ⁸ are independently substituted or unsubstituted aryls having 6 to 20 carbon atoms or heteroaryls having 5 to 20 carbon atoms, respectively.
R ⁹ is oxygen or sulfur
j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

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

R ¹ to R ³ may be the same or different, and may be the same or different, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, cycloalkylthio group, arylether group. In a fused ring formed between an arylthioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and an adjacent substituent. Is selected from.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Halogen means fluorine, chlorine, bromine and iodine.

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

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

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

The fused rings formed between the adjacent substituents are, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , and Ar ¹ . It is a conjugated or non-conjugated fused ring formed between Ar ² and the like. Here, when n is ¹ , a conjugated or non-conjugated fused ring may be formed between the two R1s. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be fused with another ring.

Specific examples of this phosphine oxide derivative include the following compounds.

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

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

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

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

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

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

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and the like. Benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. One of phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoyl, benzophosphole oxide ring Examples thereof include a valent group, a monovalent group of a dibenzophosphole oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocrabazolyl and benzobenzoindolocrazolyl.

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

Specific examples of this pyrimidine derivative include the following compounds.

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

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

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

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

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

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

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and the like. Benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. One of phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoyl, benzophosphole oxide ring Examples thereof include a valent group, a monovalent group of a dibenzophosphole oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocrabazolyl and benzobenzoindolocrazolyl.

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

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

Specific examples of this carbazole derivative include the following compounds.

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

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details can be found in US Publication No. 2011/0156013.

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

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

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

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

Specific examples of the heteroaryl include pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indrill, isoindrill, 1H-indazolyl, and the like. Benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyldinyl, prynyl, pteridinyl, carbazolyl, acridinyl, phenoxatinyl, phenoxadinyl, phenoxadinyl. One of phenazasilinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoyl, benzophosphole oxide ring Examples thereof include a valent group, a monovalent group of a dibenzophosphole oxide ring, frazanyl, thiantrenyl, indolocarbazolyl, benzoindolocrabazolyl and benzobenzoindolocrazolyl.

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

Specific examples of this triazine derivative include the following compounds.

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

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

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4. In the "benzoimidazole-based substituent", the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is benzo. It is a substituent that has been replaced with an imidazole group, and at least one hydrogen in the benzoimidazole derivative may be substituted with dehydrogen. * In the following structural formula represents the bonding position.

R ¹¹ in the benzimidazole group is hydrogen, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms or an aryl having 6 to 30 carbon atoms, and is the above formula (ETM-2-1) and the formula (ETM-2-1). The explanation of R ¹¹ in ETM-2-2) can be quoted.

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

Specific examples of this benzoimidazole derivative include 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2- (4- (10- (10-). Naphthalene-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 5- (10- (naphthalene-2-yl) anthracene-9-yl) -1,2-diphenyl-1H-benzo [d] imidazole, 1- (4) -(10- (Naphthalene-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)) Anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 1- (4- (9,10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -2- Examples thereof include phenyl-1H-benzo [d] imidazole and 5- (9,10-di (naphthalen-2-yl) anthracene-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole.

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

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

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

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

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

As the alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ , the description of R ¹¹ to R ¹⁸ in the above formula (ETM-2) can be cited. Further, in addition to the above-mentioned example, φ can be given, for example, the following structural formula. In addition, R in the following structural formulas is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl. In addition, * in each structural formula represents the bonding position.

Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di (1,10-). Phenanthroline-2-yl) anthracene, 2,6-di (1,10-phenanthroline-5-yl) pyridine, 1,3,5-tri (1,10-phenanthroline-5-yl) benzene, 9,9' -Difluoro-bi (1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis (2-phenyl-1,10-phenanthroline-9-yl) benzene, compounds represented by the following structural formulas, etc. can give.

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

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

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

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

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

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

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

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

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

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

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

<Siror derivative>
The siror derivative is, for example, a compound represented by the following formula (ETM-15). Details are described in Japanese Patent Application Laid-Open No. 9-194487.

X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. For details of these groups, the explanations in the above general formulas (1A) and (1B), and further the explanations in the above formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced with alkenyl or alkynyl, respectively, and the details of these alkenyl and alkynyl can be referred to in the above formula (ETM-7-2).
Further, X and Y may be bonded to form a cycloalkyl ring (and a ring in which a part thereof is unsaturated), and the details of the cycloalkyl ring are described in the above general formula (1A) and the general formula (1A). The description of cycloalkyl in 1B) can be referred to.

R ¹ to R ⁴ are independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyl, respectively. Oxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, It is an isothiocyanate group or a cyano, which may be substituted with an alkyl, cycloalkyl, aryl or halogen and may form a fused ring with an adjacent substituent.

For details of halogens, alkyls, cycloalkyls, alkoxys, aryloxys, aminos, aryls, heteroaryls, alkenyls and alkynyls in ^R1 to ^R4 , the explanations in the above general formulas (1A) and (1B) are cited. can.

The details of alkyl, aryl and alkoxy in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in ^R1 to ^R4 are also described above. The explanations in the general formula (1A) and the general formula (1B) can be quoted.

Examples of the silyl include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with aryl, alkyl or cycloalkyl, and trisubstituted silyl is preferable. Examples thereof include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl and alkyldicycloalkylsilyl. For details of aryl, alkyl and cycloalkyl in these, the explanations in the above general formulas (1A) and (1B) can be cited.

The fused ring formed between the adjacent substituents is, for example, a conjugated or non-conjugated fused ring formed between R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , and the like. .. These fused rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be fused with another ring.

However, preferably, when R ¹ and R ⁴ are phenyl groups, X and Y are not alkyl or phenyl. Further, preferably, when R ¹ and R ⁴ are thienyl groups, X and Y are bonded to an alkyl, and R ² and R ³ are bonded to an alkyl, aryl, alkenyl or R ² and R ³ to form a ring. It is a structure that does not satisfy cycloalkyl at the same time. Also, preferably, when R ¹ and R ⁴ are silyl groups, R ² , R ³ , X and Y are independently hydrogen or not an alkyl having 1 to 6 carbon atoms. Also, preferably, in the case of a structure in which benzene rings are condensed at R ¹ and R ² , X and Y are not alkyl and phenyl.

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

<Azolin derivative>
The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017/014226.

式（Ｌ－１）中、Ｘ^１～Ｘ^６はそれぞれ独立して＝ＣＲ^６－または＝Ｎ－であり、Ｘ^１～Ｘ^６のうちの少なくとも２つは＝ＣＲ^６－であり、Ｘ^１～Ｘ^６のうちの２つの＝ＣＲ^６－におけるＲ^６はφまたはアゾリン環と結合する部位であり、それ以外の＝ＣＲ^６－におけるＲ^６は水素であり、
式（Ｌ－２）中、Ｘ^７～Ｘ^１４はそれぞれ独立して＝ＣＲ^６－または＝Ｎ－であり、Ｘ^７～Ｘ^１４のうちの少なくとも２つは＝ＣＲ^６－であり、Ｘ^７～Ｘ^１４のうちの２つの＝ＣＲ^６－におけるＲ^６はφまたはアゾリン環と結合する部位であり、それ以外の＝ＣＲ^６－におけるＲ^６は水素であり、
Ｌの少なくとも１つの水素は炭素数１～４のアルキル、炭素数５～１０のシクロアルキル、炭素数６～１０のアリールまたは炭素数２～１０のヘテロアリールで置換されていてもよく、
ｍは１～４の整数であり、ｍが２～４であるとき、アゾリン環とＬとで形成される基は同一であっても異なっていてもよく、そして、
式（ＥＴＭ－１６）で表される化合物中の少なくとも１つの水素は重水素で置換されていてもよい。 In the formula (ETM-16),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of up to 6; a cycloalkyl of 3 to 14 carbons, an aryl of 6 to 18 carbons or a heteroaryl of 2 to 18 carbons.
Y is independently -O-, -S- or> N-Ar, and Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar. May be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R ¹ to R ⁵ are independent of each other. Hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, however, any one of Ar and R ¹ to R ⁵ in the above> N-Ar is bonded to L. It is a part to do
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In equation (L-1), X ¹ to X ⁶ are independently = CR ⁶ − or = N −, and at least two of X ¹ to X ⁶ are = CR ⁶ −, and X ¹ In two of ~ X ⁶ = CR ⁶ −, R ⁶ is a site that binds to φ or an azoline ring, and in the other = CR ⁶ −, R ⁶ is hydrogen.
In equation (L-2), X ⁷ to X ¹⁴ are independently = CR ⁶ − or = N −, and at least two of X ⁷ to X ¹⁴ are = CR ⁶ −, and X ^{7 In} two of X14 = CR ^6- , R ⁶ is a site that binds to φ or an azoline ring, and in the other = CR ^6- , R ⁶ is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16) may be substituted with deuterium.

式（ＥＴＭ－１６－１）および式（ＥＴＭ－１６－２）中、
φは炭素数６～４０の芳香族炭化水素に由来するｍ価の基または炭素数２～４０の芳香族複素環に由来するｍ価の基であり、φの少なくとも１つの水素は炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、炭素数６～１８のアリールまたは炭素数２～１８のヘテロアリールで置換されていてもよく、
式（ＥＴＭ－１６－１）中、Ｙは、それぞれ独立して、－Ｏ－、－Ｓ－または＞Ｎ－Ａｒであり、Ａｒは炭素数６～１２のアリールまたは炭素数２～１２のヘテロアリールであり、Ａｒの少なくとも１つの水素は炭素数１～４のアルキル、炭素数５～１０のシクロアルキル、炭素数６～１２のアリールまたは炭素数２～１２のヘテロアリールで置換されていてもよく、
式（ＥＴＭ－１６－１）中、Ｒ^１～Ｒ^４はそれぞれ独立して水素、炭素数１～４のアルキルまたは炭素数５～１０のシクロアルキルであり、ただし、Ｒ^１とＲ^２は同一であり、またＲ^３とＲ^４は同一であり、
式（ＥＴＭ－１６－２）中、Ｒ^１～Ｒ^５はそれぞれ独立して水素、炭素数１～４のアルキルまたは炭素数５～１０のシクロアルキルであり、ただし、Ｒ^１とＲ^２は同一であり、またＲ^３とＲ^４は同一であり、
式（ＥＴＭ－１６－１）および式（ＥＴＭ－１６－２）中、
Ｌは、それぞれ独立して、下記式（Ｌ－１）で表される２価の基、および下記式（Ｌ－２）で表される２価の基からなる群から選ばれ、

式（Ｌ－１）中、Ｘ^１～Ｘ^６はそれぞれ独立して＝ＣＲ^６－または＝Ｎ－であり、Ｘ^１～Ｘ^６のうちの少なくとも２つは＝ＣＲ^６－であり、Ｘ^１～Ｘ^６のうちの２つの＝ＣＲ^６－におけるＲ^６はφまたはアゾリン環と結合する部位であり、それ以外の＝ＣＲ^６－におけるＲ^６は水素であり、
式（Ｌ－２）中、Ｘ^７～Ｘ^１４はそれぞれ独立して＝ＣＲ^６－または＝Ｎ－であり、Ｘ^７～Ｘ^１４のうちの少なくとも２つは＝ＣＲ^６－であり、Ｘ^７～Ｘ^１４のうちの２つの＝ＣＲ^６－におけるＲ^６はφまたはアゾリン環と結合する部位であり、それ以外の＝ＣＲ^６－におけるＲ^６は水素であり、
Ｌの少なくとも１つの水素は炭素数１～４のアルキル、炭素数５～１０のシクロアルキル、炭素数６～１０のアリールまたは炭素数２～１０のヘテロアリールで置換されていてもよく、
ｍは１～４の整数であり、ｍが２～４であるとき、アゾリン環とＬとで形成される基は同一であっても異なっていてもよく、そして、
式（ＥＴＭ－１６－１）または式（ＥＴＭ－１６－２）で表される化合物中の少なくとも１つの水素は重水素で置換されていてもよい。 The specific azoline derivative is a compound represented by the following general formula (ETM-16-1) or general formula (ETM-16-2).

In the formula (ETM-16-1) and the formula (ETM-16-2),
φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ has 1 carbon atom. It may be substituted with an alkyl of up to 6; a cycloalkyl of 3 to 14 carbons, an aryl of 6 to 18 carbons or a heteroaryl of 2 to 18 carbons.
In the formula (ETM-16-1), Y is independently -O-, -S- or> N-Ar, and Ar is an aryl having 6 to 12 carbon atoms or a hetero with 2 to 12 carbon atoms. It is aryl, even if at least one hydrogen of Ar is substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms. Often,
In the formula (ETM-16-1), R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-2), R ¹ to R ⁵ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, respectively, except that R ¹ and R ² are the same. And R ³ and R ⁴ are the same,
In the formula (ETM-16-1) and the formula (ETM-16-2),
L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

In equation (L-1), X ¹ to X ⁶ are independently = CR ⁶ − or = N −, and at least two of X ¹ to X ⁶ are = CR ⁶ −, and X ¹ In two of ~ X ⁶ = CR ⁶ −, R ⁶ is a site that binds to φ or an azoline ring, and in the other = CR ⁶ −, R ⁶ is hydrogen.
In equation (L-2), X ⁷ to X ¹⁴ are independently = CR ⁶ − or = N −, and at least two of X ⁷ to X ¹⁴ are = CR ⁶ −, and X ^{7 In} two of X14 = CR ^6- , R ⁶ is a site that binds to φ or an azoline ring, and in the other = CR ^6- , R ⁶ is hydrogen.
At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and
At least one hydrogen in the compound represented by the formula (ETM-16-1) or the formula (ETM-16-2) may be substituted with deuterium.

上記式中のＺは、＞ＣＲ_２、＞Ｎ－Ａｒ、＞Ｎ－Ｌ、－Ｏ－または－Ｓ－であり、＞ＣＲ_２におけるＲは、それぞれ独立して、炭素数１～４のアルキル、炭素数５～１０のシクロアルキル、炭素数６～１２のアリールまたは炭素数２～１２のヘテロアリールであり、Ｒは互いに結合して環を形成していてもよく、＞Ｎ－ＡｒにおけるＡｒは炭素数６～１２のアリールまたは炭素数２～１２のヘテロアリールであり、＞Ｎ－ＬにおけるＬは上記一般式（ＥＴＭ－１６）、式（ＥＴＭ－１６－１）または一般式（ＥＴＭ－１６－２）におけるＬである。 Preferably, φ is a monovalent group represented by the following formulas (φ1-1) to (φ1-18) and a divalent group represented by the following formulas (φ2-1) to (φ2-34). It consists of a trivalent group represented by the following formulas (φ3-1) to (φ3-3) and a tetravalent group represented by the following formulas (φ4-1) to formula (φ4-2). Selected from the group, at least one hydrogen of φ is substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms or a heteroaryl having 2 to 18 carbon atoms. May be good. * In the following structural formula represents the bonding position.

Z in the above formula is> CR ₂ ,>N-Ar,> N-L, -O- or -S-, and R in> CR ₂ is an alkyl having 1 to 4 carbon atoms independently. , Cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 12 carbon atoms or heteroaryl with 2 to 12 carbon atoms, and R may be bonded to each other to form a ring,> Ar in N—Ar. Is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and L in> NL is the above general formula (ETM-16), formula (ETM-16-1) or general formula (ETM-). It is L in 16-2).

Preferably, L is a divalent group of rings selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthylidine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine. At least one hydrogen of L may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms.

Preferably, Ar in> N-Ar as Y or Z consists of the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazineyl, quinolinyl, isoquinolinyl, naphthyldinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl. Selected, at least one hydrogen of Ar in> N—Ar as Y may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms or an aryl having 6 to 10 carbon atoms.

Preferably, R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, where R ¹ and R ² are the same, and R ³ and R are R. ⁴ is the same, and not all of R ¹ to R ⁴ are hydrogen at the same time, and when m is 1 or 2 and m is 2, the group formed by the azoline ring and L. Are the same.

Specific examples of the azoline derivative include the following compounds. In addition, "Me" in the structural formula represents a methyl group.

Ｌは、ベンゼン、ピリジン、ピラジン、ピリミジン、ピリダジン、およびトリアジンからなる群から選択される環の２価の基であり、Ｌの少なくとも１つの水素は炭素数１～４のアルキル、炭素数５～１０のシクロアルキル、炭素数６～１０のアリールまたは炭素数２～１４のヘテロアリールで置換されていてもよく、
Ｙとしての＞Ｎ－ＡｒにおけるＡｒは、フェニル、ピリジニル、ピラジニル、ピリミジニル、ピリダジニル、およびトリアジニルからなる群から選択され、当該Ａｒの少なくとも１つの水素は炭素数１～４のアルキル、炭素数５～１０のシクロアルキルまたは炭素数６～１０のアリールで置換されていてもよく、
Ｒ^１～Ｒ^４はそれぞれ独立して水素、炭素数１～４のアルキルまたは炭素数５～１０のシクロアルキルであり、ただし、Ｒ^１とＲ^２は同一であり、Ｒ^３とＲ^４は同一であり、またＲ^１～Ｒ^４の全てが同時に水素になることはなく、そして、
ｍは２であり、アゾリン環とＬとで形成される基は同一である。 More preferably, φ is a divalent group represented by the following formula (φ2-1), formula (φ2-31), formula (φ2-32), formula (φ2-33) and formula (φ2-34). Selected from the group consisting of, at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms, where * in each structural formula represents the bond position.

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is an alkyl having 1 to 4 carbon atoms and 5 to 5 carbon atoms. It may be substituted with 10 cycloalkyl, an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 14 carbon atoms.
Ar in> N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl, and at least one hydrogen of the Ar is an alkyl having 1 to 4 carbon atoms and 5 to 5 carbon atoms. It may be substituted with 10 cycloalkyl or an aryl with 6 to 10 carbon atoms.
R ¹ to R ⁴ are independently hydrogen, an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, where R ¹ and R ² are the same and R ³ and R ⁴ are the same. And not all of ^R1 to ^R4 become hydrogen at the same time, and
m is 2, and the group formed by the azoline ring and L is the same.

Other specific examples of the azoline derivative include, for example, the following compounds. In addition, "Me" in the structural formula represents a methyl group.

For details of alkyl, cycloalkyl, aryl or heteroaryl in each of the above formulas defining this azoline derivative, the explanations in the above general formulas (1A) and (1B) can be cited.

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

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.

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

<Cathode in organic electroluminescent device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injecting layer 107 and the electron transporting layer 106.

The material for forming the cathode 108 is not particularly limited as long as it is a substance capable of efficiently injecting electrons into the organic layer, but 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.

<Binder 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.

<Method of manufacturing an organic electroluminescent device>
Each layer constituting the organic EL element is made of a thin film of the material to be composed of each layer by a thin film method such as thin film deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method or casting method, coating method, etc. By setting, it can be formed. The film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured 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.

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.

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.

<Evaporation method>
A thin film of an anode material is formed on an appropriate substrate by a vapor deposition method or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a cathode material is formed by a vapor deposition method or the like. By forming the cathode into a cathode, the desired organic EL element can be obtained. In the above-mentioned production of the organic EL 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.

<Wet film formation method>
The wet film forming method is carried out by preparing a small molecule compound capable of forming each organic layer of an organic EL device as a liquid organic layer forming composition and using the same. If there is no suitable organic solvent to dissolve this low molecular weight compound, it is highly compatible with other monomers having a soluble function as a reactive compound in which the low molecular weight compound is substituted with a reactive substituent and a main chain type polymer. A composition for forming an organic layer may be prepared from a molecularized polymer compound or the like.

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

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

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

Therefore, in general, a method is adopted in which an organic EL element is manufactured by a wet film forming method for only a few layers and a vacuum vapor deposition method for the rest.

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

<Other film formation methods>
A laser heating drawing method (LITI) can be used to form a film of the composition for forming an organic layer. LITI is a method in which a compound adhered to a substrate is heated and vapor-deposited by a laser, and an organic layer forming composition can be used as a material to be applied to the substrate.

<Arbitrary process>
Appropriate treatment steps, cleaning steps, and drying steps may be appropriately added before and after each step of film formation. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, heat treatment and the like. Further, a series of steps for forming a bank can be mentioned.

Photolithography techniques can be used to create the banks. As the bank material that can be used for photolithography, a positive resist material and a negative resist material can be used. Further, a patternable printing method such as an inkjet method, a gravure offset printing, a reverse offset printing, and a screen printing can also be used. In that case, a permanent resist material can also be used.

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

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

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

(1) Physical Properties of Organic Solvent The boiling point of at least one organic solvent is 130 ° C. to 300 ° C., more preferably 140 ° C. to 270 ° C., and even more preferably 150 ° C. to 250 ° C. When the boiling point is higher than 130 ° C., it is preferable from the viewpoint of inkjet ejection property. Further, when the boiling point is lower than 300 ° C., it is preferable from the viewpoint of defects of the coating film, surface roughness, residual solvent and smoothness. The organic solvent is more preferably configured to contain two or more kinds of organic solvents from the viewpoint of good inkjet ejection property, film forming property, smoothness and low residual solvent. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming an organic layer in consideration of transportability and the like.

Further, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP _GS ) of the good solvent (GS) is higher than the boiling point (BP _PS ) of the poor solvent (PS). Also low, configuration is particularly preferred.
By adding the poor solvent having a high boiling point, the good solvent having a low boiling point volatilizes first at the time of film formation, and the concentration of the content in the composition and the concentration of the poor solvent increase, and rapid film formation is promoted. As a result, a coating film having few defects, a small surface roughness, and high smoothness can be obtained.

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

After the film formation, the organic solvent is removed from the coating film by a drying step such as vacuum, reduced pressure, and heating. When heating is performed, it is preferable to perform heating at a glass transition temperature (Tg) of at least one of the solutes + 30 ° C. or lower from the viewpoint of improving the coating film-forming property. From the viewpoint of reducing the residual solvent, it is preferable to heat the solute at at least one glass transition point (Tg) of −30 ° C. or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Further, the drying may be performed a plurality of times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific Examples of Organic Solvents Examples of the organic solvent used in the composition for forming an organic layer include an alkylbenzene-based solvent, a phenyl ether-based solvent, an alkyl ether-based solvent, a cyclic ketone-based solvent, an aliphatic ketone-based solvent, and a monocyclic solvent. Examples thereof include a ketone solvent, a solvent having a diester skeleton and a fluorine-containing solvent, and specific examples thereof include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, and the like. Heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol Monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropylmethyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butylmethyl ether, tripropylene glycol Dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene , O-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoro Anisol, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Anisol, Fenetol, Benzodioxol, 4-Methylanisole, s-butylbenzene, 3-Methylanisole, 4-Fluoro-3-methyl Anisole, Simene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, Decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenylether, 1-fluoro-3,5-dimethoxybenzene, benzoic acid Methyl, isopentylbenzene, 3,4-dimethylanisole, o-tornitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene , 1-Methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitril, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydro Benzofuran, 1-methyl-4- (propoxymethyl) benzene, 1-methyl-4- (butyloxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) ) Benzene, 1-methyl-4- (heptyloxymethyl) benzene, benzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether and the like, but are not limited thereto. Further, the solvent may be used alone or may be mixed.

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

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

Examples of the binder used in the composition for forming an organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, and the like. Ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile -Stylite copolymer (AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the above resins and polymers include, but are not limited to.

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

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

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

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

<Composition and physical properties of the composition for forming an organic layer>
The content of each component in the composition for forming an organic layer is obtained from the good solubility, storage stability and film forming property of each component in the composition for forming an organic layer, and the composition for forming an organic layer. Good film quality of the coating film, good ejection property when the inkjet method is used, and good electrical characteristics, light emission characteristics, efficiency, and life of the organic EL element having an organic layer produced by using the composition. It is decided in consideration of the viewpoint of. For example, in the case of a composition for forming a light emitting layer, the first component is 0.0001% by weight to 2.0% by weight with respect to the total weight of the composition for forming a light emitting layer, and the second component is for forming a light emitting layer. 0.0999% by weight to 8.0% by weight based on the total weight of the composition, and 90.0% by weight to 99.9% by weight based on the total weight of the composition for forming the light emitting layer as the third component. preferable.

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

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

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

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

式（ＸＬＰ－１）において、
ＭＵｘ、ＥＣｘおよびｋは上記式（Ｈ３）におけるＭＵ、ＥＣおよびｋと同定義であり、ただし、式（ＸＬＰ－１）で表される化合物は少なくとも１つの架橋性置換基（ＸＬＳ）を有し、好ましくは架橋性置換基を有する１価または２価の芳香族化合物の含有量は、分子中０．１～８０重量％である。 <Crosslinkable polymer compound: a compound represented by the general formula (XLP-1)>
Next, a case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

In the formula (XLP-1)
MUx, ECx and k have the same definition as MU, EC and k in the above formula (H3), except that the compound represented by the formula (XLP-1) has at least one crosslinkable substituent (XLS). The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.1 to 80% by weight in the molecule.

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

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the above-mentioned polymer compound, but a substituent having the following structure is preferable. * In each structural formula indicates the bonding position.

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

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

<Manufacturing method of polymer compound and crosslinkable polymer compound>
The method for producing the polymer compound and the crosslinkable polymer compound will be described by taking as an example the compound represented by the above formula (H3) and the compound represented by the formula (XLP-1). These compounds can be synthesized by appropriately combining known production methods.

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

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

When producing the compound of the formula (H3) and the compound of the formula (XLP-1), the compound may be produced in one step or may be produced in multiple steps. Further, it may be carried out by a batch polymerization method in which the reaction is started after all the raw materials are put in the reaction vessel, or it may be carried out by a dropping polymerization method in which the raw materials are dropped and added to the reaction vessel, and the product advances the reaction. It may be carried out by a precipitation polymerization method in which precipitation is accompanied, and these can be combined and synthesized as appropriate. For example, when the compound represented by the formula (H3) is synthesized in one step, the desired product is obtained by carrying out the reaction in a state where the monomer unit (MU) and the end cap unit (EC) are added to the reaction vessel. Further, when synthesizing a compound represented by the general formula (H3) in multiple stages, the monomer unit (MU) is polymerized to a target molecular weight, and then an end cap unit (EC) is added to react the target product. obtain. By adding different types of monomer units (MUs) in multiple stages and carrying out the reaction, a polymer having a concentration gradient in the structure of the monomer units can be produced. Further, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

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

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

For specific polymer synthesis procedures, see JP 2012-036388, International Publication No. 2015/008851, JP 2012-36381, JP 2012-144722, and International Publication No. 2015/194448. , International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2011/049241 Can be done.

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

Examples of the display device include a panel display such as a color flat panel display and a flexible display such as a flexible color organic electroluminescent (EL) display (for example, JP-A-10-335066, JP-A-2003-321546). See Japanese Patent Publication No. 2004-281086, etc.). In addition, examples of the display method of the display include a matrix method and a segment method. 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-2003-277741, JP-A-2004-119211). Etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display board, a sign, and the like. In particular, as a backlight for a liquid crystal display device, especially a personal computer for which thinning is an issue, the present embodiment is considered to be difficult to thin because the conventional method consists of a fluorescent lamp and a light guide plate. The backlight using the light emitting element according to the above is characterized by being thin and lightweight.

3-2. Other Organic Devices The polycyclic aromatic compound according to the present invention can be used for manufacturing an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, 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.

Quantum dots with a narrow half-value width at half maximum are used as the phosphor of the wavelength conversion filter for the purpose of widening the color gamut of the display. On the other hand, there are problems such as instability to oxidation, high cohesiveness due to nano-sized fine particles, and the metal used is regulated as a pollutant. The polycyclic aromatic compound according to the present invention can be used as a phosphor of a wavelength conversion filter. As the matrix for dispersing this polycyclic aromatic compound, a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability is preferable, and for example, (meth) such as polymethyl (meth) acrylate is preferable. ) Acrylic polymers and cycloolefin polymers such as Zeonex can be mentioned.

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

Synthesis Example (1): Synthesis of compound (1A-18) Nitrogen atmosphere in a flask containing compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) And o-dichlorobenzene (400 ml). Below, at room temperature, boron tribromide (1.13 ml, 12 mmol, 4 eq.) Was added. After completion of the dropping, the temperature was raised to 180 ° C. and the mixture was stirred for 20 hours. Then, the mixture was cooled to room temperature again, N, N-diisopropylethylamine (7.70 ml, 45 mmol, 15 eq.) Was added, and the mixture was stirred until the exotherm subsided. Then, the reaction solution was distilled off under reduced pressure at 60 ° C. to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in this order, purified with a silica gel column (eluent: toluene), and the crude product was recrystallized twice with o-dichlorobenzene to compound (1A-18). ) Was obtained (0.84 g).

^{1 1} H-NMR ((CDCl ₂ ) _2,500 MHz): δ = 2.51 (m, 12H), 5.21 (s, 1H), 6.73 (d, 2H), 6.89 (d, 4H) ), 7.23-7.28 (m, 6H), 7.50 (t, 2H), 7.62 (t, 4H), 7.92 (d, 4H), 8.59 (s, 2H). , 8.74 (s, 2H), 9.13 (s, 2H).

The target compound (1A-18) was confirmed at m / z = 801.35 by MALDI-MS.

Synthesis Example (2): Synthesis of compound (1A-32) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-32) (3.36 g, 3. Compound (1A-32) was obtained (0.38 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

^{1 1} H-NMR (CDCl _3,500 MHz): δ = 9.16 (s, 2H), 8.96 (d, 2H), 8.68 (s, 2H), 7.91 (d, 4H), 7 .57 (t, 4H), 7.43 (t, 2H), 7.21 (t, 8H), 7.11 (d, 8H), 7.02 (t, 6H), 6.82 (s, 2H), 6.61 (s, 4H), 6.37 (d, 2H), 5.31 (s, 1H), 2.17 (s, 12H).

The target compound (1A-32) was confirmed at m / z = 1135.50 by MALDI-MS.

Synthesis Example (3): Synthesis of compound (1A-111) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-111) (2.64 g, 3. Compound (1A-111) was obtained (0.21 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

The target compound (1A-111) was confirmed at m / z = 895.33 by MALDI-MS.

Synthesis Example (4): Synthesis of compound (1A-214) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-214) (3.64 g, 3. Compound (1A-214) was obtained (0.30 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

The target compound (1A-214) was confirmed at m / z = 1229.48 by MALDI-MS.

Synthesis Example (5): Synthesis of compound (1A-303) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-303) (4.11 g, 3. Compound (1A-303) was obtained (0.60 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

^{1 1} H-NMR (CDCl _3,500 MHz): δ = 1.50 (s, 36H), 1.88 (s, 12H), 2.49 (s, 6H), 5.49 (s, 1H), 7 .04 (s, 4H), 7.08 (d, 2H), 7.33 (t, 2H), 7.42 (t, 4H), 7.50 (dd, 4H), 7.65 (d, 4H), 7.72 (dd, 2H), 7.81 (d, 4H), 8.21 (s, 4H), 8.77 (s, 2H), 9.20 (s, 2H), 9. 47 (s, 2H).

The target compound (1A-303) was confirmed at m / z = 1383.75 by MALDI-MS.

Synthesis Example (6): Synthesis of compound (1A-407) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-407) (3.35 g, 3. Compound (1A-407) was obtained (0.56 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

^{1 1} H-NMR ((CDCl ₂ ) _2,500 MHz): δ = 1.63 (s, 12H), 2.03 (s, 6H), 5.20 (s, 1H), 6.31 (s, 2H) ), 6.53 (s, 4H), 7.04-7.10 (m, 4H), 7.15 (d, 4H), 7.22-7.27 (m, 6H), 7.38- 7.45 (m, 6H), 7.48 (s, 2H), 7.57-7.60 (m, 6H), 7.66 (d, 2H), 7.76 (d, 2H), 7 .95 (d, 4H), 8.75 (s, 2H), 9.00 (d, 2H), 9.21 (s, 2H).

The target compound (1A-407) was confirmed at m / z = 1263.56 by MALDI-MS.

Synthesis Example (7): Synthesis of compound (1A-702) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-702) (1.62 g, 3. Compound (1A-702) was obtained (0.42 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

The target compound (1A-702) was confirmed at m / z = 555.25 by MALDI-MS.

Synthesis Example (8): Synthesis of compound (1A-331) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-331) (2.05 g, 3. Compound (1A-331) was obtained (0.10 g) by the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

^{1 1} H-NMR ((CDCl ₂ ) _2,500 MHz): δ = 5.01 (s, 1H), 6.74 (d, 2H), 7.00-7.01 (m, 4H), 7.27 -7.29 (m, 2H), 7.42-7.44 (m, 8H), 7.49 (t, 1H), 7.54 (t, 1H), 7.62 (t, 1H), 7.91 (d, 1H), 8.15 (d, 1H), 8.30 (d, 1H), 8.81 (d, 1H), 8.91-8.95 (m, 2H), 9 .33 (s, 1H).

The target compound (1A-331) was confirmed at m / z = 699.21 by MALDI-MS.

Synthesis Example (9): Synthesis of compound (1A-902) Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1 eq.) Is compounded with compound (Int-1A-902) (2.32 g, 3. Compound (1A-902) was obtained (0.50 g) in the same procedure as in Synthesis Example 1 except that it was changed to 0 mmol, 1 eq.).

The target compound (1A-902) was confirmed at m / z = 789.26 by MALDI-MS.

Synthesis example (10): Synthesis of compound (1A-214) (alternative method 1)
1.6 mol / L tBuLi-heptane solution in a flask containing compound (Int1-1A-214) (2.36 g, 3.0 mmol, 1 eq.) And t-butylbenzene (400 ml) while ice-cooling under a nitrogen atmosphere. (9.3 ml, 15 mmol, 5 eq.) Was added. After completion of the dropping, the mixture was stirred at room temperature for 4 hours. Then, boron tribromide (2.25 g, 9.0 mmol, 3 eq.) Was slowly added while cooling with ice. After completion of the dropping, the mixture was stirred at room temperature for 24 hours. Then, 1,2,2,6,6-pentamethylpiperidine (1.86 g, 12 mmol, 4eq.) Was added while cooling with ice. Then, the mixture was stirred at 170 ° C. for 24 hours. The temperature was returned to room temperature, and water was added until the heat generation subsided. Then, the mixture was extracted with toluene, and the organic solvents were collectively concentrated under reduced pressure to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in this order, purified with a silica gel column (eluent: toluene), and the crude product was recrystallized twice with o-dichlorobenzene to compound (1A-214). ) Was obtained (1.10 g).

The target compound (1A-214) was confirmed at m / z = 1229.4801 by MALDI-MS.

Synthesis example (11): Synthesis of compound (1A-702) (alternative method 1)
Synthetic Example 10 except that compound (Int1-1A-214) (2.36 g, 3.0 mmol, 1 eq.) Was changed to compound (Int 1-1A-702) (1.62 g, 3.0 mmol, 1 eq.). Compound (1A-702) was obtained in the same procedure (0.97 g).

The target compound (1A-702) was confirmed at m / z = 555.2522 by MALDI-MS.

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

Next, the evaluation of the basic physical properties of the compound of the present invention and the production and evaluation of an organic EL device using the compound of the present invention will be described. However, the application of the compound of the present invention is not limited to the examples shown below, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.

<Evaluation of basic physical properties>
Compound (1A-18), compound (1A-32), compound (1A-111), compound (1A-214), compound (1A-303), compound (1A-331), compound (1A-407) of the present invention. ), Compound (1A-702), and comparative compounds RGD-1, RGD-2, RGD-3, and RBD-1 are each dissolved in toluene together with PMMA (polymethylmethacrylate) so as to be 1 wt%. After that, a thin film was formed on a transparent support substrate (10 mm × 10 mm) made of quartz by a spin coating method to prepare a PMMA dispersion film.

Photoluminescence was measured by excitation at room temperature at a wavelength of 280 nm. The fluorescence lifetime was measured at 300 K using a fluorescence lifetime measuring device (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.). Specifically, a light emitting component having a fast fluorescence lifetime and a light emitting component having a slow fluorescence lifetime were observed at the maximum emission wavelength measured at an excitation wavelength of 280 nm. In the fluorescence lifetime measurement of a general organic EL material that emits fluorescence at room temperature, a slow emission component involving a triplet component derived from phosphorescence is rarely observed due to the deactivation of the triplet component due to heat. 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. The results are shown in Table 1.

The chemical structures of RGD-1, RGD-2, RGD-3, and RBD-1 in Table 1 are shown below.

<Evaluation of thin-film deposition type organic EL element>
The organic EL elements according to Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-4 were produced, and the emission wavelength, half-value width, drive voltage, and external quantum at a brightness of 500 cd / m ² . Efficiency and LT50 (time to 250 cd / m ² when continuously driven at a current density at an initial brightness of 500 cd / m ² ) were measured.

In Table 2, "NPD" is N, N'-diphenyl-N, N'-dinaphthyl-4,4'-diaminobiphenyl, and "TcTa" is 4,4', 4 "-tris (N-carbazolyl). It is a triphenylamine, "mCP" is 1,3-bis (N-carbazolyl) benzene, "Ir (ppy) ₃ " is tris (2-phenylpyridinato) iridium (III), and ""2CzBN" is 3,4-dicarbazolylbenzonitrile and "BPy-TP2" is 2,7-di ([2,2'-bipyridine] -5-yl) triphenylene. Together with "GH-1", the chemical structure is shown below.

<Example 1-1>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm was 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 NPD, TcTa, mCP, GH-1, compound (1A-18), 2CzBN, and BPy-TP2 are inserted, respectively. A molybdenum vapor deposition boat and a tungsten vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 ^-4 Pa, and first, the NPD was heated and vapor-deposited to a film thickness of 40 nm to form a hole injection layer. Next, TcTa was heated to be vapor-deposited to a film thickness of 15 nm, and mCP was further heated to be vapor-deposited to a film thickness of 15 nm to form a hole transport layer composed of two layers. Next, GH-1 and the compound (1A-18) were simultaneously heated and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of GH-1 to compound (1A-18) was approximately 99: 1. Next, 2CzBN was heated and vapor-filmed to a film thickness of 10 nm, and BPy-TP2 was further heated and vapor-filmed to a film thickness of 20 nm to form an electron transport layer composed of two layers. 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. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

<Example 1-2 to Example 1-4>
Each element was manufactured by changing the compound (1A-18) which is the dopant of Example 1 to each dopant shown in Table 2.

<Comparative Example 1-1 to Comparative Example 1-4>
Each element was manufactured by changing the compound (1A-18) which is the dopant of Example 1 to each dopant shown in Table 2.

The evaluation results of each element are shown in Table 3.

Examples 1-1 to 1-4 have green (500 to 550 nm) emission as compared with Comparative Examples 1-1 to 1-4, and have half-value width, color purity, and external emission of the emission spectrum. Balanced results were obtained with high levels of quantum efficiency and device lifetime.

The organic EL elements according to Examples 1-5 to 1-8, Comparative Example 1-5, Examples 1-9 to 1-12 and Comparative Example 1-6 were produced, and the brightness was 500 cd / m ² . , Emission wavelength, half-value width, drive voltage, external quantum efficiency, and LT50 (time to reach 250 cd / m ² when continuously driven at a current density at an initial luminance of 500 cd / m ² ) were measured.

In Table 4, the chemical structures of "HATCN", "TBB", "CBP", "GH-2" and "TPBi" are shown below.

<Example 1-5>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm was used as a transparent support substrate. A molybdenum vapor deposition boat in which this transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.) and contains HATCN, TBB, TcTa, CBP, compound (1A-32) and TPBi, respectively. A tungsten vapor deposition boat containing LiF and aluminum was installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 ^-4 Pa, and HATCN was first heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer. Next, the TBB was heated and vapor-filmed to a film thickness of 65 nm, and then TcTa was heated and vapor-filmed to a film thickness of 10 nm to form a hole transport layer composed of two layers. Next, the CBP and the compound (1A-32) were simultaneously heated and vapor-deposited to a film thickness of 30 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of CBP to compound (1A-32) was approximately 99: 1. Next, TPBi was heated and vapor-deposited to a film thickness of 50 nm to form an electron transport layer. 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. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

<Examples 1-6 to 1-8, Comparative Example 1-5, Examples 1-9 to 1-12 and Comparative Example 1-6>
Each element was manufactured by changing the host CBP of Example 1-5, the dopant compound (1A-32), and the mixing ratio to each host, each dopant, and each mixing ratio shown in Table 4.

The evaluation results of each element are shown in Table 5.

In Examples 1-5 to 1-8 and Examples 1-9 to 1-12, the half width of the emission spectrum is narrower and the efficiency is higher than that of Comparative Example 1-5 and Comparative Example 1-6. A long element life was obtained.

The organic EL elements according to Examples 1-13, Comparative Example 1-7, Example 1-14, Example 1-15, Example 1-16 and Comparative Example 1-8 were produced, and the brightness was 500 cd / m ² . , Emission wavelength, half-value width, drive voltage, external quantum efficiency, and LT50 (time to reach 250 cd / m ² when continuously driven at a current density at an initial luminance of 500 cd / m ² ) were measured.

In Table 6, the chemical structures of "4CzIPN", "BCC-TPTA", "T2T", and "Liq" are shown below.

<Example 1-13>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO formed to a thickness of 200 nm by sputtering to 50 nm was 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 is made of molybdenum containing HATCN, TBB, TcTa, 4CzIPN, compound (1A-32), T2T, TPBi and Liq, respectively. A vapor deposition boat and a tungsten vapor deposition boat containing LiF and aluminum were installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 ^-4 Pa, and HATCN was first heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer. Next, the TBB was heated and vapor-filmed to a film thickness of 65 nm, and then TcTa was heated and vapor-filmed to a film thickness of 10 nm to form a hole transport layer composed of two layers. Next, TcTa, 4CzIPN and the compound (1A-32) were simultaneously heated and vapor-deposited to a film thickness of 30 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of TcTa, 4CzIPN and compound (1A-32) was approximately 85:14: 1. Next, T2T was heated and vapor-filmed to a film thickness of 10 nm, and then TPBi and Liq were heated and vapor-deposited to a film thickness of 40 nm to form an electron transport layer composed of two layers. The deposition rate was adjusted so that the weight ratio of TPBi and Liq was about 70:30. 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. At this time, the vapor deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

<Comparative Example 1-7, Example 1-14, Example 1-15, Example 1-16 and Comparative Example 1-8>
The host TcTa of Example 1-13, the assisting dopant 4CzIPN and the dopant compound (1A-32) and the mixture ratio are changed to each of the assisting dopants and dopants and each mixture ratio shown in Table 6. Each element was manufactured.

The evaluation results of each element are shown in Table 7.

In Example 1-13, the half width of the emission spectrum was narrower than that in Comparative Example 1-7, and high efficiency and long device life were obtained.
Further, by changing the dopant of Example 1-13, a blue light emitting device can be realized as in Example 1-14.
Similarly, by changing the element configuration of Example 1-13, it is possible to realize an element using an exhibit and an assisting dopant as in Example 1-15.
Example 1-16 showed blue emission as compared with Comparative Example 1-8, the half width of the emission spectrum was narrow, and high efficiency and long device life were obtained.

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

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

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

<Example 2-1 to Example 2-9>
A coating solution of the material forming each layer is prepared to prepare a coating type organic EL device.

<Manufacturing of Organic EL Devices of Examples 2-1 to 2-3>
Table 8 shows the material composition of each layer in the organic EL device.

The structure of "ET1" in Table 8 is shown below.

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

The compound (A) is a polycyclic aromatic compound represented by the general formula (1A) or the general formula (1B) (for example, compound (1A-32)), or the polycyclic aromatic compound as a monomer (that is, the said compound). The monomer is a polymer compound polymerized as (having a reactive substituent), or a crosslinked polymer compound further crosslinked. The polymer compound for obtaining a polymer crosslinked body has a crosslinkable substituent.

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

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

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

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

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

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, ET1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

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

<Example 2-3>
An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is spin-coated with a PCz solution and fired on a hot plate at 120 ° C. for 1 hour to form a film having a film thickness of 30 nm.

<Evaluation of Organic EL Devices of Examples 2-1 to 2-3>
It can be expected that the coating type organic EL device obtained as described above also has excellent drive voltage and external quantum efficiency like the vapor deposition type organic EL device.

<Manufacturing of Organic EL Devices of Examples 2-4 to 2-6>
Table 9 shows the material composition of each layer in the organic EL element.

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

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

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

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

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

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

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

<Evaluation of Organic EL Devices of Examples 2-4 to 2-6>
It can be expected that the coating type organic EL device obtained as described above also has excellent drive voltage and external quantum efficiency like the vapor deposition type organic EL device.

<Manufacturing of Organic EL Devices of Examples 2-7 to 2-9>
Table 10 shows the material composition of each layer in the organic EL device.

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

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

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

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

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

The produced multilayer film was fixed to a substrate holder of a commercially available thin-film deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and tungsten containing aluminum. Install a vapor deposition boat. After depressurizing the vacuum chamber to 5 × 10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The vapor deposition rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec so as to have a film thickness of 1 nm. Next, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

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

<Evaluation of Organic EL Devices of Examples 2-7 to 2-9>
It can be expected that the coating type organic EL device obtained as described above also has excellent drive voltage and external quantum efficiency like the vapor deposition type organic EL device.

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

According to a preferred embodiment of the present invention, by manufacturing an organic EL device using, for example, a novel polycyclic aromatic compound as a dopant material, an organic EL device having a narrow half-value width of the emission spectrum and excellent color purity, and further a quantum It is possible to provide an organic EL element having excellent efficiency and element life. Further, since the novel polycyclic aromatic compound of the present invention has a rigid structure, the emission spectrum is sharper, the half width of the emission spectrum is narrow, and the compound which gives light emission with high color purity. There are many.

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 (31)

A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B).

In the above formula (1A) or formula (1B),
R ^a is a hydrogen or a substituent, and "-C (-R ^a ) =" in the a ring may be replaced with "-N =".
The B ring, C ring, D ring, E ring, F ring, and G ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-R are independently substituted aryls, substituted heteroaryls, substituted alkyls, or optionally substituted cycloalkyls, respectively.
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, substituted, respectively. It is an alkyl which may be substituted or a cycloalkyl which may be substituted, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is , Can be attached by a single bond or a linking group,
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ¹ can be at least one of the a ring and the B ring by a single bond or a linking group. May be combined,
The R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is at least one of the a ring and the E ring by a single bond or a linking group. May be combined,
The C and D rings, the G and B rings, and the F and E rings may be independently bonded by a single bond or a linking group, respectively.
However, in the above formula (1A), the CD bond of the C ring and the D ring and the R of> N ^— R as X1 (this R may be the substituted aryl, the substituted may be the case). Heteroaryl, or the optionally substituted cycloalkyl) and the X ¹ B bond of the B ring and> NR R as X ² (where this R is the optionally substituted aryl, said. There is one or two of the three bonds (limited to the substituted heteroaryl or the substituted cycloalkyl) and the ^X2E bond of the E ring. And
Further, in the above formula (1B), any one or one of the three bonds of the CD bond of the C ring and the D ring, the GB bond of the G ring and the B ring, and the FE bond of the F ring and the E ring. There are two bonds,
At least one of the B ring, C ring, D ring, E ring, F ring, G ring, aryl, and heteroaryl in the compound represented by the above formula (1A) or formula (1B) is at least one cyclo. It may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound represented by the above formula (1A) or the formula (1B) may be substituted with deuterium, cyano, or halogen. In the above formula (1A) or formula (1B),
^Ra is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted aryl. Heteroarylamino, optionally substituted diarylboryl (two aryls may be attached by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, substituted. An alkoxy optionally, an aryloxy optionally substituted, or a substituted silyl,
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
The B ring, C ring, D ring, E ring, F ring, and G ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted. Aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (The two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, substituted. May be substituted with aryloxy, or substituted silyl,
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-Rs are independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. ,
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least 1 in the R. One hydrogen may be substituted with alkyl or cycloalkyl, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is a single bond. , -CH = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) It may be bound by _2- or -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-Si (-). R) ₂ -Rs are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, or a heteroarylene.
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and B ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the E ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) _2- are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, or two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene.
The C and D rings, the G and B rings, and the F and E rings are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, and alkenyl. , Alkinyl, or cycloalkyl, the at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and the two adjacent Rs form a ring with the cycloalkylene, arylene, and It may form a heteroarylene,
However, in the above formula (1A), the CD bond of the C ring and the D ring and the R of> N ^- R as X1 (this R may be substituted with the alkyl or the cycloalkyl, the aryl, The X ¹ B bond of the heteroaryl or the cycloalkyl and the B ring and an R of> NR as X ² (where R may be substituted with the alkyl or cycloalkyl, said. Any one or two of the three bonds with aryl, said heteroaryl, or said cycloalkyl) and the ^X2E bond of the E ring is present.
Further, in the above formula (1B), any one or one of the three bonds of the CD bond of the C ring and the D ring, the GB bond of the G ring and the B ring, and the FE bond of the F ring and the E ring. There are two bonds,
At least one of the B ring, C ring, D ring, E ring, F ring, G ring, aryl, and heteroaryl in the compound represented by the above formula (1A) or formula (1B) is at least one cyclo. It may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH _2- in the cycloalkane may be substituted with -O-.
At least one hydrogen in the compound represented by the above formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen.
The polycyclic aromatic compound according to claim 1. The polycyclic aromatic compound according to claim 1, which is represented by the following general formula (2A) or the following general formula (2B).

In the above formula (2A) or formula (2B),
Ra is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, ^diarylboryl (two aryls may be single-bonded or bonded by a linking group), alkyl, cycloalkyl, An alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or ^{alkyldicycloalkylsilyl} , wherein at least one hydrogen in the Ra is aryl, heteroaryl, alkyl, or. May be substituted with cycloalkyl,
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two). Aryl may be attached by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. And at least one hydrogen in the R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R Adjacent groups of ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are attached to each other together with the b ring, c ring, d ring, e ring, f ring, and g ring, respectively. An aryl ring or a heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls). Substituted with a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.
Any "-C (-R) =" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f or R ^g ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N (-R)-", "-O-", "-S-", "-C (-R) _2- ", It may be replaced with "-Si (-R) _2- " or "-Se-", and the R of the above-mentioned "-N (-R)-", the R of "-C (-R) _2- ", And the R of "-Si (-R) _2- " is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. , At least one of the two Rs of "-C (-R) _2- " and the two Rs of "-Si (-R) _2- " is a single bond, -CH = CH-, -CR. = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- -CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R, respectively. Independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and two adjacent. R may form a ring with each other to form a cycloalkylene, an arylene, or a heteroarylene.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-Rs are independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. ,
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least 1 in the R. One hydrogen may be substituted with alkyl or cycloalkyl, and at least one of the two Rs of> C (-R) ₂ and the two Rs of> Si (-R) ₂ is a single bond. , -CH = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) It may be bound by _2- or -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) ₂ -R, and -Si (-Si (-). R) ₂ -Rs are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form a cycloalkylene, an arylene, or a heteroarylene.
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and b ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) _2- are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, or two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene.
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, aryl, heteroaryl, alkyl, and alkenyl. , Alkinyl, or cycloalkyl, the at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and the two adjacent Rs form a ring with the cycloalkylene, arylene, and It may form a heteroarylene,
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N ^— R as X1 (the R may be substituted with the alkyl or the cycloalkyl, the aryl, The X ¹ b bond of the heteroaryl or the cycloalkyl and the b ring and an R of> N-R as X ² (where R may be substituted with the alkyl or cycloalkyl, said. Any one or two of the three bonds with aryl, said heteroaryl, or said cycloalkyl) and the X ² e bond of the e-ring is present.
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
The b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, and the aryl in the compound represented by the formula (2A) or the formula (2B). And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms and 2 carbon atoms. It may be substituted with ~ 30 heteroaryl, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH _2- in the cycloalkane is substituted with -O-. May,
At least one hydrogen in the compound represented by the above formula (2A) or the formula (2B) may be substituted with deuterium, cyano, or halogen. In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 30 carbon atoms, ^a heteroaryl having 2 to 30 carbon atoms, a diallyl amino (where the aryl is an aryl having 6 to 12 carbon atoms), and a diallyl boryl (where the aryl is an aryl having 6 to 12 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or ^a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diarylamino (however, the aryl is). Aryl with 6 to 12 carbon atoms), diarylboryl (where the aryl is an aryl with 6 to 12 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms. , Or a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g is an aryl having 6 to 12 carbon atoms and 2 carbon atoms. It may be substituted with ~ 15 heteroaryl, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and may be substituted with R ^b , R ^c , R ^d , R ^e , R ^f , and R. Adjacent groups of ^g are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring having 9 to 16 carbon atoms or a hetero having 6 to 15 carbon atoms, respectively. An aryl ring may be formed, and at least one hydrogen in the formed ring is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, and a diarylamino (where the aryl has 6 to 12 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or an alkyl having 3 to 3 carbon atoms. It may be substituted with 24 cycloalkyls, the at least one hydrogen in these substituents being an aryl with 6-12 carbons, a heteroaryl with 2-15 carbons, an alkyl with 1-6 carbons, or carbon. It may be substituted with the number 3 to 14 cycloalkyl.
Any "-C (-R) =" in the b ring, c ring, d ring, e ring, f ring, and g ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f or R ^g ) may be replaced with "-N =" and any "-C (-R) = C (-R)-" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N (-R)-", "-O-", "-S-", "-C (-R) _2- ", It may be replaced with "-Si (-R) _2- " or "-Se-", and the R of "-N (-R)-", the R of "-C (-R) _2- ", And R of "-Si (-R) _2- " is hydrogen, aryl with 6 to 12 carbon atoms, heteroaryl with 2 to 15 carbon atoms, alkyl with 1 to 6 carbon atoms, or cyclo with 3 to 14 carbon atoms. It is an alkyl, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and the 2 of the above-mentioned "-C (-R) _2- ". At least one of the two Rs of "-Si (-R) _2- " is a single bond, -CH = CH-, -CR = CR-, -C≡C-, -N (-). R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, respectively. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, at least 1 in the R. One hydrogen may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs form a ring with each other to form a ring and a cycloalkylene having 3 to 14 carbon atoms. , An arylene having 6 to 12 carbon atoms or a heteroarylene having 2 to 15 carbon atoms may be formed.
Y ¹ , Y ² and Y ³ are independent of>B-,>P-,> P (= O)-,> P (= S)-,>Al-,>Ga-,> As. -,> C (-R)-,> Si (-R)-or> Ge (-R)-, and the above-mentioned> C (-R)-R,> Si (-R)-R, And> Ge (-R)-R are independently aryls with 6 to 12 carbon atoms, heteroaryls with 2 to 15 carbon atoms, alkyls with 1 to 6 carbon atoms, or cyclos with 3 to 14 carbon atoms. It is alkyl, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.
X ¹ and X ² are independently>N-R,>O,>S,> C (-R) ₂ ,> Si (-R) ₂ , or> Se, and the above-mentioned> N-R. R,> C (-R) ₂ R, and> Si (-R) ₂ R are independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, and carbon. It is an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the R is substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. Often,
The above-mentioned R of>N-R,> R of C (-R) ₂ , or R of> Si (-R) ₂ as X ¹ is a single bond, -CH = CH-, -CR = CR-,-. C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se-, a ring and b ring It may be bound to at least one of, and the R of> N-R, the R of> C (-R) ₂ or the R of> Si (-R) ₂ as X ² is a single bond, -CH. = CH-, -CR = CR-, -C≡C-, -N (-R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the above-CR = CR-R, -N (-R)-R, -C (-R) _2- . R and R of -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, and 1 carbon atom. An alkenyl having a number of carbon atoms of 1 to 6, an alkynyl having a carbon content of 1 to 6 or a cycloalkyl having a carbon number of 3 to 14, and at least one hydrogen in the R is an alkyl having a carbon number of 1 to 6 or a cycloalkyl having a carbon number of 3 to 14. It may be substituted with, and two adjacent Rs form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms. You may be
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -CH = CH-, -CR = CR-, -C≡C-, and -N (-". R)-, -O-, -S-, -C (-R) _2- , -Si (-R) _2- , or -Se- may be used for binding, and the above-CR = CR-R. , -N (-R)-R, -C (-R) ₂ -R, and -Si (-R) ₂ -R are independently hydrogen, an aryl having 6 to 12 carbon atoms, respectively. Heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, at least 1 in the R. One hydrogen may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs form a ring with each other to form a ring and a cycloalkylene having 3 to 14 carbon atoms. , An arylene having 6 to 12 carbon atoms or a heteroarylene having 2 to 15 carbon atoms may be formed.
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N—R as X1 (this R is the alkyl having ¹ to 6 carbon atoms or the cyclo having 3 to 14 carbon atoms). ^With the X1 b bond of the b ring (limited to the aryl having 6 to 12 carbon atoms, the heteroaryl having 2 to 15 carbon atoms, or the cycloalkyl having 3 to 14 carbon atoms, which may be substituted with an alkyl). , R of> N ^— R as X2 (where R may be substituted with the alkyl having 1 to 6 carbon atoms or the cycloalkyl having 3 to 14 carbon atoms, the aryl having 6 to 12 carbon atoms, There is one or two of the three bonds (limited to the heteroaryl having 2 to 15 carbon atoms or the cycloalkyl having 3 to 14 carbon atoms) and the ^X2e bond of the e-ring. And
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
In the compound represented by the above formula (2A) or the above formula (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and the like. And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms and 2 carbon atoms. It may be substituted with ~ 15 heteroaryl, an alkyl having 1-12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
The polycyclic aromatic compound according to claim 3. In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 16 carbon atoms, ^a heteroaryl having 2 to 20 carbon atoms, a diallyl amino (however, the aryl is an aryl having 6 to 10 carbon atoms), and a diallyl boryl (however, the aryl has 6 to 10 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or ^a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
"-C (-R ^a ) =" in the a ring may be replaced with "-N =".
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (however, the aryl is). Aryl with 6 to 10 carbon atoms), diarylboryl (where the aryl is an aryl with 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms. , Or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is an aryl having 6 to 10 carbon atoms and 2 carbon atoms. It may be substituted with up to 10 heteroaryls, 1 to 5 carbons of alkyl, or 5 to 10 carbons of cycloalkyl, as well as R ^b , R ^c , R ^d , R ^e , R ^f , and R. Adjacent groups of ^g are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring having 9 to 16 carbon atoms or a hetero having 6 to 15 carbon atoms, respectively. An aryl ring may be formed, and at least one hydrogen in the formed ring is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (where the aryl has 6 to 10 carbon atoms). Aryl), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or an alkyl having 3 to 3 carbon atoms. It may be substituted with 16 cycloalkyls, the at least one hydrogen in these substituents being an aryl 6-10 carbons, a heteroaryl 2-10 carbons, an alkyl 1-5 carbons, or carbon. It may be substituted with the number 5 to 10 cycloalkyl.
Any "-C (-R) =" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring (where R is R ^b , R ^c , R ^d , R ^e , R). ^f ), or ^Rg ) may be replaced with "-N =".
Y ¹ , Y ² and Y ³ are independently>B-,>P-,> P (= O)-or> P (= S)-, respectively.
X ¹ and X ² are independently>N-R,>O,> S, or> C (-R) ₂ , and of the above-mentioned> N-R R and> C (-R) ₂ . R is independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
The R of> N-R or the R of> C (-R) ₂ as X ¹ is a single bond, -N (-R)-, -O-, -S-, or -C (-R) ₂ . -Therefore, it may be bonded to the b ring, and the R of> N-R or the R of> C (-R) ₂ as X ² is a single bond, -N (-R)-, -O-. , -S-, or -C (-R) ₂ -may be bonded to the e-ring, and the R of -N (-R)-and the R of -C (-R) _2- are respectively. Independently, hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R. May be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are independently single-bonded, -N (-R)-, -O-, -S-, or -C (-R). ) ₂ -R may be bonded by 2-, and the -N (-R)-R and the -C (-R) ₂ -R are independently hydrogen, an aryl having 6 to 10 carbon atoms, and carbon. It is a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R is an alkyl having 1 to 5 carbon atoms or an alkyl having 5 to 10 carbon atoms. May be substituted with cycloalkyl in
However, in the above formula (2A), the cd bond of the c ring and the d ring and the R of> N—R as X1 (this R is the alkyl having ¹ to 5 carbon atoms or the cyclo having 5 to 10 carbon atoms). The X ¹ b bond of the ring (limited to the aryl having 6 to 10 carbon atoms) and the b ring, which may be substituted with an alkyl, and an R of> NR as X ² (this R is the above carbon number 1 to 1 to 10). One of the three bonds (limited to the aryl having 6 to 10 carbon atoms, which may be substituted with an alkyl of 5 or a cycloalkyl having 5 to 10 carbon atoms) and the ^X2e bond of the e-ring. There is one or two bonds,
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
In the compound represented by the above formula (2A) or the above formula (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and the like. And at least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 10 carbon atoms and 2 carbon atoms. It may be substituted with ~ 10 heteroaryl, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
The polycyclic aromatic compound according to claim 3. In the above formula (2A) or formula (2B),
Ra is hydrogen, an aryl having 6 to 16 carbon atoms, ^a heteroaryl having 2 to 20 carbon atoms, a diallyl amino (however, the aryl is an aryl having 6 to 10 carbon atoms), and a diallyl boryl (however, the aryl has 6 to 10 carbon atoms). It is an aryl, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or ^a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the Ra. May be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, and a diarylamino (however, the aryl is). Aryl having 6 to 10 carbon atoms), diarylboryl (where the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms. , Or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g is an alkyl having 1 to 5 carbon atoms, or an alkyl having 1 to 5 carbon atoms. It may be substituted with 5-10 cycloalkyls.
Y1 ^{, Y2} , and Y3 ^are > B-, and
X ¹ and X ² are> N-R, and the R of> N-R is hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, and an alkyl having 1 to 5 carbon atoms. Alternatively, it is a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R may be substituted with an alkyl having 1 to 5 carbon atoms.
The R of> N—R as X ¹ may be bonded to the b ring by a single bond, and the R of the> N—R as X ² may be bonded to the e ring by a single bond. May,
The c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring may be independently bonded by a single bond.
However, in the above formula (2A), the cd bond of the c ring and the d ring and R of> N ^— R as X1 (this R may be substituted with the alkyl having 1 to 5 carbon atoms). The X ¹ b bond of the ring (limited to aryls of number 6 to 10) and the R of> NR as X ² (this R may be substituted with the alkyl having 1 to 5 carbon atoms). One or two of the three bonds (limited to aryls of number 6 to 10) and the ^X2e bond of the e-ring are present.
Further, in the above formula (2B), any one or one of the three bonds of the cd bond of the c ring and the d ring, the gb bond of the g ring and the b ring, and the fe bond of the f ring and the e ring. There are two bonds,
At least of the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl in the compound represented by the formula (2A) or the formula (2B). One may be condensed with at least one cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 5 carbon atoms.
At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
The polycyclic aromatic compound according to claim 3. The polycyclic aromatic compound according to claim 3, which is represented by any of the following structural formulas.

In each formula,
R is independently hydrogen, aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 20 carbon atoms, diarylamino (where aryl is aryl with 6 to 10 carbon atoms), and diarylboryl (where aryl is carbon number of carbon atoms). It is an aryl of 6 to 10 and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least in the R. One hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.
o is an integer of 1 to 3 independently,
p is an integer of 1 to 4 independently of each other.
q is an independent integer of 1 to 5, respectively.
At least one hydrogen in the compound represented by each of the above formulas may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound according to claim 1, which is represented by any of the following structural formulas.

A reactive compound in which a reactive substituent is substituted on the polycyclic aromatic compound according to any one of claims 1 to 8. A polymer compound obtained by polymerizing the reactive compound according to claim 9 as a monomer, or a polymer crosslinked product obtained by further cross-linking the polymer compound. A pendant type polymer compound in which a main chain type polymer is substituted with the reactive compound according to claim 9, or a pendant type polymer crosslinked body in which the pendant type polymer compound is further crosslinked. A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 8. A material for an organic device containing the reactive compound according to claim 9. A material for an organic device containing the polymer compound or polymer crosslinked body according to claim 10. A material for an organic device containing the pendant type polymer compound or the pendant type polymer crosslinked body according to claim 11. The organic device according to any one of claims 12 to 15, wherein the material for the organic device is a material for an organic field light emitting device, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter. Material for. The material for an organic device according to claim 16, wherein the material for an organic electroluminescent element is a material for a light emitting layer. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent. An ink composition comprising the reactive compound according to claim 9 and an organic solvent. An ink composition containing a main chain polymer, the reactive compound according to claim 9, and an organic solvent. An ink composition comprising the polymer compound or the crosslinked polymer according to claim 10 and an organic solvent. An ink composition comprising the pendant type polymer compound or the pendant type polymer crosslinked body according to claim 11 and an organic solvent. The polycyclic aromatic compound according to any one of claims 1 to 8, the reactive compound according to claim 9, and the reactive compound according to claim 10, which are arranged between the pair of electrodes composed of an anode and a cathode and the pair of electrodes. An organic electric field light emitting element having an organic layer containing the polymer compound or polymer crosslinked according to claim, or the pendant type polymer compound or pendant polymer crosslinked according to claim 11. The organic electroluminescent device according to claim 23, wherein the organic layer is a light emitting layer. 24. The light emitting layer comprises a host and the polycyclic aromatic compound, a reactive compound, a polymer compound, a polymer crosslinked body, a pendant type polymer compound or a pendant type polymer crosslinked body as a dopant. The organic field light emitting element described in 1. The light emitting layer is further represented by a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), and a compound represented by the following general formula (H4). Claimed to contain at least one selected from the group consisting of a compound comprising the structure to be, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. Item 25. The organic electroluminescent element.

In the above general formula (H1), L1 is ^an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms.
In the above general formula (H2), L ² and L ³ are independently aryls having 6 to 30 carbon atoms or heteroaryls having 2 to 30 carbon atoms.
In the above general formula (H3), MU is a divalent group independently represented by removing any two hydrogen atoms from the aromatic compound, and EC is independently represented by any one hydrogen from the aromatic compound. It is a monovalent group represented by excluding atoms, two hydrogens in MU are replaced with EC or MU, k is an integer of 2 to 50,000, and
In the above general formula (H4), G is independently = C (−H) − or = N−, and H in the above = C (−H) − is a substituent or another formula (H4). It may be replaced by the structure represented.
In the above general formula (H5),
R ¹ to R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, ^{diheteroarylamino} , arylhetelloarylamino, alkyl or cycloalkyl, and at least ^one of R1 to R11. Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl.
Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring or a c ring, and at least one hydrogen in the formed ring is a hydrogen. It may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further aryl, heteroaryl, diarylamino, alkyl. Alternatively, it may be substituted with cycloalkyl.
Any "-C (-R) =" (where R is R ¹ to R ¹¹ ) in the a-ring, b-ring, and c-ring may be replaced with "-N =".
In the above general formula (H6),
R ¹ to R ¹⁶ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetelloarylamino, alkyl or cycloalkyl, and at least ^one of R1 to ^R16 . Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl.
Adjacent groups of R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with an a ring, a b ring, a c ring or a d ring, and at least one in the formed ring. Hydrogen may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further aryl, heteroaryl, diaryl. May be substituted with amino, alkyl or cycloalkyl, and
At least one hydrogen in the compound or structure represented by each of the above formulas may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, cyano, a halogen or deuterium. It has at least one layer of an electron transporting layer and an electron injecting layer arranged between the cathode and the light emitting layer, and at least one of the electron transporting layer and the electron injecting layer is a borane derivative, a pyridine derivative, or fluoranthene. Derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives The organic electric field light emitting element according to any one of claims 23 to 26, which comprises at least one selected from the group consisting of. At least one layer of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, and an alkaline soil. Contains at least one selected from the group consisting of halides of similar metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals. 27. The organic electric field light emitting element according to claim 27. At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or a polymer compound. , A polymer crosslinked product obtained by further cross-linking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain type polymer, or the pendant type polymer compound. The organic electric field light emitting element according to any one of claims 23 to 28, which comprises a pendant type polymer crosslinked body further crosslinked. A display device or a lighting device including the organic electroluminescent element according to any one of claims 23 to 29. A wavelength conversion filter including the wavelength conversion filter material according to claim 16.

Images