JP7239924B2 - Organic electroluminescence device, display device and lighting device, and compound - Google Patents

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent device, a display device and a lighting device using the organic electroluminescent device, and a compound used for the organic electroluminescent device.

Conventionally, display devices using light-emitting elements that emit electroluminescence have been studied in various ways because they can be reduced in power consumption and thickness. , has been actively studied because it is easy to reduce the weight and increase the size. In particular, the development of organic materials that emit light in blue, one of the three primary colors of light, and the combination of multiple materials that achieve optimal light emission properties have been actively pursued, regardless of whether they are high-molecular compounds or low-molecular-weight compounds. has been studied.

An organic EL element has a structure comprising a pair of electrodes consisting of an anode and a cathode, and one or more layers interposed 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. Various organic materials suitable for these layers have been developed.

Benzofluorene-based compounds, for example, have been developed as light-emitting layer materials (International Publication No. 2004/061047). Further, as a hole-transporting material, for example, a triphenylamine-based compound has been developed (JP-A-2001-172232). Further, as an electron transport material, for example, an anthracene-based compound has been developed (Japanese Unexamined Patent Application Publication No. 2005-170911).

In recent years, compounds in which a plurality of aromatic rings are condensed with boron as a central atom have also been reported (International Publication No. 2015/102118). In this document, an organic EL device evaluation using a compound obtained by condensing the plurality of aromatic rings as a dopant material for the light-emitting layer is performed. In particular, it is beneficial to examine compounds that are excellent in organic EL properties such as light emission properties.

WO 2004/061047 Japanese Patent Application Laid-Open No. 2001-172232 JP-A-2005-170911 International Publication No. 2015/102118

As described above, various materials have been developed as materials for use in organic EL devices, but in order to further improve the light-emitting properties and increase the choice of materials for the light-emitting layer, it is necessary to develop material combinations that are different from conventional materials. Desired.

The present inventors have made intensive studies to solve the above problems, and as a result, the first component consists of a group consisting of organic compounds containing a specific element in the molecule, and an inorganic compound containing a specific element in the molecule. The inventors have developed an organic EL device having a light-emitting layer containing at least one selected from the group and at least one thermally activated delayed phosphor as a second component, thereby completing the present invention.

In this specification, the chemical structure and substituents may be represented by the number of carbon atoms, but when the chemical structure is substituted with a substituent group, or when the substituent is further substituted with a substituent group, the number of carbon atoms is the number of carbon atoms in the chemical structure. and substituents, and do not mean the total number of carbon atoms in the chemical structure and the substituents, or the total number of carbon atoms in the substituents. For example, “substituent B having Y carbon atoms and substituted with substituent A having X carbon atoms” means that “substituent B having Y carbon atoms” is substituted with “substituent A having X carbon atoms”. However, the carbon number Y is not the total carbon number of the substituents A and B. Further, for example, “substituent B having Y carbon atoms and substituted with substituent A” means that “substituent B having Y carbon atoms” is substituted with “substituent A (with no carbon number limitation)”. However, the carbon number Y is not the total carbon number of the substituents A and B.

Item 1.
An organic electroluminescent device having a light-emitting layer,
The light-emitting layer contains at least one selected from organic compounds and inorganic compounds as a first component and at least one thermally activated delayed phosphor as a second component,
The organic compound is an organic compound containing one selected from Ga, Ge, Sn, As, Sb and Bi in the molecule,
The inorganic compound is an inorganic compound containing one selected from elements of the 5th period and the 6th period,
Organic electroluminescence device.

（上記一般式（Ａ－１）および式（Ａ－２）中、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、
Ｘ^１、Ｘ^２およびＸ^３は、それぞれ独立して、少なくともＹと直接結合するＣまたはＮを含む基であり、
式（Ａ－１）中のＸ^１およびＸ^２、Ｘ^２およびＸ^３ならびにＸ^３およびＸ^１を連結する連結基は、Ｙを含まない環を有していてもよく、そして、
式（Ａ－２）中のＸ^２およびＸ^３ならびにＸ^３およびＸ^１を連結する連結基は、Ｙを含まない環を有していてもよく、そして、
式（Ａ－１）または式（Ａ－２）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。） Section 2.
Item 2. The organic electroluminescence device according to item 1, wherein the first component comprises at least one organic compound represented by any one of the following general formulas (A-1) and (A-2).

(In the above general formulas (A-1) and (A-2),
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ may be bonded to each other;
X ¹ , X ² and X ³ are each independently a group containing at least C or N directly bonded to Y;
The linking groups that link X ¹ and X ² , X ² and X ³ , and X ³ and X ¹ in formula (A-1) may have a ring that does not contain Y, and
The linking group that links X ² and X ³ and X ³ and X ¹ in formula (A-2) may have a ring that does not contain Y, and
At least one hydrogen in the organic compound represented by formula (A-1) or formula (A-2) may be substituted with cyano, halogen, or deuterium. )

（上記一般式（ｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、そして、
一般式（ｉ）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（ｉｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、
Ｘ^４およびＸ^５は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記Ａ環、Ｂ環およびＣ環の少なくとも１つと結合していてもよく、そして、
一般式（ｉｉ）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（ｉｉｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、
Ｘ^４、Ｘ^５およびＸ^６は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記Ａ環、Ｂ環およびＣ環の少なくとも１つと結合していてもよく、そして、
一般式（ｉｉｉ）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。） Item 3.
Item 3. The organic electroluminescence device according to item 1 or 2, wherein the first component contains at least one organic compound represented by any one of the following general formula (i), formula (ii) and formula (iii).

(In the above general formula (i),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(--R) ₂ or Bi(--R) ₂ may be bonded to each other, and
At least one hydrogen in the organic compound represented by general formula (i) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (ii),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ may be bonded to each other;
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring, and
At least one hydrogen in the organic compound represented by general formula (ii) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (iii),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ may be bonded to each other;
X ⁴ , X ⁵ and X ⁶ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and > Each R of C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and R of said >NR and/or >C(-R) ₂ may be bonded to at least one of said A ring, B ring and C ring, and
At least one hydrogen in the organic compound represented by general formula (iii) may be substituted with cyano, halogen or deuterium. )

Section 4.
In the general formula (i), formula (ii) and formula (iii),
At least one hydrogen in ring A, ring B and ring C is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl, cyclo optionally substituted with alkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Item 4. The organic electroluminescence device according to item 3.

（上記一般式（１）中、
Ｒ^１～Ｒ^１２は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^４、Ｒ^９～Ｒ^１２およびＲ^５～Ｒ^８は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、そして、
一般式（１）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（２）中、
Ｒ^１～Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^３、Ｒ^８～Ｒ^１１およびＲ^４～Ｒ^７は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、
Ｘ^４およびＸ^５は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記ａ環、ｂ環およびｃ環の少なくとも１つと結合していてもよく、そして、
一般式（２）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（３）中、
Ｒ^１～Ｒ^９は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^３、Ｒ^７～Ｒ^９およびＲ^４～Ｒ^６は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、
Ｘ^４、Ｘ^５およびＸ^６は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記ａ環、ｂ環およびｃ環の少なくとも１つと結合していてもよく、そして、
一般式（３）で表される有機化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。） Item 5.
Item 5. The organic electroluminescence device according to any one of items 1 to 4, containing at least one organic compound represented by any one of the following general formulas (1) to (3) as the first component.

(In the above general formula (1),
R ¹ to R ¹² are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y is Ga, As, Sb, Sb=O, Bi or Bi=O, and
At least one hydrogen in the organic compound represented by general formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y is Ga, As, Sb, Sb=O, Bi or Bi=O;
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) _2, >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >N—R and/or >C(—R) ₂ may be bonded to at least one of the a ring, b ring and c ring, and
At least one hydrogen in the organic compound represented by general formula (2) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (3),
R ¹ to R ⁹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ , two groups adjacent to each other are bonded together to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y is Ga, As, Sb, Sb=O, Bi or Bi=O;
X ⁴ , X ⁵ and X ⁶ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and > Each R of C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and R of said >NR and/or >C(-R) ₂ may be bonded to at least one of said a ring, b ring and c ring, and
At least one hydrogen in the organic compound represented by general formula (3) may be substituted with cyano, halogen or deuterium. )

（上記構造式中、
Ｍｅはメチル、ｔＢｕはｔ－ブチル、ｔＡｍはｔ－アミル、ｔＯｃｔはｔ－オクチルを表し、 上記構造式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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよい。） Item 6.
Item 6. The organic electroluminescence device according to item 5, wherein the organic compound represented by any one of the general formulas (1) to (3) is substituted with at least one group represented by the following structural formula.

(In the above structural formula,
Me is methyl, tBu is t-butyl, tAm is t-amyl, tOct is t-octyl, and at least one hydrogen in the above structural formula is aryl, heteroaryl, diarylamino, or diarylboryl (wherein two may be linked via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen may further be aryl, heteroaryl, alkyl or cyclo It may be substituted with alkyl. )

Item 7.
In the general formulas (1) to (3),
R ¹ to R ¹² are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms), diarylboryl ( However, each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. ,
Two adjacent groups among R ¹ to R ¹² 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 ring a, ring b or ring c. at least one hydrogen in the ring formed is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms); diarylboryl (wherein each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cyclo having 3 to 24 carbon atoms; optionally substituted with alkyl,
Y is Sb, Sb=O, Bi, or Bi=O;
X ⁴ and X ⁵ in the general formula (2) are each independently >O, >N—R or >S, and R in >N—R is an aryl having 6 to 10 carbon atoms; alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and
X ⁴ to X ⁶ in the general formula (3) are each independently >O or >S;
7. The organic electroluminescence device according to item 5 or 6.

（上記式中、Ｙは、Ｇａ、Ａｓ、ＳｂまたはＢｉであり、
Ｒは、それぞれ独立して、炭素数６～１０のアリール、炭素数１～５のアルキルまたは炭素数５～１０のシクロアルキルである。） Item 8.
Item 6. The organic electroluminescence device according to any one of items 1 to 5, comprising an organic compound represented by any one of the following formulas as the first component.

(wherein Y is Ga, As, Sb or Bi,
Each R is independently aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. )

Item 9.
Item 6. The organic electroluminescence device according to any one of items 1 to 5, containing an organic compound represented by any one of the following formulas as the first component.

（上記一般式（４）中、
Ｒ^１～Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^３、Ｒ^８～Ｒ^１１およびＲ^４～Ｒ^７は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｘ^４およびＸ^５は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒおよび＞Ｃ（－Ｒ）_２から選ばれるが、Ｘ^４およびＸ^５は、同時に＞Ｃ（－Ｒ）_２になることはなく、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記ａ環、ｂ環およびｃ環の少なくとも１つと結合していてもよく、そして、
一般式（４）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（５）中、
Ｒ^１～Ｒ^１４は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１２～Ｒ^１４、Ｒ^９～Ｒ^１１、Ｒ^３～Ｒ^５およびＲ^６～Ｒ^８は、それぞれ、隣接する２つの基が、互いに結合して、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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、Ｒ^１３は連結基または単結合でａ環と結合してもよく、
Ｘ^４～Ｘ^７は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒおよび＞Ｃ（－Ｒ）_２から選ばれるが、Ｘ^４～Ｘ^７は、同時に＞Ｃ（－Ｒ）_２になることはなく、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは、前記ａ環、ｂ環、ｃ環およびｄ環の少なくとも１つと結合していてもよく、そして、
一般式（５）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。） Item 10.
Any one of items 1 to 9, wherein as the second component, at least one thermally activated delayed phosphor that is a compound represented by any of the following general formula (4) and formula (5) is included. The organic electroluminescent device described.

(In the above general formula (4),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
X ⁴ and X ⁵ are each independently selected from >O, >NR and >C(-R) ₂ , provided that X ⁴ and X ⁵ are >C(-R) ₂ at the same time and R in the above >NR and >C(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N—R and/or >C(—R) ₂ is bonded to at least one of ring a, ring b and ring c; well, and
At least one hydrogen in the compound represented by general formula (4) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (5),
R ¹ to R ¹⁴ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In addition, two adjacent groups of R ¹² to R ¹⁴ , R ⁹ to R ¹¹ , R ³ to R ⁵ and R ⁶ to R ⁸ are bonded to each other to form a ring, b ring, c ring or An aryl ring or heteroaryl ring may be formed together with the d ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, or diarylboryl (wherein the two aryls are a single bond or a linking group). ), optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen in these is further substituted with aryl, heteroaryl, alkyl or cycloalkyl may be, R ¹³ may be connected to the a ring with a linking group or a single bond,
X ⁴ to X ⁷ are each independently selected from >O, >N—R and >C(-R) ₂ , provided that X ⁴ to X ⁷ are simultaneously >C(-R) ₂ and R in the above >NR and >C(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N—R and/or >C(—R) ₂ is at least one of the a ring, b ring, c ring and d ring; may be combined, and
At least one hydrogen in the compound represented by general formula (5) may be substituted with cyano, halogen or deuterium. )

Item 11.
A display device or lighting device comprising the organic electroluminescence device according to any one of Items 1 to 10.

（上記一般式（ｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、そして、
一般式（ｉ）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（ｉｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｓｎ－Ｒ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、
Ｘ^４およびＸ^５は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｎ－Ｒおよび＞Ｃ（－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、また、前記＞Ｎ－Ｒおよび／または＞Ｃ（－Ｒ）_２のＲは前記Ａ環、Ｂ環およびＣ環の少なくとも１つと結合していてもよく、そして、
一般式（ｉｉ）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（ｉｉｉ）中、
Ａ環、Ｂ環およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｙは、Ｇａ、Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、Ｓｂ＝Ｓ、Ｓｂ（－Ｒ）_２、オルトクロラニル基が結合したＳｂ、Ｂｉ、Ｂｉ＝Ｏ、Ｂｉ＝Ｓ、Ｂｉ（－Ｒ）_２またはオルトクロラニル基が結合したＢｉであり、前記Ｇｅ－Ｒ、Ｓｎ－Ｒ、Ｓｂ（－Ｒ）_２およびＢｉ（－Ｒ）_２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、シクロアルキル、アルコキシ、アリールオキシ、ハロゲンまたはシアノであり、またＳｂ（－Ｒ）_２またはＢｉ（－Ｒ）_２の２つのＲは互いに結合していてもよく、
Ｘ^４、Ｘ^５およびＸ^６は、それぞれ独立して、＞Ｏ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｃ（－Ｒ）_２のＲは、それぞれ独立して、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキルまたは置換されていてもよいシクロアルキルであり、また、前記＞Ｃ（－Ｒ）_２のＲは前記Ａ環、Ｂ環およびＣ環の少なくとも１つと結合していてもよく、そして、
一般式（ｉｉｉ）で表される化合物おける少なくとも１つの水素がシアノ、ハロゲンまたは重水素で置換されていてもよい。） Item 12.
A polycyclic aromatic compound represented by any one of the following general formula (i), formula (ii) and formula (iii).

(In the general formula (i) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(--R) ₂ or Bi(--R) ₂ may be bonded to each other, and
At least one hydrogen in the compound represented by general formula (i) may be substituted with cyano, halogen or deuterium. )

(In the general formula (ii) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Sn—R, Sb, Sb═O, Sb═S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi═O, Bi═S, Bi(—R) ₂ or ortho Bi to which a chloranyl group is attached, and the Rs of Sn—R, Sb(—R) ₂ and Bi(—R) ₂ are each independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy , halogen or cyano, and the two Rs of Sb(-R) ₂ or Bi(-R) ₂ may be bonded to each other,
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) _2, >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring, and
At least one hydrogen in the compound represented by general formula (ii) may be replaced with cyano, halogen or deuterium. )

(In the above general formula (iii),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y is Ga, Ge--R, Sn--R, As, Sb, Sb=O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is bound, Bi, Bi=O, Bi=S; Bi(--R) ₂ or Bi to which an orthochloranyl group is bound, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ may be bonded to each other;
X ⁴ , X ⁵ and X ⁶ are each independently selected from >O, >C(-R) _{2 ,} >S, >Se and a single bond, wherein R of said >C(-R) ₂ is Each independently represents optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above >C(-R) R of ₂ may be bonded to at least one of the A ring, B ring and C ring, and
At least one hydrogen in the compound represented by general formula (iii) may be replaced with cyano, halogen or deuterium. )

Item 13.
In the general formula (i), formula (ii) and formula (iii),
At least one hydrogen in ring A, ring B and ring C is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl, cyclo alkyl, alkoxy or aryloxy in which at least one hydrogen may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Item 13. The polycyclic aromatic compound according to item 12.

（上記一般式（１）中、
Ｒ^１～Ｒ^１２は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^４、Ｒ^９～Ｒ^１２およびＲ^５～Ｒ^８は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、そして、
一般式（１）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（２）中、
Ｒ^１～Ｒ^１１は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^３、Ｒ^８～Ｒ^１１およびＲ^４～Ｒ^７は、それぞれ、隣接する２つの基が、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、
Ｘ^４およびＸ^５は、それぞれ独立して、＞Ｏ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｃ（－Ｒ）_２のＲは、それぞれ独立して、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキルまたは炭素数３～１４のシクロアルキルであり、そして、
一般式（２）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。）

（上記一般式（３）中、
Ｒ^１～Ｒ^９は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
また、Ｒ^１～Ｒ^３、Ｒ^７～Ｒ^９およびＲ^４～Ｒ^６は、それぞれ、隣接する２つの基、互いに結合して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、ジアリールボリル（ただし２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも１つの水素はさらに、アリール、ヘテロアリール、アルキルまたはシクロアルキルで置換されていてもよく、
Ｙは、Ｇａ、Ａｓ、Ｓｂ、Ｓｂ＝Ｏ、ＢｉまたはＢｉ＝Ｏであり、
Ｘ^４～Ｘ^６は、それぞれ独立して、＞Ｏ、＞Ｃ（－Ｒ）_２、＞Ｓ、＞Ｓｅおよび単結合から選ばれ、前記＞Ｃ（－Ｒ）_２のＲは、それぞれ独立して、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキルまたは炭素数３～１４のシクロアルキルであり、そして、
一般式（３）で表される化合物における少なくとも１つの水素は、シアノ、ハロゲンまたは重水素で置換されていてもよい。） Item 14.
A polycyclic aromatic compound represented by any one of the following general formula (1), formula (2) and formula (3).

(In the above general formula (1),
R ¹ to R ¹² are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y is Ga, As, Sb, Sb=O, Bi or Bi=O, and
At least one hydrogen in the compound represented by general formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y is Ga, As, Sb, Sb=O, Bi or Bi=O;
X ⁴ and X ⁵ are each independently selected from >O, >C(-R) ₂ , >S, >Se and a single bond, and R of said >C(-R) ₂ is each independently is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound represented by general formula (2) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (3),
R ¹ to R ⁹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In addition, R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ are respectively two groups adjacent to each other and are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, the b ring or the c ring. and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl , cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl,
Y is Ga, As, Sb, Sb=O, Bi or Bi=O;
X ⁴ to X ⁶ are each independently selected from >O, >C(-R) ₂ , >S, >Se and a single bond, and each R of >C(-R) ₂ is independently is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound represented by general formula (3) may be substituted with cyano, halogen or deuterium. )

Item 15.
In the general formulas (1) to (3),
R ¹ to R ¹² are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms), diarylboryl ( However, each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. ,
Two adjacent groups among R ¹ to R ¹² 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 ring a, ring b or ring c. at least one hydrogen in the ring formed is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms); diarylboryl (wherein each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cyclo having 3 to 24 carbon atoms; optionally substituted with alkyl,
Y is Sb, Sb=O, Bi, or Bi=O;
X ⁴ and X ⁵ in the general formula (2) are each independently >O, >N—R or >S, and R in >N—R is an aryl having 6 to 10 carbon atoms; alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and
X ⁴ to X ⁶ in the general formula (3) are each independently >O or >S;
15. A polycyclic aromatic compound according to Item 14.

Item 16.
Item 16. The polycyclic aromatic compound according to any one of Items 12 to 15, wherein the halogen is fluorine.

According to a preferred embodiment of the present invention, as the first component, at least one selected from the group consisting of organic compounds containing a specific element in the molecule and the group consisting of inorganic compounds containing the specific element in the molecule. and, as a second component, an organic EL device having a light-emitting layer containing at least one thermally activated delayed phosphor, thereby providing an organic EL device having thermally activated delayed fluorescence (TADF) activity. can be done.

1 is a schematic cross-sectional view showing an organic EL element according to this embodiment; FIG.

1. Organic electroluminescence device The organic EL device of the present invention has a light-emitting layer, and the light-emitting layer contains at least one compound selected from organic compounds and inorganic compounds as a first component and a heat-activated compound as a second component. and at least one delayed phosphor, the organic compound is an organic compound containing one selected from Ga, Ge, Sn, As, Sb and Bi in the molecule, and the inorganic compound is the fifth period and 6th period elements.
In the light-emitting layer of the organic EL device of the present invention, the first component functions as a host component and the second component functions as a dopant component.

Organic EL utilizes a phenomenon in which organic molecules are excited by an electric current and emit light when they return to a low-energy ground state. Thermally activated delayed fluorescence (TADF) is a phenomenon in which reverse energy transfer from an excited triplet state to an excited singlet state occurs using thermal energy at room temperature, leading to fluorescence emission. It is generally known that transitions between molecular orbitals with different spin multiplicity require strong spin-orbit interaction. In other words, in order to efficiently cause TADF, it is necessary to increase the spin-orbit interaction.

There are several ways to enhance the spin-orbit interaction, one of which is to use the heavy atom effect. In the presence of heavy atoms, electrons in the vicinity of heavy atoms are attracted by the strong nuclear charge, which increases their orbital angular momentum and can easily cause spin reversal. As a material utilizing this, an Ir-based phosphorescent material containing Ir (iridium), which is a heavy atom, is known. Ir-based phosphorescent materials have the property that the presence of Ir facilitates intersystem crossing from the singlet state to the triplet state. On the other hand, heavy atoms also have the effect of hastening the reverse intersystem crossing from the triplet state to the singlet state, which is the reverse process of this intersystem crossing.

Heavy atom effects can be classified into two types: internal heavy atom effects and external heavy atom effects. The internal heavy atom effect occurs when the TADF molecule that causes reverse intersystem crossing has a heavy atom, and the effect of facilitating spin reversal is very large, but the introduction of heavy atoms changes the characteristics such as the emission wavelength. Therefore, a new molecular design is required. On the other hand, the external heavy atom effect occurs when the host or additive other than the TADF molecule contains heavy atoms. , can be applied to enhance the performance of many TADF dopants.
In the light-emitting layer of the organic EL device of the present invention, at least one selected from the group consisting of organic compounds containing heavy atoms and the group consisting of inorganic compounds containing heavy atoms as a host component, and as a dopant component, By including at least one kind of thermally activated delayed phosphor, the external heavy atom effect is exhibited and the spin-orbit interaction is enhanced.

1-1. First Component The light-emitting layer of the organic EL device of the present invention contains, as a first component, at least one compound selected from organic compounds and inorganic compounds, and the organic compound includes Ga, Ge, Sn, As, Sb and Bi. and the inorganic compound is an inorganic compound containing one selected from the elements of the 5th period and the 6th period.
Since the organic compound and the inorganic compound contained as the first component in the light-emitting layer contain a specific element, it is thought that the external heavy atom effect can be exhibited and the spin-orbit interaction can be enhanced.

1-1-1. Inorganic compound as first component Elements of the fifth period contained in the inorganic compound are Rb, Sr, Y, Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Sb, and Te. , I, or Xe.
The elements of the sixth period contained in the inorganic compound are Cs, Ba, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, Tl, Pb, Bi, Po, At, or Rn.
Among these, the inorganic compounds include Rb, Sr, Y, Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Sb, Te, Cs, Ba, La, Ce, Pr , Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, Tl, Pb, Bi, Po , and At.

The form of the inorganic compound is not particularly limited, and examples include hydrogen compounds, oxides, oxoacids, hydroxides, halides, sulfates, nitrates, carbonates, acetates, metal complexes (coordination compounds). etc.

1-1-2. Organic compound as the first component The first component preferably contains at least one of the above organic compounds, and an organic compound ( Hereinafter, in this item, it is more preferable to include the term "compound" in some cases.
In addition, in the compound represented by either the following general formula (A-1) or formula (A-2), the heavy atom represented by Y in each formula is incorporated in the ring and the bond is cut. Since it has a difficult structure, it is considered to be highly stable.

In formulas (A-1) and (A-2), the code Y (hereinafter Y in the formula is the "code Y") is Ga, Ge-R, Sn-R, As, Sb, Sb= O, Sb=S, Sb(-R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi=O, Bi=S, Bi(-R) ₂ or Bi to which an orthochloranyl group is attached. Here, Y may be Ga, As, Sb, Sb=O, Bi or Bi=O.
In formulas (A-1) and (A-2), compounds in which Y is "Sb to which an orthochloranyl group is bonded" have the following structure. The same applies to compounds in which Y is "Bi to which an orthochloranyl group is bound".

R of Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ above is each independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano; , and two R's of Sb(-R) ₂ or Bi(-R) ₂ may be bonded to each other.
In addition, "aryl", "heteroaryl", "alkyl", "cycloalkyl", "alkoxy" and "aryloxy" as the above R are the same groups as the groups selected as the "first substituent" described later. and "halogen" includes fluorine, chlorine, bromine and iodine.

In addition, X ¹ , X ² and X ³ are each independently a group containing at least C or N directly bonded to Y, and X ¹ and X 2 , X ^{2 and} X in formula (A-1) ³ and the linking group linking X ³ and X ¹ may have a ring that does not contain Y, and linking X ² and X 3 and X ^{3 and} X ¹ in formula (A-2) The linking group may have a ring that does not contain Y.

In formula (A-1), for example, when X ¹ is a group containing C (carbon atom), the bond of C (carbon atom) includes the following formulas (A-1-c1) to formula (A- The embodiment represented by 1-c3) is exemplified.

As shown in formulas (A-1-c1) to (A-1-c3), when X ¹ is a group containing C (carbon atom), the first C (carbon atom) of the group The bond is directly bonded to Y, the second bond is linked to ^X2 via linking group a, and the third bond is linked to ^X3 via linking group c.
The fourth bond may be bonded to any substituent R without a linking group as in formula (A-1-c1), formula (A-1-c2) or formula (A- As in 1-c3), a linking group a or a linking group c containing a double bond may be formed. In addition, when the fourth bond is bound to any substituent R as in formula (A-1-c1), the substituent R is bound to any of the linking groups a to c to form a ring. You may

Further, in formula (A-1), for example, when X ¹ is a group containing N (nitrogen atom), as shown in the following formula (A-1-n1), N (carbon atom) of the group The first bond was directly linked to Y, the second bond was linked to ^X2 via linking group a, and the third bond was linked to ^X3 via linking group c. Configuration.

These explanations also apply to X ² and X ³ in formula (A-1).

On the other hand, in formula (A-2), when X ¹ is a group containing C (carbon atom), the bond of the C (carbon atom) is represented by the following formula (A-2-c1) or formula (A- 2-c2) can be mentioned.

As shown in formula (A-2-c1) or formula (A-2-c2), when X ¹ is a group containing C (carbon atom), the first C (carbon atom) of the group The bond is directly bonded to Y, and the second bond is bonded to ^X3 via the linking group e.
The third and fourth bonds may be bonded to optional substituents R ^a and R ^b without a linking group as in formula (A-2-c1), and formula (A-1 As in -c2), one may form a linking group a containing a double bond, and the other may bond to an optional substituent R ^a without a linking group. In addition, when at least one of the third and fourth bonds is bonded to any substituents R ^a and R ^b , the substituents R ^a and R ^b are bonded to the linking group d or e to form a ring may be formed.

Further, in formula (A-2), when X ¹ is a group containing N (nitrogen atom), the bond of said N (carbon atom) is represented by the following formula (A-2-n1) or formula (A- 2-n2).

As shown in formula (A-2-c1) or formula (A-2-c2), when X ¹ is a group containing N (nitrogen atom), the first N (carbon atom) of the group A bond is directly attached to Y and a second bond is attached to ^X3 via linking group e.
The third bond may be bonded to any substituent R without a linking group as in formula (A-2-n1), and as in formula (A-2-n2), two A linking group e containing a double bond may be formed. In addition, when the third bond is bonded to any substituent R, the substituent R may be bonded to the linking group d or e to form a ring.

In formula (A-2), X ² is the same as X ¹ .
In formula (A-2), when X ³ is a group containing C (carbon atom), X ¹ in the above formula (A-1) is a group containing C (carbon atom), and It is the same, and when X ³ is a group containing N (nitrogen atom), it is the same as when X ¹ in the above formula (A-1) is a group containing N (nitrogen atom).

In formula (A-1), “linking group a” that connects X ¹ and X ² , “linking group b” that connects X ² and X ³ , and “linking group c” that connects X ³ and X ¹ ” may have a ring that does not contain Y. In formula (A-2), the “connecting group e” connecting X ² and X ³ and the “connecting group d” connecting X ³ and X ¹ also have rings that do not contain Y. may be
Here, "a ring not containing Y" means a ring structure formed by bonding two substituents of these linking groups without intervening Y, and two substituents of the same linking group. The substituents may be formed by bonding to each other without Y interposed therebetween, or one substituents on different linking groups may be bonded to each other without Y intervening.

At least one hydrogen in the compound represented by formula (A-1) or formula (A-2) may be substituted with cyano, halogen or deuterium. For example, in formulas (A-1) and (A-2), linking group a to linking group c, linking group d to linking group e, and substituents to these linking groups, X ¹ and X ² and the hydrogen in R when Y is Ge--R, Sn--R, Sb(--R) ₂ or Bi(--R) ₂ and are substituted with cyano, halogen or deuterium can be Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

Compounds in which such a ring is formed include compounds represented by the following formulas (i), (ii) and (iii), and furthermore, the following formulas (1), (2) and ( A compound represented by 3) is exemplified.
Ring A (ring a), Ring B (ring b) and Ring C (ring c) of formula (i) and formula (1), and ring B (ring b) of formula (ii) and formula (2) and Ring C (ring c) corresponds to "a ring formed by bonding two substituents on the same linking group without intervening Y".
Further, ring A (ring a) of formula (ii) and formula (2), and ring A (ring a), ring B (ring b) and ring C (ring c) of formula (iii) and formula (3) ) corresponds to the above-mentioned "ring formed by binding one substituents of different linking groups to each other without intervening Y".
Such compounds are considered to have higher stability because the heavy atom represented by Y in each formula is incorporated in the ring and has a structure in which the bond is more difficult to break.
Therefore, in the present invention, the first component preferably contains at least one compound represented by any one of the following formulas (i), (ii) and (iii). More preferably, it contains at least one compound represented by either formula (2) or formula (3).

In the present invention, the first component preferably contains a compound represented by the following formula (i), and more preferably contains a compound represented by the following formula (1).

The compounds represented by formula (i) and formula (1) are one embodiment of the compound represented by formula (A-1).
That is, as shown below, the compounds represented by formulas (i) and (1) are such that X ¹ , X ² and X ³ in formula (A-1) are "at least N directly bonded to Y (nitrogen atom)", and the two substituents of the linking group c that links X ¹ and X ³ are bonded to each other to form a "ring A (ring a)" that does not contain Y, and X ² and the two substituents of the linking group b that links X ³ are bonded to each other to form a "ring B (ring b)" that does not contain Y, and the two substituents of the linking group c that links X ¹ and X ² It corresponds to a compound in which groups are bonded together to form a "ring C (ring c)" that does not contain Y.

A ring, B ring and C ring in general formula (i) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted. This substituent may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diarylboryl (wherein the two aryls are bonded via a single bond or a linking group). optionally), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy (the above are also referred to as "first substituents") are preferable. . When these "first substituents" have substituents, examples of substituents include aryl, heteroaryl, alkyl, and cycloalkyl (these are also referred to as "second substituents").
In addition, the aryl ring or heteroaryl ring shares a bond with the central condensed three-ring structure of general formula (i) comprising Y and three Ns (hereinafter, this structure is also referred to as "D1 structure") It is preferred to have a 5-membered or 6-membered ring.

Here, the "condensed three-ring structure (D1 structure)" means a structure in which three rings composed of Y and three N shown in the center of general formula (i) are condensed. Further, "a 6-membered ring sharing a bond with the condensed 3-ring structure" means an a-ring (benzene ring (6-membered ring)) fused to the D1 structure, for example, as shown in the above general formula (1). . Further, "the aryl ring or heteroaryl ring (which is the A ring) has this 6-membered ring" means that the A ring is formed only by this 6-membered ring, or that the 6-membered ring is included. It means that the A ring is formed by further condensing another ring and the like to this 6-membered ring. In other words, the “aryl ring or heteroaryl ring having a 6-membered ring (which is the A ring)” as used herein means that the 6-membered ring constituting all or part of the A ring is fused to the D1 structure. means that there is The same description applies to "B ring (b ring)", "C ring (c ring)", and "5-membered ring".

The A ring (or B ring, C ring) in formula (i) is the a ring and its substituents R ¹ to R ⁴ (or b ring and its substituents R ⁹ to R ¹² , c ring and corresponding to its substituents R ⁵ -R ⁸ ). That is, formula (1) corresponds to formula (i) in which "A to C rings having a 6-membered ring" are selected as the A to C rings. In this sense, each ring in Formula (1) is represented by lower case letters a to c.

The "aryl ring" which is the A ring, B ring and C ring of formula (i) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, and 6 carbon atoms. An aryl ring having up to 12 carbon atoms is more preferable, and an aryl ring having 6 to 10 carbon atoms is more preferable, and specific examples include the "aryl ring" described later.
The “aryl ring” is defined as “R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ defined in formula (1), and two adjacent groups are bonded to each other. aryl ring formed together with the a-ring, b-ring or c-ring”, and since the a-ring (or b-ring or c-ring) is already composed of a benzene ring having 6 carbon atoms, The total number of carbon atoms of the condensed rings in which the rings are condensed is 9, which is the lower limit of the number of carbon atoms.

Further, the "heteroaryl ring" which is the A ring, B ring and C ring of formula (i) includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms. Preferred are heteroaryl rings having 2 to 20 carbon atoms, more preferred are heteroaryl rings having 2 to 15 carbon atoms, and particularly preferred are heteroaryl rings having 2 to 10 carbon atoms. Further, the "heteroaryl ring" includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon atoms as ring-constituting atoms. heteroaryl ring”.
This "heteroaryl ring" is defined by the general formula (1), wherein two adjacent groups of "R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ are bonded to each other. heteroaryl ring formed together with the a-ring, b-ring or c-ring”, and since the a-ring (or b-ring or c-ring) already consists of a benzene ring having 6 carbon atoms, this The total carbon number of the condensed ring in which a 5-membered ring is condensed to is 6, which is the lower limit of the carbon number.

In formula (1), the substituents R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ of the a ring, the b ring and the c ring each have two adjacent groups bonded to each other to form a An aryl ring or heteroaryl ring may be formed together with the ring, b ring or c ring, and at least one hydrogen in the formed ring may be substituted with the above-mentioned "first substituent", The "first substituent" may be further substituted with the "second substituent" described above.
Therefore, the compound represented by the general formula (1) constitutes a compound as shown in the following formulas (1a) and (1b) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring changes the ring structure. A' ring, B' ring and C' ring in each formula respectively correspond to A ring, B ring and C ring in general formula (i). In formulas (1a) and (1b) below, the definition of each symbol is the same as the definition described above.

The A' ring, B' ring and C' ring in the above formulas (1a) and (1b) are explained in terms of the general formula (1), and the adjacent groups among the substituents R ¹ to R ¹² are An aryl ring or a heteroaryl ring formed together with the a-ring, b-ring and c-ring (it can also be said to be a condensed ring formed by condensing the a-ring, b-ring or c-ring with another ring structure). Although not shown in the formula, there are compounds in which all of the a-ring, b-ring and c-ring are changed to A'-ring, B'-ring and C'-ring. Further, as can be seen from the above formulas (1a) and (1b), for example, R ⁹ of the b ring and R ⁸ of the c ring, R ¹² of the b ring and R ¹ of the a ring, R ⁵ of the c ring and a Ring R ⁴ and the like do not correspond to "adjacent groups", and they are not bonded. That is, "adjacent groups" mean groups that are adjacent on the same ring.

The compounds represented by general formulas (1a) and (1b) have, for example, a benzene ring, an indane ring, an indole ring, a pyrrole ring, and a benzofuran ring with respect to the benzene ring which is the a ring (or b ring or c ring). Or a compound having an A' ring (or B' ring or C' ring) formed by condensing a benzothiophene ring, and the formed condensed ring A' (or condensed ring B' or condensed ring C') ) is a naphthalene ring, a fluorene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

In formula (1), two adjacent groups among R ¹ to R ¹² are bonded together to form an aryl ring having 9 to 16 carbon atoms or an aryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c. may form a heteroaryl ring of, at least one hydrogen in the formed ring may be substituted with the first substituent described above, and the first substituent may be the second substituent described above may be substituted with a group.

Y in formula (i) has the same definition as Y in general formula (A-1) above, but may be Ga, As, Sb, Sb=O, Bi or Bi=O, Sb, It may be Sb=O, Bi or Bi=O.

Y in formula (1) is Ga, As, Sb, Sb=O, Bi or Bi=O, but may be Sb, Sb=O, Bi or Bi=O.

At least one hydrogen in the compounds represented by formula (i) and formula (1) may be replaced with cyano, halogen or deuterium. For example, in formulas (i) and (1), A ring (a ring), B ring (b ring), C ring (c ring), and substituents on these rings, and Y is Ge—R , Sn--R, Sb(--R) ₂ or Bi(--R) ₂ can be replaced with cyano, halogen or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

In the present invention, the first component preferably contains a compound represented by the following formula (ii), and more preferably contains a compound represented by the following formula (2).

The compounds represented by formula (ii) and formula (2) are one embodiment of the compound represented by formula (A-2).
In other words, as shown below, the compounds represented by formulas (ii) and (2) are such that X ¹ , X ² and X ³ in formula (A-2) are "at least a C (a group containing (a carbon atom)", wherein the substituent of the linking group d that links ^X2 and ^X3 and the substituent of the linking group e that links ^X1 and ^X3 are bonded to each other to include Y The two substituents of the linking group e are bonded to each other to form a "ring B (ring b)" that does not contain Y, and the two substituents of the linking group d It corresponds to a compound in which substituents are bonded to each other to form a "ring C (ring c)" that does not contain Y.
In formulas (ii) and (2), X ⁴ corresponds to a group included in the linking group e that links X ¹ and X ³ in formula (A-2), and X ⁵ corresponds to the group represented by formula (A It corresponds to the group included in the linking group d linking X ² and X ³ in -2).

A ring, B ring and C ring in formula (ii) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted. This substituent is preferably selected from the first substituents described above, and examples of the substituent when the "first substituent" has a substituent include the second substituents described above.
In addition, the aryl ring or heteroaryl ring is bonded to the central condensed two-ring structure of general formula (ii) comprising Y, X ⁴ and X ⁵ (hereinafter this structure is also referred to as "D2 structure") It is preferred to have a 5- or 6-membered ring sharing

Here, the “condensed two-ring structure (D2 structure)” means a structure in which two rings composed of Y, ^X4 and ^X5 shown in the center of formula (ii) are condensed. Further, the "6-membered ring sharing a bond with the condensed two-ring structure" means, for example, the a-ring (benzene ring (6-membered ring)) fused to the D2 structure as shown in the above formula (2). . Further, "the aryl ring or heteroaryl ring (which is the A ring) has this 6-membered ring" means that the A ring is formed only by this 6-membered ring, or such that the 6-membered ring is included It means that the A ring is formed by further condensing another ring and the like to this 6-membered ring. In other words, the “aryl ring or heteroaryl ring having a 6-membered ring (which is the A ring)” as used herein means that the 6-membered ring constituting all or part of the A ring is fused to the D2 structure. means that there are The same description applies to "B ring (b ring)", "C ring (c ring)", and "5-membered ring".

Ring A (or ring B, ring C) in formula (ii) is ring a in formula (2) and its substituents R ¹ to R ³ (or ring b and its substituents R ⁸ to R ¹¹ , ring c and corresponding to its substituents R ⁴ -R ⁷ ). That is, formula (2) corresponds to formula (ii) in which "A to C rings having a 6-membered ring" are selected as A to C rings. In that sense, each ring in formula (2) is represented by lower case letters a to c.

The "aryl ring" which is the A ring, B ring and C ring of formula (ii) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, and 6 carbon atoms. An aryl ring having up to 12 carbon atoms is more preferable, and an aryl ring having 6 to 10 carbon atoms is more preferable, and specific examples include the "aryl ring" described later.
The “aryl ring” is defined as “R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ defined in formula (2), and two adjacent groups are bonded to each other. aryl ring formed together with a ring, b ring, or c ring", and since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, The total number of carbon atoms of the condensed rings in which the rings are condensed is 9, which is the lower limit of the number of carbon atoms.

Further, the "heteroaryl ring" which is the A ring, B ring and C ring of formula (ii) includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms. Preferred are heteroaryl rings having 2 to 20 carbon atoms, more preferred are heteroaryl rings having 2 to 15 carbon atoms, and particularly preferred are heteroaryl rings having 2 to 10 carbon atoms. Further, the "heteroaryl ring" includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon atoms as ring-constituting atoms. heteroaryl ring”.
The "heteroaryl ring" is defined by the general formula (2), wherein each of "R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ is a heteroaryl ring formed together with the a ring, b ring or c ring", and since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, this The total carbon number of the condensed ring in which a 5-membered ring is condensed to is 6, which is the lower limit of the carbon number.

In formula (2), the substituents R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ of the a ring, the b ring and the c ring each have two adjacent groups bonded to each other to form a An aryl ring or heteroaryl ring may be formed together with the ring, b ring or c ring, and at least one hydrogen in the formed ring may be substituted with the above-mentioned "first substituent", The "first substituent" may be further substituted with the "second substituent" described above.
Therefore, the compound represented by the formula (2) constitutes a compound as shown in the following formulas (2a) and (2b) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring The ring structure changes. A' ring, B' ring and C' ring in each formula respectively correspond to A ring, B ring and C ring in formula (ii). In formulas (2a) and (2b) below, the definition of each symbol is the same as the definition described above.

The A' ring, B' ring and C' ring in the above formulas (2a) and (2b) are, if explained in general formula (2), adjacent groups among the substituents R ¹ to R ¹¹ An aryl ring or a heteroaryl ring formed together with the a-ring, b-ring and c-ring (it can also be said to be a condensed ring formed by condensing the a-ring, b-ring or c-ring with another ring structure). Although not shown in the formula, there are compounds in which all of the a-ring, b-ring and c-ring are changed to A'-ring, B'-ring and C'-ring. Further, as can be seen from the above formulas (2a) and (2b), for example, R ⁸ of the b ring and R ⁷ of the c ring, R ¹¹ of the b ring and R ¹ of the a ring, R ⁴ and a of the c ring Ring R ³ and the like do not correspond to "adjacent groups", and they are not bonded. That is, "adjacent groups" mean groups that are adjacent on the same ring.

The compounds represented by formulas (2a) and (2b) have, for example, a benzene ring, indane ring, indole ring, pyrrole ring, benzofuran ring or A compound having an A' ring (or B' ring or C' ring) formed by condensing a benzothiophene ring, and the formed condensed ring A' (or condensed ring B' or condensed ring C') is a naphthalene ring, fluorene ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring, respectively.

In formula (2), two adjacent groups among R ¹ to R ¹¹ are bonded together to form an aryl ring having 9 to 16 carbon atoms or an aryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c. may form a heteroaryl ring, at least one hydrogen in the formed ring may be substituted with the first substituent described above, and the first substituent may be the second substituent described above may be substituted with a group.

Y in formula (ii) has the same definition as Y in formula (A-2) above, but may be Ga, As, Sb, Sb=O, Bi or Bi=O, Sb, It may be Sb=O, Bi or Bi=O.
In another aspect, Y in formula (ii) is Sn—R, Sb, Sb=O, Sb=S, Sb(—R) ₂ , Sb, Bi, Bi=O to which an orthochloranyl group is bonded. , Bi=S, Bi(-R) ₂ or Bi to which an orthochloranyl group is attached.

Y in Formula (2) is Ga, As, Sb, Sb=O, Bi or Bi=O, but may be Sb, Sb=O, Bi or Bi=O.

X ⁴ and X ⁵ in formula (ii) and formula (2) are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond; , >O, >NR and >S, and may be selected from >O, >C(-R) ₂ , >S, >Se and a single bond.

and each R in >NR and >C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl.
In addition, "aryl", "heteroaryl", "alkyl" and "cycloalkyl" as R are the same as the above-mentioned "first substituents".
Further, when "aryl", "heteroaryl", "alkyl" and "cycloalkyl" as R have a substituent, examples of the substituent include the same groups as the above-mentioned "second substituent". .
R in the above >NR may be aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. In addition, R in the above >C(-R) ₂ is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, good too.

In formula (ii), R in the above >NR and/or >C(-R) ₂ may be bonded to at least one of the above A ring, B ring and C ring. In formula (2), R in >NR and/or >C(-R) ₂ may be bonded to at least one of ring a, ring b and ring c.
Here, the provision that "R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring" in the formula (ii). is the definition that "R of the >NR and/or >C(-R) ₂ may be bonded to at least one of the a ring, b ring and c ring" in formula (2). corresponds to
This definition can be expressed by a compound having a ring structure in which X ⁴ and X ⁵ are incorporated in condensed ring B' and condensed ring C', represented by the following formula (2c). That ^is , for ^example , the B' ring (or C' ring).
The above definition can also be expressed by compounds having a ring structure in which X ⁴ and/or X ⁵ are incorporated in a condensed ring A', represented by the following formula (2d) or (2e). That is, for example, it is a compound having an A' ring formed by condensing another ring such that X ⁴ (and/or X ⁵ ) is incorporated into the benzene ring, which is the a ring in formula (2). .
R ¹ to R ¹¹ , Y, X ⁴ and X ⁵ in formulas (2c), (2d) and (2e) are the same as defined in formula (2).

At least one hydrogen in the compounds represented by formula (ii) and formula (2) may be replaced with cyano, halogen or deuterium. For example, in formulas (ii) and (2), A ring (a ring), B ring (b ring), C ring (c ring), and substituents on these rings, Y is Ge—R, Sn —R, R when Sb(—R) ₂ or Bi(—R) ₂ , and hydrogen at R when X ⁴ and X ⁵ are >N—R or >C(—R) ₂ It can be substituted with cyano, halogen or deuterium.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

In the present invention, the first component preferably contains a compound represented by the following formula (iii), and more preferably contains a compound represented by the following formula (3).

The compounds represented by formula (iii) and formula (3) are one embodiment of the compound represented by formula (A-1).
In other words, as shown below, the compounds represented by formulas (iii) and (3) are such that X ¹ , X ² and X ³ in formula (A-1) are "at least a C (a group containing (a carbon atom)", wherein the substituent of the linking group b that links ^X2 and ^X3 and the substituent of the linking group c that links ^X1 and ^X3 are bonded to each other to include Y The substituent of the linking group c and the substituent of the linking group a that links X ¹ and X ² are bonded to each other to form a "ring B (ring a)" that does not contain Y. It corresponds to a compound in which the substituent of the linking group a and the substituent of the linking group b combine with each other to form a "ring C (ring c)" that does not contain Y.
In formulas (iii) and (3), X ⁴ corresponds to a group included in the connecting group c that connects X ¹ and X ³ in formula (A-1), and X ⁵ corresponds to the group of formula (A -1) corresponds to a group included in the linking group b that links X ² and X ³ , and X ⁶ corresponds to a group included in the linking group a that links X ¹ and X ² in formula (A-1) Applicable.

Ring A, ring B and ring C in formula (iii) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted. This substituent is preferably selected from the first substituents described above, and examples of the substituent when the "first substituent" has a substituent include the second substituents described above.
In addition, the aryl ring or heteroaryl ring is a condensed three-ring structure in the center of general formula (iii) comprising Y, X ⁴ , X ⁵ and X ⁶ (hereinafter, this structure is also referred to as “D3 structure” ) to share a bond with the 5- or 6-membered ring.

Here, the “fused three-ring structure (D3 structure)” means a structure in which three rings composed of Y, X ⁴ , X ⁵ and X ⁶ shown in the center of formula (iii) are condensed. means. Further, "a 6-membered ring sharing a bond with the condensed 3-ring structure" means, for example, an a-ring (benzene ring (6-membered ring)) fused to the D3 structure as shown in the above formula (3). . Further, "the aryl ring or heteroaryl ring (which is the A ring) has this 6-membered ring" means that the A ring is formed only by this 6-membered ring, or such that the 6-membered ring is included It means that the A ring is formed by further condensing another ring and the like to this 6-membered ring. In other words, the “aryl ring or heteroaryl ring having a 6-membered ring (A ring)” as used herein means that the 6-membered ring constituting all or part of the A ring is fused to the D3 structure. means that there is The same description applies to "B ring (b ring)", "C ring (c ring)", and "5-membered ring".

The A ring (or B ring, C ring) in formula (iii) is the a ring and its substituents R ¹ to R ³ (or b ring and its substituents R ⁷ to R ⁹ , c ring and corresponding to its substituents R ⁴ -R ⁶ ). That is, formula (3) corresponds to formula (iii) in which "A to C rings having a 6-membered ring" are selected as the A to C rings. In this sense, each ring in formula (3) is represented by lower case letters a to c.

The "aryl ring" which is the A ring, B ring and C ring of formula (iii) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, and 6 carbon atoms. An aryl ring having up to 12 carbon atoms is more preferable, and an aryl ring having 6 to 10 carbon atoms is more preferable, and specific examples include the "aryl ring" described later.
The “aryl ring” is defined as “R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ defined in formula (3), and two adjacent groups are bonded to each other. aryl ring formed together with a ring, b ring, or c ring", and since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, The total number of carbon atoms of the condensed rings in which the rings are condensed is 9, which is the lower limit of the number of carbon atoms.

Further, the "heteroaryl ring" which is the A ring, B ring and C ring of formula (iii) includes, for example, a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms. Preferred are heteroaryl rings having 2 to 20 carbon atoms, more preferred are heteroaryl rings having 2 to 15 carbon atoms, and particularly preferred are heteroaryl rings having 2 to 10 carbon atoms. Further, the "heteroaryl ring" includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon atoms as ring-constituting atoms. heteroaryl ring”.
The "heteroaryl ring" is defined by the general formula (3), wherein each of "R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ is a heteroaryl ring formed together with the a ring, b ring or c ring", and since the a ring (or b ring, c ring) is already composed of a benzene ring having 6 carbon atoms, this The total carbon number of the condensed ring in which a 5-membered ring is condensed to is 6, which is the lower limit of the carbon number.

In formula (3), the substituents R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ of rings a, b and c each have two adjacent groups bonded together to form a An aryl ring or heteroaryl ring may be formed together with the ring, b ring or c ring, and at least one hydrogen in the formed ring may be substituted with the above-mentioned "first substituent", The "first substituent" may be further substituted with the "second substituent" described above.
Therefore, the compound represented by the formula (3) constitutes a compound as shown in the following formulas (3a) and (3b) depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring The ring structure changes. A' ring, B' ring and C' ring in each formula respectively correspond to A ring, B ring and C ring in formula (iii). Definitions of symbols in the following formulas (3a) and (3b) are the same as those defined above.

The A' ring, B' ring and C' ring in the above formulas (3a) and (3b) are, if explained in general formula (3), adjacent groups among the substituents R ¹ to R ⁹ An aryl ring or a heteroaryl ring formed together with the a-ring, b-ring and c-ring (it can also be said to be a condensed ring formed by condensing the a-ring, b-ring or c-ring with another ring structure). Although not shown in the formula, there are compounds in which all of the a-ring, b-ring and c-ring are changed to A'-ring, B'-ring and C'-ring. Further, as can be seen from the above formulas (3a) and (3b), for example, R ⁷ of the b ring and R ⁶ of the c ring, R ⁹ of the b ring and R ¹ of the a ring, R ⁴ of the c ring and a Ring R ³ and the like do not correspond to "adjacent groups", and they are not bonded. That is, "adjacent groups" mean groups that are adjacent on the same ring.

The compounds represented by formulas (3a) and (3b) have, for example, a benzene ring, indane ring, indole ring, pyrrole ring, benzofuran ring or A compound having an A' ring (or B' ring or C' ring) formed by condensing a benzothiophene ring, and the formed condensed ring A' (or condensed ring B' or condensed ring C') is a naphthalene ring, fluorene ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring, respectively.

In formula (3), two adjacent groups among R ¹ to R ⁹ are bonded together to form an aryl ring having 9 to 16 carbon atoms or an aryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c. may form a heteroaryl ring, at least one hydrogen in the formed ring may be substituted with the first substituent described above, and the first substituent may be the second substituent described above may be substituted with a group.

Y in formula (iii) has the same definition as Y in formula (A-1) above, but may be Ga, As, Sb, Sb=O, Bi or Bi=O, Sb, It may be Sb=O, Bi or Bi=O.

Y in Formula (3) is Ga, As, Sb, Sb=O, Bi or Bi=O, but may be Sb, Sb=O, Bi or Bi=O.

X ⁴ , X ⁵ and X ⁶ in formula (iii) and formula (3) are each independently from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond is selected, may be >O or >S, and may be selected from >O, >C(-R) ₂ , >S, >Se and a single bond.

and each R in >NR and >C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl.
"Aryl", "heteroaryl", "alkyl" and "cycloalkyl" as R above are the same as the above-mentioned "first substituent".
Further, when "aryl", "heteroaryl", "alkyl" and "cycloalkyl" as R have a substituent, examples of the substituent include the same groups as the above-mentioned "second substituent". .
R in >C(-R) ₂ is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, good too.

In formula (iii), R in the above >NR and/or >C(-R) ₂ may be bonded to at least one of the above A ring, B ring and C ring. Further, in formula (3), R in the above >NR and/or >C(-R) ₂ may be bonded to at least one of the above ring a, ring b and ring c.
Here, the provision that "the R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring" in the formula (iii). is the definition that "R of the >NR and/or >C(-R) ₂ may be bonded to at least one of the a ring, b ring and c ring" in formula (3). corresponds to
This definition can be expressed by a compound having a ring structure in which X ⁴ and X ⁵ are incorporated in condensed ring B' and condensed ring C', represented by the following formula (3c). That ^is , for example ^, the B' ring (or C' ring).
The above definition can also be expressed by compounds having a ring structure in which X ⁴ and/or X ⁵ are incorporated in a condensed ring A', represented by the following formulas (3d) and (3e). That is, for example, it is a compound having an A' ring formed by condensing another ring such that X ⁴ (and/or X ⁵ ) is incorporated into the benzene ring, which is the a ring in formula (3). .
R ¹ to R ⁹ , Y, X ⁴ , X ⁵ and X ⁶ in formulas (3c), (3d) and (3e) are the same as defined in formula (3).

At least one hydrogen in the compounds represented by formula (iii) and formula (3) may be replaced with cyano, halogen or deuterium. For example, in formulas (iii) and (3), A ring (a ring), B ring (b ring), C ring (c ring), and substituents on these rings, Y is Ge—R, Sn R when —R, Sb(—R) ₂ or Bi(—R) ₂ and R when X ⁴ , X ⁵ and X ⁵ are >NR or >C(—R) ₂ can be replaced with cyano, halogen or deuterium.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

Specific " The aryl ring" includes a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-Terphenyl), condensed tricyclic system, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, benzofluorene ring, condensed pentacyclic ring system A perylene ring, a pentacene ring, and the like can be mentioned. The fluorene ring and benzofluorene ring also include structures in which fluorene rings and benzofluorene rings are spiro-bonded.

Further, specific "heteroaryl rings" which are rings A, B and C of formula (i), formula (ii) and formula (iii) include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H -indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring , dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole oxide ring, dibenzophosphole oxide ring, furazane ring, oxadiazole ring, thianthrene ring, indolocarbazole ring, benzoindolo A carbazole ring, a benzobenzoindolocarbazole ring, and the like are mentioned.

At least one hydrogen in the above "aryl ring" or "heteroaryl ring" is the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted " diarylamino", substituted or unsubstituted "diarylboryl (wherein the two aryls may be linked via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted " cycloalkyl”, substituted or unsubstituted “alkoxy”, or substituted or unsubstituted “aryloxy”.

As the first substituent, "aryl", "heteroaryl", aryl of "diarylamino", aryl of "diarylboryl", and aryl of "aryloxy" are the above-mentioned "aryl ring" or "heteroaryl A monovalent group of "ring" may be mentioned.

"Diarylboryl" as the first substituent is a boryl group substituted with aryl, and two aryls may be bonded via a single bond or a linking group.
Here, examples of the linking group for linking two aryls include groups selected from >C(--R) ₂ , >O, >S and >NR. Here, R of >C(-R) ₂ and >N-R is each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the first substituent ), and these groups may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (these are the second substituents), and the above descriptions can be referred to for the details of these groups.
More specifically, the "diarylboryl in which two aryls are bonded via a single bond or a linking group" includes groups shown below.

The "alkyl" as the first substituent may be either linear or branched, and examples thereof include alkyl having 1 to 24 carbon atoms (branched alkyl having 3 to 24 carbon atoms). Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 8 carbon atoms (Branched chain alkyl having 3 to 8 carbon atoms) is more preferable, alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is particularly preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is more preferable. branched chain alkyl) are most preferred.

Examples of specific alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3 ,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethyl Hexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl etc.
Examples of alkyl include 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. .

Examples of "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, Examples include alkyl, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms and cycloalkyl having 5 carbon atoms.

Specific cycloalkyls include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, alkyl (especially methyl)-substituted products thereof having 1 to 5 carbon atoms, norbornyl, bicyclo [1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo [2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

Examples of "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and 1 to 6 carbon atoms. (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

Examples of specific alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy and octyloxy.

The first substituent, substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, substituted or unsubstituted “diarylamino”, substituted or unsubstituted “diarylboryl (where two aryl may be linked via a single bond or a linking group)”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “cycloalkyl”, substituted or unsubstituted “alkoxy”, substituted or unsubstituted "Aryloxy", as described as substituted or unsubstituted, optionally have at least one hydrogen in them replaced with a second substituent.
Examples of the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl, and specific examples thereof include the above-described monovalent group of "aryl ring" or "heteroaryl ring", and the first Reference may be made to the description of "alkyl" or "cycloalkyl" as substituents. In the aryl or heteroaryl as the second substituent, at least one hydrogen in them is substituted with aryl such as phenyl (specific examples are the groups described above) or alkyl such as methyl (specific examples are the groups described above). groups are also included. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl or an alkyl such as methyl is also a heteroaryl as the second substituent. included.

Aryl, heteroaryl, diarylamino aryl, diarylboryl aryl, aryl in R ¹ to R ¹² of formula (1), R ¹ to R ¹¹ of formula (2), and R ¹ to R ⁹ of formula (3) Aryl of oxy includes the above-mentioned monovalent group of "aryl ring" or "heteroaryl ring", and "two aryls may be bonded via a single bond or a linking group" of diarylboryl. For the definition of , alkyl, cycloalkyl, and alkoxy, reference can be made to the description of "diarylboryl", "alkyl", "cycloalkyl" and "alkoxy" as the "first substituent" above.
Furthermore, the same applies to aryl, heteroaryl, alkyl or cycloalkyl as substituents which may be substituted on these groups.

R ¹ to R ¹² in formula (1), R ¹ to R ¹¹ in formula (2), and R ¹ to R ⁹ in formula (3) are each independently hydrogen or an aryl having 6 to 30 carbon atoms. , heteroaryl having 2 to 30 carbon atoms, diarylamino (where each aryl is aryl having 6 to 12 carbon atoms), diarylboryl (where each aryl is aryl having 6 to 12 carbon atoms, and these are single bonds or linking groups ), preferably alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms.

In addition, the compound represented by any one of the formulas (1) to (3) can adjust the emission wavelength by the steric hindrance, electron-donating and electron-withdrawing properties of the structure of the substituent. Specifically, groups represented by the following structural formulas are preferable.
In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl. Further, at least one hydrogen in the following structural formula is the first substituent aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), It may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be further substituted with a second substituent aryl, heteroaryl, alkyl or cycloalkyl. Here, the above description can be referred to for the "first substituent" and the "second substituent".

Among the groups represented by the above structural formulas, the compounds represented by any of formulas (1) to (3) are methyl, t-butyl, t-amyl, t-octyl, phenyl, o- tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl) It is more preferably substituted with at least one selected from phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, methyl, t-butyl , t-amyl, t-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino , carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl.

On the other hand, from the viewpoint of ease of synthesis, the compounds represented by any of formulas (1) to (3) are t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl , 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6- It is more preferably substituted with at least one selected from dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl.

Further, the compound represented by any one of formulas (1) to (3) is more preferably substituted with at least one group represented by the following structural formula.
In the following structural formulas, Me is methyl, tBu is t-butyl, tAm is t-amyl, tOct is t-octyl, and * represents a bonding position. and at least one hydrogen in the following structural formula is the first substituent, aryl, heteroaryl, diarylamino, or diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), It may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be further substituted with a second substituent aryl, heteroaryl, alkyl or cycloalkyl. Here, the above description can be referred to for the "first substituent" and the "second substituent".

In the present invention, among the compounds represented by any one of formulas (1) to (3), it is preferable that the first component contains a compound represented by any one of the following formulas.

In the above formula, Y is Ga, As, Sb or Bi.
Each R is independently aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. As for "aryl", "alkyl" and "cycloalkyl" which are R, the explanation of the above-mentioned "first substituent" or "second substituent" can be referred to.

More specific examples of the compound that can be used as the first component hereinafter include compounds represented by the following chemical structural formulas. "Me" in the following structural formulas represents methyl.

1-2. Method for producing the organic compound of the first component The organic compounds represented by formulas (A-1) to (A-2), formulas (i) to (iii), and formulas (1) to (3) are For example, it can be synthesized by applying the method disclosed in WO 2015/102118.

For example, organic compounds represented by formulas (A-1) and (A-2) can be synthesized by synthesizing an intermediate of the following scheme and cyclizing the intermediate as shown in the scheme below. can be done. In the scheme below, X represents halogen or hydrogen, and the definitions of other symbols are the same as those described above.

In the organic compound represented by formula (i) or formula (1), basically, the A ring (a ring), the B ring (b ring) and the C ring (c ring) are bonded by -NH- to produce an intermediate (first reaction), followed by linking the A-ring (a-ring), B-ring (b-ring) and C-ring (c-ring) with a linking group (a group containing Y) can produce the final product (second reaction). In the first reaction, for example, an amination reaction such as the Buchwald-Hartwig reaction can be used. Also, in the second reaction, a tandem hetero Friedel-Crafts reaction can be used. In the scheme below, X represents halogen or hydrogen, and the definitions of other symbols are the same as those of formula (i) and formula (1) described above.

Further, in the organic compounds represented by formulas (ii) and (2), A ring (a ring) and B ring (b ring) and A ring (a ring) and C ring (c ring) are X ⁴ Alternatively, it can be synthesized by synthesizing an intermediate linked at ^X5 (first reaction) and cyclizing it in a tandem hetero Friedel-Crafts reaction (sequential electrophilic aromatic substitution reactions). In the scheme below, X represents halogen or hydrogen, and the definitions of other symbols are the same as those defined above.

Furthermore, the organic compounds represented by formula (iii) and formula (3) include A ring (a ring) and B ring (b ring), B ring (b ring) and C ring (c ring), and C An intermediate in which ring (c-ring) and A-ring (a-ring) are bonded at X ⁴ , X ⁵ or X ⁶ is synthesized (first reaction), and then subjected to tandem hetero-Friedel-Crafts reaction (successive aromatic It can be synthesized by cyclization with group electrophilic substitution reaction). In the scheme below, X represents halogen or hydrogen, and the definitions of other symbols are the same as those defined above.

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

The cyclization by the tandem hetero Friedel-Crafts reaction shown in the above scheme is a reaction to introduce Y. First, the terminal hydrogen atom of C (carbon atom) or N (nitrogen atom) to be bonded to Y is ortho-metallated with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Next, boron trichloride, boron tribromide, or the like is added to perform lithium-boron metal exchange, and then a Bronsted base such as N,N-diisopropylethylamine is added to cause a tandem bolus Friedel-Crafts reaction to achieve the desired can get things. A Lewis acid such as aluminum trichloride may be added here to accelerate the reaction.

In addition to the method of introducing lithium to the desired position by ortho-metallation, it is also possible to introduce a halogen such as a bromine atom to the position where lithium is to be introduced, and to introduce lithium to the desired position by halogen-metal exchange. can.

Further, in the organic compounds represented by formulas (A-1) to (A-2), formulas (i) to (iii), and formulas (1) to (3), at least some hydrogen atoms is substituted with deuterium, and organic compounds substituted with halogen such as fluorine and chlorine are also included, and such organic compounds are deuterated, fluorinated or chlorine Synthesis can be performed in the same manner as described above by using a raw material that has been synthesized.

1-3. Second Component The light-emitting layer of the organic EL device of the present invention contains at least one thermally activated delayed phosphor as the second component.
"Thermal activated delayed fluorescent material" absorbs thermal energy to cause reverse intersystem crossing from the excited triplet state to the excited singlet state, and radiatively deactivates from the excited singlet state to emit delayed fluorescence. Means a compound that can emit radiation. However, the term “thermally activated delayed fluorescence” also includes the case of passing through a higher triplet in the excitation process from the excited triplet state to the excited singlet state.
For example, a paper by Monkman et al., University of Durham (NATURE COMMUNICATIONS, 7:13680, DOI: 10.1038/ncomms13680), a paper by Hosokai et al., National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282) , a paper by Sato et al. of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7) and an academic presentation by Sato et al. No.: 2I4-15, Mechanism of high-efficiency luminescence in organic EL using DABNA as a light-emitting molecule, Graduate School of Engineering, Kyoto University). In the present invention, when the fluorescence lifetime is measured at 300 K for a sample containing the target compound, the target compound is determined to be a "heat-activated delayed phosphor" based on the fact that a slow fluorescent component is observed. . Here, the term "slow fluorescence component" refers to a component having a fluorescence lifetime of 0.1 μsec or longer. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measurement device (C11367-01, manufactured by Hamamatsu Photonics K.K.).

E (2, S, PT) is the excited singlet energy level obtained from the peak top on the short wavelength side of the fluorescence spectrum of the second component, and the excited triplet energy level obtained from the peak top on the short wavelength side of the phosphorescence spectrum of the second component Assuming that the term energy level is E(2, T, PT), the singlet/triplet energy difference (ΔE(2, ST, PT)) obtained therefrom preferably satisfies the following relationship.
ΔE (2, ST, PT) = E (2, S, PT) - E (2, T, PT) ≤ 0.20 eV
That is, for the second component, the magnitude of ΔE(ST) is used as an index of TADF activity. A smaller ΔE(ST) is advantageous for exhibiting TADF activity.
Here, ΔE(2, ST, PT) is preferably 0.20 eV or less, more preferably 0.15 eV or less, and even more preferably 0.10 eV or less.

Reverse Intersystem Crossing Rate The reverse intersystem crossing rate indicates the rate of reverse intersystem crossing from an excited triplet to an excited singlet. The reverse intersystem crossing rate of the second component can be calculated by transient fluorescence spectrometry using the method described in Nat. Commun. 2015, 6, 8476. or Organic Electronics 2013, 14, 2721-2726, Specifically, the reverse intersystem crossing rate of the assisting dopant is preferably 10 ⁵ s ⁻¹ or more, more preferably 10 ⁶ s ⁻¹ or more.

Emission Rate Emission rate indicates the rate of transition from an excited singlet to the ground state via fluorescence emission without going through the TADF process. The luminescence rate of the second component, like the reverse intersystem crossing rate, can be calculated using the method described in Nat. Specifically, the reverse intersystem crossing rate of the second component is preferably 10 ⁷ s ⁻¹ or more, more preferably 10 ⁸ s ⁻¹ or more.

The second component preferably contains at least one thermally-activated delayed phosphor containing a boron atom, more specifically, represented by either the following general formula (4) or formula (5) It is more preferable to include at least one thermally activated delayed phosphor that is a compound that The compound represented by the following general formula (4) and the compound represented by the following general formula (5) are described below.

1-3-1. The compound represented by the general formula (4) preferably contains a compound represented by the following general formula (4) as the heat-activated delayed phosphor, which is the second component.

In the above formula (4), R ¹ to R ¹¹ each independently represent hydrogen, aryl, heteroaryl, diarylamino, or diarylboryl (wherein two aryls may be bonded via a single bond or a linking group). ), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), and at least one hydrogen in these is further aryl, heteroaryl, alkyl, or cycloalkyl (above, second substituent) may be substituted.

“aryl”, “heteroaryl”, “diarylamino”, “diarylboryl”, “alkyl”, “cycloalkyl”, “alkoxy” and “aryloxy” as the first substituents of R ¹ to R ¹¹ and , “aryl”, “heteroaryl”, “alkyl” and “cycloalkyl” as the second substituents of R ¹ to R ¹¹ are the “first substituents” and Reference may be made to the description of these groups as "secondary substituents".

In the above formula (4), the emission wavelength can be adjusted by the steric hindrance, electron donating and electron withdrawing properties of the structure of R ¹ to R ¹¹ (first substituents). Therefore, in formula (4), at least one of R ¹ to R ¹¹ is preferably a group represented by the following formula.
In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl. At least one hydrogen in the following structural formula may be further substituted with a second substituent, aryl, heteroaryl, alkyl or cycloalkyl. Here, as to the “second substituent”, the description of formulas (1) to (3) above can be referred to.

Among the groups represented by the above structural formulas, in the above formula (4), at least one of R ¹ to R ¹¹ is methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl. , p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl ) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl or phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, phenyl , o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl more preferably 3,6-di-t-butylcarbazolyl.

On the other hand, from the viewpoint of ease of synthesis, at least one of R ¹ to R ¹¹ in the above formula (4) is t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethyl More preferred is carbazolyl or 3,6-di-t-butylcarbazolyl.

In the above formula (4), each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ has two adjacent groups bonded to each other together with the a ring, the b ring or the c ring. An aryl ring or heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (provided that two aryls are bonded via a single bond or a linking group). may be substituted), alkyl, cycloalkyl, alkoxy or aryloxy (above, the first substituent), at least one hydrogen of which is further aryl, heteroaryl, alkyl or cycloalkyl (above, the second substituent) may be substituted.
That is, the compound represented by formula (4) constitutes a compound as shown in the following general formulas (4a) and (4b), depending on the mutual bonding form of the substituents on rings a, b and c. changes the ring structure. The a', b' and c' rings in formulas (4a) and (4b) correspond to the a, b and c rings in general formula (4), respectively. The definition of each symbol in the following general formulas (4a) and (4b) is the same as that of general formula (4).

Rings a′, b′ and c′ in formulas (4a) and (4b) are the substituents R ¹ to R ³ , the substituents R ⁸ to R ¹¹ and the substituents R ⁴ to R ⁷ An aryl ring or a heteroaryl ring formed by bonding adjacent groups together with a ring, b ring, and c ring, respectively (a condensed ring formed by condensing another ring structure to the a ring, b ring, or c ring) can be called a ring). Although not shown in the formula, there are compounds in which all of the a-ring, b-ring and c-ring are changed to a'-ring, b'-ring and c'-ring. Further, as can be seen from the formulas (4a) and (4b), for example, R ³ of the a ring and R ⁴ of the c ring, R ¹¹ of the b ring and R ¹ of the a ring are “adjacent groups”. are not applicable and they are not combined. That is, "adjacent groups" mean groups that are adjacent on the same ring. Also, R ⁸ of ring b and R ⁷ of ring c are not bound to adjacent groups and are not part of the above aryl or heteroaryl ring formed.

The formed "aryl ring" (a' ring, b' ring or c' ring) or "heteroaryl ring" (a' ring, b' ring or c' ring) is the above-mentioned aryl as the first substituent or a heteroaryl, nonvalent ring. However, since the a ring (or b ring or c ring) that constitutes a part of the a' ring (b' ring or c' ring) is already a benzene ring having 6 carbon atoms, the "aryl ring" The total carbon number of the condensed ring in which a 5-membered ring is condensed to the ring is 9, and for the "heteroaryl ring", the total carbon number of the condensed ring in which the 5-membered ring is condensed to the benzene ring is 6. number.

Compounds represented by formulas (4a) and (4b) have, for example, a benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring with respect to the a ring (or b ring or c ring). is a compound having an a' ring (or b' ring or c' ring) formed by condensation, and the formed condensed ring a' (or condensed ring b' or condensed ring c') is a naphthalene ring, It is a carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring.

"Aryl", "Heteroaryl", "Diarylamino", "Diarylboryl", "Alkyl", "Cycloalkyl", "Alkoxy" as the First Substituent Substituting on the Formed Aryl Ring or Heteroaryl Ring and "aryloxy", and "aryl", "heteroaryl", "alkyl" and "cycloalkyl" as the second substituent that can be further substituted on the first substituent are the above-described formulas (1) to Reference can be made to the description of these groups as "first substituent" and "second substituent" in (3).

In general formula (4), X ⁴ and X ⁵ are each independently selected from >O, >N—R and >C(—R) ₂ , but X ⁴ and X ⁵ are simultaneously >C( —R) ₂ and each R in the above >N—R and >C(—R) ₂ is independently optionally substituted aryl, optionally substituted heteroaryl, substituted optionally substituted alkyl or optionally substituted cycloalkyl, and the >N—R and >C(—R) ₂ are bonded to at least one of the a, b and c rings. may

X ⁴ and X ⁵ are both >N-R, both are >O, both are >N-R, or one is >N-R and the other is >O Preferably, both are >O, or both are more preferably >NR, and more preferably both are >NR.

R in the above >NR and >C(-R) ₂ is each independently aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or 3 carbon atoms. -6 cycloalkyl is preferred.
The substituents that can be substituted for R in >N—R and R in >C(—R) ₂ include “aryl”, “heteroaryl” and “alkyl” as the “second substituent” described above. or "cycloalkyl".

The provision that "the >N-R and >C(-R) ₂ may be bonded to at least one of the a-ring, b-ring and c-ring" is represented by the following formula (4c): It can be represented by a compound having a ring structure in which X ⁴ and X ⁵ are incorporated in condensed ring B' and condensed ring C'. That is, for ^example , ^the B' ring (or C' ring).
The above definition can also be expressed by compounds having a ring structure in which X ⁴ and/or X ⁵ are incorporated in a condensed ring A', represented by the following formula (4d) or (4e). That is, for example, it is a compound having an A' ring formed by condensing another ring such that X ⁴ (and/or X ⁵ ) is incorporated into the benzene ring, which is the a ring in formula (4). .
R ¹ to R ¹¹ , X 4 and X ⁵ in formulas (4c), ( ^4d ) and (4e) below are the same as defined in formula (4).

At least one hydrogen in the compound represented by general formula (4) may be substituted with cyano, halogen or deuterium. For example, in general formula (4), when ring a, ring b, ring c, substituents on these rings, and X ⁴ and X ⁵ are >N—R or >C(—R) ₂ can be replaced with cyano, halogen or deuterium.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

The compound represented by general formula (4) can be produced according to the production method described in International Publication No. 2015/102118. In addition, referring to the method for producing the compound represented by the above formula (2), it can be produced using a general amination reaction such as the Buchwald-Hartwig reaction instead of the etherification reaction in the first reaction. .

Specifically, the compound represented by the general formula (4) includes the specifications of Japanese Patent Application No. 2017-199617, Japanese Patent Application No. 2018-107092, International Application No. PCT/JP2015/054426, and International Application No. PCT/JP2017/001089. Examples include the compounds described in the book, and specifically, the compounds shown below are preferable. "Me" in the following structural formulas represents methyl.

1-3-2. The compound represented by the general formula (5) preferably contains a compound represented by the following general formula (5) as the heat-activated delayed phosphor, which is the second component. The compound represented by general formula (5) corresponds to a dimer of a compound having two unit structures represented by general formula (4) described above.

In general formula (5) above, R ¹ to R ¹⁴ each independently represent hydrogen, aryl, heteroaryl, diarylamino, or diarylboryl (provided that the two aryls are bonded via a single bond or a linking group). ), alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), wherein at least one hydrogen is further aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) may be substituted with

R ⁴ and R ¹³ in formula (5) each independently represent aryl, heteroaryl, diarylamino, or diarylboryl (however, the two aryls may be bonded via a single bond or a linking group). , alkyl, cycloalkyl, alkoxy or aryloxy (above, first substituent), at least one hydrogen of which is substituted with aryl, heteroaryl, alkyl or cycloalkyl (above, second substituent) may have been

“aryl”, “heteroaryl”, “diarylamino”, “diarylboryl”, “alkyl”, “cycloalkyl”, “alkoxy” and “aryloxy” as the first substituents of R ¹ to R ¹⁴ and , “aryl”, “heteroaryl”, “alkyl” and “cycloalkyl” as the second substituents of R ¹ to R ¹⁴ are the “first substituents” and Reference may be made to the description of these groups as "secondary substituents".

In the above formula (5), the emission wavelength can be adjusted by the steric hindrance, electron donating and electron withdrawing properties of the structures of R ¹ to R ¹⁴ (first substituents). Therefore, in formula (5), at least one of R ¹ to R ¹⁴ is preferably a group represented by the following formula.
In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl. At least one hydrogen in the following structural formula may be further substituted with a second substituent, aryl, heteroaryl, alkyl or cycloalkyl. Here, as to the “second substituent”, the description of formulas (1) to (3) above can be referred to.

Among the groups represented by the above structural formulas, in the above formula (5), at least one of R ¹ to R ¹⁴ is methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl. , p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl ) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl or phenoxy, more preferably methyl, t-butyl, t-amyl, t-octyl, phenyl , o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl more preferably 3,6-di-t-butylcarbazolyl.

On the other hand, from the viewpoint of ease of synthesis, at least one of R ¹ to R ¹⁴ in the above formula (5) is t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethyl More preferred is carbazolyl or 3,6-di-t-butylcarbazolyl.

In the above formula (5), two adjacent groups of R ¹² to R ¹⁴ , R ⁹ to R ¹¹ , R ³ to R ⁵ and R ⁶ to R ⁸ are bonded to each other to form a ring , b ring, c ring or d ring may form an aryl ring or heteroaryl ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (provided that two aryl may be bonded via a single bond or a linking group), may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy (above, the first substituent), at least one hydrogen in which is further , aryl, heteroaryl, alkyl or cycloalkyl (these are the second substituents).
That is, the compound represented by the general formula (5) is a compound represented by the following general formula (5a), for example, depending on the mutual bonding form of the substituents on the a ring, b ring, c ring, or d ring. The constituent ring structure changes. The following formula (5a) shows a state in which the ring structure constituting the compound is changed to a b' ring and a d' ring depending on the mutual binding form of the substituents on the b ring and the d ring. The b' ring and d' ring in formula (5a) correspond to the b ring and d ring in general formula (5), respectively. Also, the definition of each symbol in the following general formula (5a) is the same as that in general formula (5).

In the b′ ring and the d′ ring in the above formula (5a), adjacent groups among the substituents R ⁹ to R ¹¹ of the b ring and the substituents R ⁶ to R ⁸ of the d ring are bonded to It represents an aryl ring or heteroaryl ring formed together with the b ring and the d ring (it can also be said to be a condensed ring formed by condensing the b ring or the d ring with another ring structure).
Further, as can be seen from the above formula (5a), for example, R ⁹ of the b ring and R ⁸ of the d ring in the formula (5) do not correspond to "adjacent groups", and they do not bond. . That is, "adjacent groups" mean groups that are adjacent on the same ring.

The formed “aryl ring” (b′ ring or d′ ring) or “heteroaryl ring” (b′ ring or d′ ring) is a nonvalent is a ring. However, since the b ring or d ring that constitutes a part of the b' ring or d' ring is already a benzene ring having 6 carbon atoms, the "aryl ring" is a condensed ring in which a 5-membered ring is condensed to the benzene ring is the lower limit of the total carbon number of 9, and for the "heteroaryl ring", the lower limit of the carbon number is 6, the total carbon number of the condensed ring in which a 5-membered ring is condensed to the benzene ring.

The compound represented by the formula (5a) has a b′ ring or a It is a compound having a d' ring, and the formed condensed ring b' or condensed ring d' is naphthalene ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring, respectively.

"Aryl", "Heteroaryl", "Diarylamino", "Diarylboryl", "Alkyl", "Cycloalkyl", "Alkoxy" as the First Substituent Substituting on the Formed Aryl Ring or Heteroaryl Ring and "aryloxy", and "aryl", "heteroaryl", "alkyl" or "cycloalkyl" as the second substituent that can be further substituted on the first substituent are represented by the above-described formulas (1) to Reference can be made to the description of these groups as "first substituent" and "second substituent" in (3).

In the above formula (5a), the ring structure changes depending on the mutual bonding form of the substituents in the b ring and the d ring. Structure can vary.

In general formula (5), X ⁴ to X ⁷ are each independently selected from >O, >NR and >C(-R) ₂ , but X ⁴ to X ⁷ are simultaneously >C( —R) ₂ and each R in the above >N—R and >C(—R) ₂ is independently hydrogen, optionally substituted aryl, or optionally substituted heteroaryl , optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N—R and/or >C(—R) ₂ is the a ring, the b ring, or the c ring and at least one of the d rings.

R in the above >NR and >C(-R) ₂ is each independently aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or 3 carbon atoms. -6 cycloalkyl is preferred.
The substituents that can be substituted for R in >N—R and R in >C(—R) ₂ include “aryl”, “heteroaryl” and “alkyl” as the “second substituent” described above. or "cycloalkyl".

The provision that "R of the >NR and/or >C(-R) ₂ may be bonded to at least one of the a ring, b ring, c ring and d ring" is, for example, It can be represented by a compound having a ring structure in which X ⁴ and X ⁷ are incorporated in condensed ring b' and condensed ring d', represented by the following formula (5b). That is, ^{for example} , the b' ring (or d' ring).
The formed condensed ring b' (or condensed ring d') is, for example, a carbazole ring, phenoxazine ring, phenothiazine ring or acridine ring. In addition, the definition of each code|symbol in Formula (5b) is the same as the definition in General formula (5).

In formula (5b), X ⁴ and X ⁷ represent a ring structure incorporated into condensed ring b' and condensed ring d', but >NR or >C(-R) as X ⁵ and X ⁶ ) The R of ₂ can be similarly bonded to the a ring and the c ring, and when it is bonded, the ring structure changes in the same manner as the above b' ring and d' ring.

At least one hydrogen in the compound represented by formula (5) may be substituted with cyano, halogen or deuterium. For example, in formula (5), ring a, ring b, ring c, ring d, substituents on these rings, X ⁴ to X ⁷ are >NR or -C(-R) ₂ - The hydrogen in R when can be replaced with cyano, halogen or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.

The compound represented by the general formula (5) is manufactured by applying the manufacturing method described in WO 2015/102118 and referring to the manufacturing method of the compound represented by the above formula (2). be able to.
The compound represented by the general formula (5) is basically produced by bonding the respective ring structures to each other to produce an intermediate (first reaction), and then bonding the respective ring structures with a boron atom. The final product can be produced by allowing the reaction to proceed (second reaction). In the first reaction, for example, general etherification reactions such as nucleophilic substitution reaction and Ullmann reaction, and general amination reactions such as Buchwald-Hartwig reaction can be used. Moreover, in the second reaction, a tandem hetero Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction) can be used.

Specific examples of the compound represented by formula (5) include the compounds described in the specification of International Application No. PCT/JP2018/018731, and the compounds shown below are preferred.

2. Structure of Organic Electroluminescence Device Hereinafter, the organic EL device according to the present embodiment will be described in detail with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.
The organic electroluminescence device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103 on the hole injection layer 103. a hole-transporting layer 104 provided on the hole-transporting layer 104; a light-emitting layer 105 provided on the hole-transporting layer 104; an electron-transporting layer 106 provided on the light-emitting layer 105; and a cathode 108 provided on the electron injection layer 107 .

Note that the organic electroluminescent device 100 is fabricated in 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 The electron-transporting layer 106 provided on the electron-transporting layer 107, the light-emitting layer 105 provided on the electron-transporting layer 106, the hole-transporting layer 104 provided on the light-emitting layer 105, and the hole-transporting layer 104 A structure having a hole-injection layer 103 provided thereon and an anode 102 provided on the hole-injection layer 103 may be employed.

All of the above layers are not 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 Layer 107 is an optional layer. Moreover, each of the above layers may be composed of a single layer, or may be composed of a plurality of layers.

In addition to the configuration of the above-described "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", the layers constituting the organic electroluminescent device may be "Substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate /anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-injection layer/cathode”, “substrate/anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-transport layer/cathode”, “substrate /anode/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light emitting layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light emitting layer/ electron-transporting layer/cathode", "substrate/anode/hole-injection layer/light-emitting layer/electron-injection layer/cathode", "substrate/anode/hole-injection layer/light-emitting layer/electron-transporting layer/cathode", "substrate/ Anode/light-emitting layer/electron-transporting layer/cathode” or “substrate/anode/light-emitting layer/electron-injecting layer/cathode” may be employed.

<Substrate in Organic Electroluminescent Device>
The substrate 101 is a support for the organic electroluminescence device 100, and is usually made of quartz, glass, metal, plastic, or the like. 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, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate and polysulfone are preferred. If it is a glass substrate, soda-lime glass, alkali-free glass, or the like is used, and the thickness should be sufficient to maintain the mechanical strength. 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, it is preferable to use non-alkali glass because the fewer ions eluted from the glass, the better. However, soda-lime glass with a barrier coating such as SiO ₂ is also available on the market and can be used. can. In addition, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side thereof in order to enhance gas barrier properties. When used, it is preferable to provide a gas barrier film.

<Anode in Organic Electroluminescent Device>
Anode 102 serves to inject holes into light-emitting layer 105 . When the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. .

Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide metal (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, and the like. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from substances used as anodes of organic electroluminescence devices.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but a low resistance is desirable 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 it is now possible to supply a substrate of about 10 Ω/□. It is particularly desirable to use a low resistance product of /□. Although the thickness of ITO can be arbitrarily selected according to the resistance value, 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-injecting layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole-transporting layer 104 . The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105 . The hole injection layer 103 and the hole transport layer 104 are each formed by stacking and mixing one or more kinds of hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. be done. Also, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form the layer.

As a hole-injecting/transporting substance, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied. It is desirable to For this purpose, it is preferable that the ionization potential is low, the hole mobility is high, the stability is excellent, and impurities that become traps are less likely to occur during manufacture and use.

Materials for forming the hole injection layer 103 and the hole transport layer 104 include compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and hole injection materials for organic electroluminescent elements. Any compound can be selected and used from known compounds used for the layer and the hole transport layer.

Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (aromatic tertiary Polymers with amino in the main or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 ,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 ,4′-diphenyl-1,1′-diamine, N,N′-dinaphthyl-N,N′-diphenyl-4,4′-diphenyl-1,1′-diamine, N ⁴ ,N ⁴ ′ -diphenyl- N ⁴ ,N ^4′ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]-4,4′-diamine, N ⁴ ,N ⁴ ,N ^4′ ,N ^{4 '} -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4''-tris(3-methylphenyl(phenyl) triphenylamine derivatives such as amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives , quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. Polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane and the like having the above-mentioned monomers in the side chains are preferable for polymer systems, but a thin film necessary for manufacturing a light-emitting device can be formed and holes can be injected from the anode. Further, the compound is not particularly limited as long as it is a compound capable of transporting holes.

It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such an organic semiconductor matrix material is composed of a compound with good electron-donating property or a compound with good electron-accepting property. Strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known for doping electron donors. (For example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)” and the literature “J. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). They generate so-called holes by an electron transfer process in an electron donating base material (hole transport material). The conductivity of the base material varies considerably depending on the number and mobility of holes. As matrix substances having hole-transporting properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.) or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Unexamined Patent Application Publication No. 2005-167175).

<Light Emitting Layer in Organic Electroluminescent Device>
The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As a material for forming the light-emitting layer 105, any compound (light-emitting compound) that emits light when excited by recombination of holes and electrons can be used. It is preferably a compound that exhibits strong luminescence (fluorescence) efficiency at . For example, a light-emitting layer material containing the above-described first component as a host material and the above-described second component as a dopant material can be used.

The light-emitting layer may be a single layer or a plurality of layers, each of which is formed of a light-emitting layer material (host material, dopant material). The host material and the dopant material may be of one kind, or may be a combination of a plurality of them. The dopant material may be included entirely or partially in the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may be mixed with the host material in advance and then vapor-deposited simultaneously.

The amount of host material to be used varies depending on the type of host material, and may be determined according to the properties of the host material. A guideline for the amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and still more preferably 90 to 99.9% by weight of the total light-emitting layer material. is.

The amount of dopant material used varies depending on the type of dopant material, and may be determined according to the properties of the dopant material. A guideline for the amount of dopant to be used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight of the total light-emitting layer material. be. The above range is preferable in that, for example, the phenomenon of concentration quenching can be prevented.

As the host material, in addition to the above-mentioned first component, condensed ring derivatives such as anthracene and pyrene, bisstyrylanthracene derivatives and distyrylbenzene, which have been known as light emitters, are used as long as they do not impair the effects of the present invention. Other host materials such as bisstyryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, etc. can also be used.

上記式中、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。
アリーレンとしては、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環構造を有する二価の基があげられる。
また、ヘテロアリーレンとしては、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、ナフトベンゾフラン環、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、ナフトベンゾチオフェン環、ベンゾホスホール環、ジベンゾホスホール環、ベンゾホスホールオキシド環、ジベンゾホスホールオキシド環、フラザン環、オキサジアゾール環、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およびベンゾベンゾインドロカルバゾール環などの環構造を有する二価の基が挙げられる。 Other host materials include, for example, carbazole-based compounds and anthracene-based compounds represented by the following formulas.

In the above formula, L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms, preferably arylene having 6 to 24 carbon atoms, more preferably arylene having 6 to 16 carbon atoms, and 6 carbon atoms. Arylene having 1 to 12 carbon atoms is more preferable, arylene having 6 to 10 carbon atoms is particularly preferable, heteroarylene having 2 to 25 carbon atoms is preferable, heteroarylene having 2 to 20 carbon atoms is more preferable, and heteroarylene having 2 to 20 carbon atoms is more preferable. Heteroarylene is more preferred, and heteroarylene having 2 to 10 carbon atoms is particularly preferred.
Specific examples of arylene include benzene ring, biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perylene ring and pentacene ring. A divalent group having a ring structure can be mentioned.
Further, as heteroarylene, specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacilline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole oxide ring, dibenzophos Divalent groups having ring structures such as hole oxide ring, furazane ring, oxadiazole ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring and benzobenzoindolocarbazole ring are included.

In the above formula, L ² and L ³ are each independently aryl having 6 to 30 carbon atoms or heteroaryl having 2 to 30 carbon atoms. As aryl, aryl having 6 to 24 carbon atoms is preferable, aryl having 6 to 16 carbon atoms is more preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable. is a monovalent ring structure having a ring structure such as benzene ring, biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perylene ring and pentacene ring A basis is given.
As heteroaryl, heteroaryl having 2 to 25 carbon atoms is preferable, heteroaryl having 2 to 20 carbon atoms is more preferable, heteroaryl having 2 to 15 carbon atoms is further preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Preferably, specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring , quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophosphole oxide ring, dibenzophosphole oxide ring, furazane Examples include monovalent groups having a ring structure such as a ring, oxadiazole ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring and benzobenzoindolocarbazole ring.

At least one hydrogen in the carbazole-based compound or anthracene-based compound represented by the above formula may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium. .

Further, regarding other host materials, another example is Advanced Materials, 2017, 29, 1605444, Journal of Material Chemistry C, 2016, 4, 11355-11381, Chemical Science, 2016, 7, 3355-3363, A host material described in Thin Solid Films, 2016, 619, 120-124 and the like can be used. In addition, since the TADF organic EL device requires a high T1 energy for the host material of the light emitting layer, the host material for the phosphorescent organic EL device described in Chemistry Society Reviews, 2011, 40, 2943-2970 is also a TADF organic EL. It can be used as a host material for devices.

More specifically, the host compound is a compound having at least one structure selected from the partial structure (HA) group represented by the following formula, wherein each At least one hydrogen atom in the structure may be substituted with any structure in the partial structure (HA) group or the partial structure (HB) group, and at least one hydrogen in these structures is It may be substituted with deuterium, halogen, cyano, alkyl having 1 to 4 carbon atoms (eg methyl or t-butyl), cycloalkyl having 5 to 10 carbon atoms (eg cyclohexyl or adamantyl), trimethylsilyl or phenyl.

The host compound is preferably a compound represented by any of the structural formulas listed below, and among these, more preferably 1 to 3 structures selected from the above partial structure (HA) group , and a compound having one structure selected from the partial structure (HB) group, more preferably a compound having a carbazole group as the partial structure (HA) group, particularly preferably the following Formula (Cz-201), Formula (Cz-202), Formula (Cz-203), Formula (Cz-204), Formula (Cz-212), Formula (Cz-221), Formula (Cz-222), Formula (Cz-261) or a compound represented by the formula (Cz-262). In the structural formulas listed below, at least one hydrogen is halogen, cyano, alkyl having 1 to 4 carbon atoms (eg methyl or t-butyl), cycloalkyl having 5 to 10 carbon atoms (eg cyclohexyl or adamantyl ), phenyl or naphthyl.

As the dopant material, other dopant materials than the second component can be used as long as the effects of the present invention are not impaired.
Other dopant materials are not particularly limited, and known compounds can be used, and can be selected from various materials depending on the desired emission color. Specifically, for example, phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene condensed ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP-A-1-245087), bisstyrylarylene derivatives (JP-A-2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl) isobenzofuran derivatives such as isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7- Coumarin derivatives such as methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, benzofluorene derivatives and the like.

Examples of blue to blue-green dopant materials for each colored light include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, derivatives thereof, furan, pyrrole, thiophene, Heteroaromatic compounds such as silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthene, etc. Cyclic compounds and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, triazole and their metal complexes and N , N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine and the like.

Examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Suitable examples include compounds obtained by introducing substituents such as aryl, heteroaryl, arylvinyl, amino, and cyano into the compounds exemplified as blue-green dopant materials, which enable wavelength lengthening.

Furthermore, as orange to red dopant materials, naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands; -(Dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogues, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives and thiadiazolopyrene derivatives, and the like, and further exemplified as the blue to blue-green and green to yellow dopant materials. Preferable examples also include compounds obtained by introducing substituents such as aryl, heteroaryl, arylvinyl, amino, and cyano into the above compounds that enable longer wavelengths.

In addition, as the dopant, it is possible to appropriately select and use compounds such as those described in Kagaku Kogyo June 2004, p.

Among these other dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives or pyrene derivatives are particularly preferred.

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／またはシクロアルキル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。 An 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 aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ are each independently aryl having 6 to 30 carbon atoms, and Ar ¹ to Ar ³ has a stilbene structure, and Ar ¹ to Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and/or cycloalkyl) or cyano and m is an integer from 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／またはシクロアルキル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。 The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula.

In the formula, Ar ² and Ar ³ are each independently aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (aryl, alkyl and /or silyl trisubstituted with cycloalkyl) or cyano.

Specific examples of aryl having 6 to 30 carbon atoms are phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl and distyrylbiphenylyl. , distyrylfluorenyl, and the like.

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-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis[4''-bis (diphenylamino)styryl]-biphenyl, 1,4-bis[4′-bis(diphenylamino)styryl]-benzene, 2,7-bis[4′-bis(diphenylamino)styryl]-9,9-dimethyl fluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl and the like.
Also, amines having a stilbene structure described in JP-A-2003-347056 and JP-A-2001-307884 may be used.

Perylene derivatives include, for example, 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 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′-anthryl)-8,11-di(t-butyl)perylene, 3,3′-bis(8,11-di(t-butyl)perylenyl) 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, and JP-A-2001-217077 may also be used.

Borane derivatives include, for example, 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, 9-(4'-(N-carbazolyl)phenyl) -10-(dimesitylboryl)anthracene and the like.
Borane derivatives described in International Publication No. 2000/40586 and the like may also 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／またはシクロアルキル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。 An aromatic amine derivative is represented, for example, by the following formula.

In the formula, Ar ⁴ is an n-valent group derived from aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are , aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and/or cycloalkyl) or cyano, and n is an integer from 1 to 4 be.

In particular, Ar ⁴ is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and/or cycloalkyl) or cyano, and n is 2, aromatic Group amine derivatives are more preferred.

Specific examples of aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl and pentacenyl.

Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl) chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene -6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-di(p-tolyl ) chrysene-6,12-diamine, N,N′-diphenyl-N,N′-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N′-diphenyl-N,N′-bis( 4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N '-Bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine etc.

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

Examples of anthracene-based compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine and N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine. , N,N,N′,N′-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N′,N′-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10- Diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene- 9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t -butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di- t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl-N,N'- Bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene -9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl -N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene , 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-( 4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino- 9-(6-diphenylamino-2-naphthyl)anthracene and the like.

In addition, [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-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.
Also, aromatic amine derivatives described in JP-A-2006-156888 may be used.

Coumarin derivatives include coumarin-6 and coumarin-334.
In addition, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, and JP-A-6-298758 may also 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 pyran derivatives include the following DCM and DCJTB.

In addition, 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 A pyran derivative described in, for example, may be used.

<Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106 . The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or 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 stacking and mixing one or more electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are efficiently transported. For this purpose, it is preferable to use a substance that has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapping impurities during production and use. However, when considering the transport balance of holes and electrons, if the function mainly plays the role of efficiently preventing holes from the anode from flowing to the cathode side without recombination, the electron transport capacity is not so high. Even if it is not high, the effect of improving the luminous efficiency is equivalent to that of a material with a high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also have the function of a layer capable of efficiently blocking the movement of holes.

Materials (electron transport materials) forming the electron transport layer 106 or the electron injection layer 107 include compounds conventionally used as electron transport compounds in photoconductive materials, and those used in the electron injection layer and electron transport layer of organic EL elements. It can be used by arbitrarily selecting from among the known compounds that are known.

Materials used for the electron transport layer or the electron injection layer include compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, It preferably contains at least one selected from pyrrole derivatives, condensed ring derivatives thereof, and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4′-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide. derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes. These materials may be used alone, but may be used in combination with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, and 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.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole- 2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4′-(2,2′:6′2 "-terpyridinyl)) benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives , and bis-styryl derivatives.

Metal complexes having electron-accepting nitrogen can also be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, benzoquinoline metal complexes, and the like. can give.

Although the above materials can be used alone, they may be used in combination with different materials.

Borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metals, among the materials mentioned above. 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一つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、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), which is disclosed in detail in JP-A-2007-27587.

In the above formula (ETM-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen-containing at least one of heterocycle and cyano, and R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl , X is optionally substituted arylene, Y is optionally substituted aryl having up to 16 carbon atoms, optionally substituted boryl, or optionally substituted carbazolyl, and n are each independently an integer of 0 to 3. Also, substituents in the case of "optionally 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一つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、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一つであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、ｎはそれぞれ独立して０～３の整数であり、そして、ｍはそれぞれ独立して０～４の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどがあげられる。

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一つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、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 above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferable.

In formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen at least one of heterocyclic ring-containing or cyano, and R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl and R ²¹ and R ²² are each independently at least hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano X ¹ is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4 is an integer. Also, substituents in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl and the like.

In formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, optionally substituted silyl, optionally substituted nitrogen at least one of heterocyclic ring-containing or cyano, and R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl , X ¹ is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Also, substituents in the case of "optionally 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 the following formulas (X-1) to (X-9).

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

Specific examples of this borane derivative include the following compounds.

This borane derivative can be produced using known raw materials and known synthetic methods.

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

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

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

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

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

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

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

The “alkyl” for 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. Preferred "alkyl" are alkyls of 1 to 18 carbon atoms (branched alkyls of 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

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

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

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

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

The “aryl” for R ¹¹ to R ¹⁸ is preferably aryl having 6 to 30 carbon atoms, more preferably aryl having 6 to 18 carbon atoms, still more preferably aryl having 6 to 14 carbon atoms, Aryl having 6 to 12 carbon atoms is particularly preferred.

Specific examples of "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, condensed bicyclic aryl (1-,2-) naphthyl, condensed tricyclic aryl acenaphthylene-( 1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -,3-,4-,9-)phenanthryl, condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1- ,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl and the like. .

Preferable "aryl having 6 to 30 carbon atoms" includes phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, more preferably phenyl, 1- Naphthyl or 2-naphthyl may be mentioned.

R ¹¹ and R ¹² in the above formula (ETM-2-2) may combine to form a ring, and as a result, the 5-membered ring of the fluorene skeleton includes cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, 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 using known raw materials and known synthetic methods.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), which is disclosed in detail in WO2010/134352.

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

Specific examples of this fluoranthene derivative include the following compounds.

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

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are bonded via a single bond or a linking group). optionally), alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen is optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Adjacent groups among R ¹ to R ¹¹ may be combined to form an aryl ring or heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or It may be substituted with aryloxy and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

At least one hydrogen in the compound or structure represented by formula (ETM-4) may be replaced with halogen or deuterium.

Regarding the explanation of the substituents and ring formation forms in the formula (ETM-4), and the multimer formed by combining multiple structures of the formula (ETM-4), refer to the compound represented by the above general formula (2) and its large amount A description of the body can be quoted.

Specific examples of this BO derivative include the following compounds.

This BO-based derivative can be produced using known raw materials and known synthetic methods.

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

Ar is each independently divalent benzene or naphthalene, R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or carbon atoms 6-20 aryl.

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

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

The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be straight chain or branched chain. That is, it is straight chain alkyl of 1 to 6 carbon atoms or branched chain alkyl of 3 to 6 carbon atoms. Preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl , methyl, ethyl, or t-butyl are more preferred.

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

The aryl having 6 to 20 carbon atoms in R ¹ to R ⁴ is preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryl phenyl, (o-, m-, p-)tolyl, (2,3-,2,4-,2,5- , 2,6-,3,4-,3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-,m-,p-)cumenyl, bicyclic aryl (2 -,3-,4-)biphenylyl, condensed bicyclic aryl (1-,2-)naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4 '-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, anthracen-(1-,2-,9-)yl, acenaphthylene- (1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-, 2-,3-,4-,9-)phenanthryl, condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracene-(1 -,2-,5-)yl, and perylene-(1-,2-,3-)yl which is a condensed pentacyclic aryl.

"Aryl having 6 to 20 carbon atoms" is preferably phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl , more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, particularly preferably phenyl.

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

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

Each Ar ² is independently an aryl having 6 to 20 carbon atoms, and the same explanation as for the "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

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

Specific examples of these anthracene derivatives include the following compounds.

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

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

Each Ar ¹ is independently an aryl having 6 to 20 carbon atoms, and the same explanation as for the "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

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

“Alkyl” for Ar ² may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms and branched chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" are alkyls of 1 to 18 carbon atoms (branched alkyls of 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific “alkyl” include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

“Cycloalkyl” for Ar ² includes, for example, cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl and the like.

The “aryl” for Ar ² is preferably aryl having 6 to 30 carbon atoms, more preferably aryl having 6 to 18 carbon atoms, still more preferably aryl having 6 to 14 carbon atoms, particularly preferably It is an aryl having 6 to 12 carbon atoms.

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

Two ^Ar2 may be joined to form a ring, so that the 5-membered ring of the fluorene skeleton is spiro-bonded with cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene, etc. may

Specific examples of this benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced using known raw materials and known synthetic methods.

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>
A 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.

R ⁵ is substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms or 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, aryl having 5 to 20 carbon atoms, 20 heteroaryl, alkoxy having 1 to 20 carbon atoms or aryloxy having 6 to 20 carbon atoms,
R ⁷ and R ⁸ are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms;
^R9 is oxygen or sulfur,
j is 0 or 1, k is 0 or 1, r is an integer of 0-4, and q is an integer of 1-3.
Here, examples of substituents when substituted include aryl, heteroaryl, alkyl, cycloalkyl and the like.

A 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, hydrogen, alkyl group, cycloalkyl group, aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, cycloalkylthio group, arylether group , arylthioether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, amino group, nitro group, silyl group, and condensed ring formed between adjacent substituents selected from

Ar ¹ may be the same or different and is an arylene group or a heteroarylene group, and 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 condensed ring with an adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural moiety, and when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group means, for example, a saturated aliphatic hydrocarbon group such as methyl group, ethyl group, propyl group and butyl group, which may be unsubstituted or substituted. There are no particular restrictions on the substituents in the case of substitution, and examples thereof include alkyl groups, aryl groups, heterocyclic groups, and the like, and this point is also common to the following description. Although the number of carbon atoms in the alkyl group is not particularly limited, it is usually in the range of 1 to 20 from the standpoint of availability and cost.

The cycloalkyl group is, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl and adamantyl, which may be unsubstituted or substituted. Although the number of carbon atoms in the alkyl group portion is not particularly limited, it is usually in the range of 3-20.

An aralkyl group is, for example, 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 may be unsubstituted or substituted. I don't mind. Although the number of carbon atoms in the aliphatic portion is not particularly limited, it is usually in the range of 1-20.

The alkenyl group is, for example, an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl group, allyl group, butadienyl group, etc., which may be unsubstituted or substituted. Although the number of carbon atoms in the alkenyl group is not particularly limited, it is usually in the range of 2-20.

In addition, the cycloalkenyl group is, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexene group, which may be unsubstituted or substituted. I don't mind.

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

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

An alkylthio group is a group in which an oxygen atom in an ether bond of an alkoxy group is substituted with a sulfur atom.

A cycloalkylthio group is a group in which an oxygen atom in an ether bond of a cycloalkoxy group is substituted with a sulfur atom.

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

An arylthioether group is a group in which an oxygen atom in an ether bond of an arylether group is substituted with a sulfur atom.

Further, the aryl group means, for example, aromatic hydrocarbon groups such as phenyl group, naphthyl group, biphenylyl group, phenanthryl group, terphenyl group and pyrenyl group. An aryl group can be unsubstituted or substituted. Although the number of carbon atoms in the aryl group is not particularly limited, it is usually in the range of 6-40.

In addition, the heterocyclic group refers to, for example, a cyclic structural group having atoms other than carbon atoms such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group, which may be unsubstituted or substituted. I don't mind. Although the number of carbon atoms in the heterocyclic group is not particularly limited, it is usually in the range of 2-30.

Halogen means fluorine, chlorine, bromine and iodine.

Aldehyde groups, carbonyl groups, and amino groups can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic rings, and the like.

Aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be substituted or unsubstituted.

A silyl group is, for example, a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. Although the number of carbon atoms in the silyl group is not particularly limited, it is usually in the range of 3-20. Also, the silicon number is usually 1-6.

Condensed rings formed between 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 , Ar ^{1 and} Conjugated or non-conjugated fused rings formed between Ar ² and the like. Here, when n is 1, two R ^1s may form a conjugated or non-conjugated condensed ring. These condensed rings may contain a nitrogen, oxygen or sulfur atom in the ring structure, or may be condensed with another ring.

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

This phosphine oxide derivative can be produced using known raw materials and known synthetic methods.

<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.

Each Ar is independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1-4, preferably an integer of 1-3, more preferably 2 or 3;

The "aryl" of "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, Aryl having 6 to 12 carbon atoms is more preferable.

Specific “aryl” includes monocyclic aryl phenyl, bicyclic aryl (2-,3-,4-)biphenylyl, condensed bicyclic aryl (1-,2-)naphthyl , tricyclic aryl terphenylyl (m-terphenyl-2′-yl, m-terphenyl-4′-yl, m-terphenyl-5′-yl, o-terphenyl-3′-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(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), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a condensed pentacyclic aryl )yl, pentacene-(1-,2-,5-,6-)yl, etc.

"Heteroaryl" of "optionally substituted heteroaryl" includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl , pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl and the like.

Also, the above aryl and heteroaryl may be substituted, and each may be substituted, for example, by the above aryl or heteroaryl.

Specific examples of this pyrimidine derivative include the following compounds.

This pyrimidine derivative can be produced using known raw materials and known synthetic methods.

<Carbazole derivative>
A carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which multiple such compounds are bonded via single bonds. Details are described in US Publication No. 2014/0197386.

Each Ar is independently optionally substituted aryl or optionally substituted heteroaryl. n is independently an integer of 0-4, preferably an integer of 0-3, more preferably 0 or 1;

The "aryl" of "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, Aryl having 6 to 12 carbon atoms is more preferable.

Specific “aryl” includes monocyclic aryl phenyl, bicyclic aryl (2-,3-,4-)biphenylyl, condensed bicyclic aryl (1-,2-)naphthyl , tricyclic aryl terphenylyl (m-terphenyl-2′-yl, m-terphenyl-4′-yl, m-terphenyl-5′-yl, o-terphenyl-3′-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(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), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a condensed pentacyclic aryl )yl, pentacene-(1-,2-,5-,6-)yl, etc.

"Heteroaryl" of "optionally substituted heteroaryl" includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl , pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl and the like.

Also, the above aryl and heteroaryl may be substituted, and each may be substituted, for example, by the above aryl or heteroaryl.

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

Specific examples of this carbazole derivative include the following compounds.

This carbazole derivative can be produced using known starting materials and known synthetic methods.

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

Each Ar is independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1-4, preferably an integer of 1-3, more preferably 2 or 3;

The "aryl" of "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, Aryl having 6 to 12 carbon atoms is more preferable.

Specific “aryl” includes monocyclic aryl phenyl, bicyclic aryl (2-,3-,4-)biphenylyl, condensed bicyclic aryl (1-,2-)naphthyl , tricyclic aryl terphenylyl (m-terphenyl-2′-yl, m-terphenyl-4′-yl, m-terphenyl-5′-yl, o-terphenyl-3′-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(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), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a condensed pentacyclic aryl )yl, pentacene-(1-,2-,5-,6-)yl, etc.

"Heteroaryl" of "optionally substituted heteroaryl" includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Heteroaryl includes, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl , pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl and the like.

Also, the above aryl and heteroaryl may be substituted, and each may be substituted, for example, by the above aryl or heteroaryl.

Specific examples of this triazine derivative include the following compounds.

This triazine derivative can be produced using known raw materials and known synthetic methods.

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

φ is an n-valent aryl ring (preferably n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4; , and the "benzimidazole-based substituent" is 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 substituted for the imidazole group, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

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

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can refer to the description of the above formula (ETM-2-1) or formula (ETM-2-2). For R ¹¹ to R ¹⁸ in the formula, the description of the above formula (ETM-2-1) or (ETM-2-2) can be cited. In addition, the above formula (ETM-2-1) or formula (ETM-2-2) is described in a form in which two pyridine-based substituents are bonded, but when replacing these with a benzimidazole-based substituent, both may be replaced with a benzimidazole-based substituent (i.e., n=2), or any one pyridine-based substituent may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced by R ¹¹ ~ ^R18 may be substituted (ie n=1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) may be replaced with a benzimidazole-based substituent, and the “pyridine-based substituent” may be replaced with R ¹¹ to R ¹⁸ .

Specific examples of this benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-( Naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl) -1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, 1-(4 -(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2- phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole and the like.

This benzimidazole derivative can be produced using known raw materials and known synthetic methods.

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

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

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

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

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

Specific examples of this phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10- phenanthrolin-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-bis(1,10-phenanthroline-5-yl), bathocuproine and 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene.

This phenanthroline derivative can be produced using known raw materials and known synthetic methods.

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。 <Quinolinol-based metal complex>
A quinolinol-based metal complex is, for example, a compound represented by the following general formula (ETM-13).

wherein R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; n is an integer of 1-3.

Specific examples of quinolinol-based metal complexes include 8-quinolinollithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3 ,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato) ( phenolate)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(3-methylphenolate)aluminum, bis(2-methyl-8- quinolinolato)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(3-phenylphenolate)aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2,3-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolato) ( 2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethylphenolate) Aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolate)aluminum, bis( 2-methyl-8-quinolinolato)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl -8-quinolinolato)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinolato)(2 -naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolato) ) (3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolato)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-dimethylphenolate) lacto)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolato)aluminum-μ-oxo-bis(2 -methyl-8-quinolinolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)aluminum, μ-oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-4-ethyl -8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolato)aluminum, bis(2-methyl-4-methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2 -methyl-4-methoxy-8-quinolinolato)aluminum, bis(2-methyl-5-cyano-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolato)aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolato)aluminum, bis(10-hydroxybenzo[h]quinoline) beryllium, etc.

This quinolinol-based metal complex can be produced using known raw materials and known synthetic methods.

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 Derivatives and Benzothiazole Derivatives>
A thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

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

φ in each formula is an n-valent aryl ring (preferably 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 is an integer, and the “thiazole-based substituent” or “benzothiazole-based substituent” is the “pyridine-based The pyridyl group in "substituent" is a substituent substituted with a thiazole group or a benzothiazole group, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with deuterium.

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can refer to the description of the above formula (ETM-2-1) or formula (ETM-2-2). For R ¹¹ to R ¹⁸ in the formula, the description of the above formula (ETM-2-1) or (ETM-2-2) can be cited. In addition, the above formula (ETM-2-1) or formula (ETM-2-2) is described in the form of two pyridine-based substituents bonded, but these are thiazole-based substituents (or benzothiazole-based substituents group), both pyridine-based substituents may be replaced with thiazole-based substituents (or benzothiazole-based substituents) (i.e., n=2), or any one pyridine-based substituent may be replaced with a thiazole-based substituent. (or benzothiazole-based substituents) and the other pyridine-based substituents may be replaced with R ¹¹ to R ¹⁸ (ie n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a “pyridine-based substituent” of R ¹¹ to R ¹⁸ . can be replaced with

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

The electron-transporting layer or electron-injecting layer may further contain a substance capable of reducing the material forming the electron-transporting layer or electron-injecting layer. Various substances are used as the reducing substance as long as they have a certain reducing property. from the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one selected can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and Ca (2.95 eV). 9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and materials with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals 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, it is possible to improve the emission luminance and extend the life of the organic EL device. As a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, particularly a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By containing Cs, the reduction ability can be efficiently exhibited, and by addition to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL device can be improved and the life of the device can be extended.

<Cathode in Organic Electroluminescent Device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. 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 alloys, magnesium - indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum, etc.). Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective in increasing the electron injection efficiency and improving device characteristics. However, these low work function metals are generally unstable in the atmosphere. In order to improve this point, for example, a method of doping an organic layer with a small amount of lithium, cesium, or magnesium to use a highly stable electrode is known. Other dopants can also be inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide. However, it is not limited to these.

Furthermore, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride A preferable example is lamination of a hydrocarbon-based polymer compound or the like. The method of manufacturing these electrodes is not particularly limited, either by resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like, as long as it can provide electrical continuity.

<Binder that may be used in each layer>
The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer described above can form each layer alone. Polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It can also be used by dispersing it in solvent-soluble resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, and other curable resins. be.

<Method for producing organic electroluminescent element>
Each layer constituting the organic electroluminescence element is formed by depositing a material for each layer by vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating, casting, coating, or the like. It can be formed by using a thin film. The thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation film thickness measuring device or the like. When thin film formation is performed using a vapor deposition method, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, and the like. The vapor deposition conditions are generally a crucible heating temperature of +50 to +400° C., a degree of vacuum of 10 ⁻⁶ to 10 ⁻³ Pa, a vapor deposition rate of 0.01 to 50 nm/sec, a substrate temperature of −150 to +300° C., and a film thickness of 2 nm. It is preferable to appropriately set the thickness in the range of up to 5 μm.

Next, as an example of a method for producing an organic electroluminescent device, an organic electric field consisting of an anode/hole injection layer/hole transport layer/light emitting layer composed of a host material and a dopant material/electron transport layer/electron injection layer/cathode. A method for manufacturing a light-emitting element will be described. A thin film of an anode material is formed on a suitable 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 thereon to form a thin film to form a light-emitting layer, an electron-transporting layer and an electron-injecting layer are formed on the light-emitting layer, and a thin film of a cathode material is formed by vapor deposition or the like. By forming and using it as a cathode, the desired organic electroluminescence device can be obtained. In the production of the organic electroluminescent device described above, the order of production may be reversed to produce 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. It is possible.

When a DC voltage is applied to the organic electroluminescence device thus obtained, it is sufficient to apply the positive polarity to the positive electrode and the negative polarity to the negative electrode. Light emission can be observed from the electrode side (anode or cathode, and both). Moreover, this organic electroluminescence device emits light even when a pulse current or an alternating current is applied. Note that the AC waveform to be applied may be arbitrary.

<Application example of organic electroluminescence device>
The present invention can also be applied to a display device having an organic electroluminescence element, a lighting device having an organic electroluminescence element, or the like.
A display device or a lighting device equipped with an organic electroluminescent device can be manufactured by a known method such as connecting the organic electroluminescent device according to the present embodiment and a known driving device. It can be driven by appropriately using a known driving method such as driving.

Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (for example, JP-A-10-335066 and JP-A-2003-321546). (See Japanese Patent Laid-Open No. 2004-281086, etc.). Moreover, the display method of the display includes, for example, a matrix and/or a segment method. Note that matrix display and segment display may coexist in the same panel.

In the matrix, pixels for display are arranged in a two-dimensional pattern such as a grid pattern or a mosaic pattern, and a set of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, in the image and character display of personal computers, monitors, and televisions, square 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, a pixel with a side of mm order is used. become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are displayed side by side. In this case, there are typically delta type and stripe type. As a method for driving this matrix, either a line-sequential driving method or an active matrix method may be used. The line-sequential drive has the advantage of being simpler in structure, but 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 illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating state displays in audio equipment and electromagnetic cookers, and panel displays in automobiles.

Examples of lighting devices include lighting devices such as indoor lighting, backlights for liquid crystal display devices, and the like (for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, and the like). etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light by themselves, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, and the like. In particular, as a liquid crystal display device, especially a backlight for a personal computer, for which thinning is a problem, it is difficult to reduce the thickness of the conventional method because it is made of a fluorescent lamp or a light guide plate. The backlight using the light-emitting element according to 1 is characterized by its thinness and light weight.

EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these.

Example A
<Delayed fluorescence lifetime measurement using triphenylbismuth>
Using triphenylbismuth as an additive containing heavy atoms, a PMMA (polymethyl methacrylate) dispersion film mixed with a TADF dopant represented by the following structural formula was formed on a quartz substrate to prepare a sample. The samples were prepared as sample (1) in which a PMMA dispersed film was formed by mixing 10% by mass of triphenylbismuth and 1% by mass of TADF dopant, and sample (2) in which a PMMA dispersed film containing only 1% by mass of TADF dopant was formed. bottom.

Then, the delayed fluorescence lifetimes of the prepared samples (1) and (2) were measured using a delayed fluorescence lifetime measurement device (product name: "Quantaurus-Tau", manufactured by Hamamatsu Photonics K.K.).
As a result, sample (1) had a delayed fluorescence lifetime of 8 μs, while sample (2) had a delayed fluorescence lifetime of 34 μs.
In other words, it is believed that the bismuth atoms of triphenylbismuth exerted an external heavy atom effect on the TADF dopant, accelerating the reverse intersystem crossing process.
From this result, it can be understood that the delayed fluorescence lifetime of the TADF dopant is shortened by the heavy atom effect by including a compound containing a heavy atom such as triphenylbismuth as a host in the light-emitting layer.

Example B
<Evaluation as a host compound or additive>
It was estimated by DFT calculation whether or not the compound shown below is a light-emitting material having TADF activity when used as a host.

After optimizing the structure of the ground state according to the PBE0/6-31G(d) (heavy atom basis function is SBKJC+p) method, the vertical excitation energy from the ground state is calculated according to the Time-dependent DFT method. Calculated. All calculations were performed using the quantum chemical calculation program Firefly (AA Granovsky, Firefly version 8).

It should be noted that a practical host or additive for the TADF dopant should have higher singlet and triplet energy levels than the TADF dopant. Here, assuming a compound with an emission wavelength of 450 nm and ΔE _ST =0.1 as a practical TADF dopant, its S ₁ excitation energy is 2.75 eV and T ₁ excitation energy is 2.85 eV.
Therefore, when the calculated "S ₁ excitation energy is 2.75 eV or more" of the compound to be measured and "T ₁ excitation energy is 2.85 eV or more", the compound is used as a host or additive determined that it was possible.

Example B-1
The S ₁ excitation energy of the following compound (1-1) was calculated to be 3.16 eV (393 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 2.90 eV (427 nm in terms of wavelength). Therefore, it can be judged that the following compound (1-1) can be used as a host or an additive.

Example B-2
The S ₁ excitation energy of the following compound (2-241) was calculated to be 4.53 eV (274 nm in terms of wavelength) and the T ₁ excitation energy was calculated to be 3.53 eV (351 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-241) can be used as a host or additive.

Example B-3
The S ₁ excitation energy of the following compound (2-481) was calculated to be 4.56 eV (272 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.50 eV (354 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-481) can be used as a host or additive.

Example B-4
The S ₁ excitation energy of the following compound (2-601) was calculated to be 4.70 eV (264 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.48 eV (356 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-601) can be used as a host or additive.

Example B-5
The S ₁ excitation energy of the following compound (2-681) was calculated to be 3.70 eV (335 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.28 eV (378 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-681) can be used as a host or additive.

Example B-6
The S ₁ excitation energy of the following compound (2-401) was calculated to be 3.94 eV (315 nm in terms of wavelength) and the T ₁ excitation energy was 3.32 eV (373 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-401) can be used as a host or additive.

Example B-7
The S ₁ excitation energy of the following compound (2-361) was calculated to be 3.86 eV (321 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.26 eV (380 nm in terms of wavelength). Therefore, it can be determined that the following compound (2-361) can be used as a host or additive.

Example B-8
The S ₁ excitation energy of the following compound (3-761) was calculated to be 4.98 eV (249 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.46 eV (358 nm in terms of wavelength). Therefore, it can be determined that the following compound (3-761) can be used as a host or additive.

Example B-9
The S ₁ excitation energy of the following compound (3-881) was calculated to be 4.98 eV (249 nm in terms of wavelength) and the T ₁ excitation energy was calculated to be 3.46 eV (358 nm in terms of wavelength). Therefore, it can be determined that the following compound (3-881) can be used as a host or additive.

Example B-10
The S ₁ excitation energy of the following compound (3-1001) was calculated to be 5.00 eV (248 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 3.49 eV (355 nm in terms of wavelength). Therefore, it can be determined that the following compound (3-1001) can be used as a host or additive.

Example B-11
The S ₁ excitation energy of the following compound (3-1081) was calculated to be 3.15 eV (394 nm in terms of wavelength), and the T ₁ excitation energy was calculated to be 2.84 eV (437 nm in terms of wavelength). Therefore, it can be determined that the following compound (3-1081) can be used as a host or additive.

Example B-11
The S ₁ excitation energy of the following compound (3-1161) was calculated to be 4.31 eV (288 nm in terms of wavelength) and the T ₁ excitation energy was 3.37 eV (368 nm in terms of wavelength). Therefore, it can be determined that the following compound (3-1161) can be used as a host or additive.

As described above, some of the compounds that can be used in the present invention have been evaluated and shown to be excellent organic device materials, but other compounds that have not been evaluated have the same basic skeleton and are similar overall. It can be understood by those skilled in the art that the compound having the structure of is also an excellent organic device material.

According to a preferred embodiment of the present invention, as the first component, at least one organic compound or inorganic compound containing a specific element in the molecule, and as the second component, at least one thermally activated delayed phosphor. By producing an organic EL device having a light-emitting layer containing the organic EL device, it is possible to provide an organic EL device having thermally activated delayed fluorescence (TADF) activity.

REFERENCE SIGNS LIST 100 organic electroluminescent element 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 (15)

An organic electroluminescent device having a light-emitting layer,
The light-emitting layer contains at least one selected from organic compounds and inorganic compounds as a first component and at least one thermally activated delayed phosphor as a second component,
The organic compound is an organic compound represented by either the following general formula (A-1) or formula (A-2) ,
The inorganic compound is an inorganic compound containing one selected from elements of the 5th period and the 6th period,
Organic electroluminescence device.

(In the above general formulas (A-1) and (A-2),
Y ¹ is Ga, Ge—R, Sn—R, As, Sb, Sb=O, Sb=S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi=O, Bi=S , Bi(--R) ₂ or Bi to which an orthochloranyl group is attached, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently an aryl , heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ are optionally bonded to each other,
Y ² is Sn—R, Sb, Sb═O, Sb═S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi═O, Bi═S, Bi(—R) ₂ or Bi to which an orthochloranyl group is attached, and the Rs of Sn—R , Sb(—R) ₂ and Bi(—R) ₂ are each independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryl oxy, halogen or cyano, and the two Rs of Sb(-R) ₂ or Bi(-R) ₂ may be bonded to each other;
X ¹ , X ² and X ³ are each independently a group containing C or N directly bonded to at least Y ¹ or Y ² ;
The linking group linking X ¹ and X ² , X ² and X ³ and X ³ and X ¹ in formula (A-1) may have a ring that does not contain Y ¹ ,
The linking group that links X ² and X ³ and X ³ and X ¹ in formula (A-2) may have a ring that does not contain Y ² , and
At least one hydrogen in the organic compound represented by formula (A-1) or formula (A-2) may be substituted with cyano, halogen, or deuterium. ) 2. The organic electroluminescence device according to claim 1 , comprising at least one organic compound represented by any one of the following general formula (i), formula (ii) and formula (iii) as the first component.

(In the general formula (i) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ¹ is Ga, Ge—R, Sn—R, As, Sb, Sb=O, Sb=S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi=O, Bi=S , Bi(--R) ₂ or Bi to which an orthochloranyl group is attached, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently an aryl , heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(--R) ₂ or Bi(--R) ₂ may be bonded to each other, and
At least one hydrogen in the organic compound represented by general formula (i) may be substituted with cyano, halogen or deuterium. )

(In the general formula (ii) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ² is Sn—R, Sb, Sb═O, Sb═S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi═O, Bi═S, Bi(—R) ₂ or Bi to which an orthochloranyl group is attached, and the Rs of Sn—R , Sb(—R) ₂ and Bi(—R) ₂ are each independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryl oxy, halogen or cyano, and the two Rs of Sb(-R) ₂ or Bi(-R) ₂ may be bonded to each other;
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring, and
At least one hydrogen in the organic compound represented by general formula (ii) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (iii),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ¹ is Ga, Ge—R, Sn—R, As, Sb, Sb=O, Sb=S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi=O, Bi=S , Bi(--R) ₂ or Bi to which an orthochloranyl group is attached, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently an aryl , heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(—R) ₂ or Bi(—R) ₂ are optionally bonded to each other,
X ⁴ , X ⁵ and X ⁶ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and > Each R of C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and R of said >NR and/or >C(-R) ₂ may be bonded to at least one of said A ring, B ring and C ring, and
At least one hydrogen in the organic compound represented by general formula (iii) may be substituted with cyano, halogen or deuterium. ) In the general formula (i), formula (ii) and formula (iii),
At least one hydrogen in ring A, ring B and ring C is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl, cyclo optionally substituted with alkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
The organic electroluminescence device according to claim 2 . 2. The organic electroluminescence device according to claim 1, comprising at least one organic compound represented by any one of the following general formula (1), formula (2) and formula (3) as the first component .

(In the above general formula (1),
R ¹ to R ¹² are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y ¹ is Ga, As, Sb, Sb=O, Bi or Bi=O, and
At least one hydrogen in the organic compound represented by general formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y ² is Sb , Sb=O, Bi or Bi=O;
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) _2, >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >N—R and/or >C(—R) ₂ may be bonded to at least one of the a ring, b ring and c ring, and
At least one hydrogen in the organic compound represented by general formula (2) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (3),
R ¹ to R ⁹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁷ to R ⁹ and R ⁴ to R ⁶ , two groups adjacent to each other are bonded together to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y ¹ is Ga, As, Sb, Sb=O, Bi or Bi=O,
X ⁴ , X ⁵ and X ⁶ are each independently selected from >O, >NR, >C(-R) ₂ , >S, >Se and a single bond, wherein said >NR and > Each R of C(-R) ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and R of said >NR and/or >C(-R) ₂ may be bonded to at least one of said a ring, b ring and c ring, and
At least one hydrogen in the organic compound represented by general formula (3) may be substituted with cyano, halogen or deuterium. ) The organic compound represented by any one of the general formula (1), formula (2) and formula (3) (however, options for Y ² in formula (2) in this case include Sb, Sb=O, 5. The organic electroluminescence device according to claim 4 , wherein Bi and Bi═O, including Ga and As, are substituted with at least one group represented by the following structural formula.

(In the above structural formula,
Me represents methyl, tBu represents t-butyl, tAm represents t-amyl, tOct represents t-octyl,
At least one hydrogen in the above structural formula is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl optionally substituted with oxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl. ) In the general formulas (1), (2) and (3) ,
R ¹ to R ¹² are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (where each aryl is aryl having 6 to 12 carbon atoms), diarylboryl ( However, each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. ,
Two adjacent groups among R ¹ to R ¹² 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 ring a, ring b or ring c. at least one hydrogen in the ring formed is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms); diarylboryl (wherein each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cyclo having 3 to 24 carbon atoms; optionally substituted with alkyl,
Y ¹ and Y ² are Sb, Sb=O , Bi, or Bi=O;
X ⁴ and X ⁵ in the general formula (2) are each independently >O, >NR or >S, and R in >NR is an aryl having 6 to 10 carbon atoms; alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and
X ⁴ to X ⁶ in the general formula (3) are each independently >O or >S;
6. The organic electroluminescence device according to claim 4 or 5 . 2. The organic electroluminescence device according to claim 1, comprising an organic compound represented by any one of the following formulas as the first component.

(In the above formula,
Y ¹ and Y ² are Ga, As, Sb or Bi;
Each R is independently aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. ) 2. The organic electroluminescence device according to claim 1, comprising an organic compound represented by any one of the following formulas as the first component.

Any one of claims 1 to 8 , wherein the second component comprises at least one thermally-activated delayed phosphor that is a compound represented by any one of the following general formulas (4) and (5): 3. The organic electroluminescence device according to .

(In the above general formula (4),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
X ⁴ and X ⁵ are each independently selected from >O, >NR and >C(-R) ₂ , provided that X ⁴ and X ⁵ are >C(-R) ₂ at the same time and R in the above >NR and >C(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N—R and/or >C(—R) ₂ is bonded to at least one of ring a, ring b and ring c; well, and
At least one hydrogen in the compound represented by general formula (4) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (5),
R ¹ to R ¹⁴ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In addition, two adjacent groups of R ¹² to R ¹⁴ , R ⁹ to R ¹¹ , R ³ to R ⁵ and R ⁶ to R ⁸ are bonded to each other to form a ring, b ring, c ring or An aryl ring or heteroaryl ring may be formed together with the d ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, or diarylboryl (wherein the two aryls are a single bond or a linking group). ), optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, wherein at least one hydrogen in these is further substituted with aryl, heteroaryl, alkyl or cycloalkyl well,
X ⁴ to X ⁷ are each independently selected from >O, >N—R and >C(-R) ₂ , provided that X ⁴ to X ⁷ are simultaneously >C(-R) ₂ and R in the above >NR and >C(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and R in >N—R and/or >C(—R) ₂ is at least one of the a ring, b ring, c ring and d ring; may be combined, and
At least one hydrogen in the compound represented by general formula (5) may be substituted with cyano, halogen or deuterium. ) A display device or lighting device comprising the organic electroluminescence device according to any one of claims 1 to 9 . A polycyclic aromatic compound represented by any one of the following general formula (i) and formula (ii) .

(In the general formula (i) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ¹ is Ga, Ge—R, Sn—R, As, Sb, Sb=O, Sb=S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi=O, Bi=S , Bi(--R) ₂ or Bi to which an orthochloranyl group is attached, wherein each R of said Ge--R, Sn--R, Sb(--R) ₂ and Bi(--R) ₂ is independently an aryl , heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, halogen or cyano, and the two Rs of Sb(--R) ₂ or Bi(--R) ₂ may be bonded to each other, and
At least one hydrogen in the compound represented by general formula (i) may be substituted with cyano, halogen or deuterium. )

(In the general formula (ii) above,
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ² is Sn—R, Sb, Sb═O, Sb═S, Sb(—R) ₂ , Sb to which an orthochloranyl group is attached, Bi, Bi═O, Bi═S, Bi(—R) ₂ or Bi to which an orthochloranyl group is attached, and the Rs of Sn—R, Sb(—R) ₂ and Bi(—R) ₂ are each independently aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryl oxy, halogen or cyano, and the two Rs of Sb(-R) ₂ or Bi(-R) ₂ may be bonded to each other;
X ⁴ and X ⁵ are each independently selected from >O, >NR, >C(-R) _2, >S, >Se and a single bond, wherein said >NR and >C(- R) each R of ₂ is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; In addition, R in the >NR and/or >C(-R) ₂ may be bonded to at least one of the A ring, the B ring and the C ring, and
At least one hydrogen in the compound represented by general formula (ii) may be replaced with cyano, halogen or deuterium. ) In the general formula (i) and formula (ii) ,
At least one hydrogen in ring A, ring B and ring C is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group), alkyl, cyclo alkyl, alkoxy or aryloxy in which at least one hydrogen may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
The polycyclic aromatic compound according to claim 11 . A polycyclic aromatic compound represented by any one of the following general formula (1) and formula (2) .

(In the above general formula (1),
R ¹ to R ¹² are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ⁴ , R ⁹ to R ¹² and R ⁵ to R ⁸ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y ¹ is Ga, As, Sb, Sb=O, Bi or Bi=O, and
At least one hydrogen in the compound represented by general formula (1) may be substituted with cyano, halogen or deuterium. )

(In the above general formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diarylboryl (wherein two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl , alkoxy or aryloxy, wherein at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl;
In each of R ¹ to R ³ , R ⁸ to R ¹¹ and R ⁴ to R ⁷ , two adjacent groups are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diarylboryl (wherein the two aryls may be bonded via a single bond or a linking group); optionally substituted with alkyl, cycloalkyl, alkoxy or aryloxy, at least one hydrogen in which is further optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl;
Y ² is Sb , Sb=O, Bi or Bi=O;
X ⁴ and X ⁵ are each independently selected from >O, >C(-R) ₂ , >S, >Se and a single bond, and R of said >C(-R) ₂ is each independently is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound represented by general formula (2) may be substituted with cyano, halogen or deuterium. ) In the general formulas (1) and (2) ,
R ¹ to R ¹² are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (where each aryl is aryl having 6 to 12 carbon atoms), diarylboryl ( However, each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. ,
Two adjacent groups among R ¹ to R ¹² 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 ring a, ring b or ring c. at least one hydrogen in the ring formed is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl is aryl having 6 to 12 carbon atoms); diarylboryl (wherein each aryl is an aryl having 6 to 12 carbon atoms, which may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cyclo having 3 to 24 carbon atoms; optionally substituted with alkyl,
Y ¹ and Y ² are Sb, Sb=O , Bi, or Bi=O;
X ⁴ and X ⁵ in the general formula (2) are each independently >O, >NR or >S, and R in >NR is an aryl having 6 to 10 carbon atoms; alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and
X ⁴ to X ⁶ in the general formula (3) are each independently >O or >S;
The polycyclic aromatic compound according to claim 13 . The polycyclic aromatic compound according to any one of claims 11 to 14 , wherein said halogen is fluorine.

Images