WO2021095729A1 - Nitrogen-containing heterocyclic compound having perfluoroalkyl group, and use therefor - Google Patents

Abstract

A nitrogen-containing heterocyclic compound having a perfluoroalkyl group and having a suitable light emission wavelength, and a use therefor are provided. This nitrogen-containing heterocyclic compound having a perfluoroalkyl group has N carbazole rings (N being an integer greater than or equal to 2), wherein two adjacent carbazole rings are linked by (A) a direct bond, (B) a bond mediated by a π-conjugated linking group or (C) a condensation bond, and the total number of perfluoroalkyl groups substituent in the N carbazole rings is greater than or equal to 1 and less than 2N.

Description

Nitrogen-containing heterocyclic compounds having a perfluoroalkyl group and their use

A nitrogen-containing heterocyclic compound having a perfluoroalkyl group and a technique related to its utilization are disclosed.

A search for light emitting materials for organic light emitting elements such as organic light emitting diodes (OLEDs) is being conducted. As the light emitting material, it is required that various characteristics such as light emitting color (light emitting maximum wavelength), light emitting efficiency (light emitting quantum yield), and excited state stability (durability) are preferable. Among the light emitting materials for OLED, compounds showing Thermally Activated Delayed Fluorescence (TADF) are expected as next-generation light emitting materials because they show high luminous efficiency even though they are pure organic substances.

Regarding TADF materials, for example, Patent Document 1 describes that a compound having a carbazole ring represented by the following formula has high luminous efficiency.

Further, Patent Document 2 describes that a compound having a carbazole ring having a perfluoroalkyl group represented by the following formula has high luminous efficiency.

International Publication No. 2016/181846 International Publication No. 2018/0479848

The present inventors have substituted compounds having a trifluoromethyl group in all carbazole rings (compounds described in Patent Document 2) and compounds having the same skeleton in which trifluoromethyl groups have not been substituted in carbazole rings (Patent Documents). It has been found that the compound described in 1) has a problem that the emission wavelength sometimes reaches the ultraviolet region and includes light emission that adversely affects the human body known as blue light.

Therefore, one object of the present invention is to provide a nitrogen-containing heterocyclic compound having a perfluoroalkyl group having a suitable emission wavelength, and a technique relating to its use.

（式中、Ｑは、単結合又は－ＣＨ₂－である。）
で表される環Ｘを有する化合物において、隣り合う２個の環Ｘが、(A)直接連結、(B)π共役連結基を介した連結、及び(C)縮合連結のいずれかにより連結しており、Ｎ個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個以上２Ｎ個未満であると、Ｎ個の環Ｘに置換するパーフルオロアルキル基の合計の数が０個又は２Ｎ個である点を除き同じ構造を有する化合物よりも発光波長が長くなり、好適な発光波長を有することを見出した。本発明は、この知見に基づいてさらに検討を重ねて完成したものである。 As a result of diligent studies to solve the above problems, the present inventors have obtained N equations (X): N (N is an integer of 2 or more):

(In the equation, Q is a single bond or -CH _2- .)
In a compound having a ring X represented by, two adjacent rings X are linked by either (A) direct linking, (B) linking via a π-conjugated linking group, or (C) condensation linking. If the total number of perfluoroalkyl groups substituted with N rings X is 1 or more and less than 2N, the total number of perfluoroalkyl groups substituted with N rings X is 0. Alternatively, it has been found that the emission wavelength is longer than that of the compound having the same structure except that the number is 2N, and the compound has a suitable emission wavelength. The present invention has been further studied and completed based on this finding.

（式中、Ｑは、単結合又は－ＣＨ₂－である。）
で表される環Ｘを有する化合物であって、隣り合う２個の環Ｘが、(A)直接連結、(B)π共役連結基を介した連結、及び(C)縮合連結のいずれかにより連結しており、Ｎ個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個以上２Ｎ個未満である、化合物［但し、下記の化合物：

（式中、Ｙは、シアノ基又はパーフルオロメチル基である。）
を除く］。
項２．
　(A)直接連結の場合、一方の環Ｘの窒素原子と、他方の環Ｘに含まれるベンゼン環に結合する窒素原子に対してパラ位にある炭素原子とが単結合により連結し、
　(B)π共役連結基を介した連結の場合、双方の環Ｘの窒素原子同士がπ共役連結基を介して連結し、
　(C)縮合連結の場合、双方の環Ｘが縮合して式：

（式中、Ｑ¹及びＱ²は、それぞれ独立して、単結合又は－ＣＨ₂－である。）
で表される環を形成することにより連結する、
項１に記載の化合物。
項３．
　π共役連結基が、芳香環基である、項１又は２に記載の化合物。
項４．
　１個以上Ｎ個未満の環Ｘの各々に含まれる少なくとも１個のベンゼン環が、当該ベンゼン環に結合する窒素原子に対してメタ位にパーフルオロアルキル基を有する、項１～３のいずれか一項に記載の化合物。
項５．
　１個以上Ｎ個未満の環Ｘの各々に含まれる少なくとも１個のベンゼン環が、当該ベンゼン環に結合する窒素原子に対してパラ位にパーフルオロアルキル基を有する、項１～３のいずれか一項に記載の化合物。
項６．
　パーフルオロアルキル基が、パーフルオロＣ_1-4アルキル基である、項１～５のいずれか一項に記載の化合物。
項７．
　１個以上の環Ｘに電子供与性基が置換している、項１～６のいずれか一項に記載の化合物。
項８．
　Ｑが、単結合である、項１～７のいずれか一項に記載の化合物。
項９．
　下記式（１）～（３）：

［式中、
Ｒ¹⁰は、１価の芳香環基であり、
Ｒ¹¹～Ｒ²⁰は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、３個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個～５個である）、
Ｑ¹¹～Ｑ¹³は、それぞれ独立して、単結合又は－ＣＨ₂－であり、
Ｒ²¹及びＲ²²は、それぞれ独立して、水素原子、アルキル基、又は１価の芳香環基であり、
Ｒ²³～Ｒ²⁶は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、ｍ個のＬに置換する環Ｘに置換するパーフルオロアルキル基の合計の数が、１個以上２ｍｎ個未満である）、
Ｑ²¹は、単結合又は－ＣＨ₂－であり、
Ｌは、１個の芳香環で構成される連結基であり、
ｍは、１以上の整数であり、
ｎは、２以上Ｌに置換可能な最大数以下の整数であり、
ｐ及びｑは、それぞれ独立して、０又はＬに置換可能な最大数であり、
Ｒ³¹、Ｒ³⁵、及びＲ³⁹は、それぞれ独立して、１価の芳香環基であり、
Ｒ³²～Ｒ³⁴、Ｒ³⁶～Ｒ³⁸、及びＲ⁴⁰～Ｒ⁴⁸は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、６個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個～８個である）、
Ｑ³¹～Ｑ³³及びＱ⁴¹～Ｑ⁴³は、それぞれ独立して、単結合又は－ＣＨ₂－である］のいずれかで表される、項１に記載の化合物。
項１０．
　下記式（a）を満たす、項１～９のいずれか一項に記載の化合物：
Ｗ₁＞Ｗ₀　（a）
［式（a）のＷ₁は、下記式（b）：
Ｗ＝863.2－0.4440×SMR_VSA9[Ų]＋2.109×fr_para_hydroxylation[-]－115.4×HOMO-LUMO Gap[eV]　（b）
において、前記化合物の記述子SMR_VSA9、fr_para_hydroxylation、及びHOMO-LUMO Gapの値を代入して得られるＷであり、
式（a）のＷ₀は、式（b）において、前記化合物に含まれる環Ｘの合計の数をＮ個としたとき、Ｎ個の環Ｘに置換するパーフルオロアルキル基の合計の数が２Ｎ個である以外、前記化合物と同じ構造を有する比較化合物の記述子SMR_VSA9、fr_para_hydroxylation、及びHOMO-LUMO Gapの値を代入して得られるＷである］。
項１１．
　項１～１０のいずれか一項に記載の化合物を含む遅延蛍光材料。
項１２．
　項１～１０のいずれか一項に記載の化合物を含む有機発光素子。
項１３．
　有機ＥＬ素子である、請求項１２に記載の有機発光素子。
項１４．
　下記式（４）：

［式中、
Ｒ^1aは、１価の芳香環基であり、
Ｒ^1c及びＲ^1hが、パーフルオロアルキル基であり、Ｒ^1b、Ｒ^1d、Ｒ^1e、Ｒ^1f、Ｒ^1g、及びＲ¹ⁱのうち、１又は２個が臭素原子であり、残りが水素原子又は電子供与性基であるか、又は
Ｒ^1d及びＲ^1gが、パーフルオロアルキル基であり、Ｒ^1b、Ｒ^1c、Ｒ^1e、Ｒ^1f、Ｒ^1h、及びＲ¹ⁱのうち、１又は２個が臭素原子であり、残りが水素原子又は電子供与性基であり、Ｑ^1aは、単結合又は－ＣＨ₂－である］
で表される化合物。
項１４．
　下記式（５）：

［式中、
Ｒ²¹及びＲ²²は、それぞれ独立して、水素原子、アルキル基、又は１価の芳香環基であり、
Ｒ²³～Ｒ²⁶は、それぞれ独立して、水素原子又はパーフルオロアルキル基であり（但し、ｍ個のＬに置換する環のうち、少なくとも１個の環において、Ｒ²³～Ｒ²⁶の少なくとも１個は、パーフルオロアルキル基であり、Ｒ²³～Ｒ²⁶の全てがパーフルオロアルキル基ではない）、
Ｑ²¹は、単結合又は－ＣＨ₂－であり、
Ｌは、１個の芳香環で構成される連結基であり、
Ｘは、ハロゲン原子であり、
ｍは、１以上の整数であり、
ｎは、２以上Ｌに置換可能な最大数以下の整数であり、
ｐ及びｑは、それぞれ独立して、０又はＬに置換可能な最大数であり、
ａは、１以上ｎ未満の整数である］
で表される化合物。 The present invention includes the following aspects.
Item 1.
Expression (X) of N (N is an integer of 2 or more):

(In the equation, Q is a single bond or -CH _2- .)
A compound having a ring X represented by, in which two adjacent rings X are linked by either (A) direct linking, (B) linking via a π-conjugated linking group, or (C) condensation linking. Compounds in which the total number of perfluoroalkyl groups that are linked and substituted with N rings X is 1 or more and less than 2N [However, the following compounds:

(In the formula, Y is a cyano group or a perfluoromethyl group.)
except for].
Item 2.
(A) In the case of direct connection, the nitrogen atom of one ring X and the carbon atom at the para position with respect to the nitrogen atom bonded to the benzene ring contained in the other ring X are connected by a single bond.
(B) In the case of connection via a π-conjugated linking group, the nitrogen atoms of both rings X are linked via the π-conjugated linking group.
(C) In the case of condensation connection, both rings X are condensed and the formula:

(In the equation, Q ¹ and Q ² are independently single-bonded or -CH _2- .)
Connected by forming a ring represented by,
Item 2. The compound according to Item 1.
Item 3.
Item 2. The compound according to Item 1 or 2, wherein the π-conjugated linking group is an aromatic ring group.
Item 4.
Any of Items 1 to 3, wherein at least one benzene ring contained in each of one or more and less than N rings X has a perfluoroalkyl group at the meta position with respect to the nitrogen atom bonded to the benzene ring. The compound according to one item.
Item 5.
Any of Items 1 to 3, wherein at least one benzene ring contained in each of one or more and less than N rings X has a perfluoroalkyl group at the para position with respect to the nitrogen atom bonded to the benzene ring. The compound according to one item.
Item 6.
Item 6. The compound according to any one of Items 1 to 5, wherein the perfluoroalkyl group is a perfluoroC _{1-4 alkyl group.}
Item 7.
Item 6. The compound according to any one of Items 1 to 6, wherein one or more rings X are substituted with an electron donating group.
Item 8.
Item 2. The compound according to any one of Items 1 to 7, wherein Q is a single bond.
Item 9.
The following formulas (1) to (3):

[During the ceremony,
R ¹⁰ is a monovalent aromatic ring group and
R ¹¹ to R ²⁰ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (however, the total number of perfluoroalkyl groups substituted with three rings X is one. ~ 5),
Q ¹¹ ~ Q ¹³ are each independently a single bond or -CH ₂ -,
R ²¹ and R ²² are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
R ²³ to R ²⁶ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (provided that the total number of perfluoroalkyl groups substituted with ring X substituted with m Ls). Is 1 or more and less than 2 mn),
Q ²¹ is a single bond or -CH _2-
L is a linking group composed of one aromatic ring.
m is an integer greater than or equal to 1 and
n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
p and q are the maximum numbers that can be independently replaced with 0 or L, respectively.
R ³¹ , R ³⁵ , and R ³⁹ are independently monovalent aromatic ring groups, respectively.
R ³² to R ³⁴ , R ³⁶ to R ³⁸ , and R ⁴⁰ to R ⁴⁸ are independently hydrogen atoms, perfluoroalkyl groups, or electron donating groups (provided that they are replaced with 6 rings X). The total number of perfluoroalkyl groups to be produced is 1 to 8),
Item 2. The compound according to Item 1, wherein Q ³¹ to Q ³³ and Q ⁴¹ to Q ⁴³ are each independently represented by either a single bond or -CH _2-].
Item 10.
The compound according to any one of Items 1 to 9, which satisfies the following formula (a):
W ₁ > W ₀ (a)
_{[W 1 in} equation (a) is the following equation (b):
W = 863.2-0.4440 x SMR_VSA9 [Å ² ] + 2.109 x fr_para_hydroxylation [-] -115.4 x HOMO-LUMO Gap [eV] (b)
W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the compound in
_{W 0 in the} formula (a) is the total number of perfluoroalkyl groups substituted with N rings X, where N is the total number of rings X contained in the compound in the formula (b). W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the comparative compound having the same structure as the compound except that the number is 2N].
Item 11.
A delayed fluorescent material containing the compound according to any one of Items 1 to 10.
Item 12.
An organic light emitting device containing the compound according to any one of Items 1 to 10.
Item 13.
The organic light emitting element according to claim 12, which is an organic EL element.
Item 14.
The following formula (4):

[During the ceremony,
R ^1a is a monovalent aromatic ring group and
R ^1c and R ^1h are perfluoroalkyl groups, and ^{one or two of R 1b} , R ^1d , R ^1e , R ^1f , R ^1g , and R ¹ⁱ are bromine atoms, and the rest are hydrogen atoms or An electron donating group, or R ^1d and R ^1g are perfluoroalkyl groups, and one or two of ^{R 1b} , R ^1c , R ^1e , R ^1f , R ^1h , and R ^{1i are bromine.} It is an atom, the rest is a hydrogen atom or an electron donating group, and Q ^1a is a single bond or -CH _2- ].
The compound represented by.
Item 14.
The following formula (5):

[During the ceremony,
R ²¹ and R ²² are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
R ²³ to R ²⁶ are independently hydrogen atoms or perfluoroalkyl groups (provided that at least one of the m rings substituted with L has at least one of R ²³ to R ²⁶ . The individual is a perfluoroalkyl group, and ^{not all of R 23} to R ²⁶ are perfluoroalkyl groups),
Q ²¹ is a single bond or -CH _2-
L is a linking group composed of one aromatic ring.
X is a halogen atom,
m is an integer greater than or equal to 1 and
n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
p and q are the maximum numbers that can be independently replaced with 0 or L, respectively.
a is an integer greater than or equal to 1 and less than n]
The compound represented by.

According to the present invention, a nitrogen-containing heterocyclic compound having a perfluoroalkyl group having a suitable emission wavelength, and a technique relating to its use are provided.

FIG. 1A is a diagram showing ^{a 1} H NMR spectrum of the learning compound S5. FIG. 1B is a partially enlarged view of FIG. 1A. FIG. 2 is a diagram showing ^{a 1} H NMR spectrum of the learning compound S6. FIG. 3A is a diagram showing ^{a 1} H NMR spectrum of the learning compound S7. FIG. 3B is a partially enlarged view of FIG. 3A. FIG. 3C is a diagram showing ^{a 19} F NMR spectrum of the learning compound S7. ^{FIG. 4A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T1. ^{FIG. 4B is a diagram showing a 19} F NMR spectrum of an intermediate of the test compound T1. FIG. 4C is a diagram showing an IR spectrum of an intermediate of the test compound T1. ^{FIG. 5A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T4. FIG. 5B is a partially enlarged view of FIG. 5A. FIG. 5C is a diagram showing an IR spectrum of an intermediate of the test compound T4. ^{FIG. 6A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T19. FIG. 6B is a partially enlarged view of FIG. 6A. FIG. 6C is a diagram showing an IR spectrum of an intermediate of the test compound T19. FIG. 7A is ^{a diagram showing a 1} H NMR spectrum of the test compound T19. FIG. 7B is a partially enlarged view of FIG. 7A. FIG. 7C is a diagram showing an IR spectrum of the test compound T19. FIG. 8A is a diagram showing ^{a 1} H NMR spectrum of the test compound T19-2. FIG. 8B is a partially enlarged view of FIG. 8A. FIG. 8C is a diagram showing ^{a 19} F NMR spectrum of the test compound T19-2. FIG. 8D is a diagram showing an IR spectrum of the test compound T19-2. FIG. 9 is ^{a diagram showing a 1} H NMR spectrum of the test compound T21. ^{FIG. 10A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T22. FIG. 10B is a partially enlarged view of FIG. 10A. ^{FIG. 10C is a diagram showing a 19} F NMR spectrum of an intermediate of the test compound T22. ^{FIG. 11A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T25. FIG. 11B is a partially enlarged view of FIG. 11A. ^{FIG. 11C is a diagram showing a 19} F NMR spectrum of an intermediate of the test compound T25. ^{FIG. 12A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T28. 12B is a partially enlarged view of FIG. 12A. ^{FIG. 12C is a diagram showing a 19} F NMR spectrum of an intermediate of the test compound T28. FIG. 13A is ^{a diagram showing a 1} H NMR spectrum of the test compound T28. FIG. 13B is ^{a diagram showing a 19} F NMR spectrum of the test compound T28. FIG. 13C is a diagram showing an IR spectrum of the test compound T28. ^{FIG. 14A is a diagram showing a 1} H NMR spectrum of an intermediate of the test compound T31. 14B is a partially enlarged view of FIG. 14A. ^{FIG. 14C is a diagram showing a 19} F NMR spectrum of an intermediate of the test compound T31. FIG. 14D is a diagram showing an IR spectrum of an intermediate of the test compound T31. FIG. 15A is ^{a diagram showing a 1} H NMR spectrum of the test compound T34. FIG. 15B is a partially enlarged view of FIG. 15A. FIG. 15C is ^{a diagram showing a 19} F NMR spectrum of the test compound T34. FIG. 15D is a diagram showing an IR spectrum of the test compound T34.

<Definition>
In the present specification, unless otherwise specified, "halogen atom" is used in the sense of including a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

In the present specification, unless otherwise specified, the "alkyl group" means a chain saturated hydrocarbon group, and specifically, for example, a methyl group, an ethyl group, or a propyl group (n-propyl group, isopropyl). Groups), butyl groups (n-butyl group, isobutyl group, sec-butyl group, tert-butyl group), pentyl group, hexyl and other linear or branched C _1-20 alkyl groups.

In the present specification, unless otherwise specified, the "perfluoroalkyl group" means a group in which all hydrogen atoms of the alkyl group are substituted with fluorine atoms, and specifically, for example, a trifluoromethyl group. , Pentafluoroethyl group, heptafluoropropyl group (heptafluoro n-propyl group or heptafluoro i-propyl group) and other perfluoroC _1-12 alkyl groups.

In the present specification, unless otherwise specified, the "alkoxy group" means a group in which an oxygen atom is bonded to the terminal of the alkyl group, and specifically, for example, a methoxy group, an ethoxy group, or a propoxy group (n). -Propoxy group, isopropoxy group), butoxy group (n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group) and other linear or branched C _1-12 alkoxy groups can be mentioned.

In the present specification, unless otherwise specified, "aromatic ring" is used in the sense of including an aromatic hydrocarbon ring and an aromatic heterocycle.

The number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but is, for example, 6 to 40. The aromatic hydrocarbon ring is preferably a benzene ring or a condensed ring having a structure in which a plurality of benzene rings are condensed. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an anthracene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a tetracene ring, a benzopyrene ring, a perylene ring, a coronene ring, a phenanthrene ring, and a phenalene ring. Rings, triphenylene rings, etc. can be mentioned. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.

The number of ring-constituting atoms in the aromatic heterocycle is not particularly limited, but is, for example, 5 to 40 members. The aromatic heterocycle is preferably an aromatic heterocycle containing at least one heteroatom selected from an oxygen atom, a sulfur atom, and a nitrogen atom as a ring-constituting atom. Examples of the aromatic heterocycle include an oxygen-containing aromatic heterocycle (eg, furan ring, benzofuran ring, dibenzo [b, d] furan ring), and a sulfur-containing aromatic heterocycle (eg, thiophene ring, benzothiophene ring, etc.). Dibenzo [b, d] thiophene ring), nitrogen-containing aromatic heterocycle (eg, pyrrol ring, pyrazole ring, imidazole ring, 1,2,3-triazole ring, 1,2,4-triazole ring, pyridine ring, pyridazine) Ring, pyrimidine ring, pyrazine ring, 1,3,5-triazine ring, indole ring, indazole ring, benzoimidazole ring, quinoline ring, isoquinoline ring, sinoline ring, quinoxaline ring, phthalazine ring, naphthylidine ring, purine ring, acrydin ring , Phenazine ring, phenanthroline ring), oxygen-containing and nitrogen-aromatic heterocycle (eg, oxazole ring, isooxazole ring, benzoxazole ring, phenoxazine ring), sulfur-containing and nitrogen-aromatic heterocycle (eg, thiazole ring, iso) Thiazol ring, benzothiazole ring, phenothiazine ring). The aromatic heterocycle is usually other than a carbazole ring, preferably a 5- or 6-membered aromatic heterocycle, more preferably a 5- or 6-membered nitrogen-containing aromatic heterocycle, and pyridine. More preferably, it is a ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a 1,3,5-triazine ring.

The "aromatic ring" also includes an aromatic ring having one or more substituents. Examples of the substituent include an alkyl group, a perfluoroalkyl group, an alkoxy group, a cyano group, an aryl group, a heteroaryl group and the like, and these may be further substituted. The number of substituents is selected from a range of 0 or more and not more than the maximum number substitutable for aromatic rings, and may be, for example, 1, 2, 3, or 4.

In the present specification, unless otherwise specified, "monovalent aromatic ring group" means a group obtained by removing one hydrogen atom from the aromatic ring. The monovalent aromatic ring group includes a group obtained by removing one hydrogen atom from the aromatic hydrocarbon ring (aryl group) and a group obtained by removing one hydrogen atom from the aromatic heterocycle (heteroaryl group).

_{Examples of the aryl group include a C 6-18} aryl group such as a phenyl group and a naphthyl group.

Examples of the heteroaryl group include a fryl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazil group, a pyridyl group, a pyridadyl group, a pyrimidyl group, a pyrazil group, a triazinyl group, an oxazolyl group, an isooxazolyl group and a thiazolyl group. Examples thereof include an isothiazolyl group.

In the present specification, unless otherwise specified, the "electron donating group (donor group)" represents a group in which Hammett's σp is negative. Hansch, C.et.al., Chem.Rev., 91,165-195 (1991) can be referred to for a description of Hammett's σp and the numerical values of each group. Preferred electron donating groups include, for example, an alkyl group such as a methyl group, an aryl group such as a phenyl group, an alkoxyl group such as a methoxy group, an alkylsulfanyl group such as a methionyl group, and a ring X such as an N-phenylcarbazolyl group. Examples include groups having.

<Compound>
In one embodiment, the compound of the present invention is a compound having N rings (N is an integer of 2 or more) in which two adjacent rings X are (A) directly linked, (B). ) The total number of perfluoroalkyl groups substituted by N ring X, which is linked by either π-conjugated linking group or (C) condensation linking, is 1 or more and less than 2N. It is preferably a compound. It is preferable that one or more rings X are carbazole rings (Q is a single bond). The N rings X are preferably only carbazole rings, and preferably a combination of _{carbazole rings and acridine rings (Q is −CH 2-).} Ring X may have one or more substituents (perfluoroalkyl group, electron donating group, etc.). At least one (preferably two) benzene rings contained in each of one or more and less than N rings X are in the meta-position or para-position (preferably the meta-position) with respect to the nitrogen atom bonded to the benzene ring. It is preferable to have a perfluoroalkyl group in. Further, at least one (preferably two) benzene rings contained in each of one or more and less than N rings X have a perfluoroalkyl group at the meta position with respect to the nitrogen atom bonded to the benzene ring. However, it is also preferable to have an electron donating group at the para position.

(A) In the case of direct linking, of the two adjacent rings X, any atom of one ring X and any atom of the other ring X can be linked by a single bond. Among them, the nitrogen atom of one ring X and the carbon atom in the meta position or the para position (preferably the meta position) with respect to the nitrogen atom bonded to the benzene ring contained in the other ring X are connected by a single bond. It is preferable to do so.

When the ring X is a carbazole ring, it is preferable that the nitrogen atom at the 9-position of one carbazole ring and an arbitrary atom of the other carbazole ring are linked by a single bond, and the nitrogen atom at the 9-position of one carbazole ring is linked. It is more preferable that the carbon atoms at the 2-position, 3-position, 6-position, or 7-position of the other carbazole ring are linked by a single bond, and the nitrogen atom at the 9-position of one carbazole ring and the 3-position of the other carbazole ring are further preferable. Alternatively, it is particularly preferable that the carbon atom at the 6-position is connected by a single bond.

(B) In the case of connection via a π-conjugated linking group, of two adjacent rings X, an arbitrary atom of one ring X and an arbitrary atom of the other ring X are connected via a π-conjugated linking group. Can be linked. Among them, it is preferable that the nitrogen atoms of both rings X (when the ring X is a carbazole ring, the nitrogen atoms at the 9-position) are linked via a π-conjugated linking group.

The type of the π-conjugated connecting group is not particularly limited as long as it can form a π-electron conjugated system, and the electrons of the σ orbital interact with the π * orbital or the empty p-orbital located at spatially close positions. By doing so, it may be possible to form hyperconjugation. The π-conjugated linking group may be a non-aromatic π-conjugated linking group or an aromatic π-conjugated linking group.

Examples of the non-aromatic π-conjugated linking group include hyperconjugated methylene (CH ₂ ) group, CF ₂ group, C (CF ₃ ) ₂ group and the like.

The aromatic π-conjugated linking group may be a linking group composed of one aromatic ring, or may be a linking group composed of two or more aromatic rings directly bonded to each other.

In a linking group composed of one aromatic ring, the aromatic ring is a benzene ring, a naphthalene ring, a 5- or 6-membered aromatic heterocycle, a dibenzo [b, d] furan ring, or a dibenzo [b, d]. ] A thiophene ring is preferable, and a benzene ring or a 5- or 6-membered nitrogen-containing aromatic heterocycle is more preferable, and a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or 1, It is more preferably a 3,5-triazine ring.

（式中、Ａｒ¹～Ａｒ⁶は、それぞれ独立して芳香環であり、ａ２、ａ３、ａ４、及びａ６は、それぞれ独立して０以上の整数である。）
で表される構造に基づく。 A linking group composed of two or more aromatic rings directly bonded to each other is, for example, the following formula:

(In the equation, Ar ¹ to Ar ⁶ are independently aromatic rings, and a2, a3, a4, and a6 are independently integers of 0 or more.)
Based on the structure represented by.

The ^{aromatic ring represented by Ar 1} to Ar ⁶ is preferably a benzene ring or a 5- or 6-membered nitrogen-containing aromatic heterocycle, and is preferably a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring. Alternatively, it is more preferably a 1,3,5-triazine ring.

A2 and a6 are preferably 0, 1, 2, 3, or 4, more preferably 0, 1, 2, or 3, and even more preferably 0, 1, or 2.

A3 is preferably 0 or 1.

When a3 is 1 or more, a4 is preferably 0, 1, or 2, and more preferably 0 or 1.

In one embodiment, a3 and a4 are preferably 0. In this embodiment, it is preferable that Ar ¹ , Ar ² , and Ar ⁶ are benzene rings, and Ar ⁵ is a benzene ring or a 1,3,5-triazine ring.

In another embodiment, it is preferable that a3 is 1 and a4 is 0. In this embodiment, it is preferable that a2 and a6 are 0, and Ar ¹ , Ar ³ , and Ar ⁵ are benzene rings.

（式中、
Ｘ¹～Ｘ⁵は、それぞれ独立して、ＣＲ⁶又はＮであり、
Ｒ¹～Ｒ⁶は、それぞれ独立して、水素原子、アルキル基、パーフルオロアルキル基、シアノ基、又はアリール基であり、
破線は、芳香族性を示す。）
で表される構造、又は

（式中、
Ｒ^1'、Ｒ^2'、Ｒ^4'、及びＲ^5'は、それぞれ独立して、水素原子、アルキル基、パーフルオロアルキル基、シアノ基、又はアリール基であり、
Ｘ¹～Ｘ⁵、Ｒ¹～Ｒ⁵、及び破線は、前記と同じである。）
で表される構造
に基づく。 A linking group composed of two or more aromatic rings directly bonded to each other preferably has the following formula:

(During the ceremony,
X ¹ to X ⁵ are independently CR ⁶ or N, respectively.
R ¹ to R ⁶ are independently hydrogen atoms, alkyl groups, perfluoroalkyl groups, cyano groups, or aryl groups.
The dashed line indicates aromaticity. )
Structure represented by, or

(During the ceremony,
^{R 1 ', R 2',} R 4 ', and R ^5' are each independently a hydrogen atom, an alkyl group, a perfluoroalkyl group, a cyano group, or an aryl group,
X ¹ to X ⁵ , R ¹ to R ⁵ , and the broken line are the same as described above. )
Based on the structure represented by.

As a combination of ^{X 1} to X ^5,
Combinations where X ¹ to X ⁵ are CR ^6,
A combination where X ¹ , X ² , X ⁴ , and X ⁵ are CR ⁶ and X ³ is N, or where X ¹ , X ³ , and X ⁵ are N and X ² and X ⁴ are CR ⁶ . Certain combinations are preferred.
As R ⁶ , a hydrogen atom or a phenyl group is preferable.

As a combination of ^{R 1} to R ^5,
A combination in which R ¹ , R ² , R ⁴ , and R ⁵ are hydrogen atoms and R ³ is an alkyl group, a perfluoroalkyl group, a cyano group, or an aryl group is preferable.

（式中、Ｑ¹及びＱ²は、それぞれ独立して、単結合又は－ＣＨ₂－である。）
で表される環を形成することにより連結することが好ましく、式：

で表される環を形成することにより連結することがさらに好ましい。これらの縮合環は、さらに隣り合う環Ｘと連結してもよい。この場合は環Ｘの数を３個とカウントする。 (C) In the case of condensation connection, the condensation form of two adjacent rings X is not particularly limited. Both rings X are condensed, and the formula:

(In the equation, Q ¹ and Q ² are independently single-bonded or -CH _2- .)
It is preferable to connect by forming a ring represented by the formula:

It is more preferable to connect by forming a ring represented by. These fused rings may be further connected to adjacent rings X. In this case, the number of rings X is counted as three.

When ring X is a carbazole ring, both carbazole rings are fused to indro [3,2-a] carbazole ring, indro [3,2-b] carbazole ring, indro [2,3-a] carbazole ring. , Indro [2,3-b] carbazole ring, or indro [2,3-c] carbazole ring may be linked. Of these, it is preferable that both carbazole rings are condensed to form an indro [3,2-a] carbazole ring to form a link. These fused rings are further linked to adjacent carbazole rings to form a diindro [2,3-a: 2', 3'-c] carbazole ring or diindro [3,2-a: 3', 2'-c. ] It may be linked by forming a carbazole ring.

N is not particularly limited as long as it is 2 or more, but is preferably 12 or less, 10 or less, or 8 or less.

The number of perfluoroalkyl groups that can be substituted with one ring X is preferably 4 or less, more preferably 3 or less, still more preferably 2 or less.

The total number of perfluoroalkyl groups substituted with N rings X may be even or odd. When the number is odd, a plurality of stereoisomers exist and each structure contributes to TADF, so that the inverse intersystem crossing speed can be improved and the durability of the light emitting material can be improved. When the total number of perfluoroalkyl groups substituted on N rings X is 1 or more and less than 2N, and when the total number of perfluoroalkyl groups substituted on N rings X is 0 or 2N. The emission wavelength tends to be longer than that of the above, and the emission wavelength tends to become longer as the total number of perfluoroalkyl groups substituted with N rings X increases.

Of the N rings X, the ring X substituted by the perfluoroalkyl group is preferably substituted with two perfluoroalkyl groups, and the two substitution positions are not particularly limited, but the ring X is substituted. It is preferably in the meta-position or the para-position with respect to the nitrogen atom bonded to the contained benzene ring. That is, when the ring X is an acridine ring or a carbazole ring, the two substitution positions are preferably 2-positions and 7-positions, or 3-positions and 6-positions. Further, it is preferable that the perfluoroalkyl group is substituted at the 2-position and 7-position, or the 3-position and 6-position of one or more and less than N carbazole rings, and 2 of the carbazole ring having 1 or more and less than N It is more preferable that the perfluoroalkyl group is substituted at the position and the 7-position. Compounds in which the perfluoroalkyl group is substituted at the 2- and 7-positions of the carbazole ring are compounds in which the perfluoroalkyl group is not substituted in the carbazole ring, and the perfluoroalkyl group is substituted in the 3- and 6-positions of the carbazole ring. The excitation triplet state (T1) energy is lower than that of the compound. Therefore, the TADF material having this as a partial structure has a small energy difference between the excited triplet CT state and the excited triplet state of the carbazole portion, and mixing between orbitals is likely to occur. Therefore, the inverse intersystem crossing from the excited triplet state to the excited singlet state is promoted, and the delayed fluorescence lifetime tends to be shortened.

As the perfluoroalkyl group, a perfluoroC _1-6 alkyl group is preferable, and a perfluoroC _1-4 alkyl group is more preferable.

［式中、
Ｒ¹⁰は、１価の芳香環基であり、
Ｒ¹¹～Ｒ²⁰は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、３個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個～５個である）、
Ｑ¹¹～Ｑ¹³は、それぞれ独立して、単結合又は－ＣＨ₂－であり、
Ｒ²¹及びＲ²²は、それぞれ独立して、水素原子、アルキル基、又は１価の芳香環基であり、
Ｒ²³～Ｒ²⁶は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、ｍ個のＬに置換する環Ｘに置換するパーフルオロアルキル基の合計の数が、１個以上２ｍｎ個未満である）、
Ｑ²¹は、単結合又は－ＣＨ₂－であり、
Ｌは、１個の芳香環で構成される連結基であり、
ｍは、１以上の整数であり、
ｎは、２以上Ｌに置換可能な最大数以下の整数であり、
ｐ及びｑは、それぞれ独立して、０（不存在）又はＬに置換可能な最大数（存在）であり、
Ｒ³¹、Ｒ³⁵、及びＲ³⁹は、それぞれ独立して、１価の芳香環基であり、
Ｒ³²～Ｒ³⁴、Ｒ³⁶～Ｒ³⁸、及びＲ⁴⁰～Ｒ⁴⁸は、それぞれ独立して、水素原子、パーフルオロアルキル基、又は電子供与性基であり（但し、６個の環Ｘに置換するパーフルオロアルキル基の合計の数が、１個～８個である）、
Ｑ³¹～Ｑ³³及びＱ⁴¹～Ｑ⁴³は、それぞれ独立して、単結合又は－ＣＨ₂－である］のいずれかで表される化合物であることが好ましい。 In one embodiment, the compound of the present invention has the following formulas (1) to (3):

[During the ceremony,
R ¹⁰ is a monovalent aromatic ring group and
R ¹¹ to R ²⁰ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (however, the total number of perfluoroalkyl groups substituted with three rings X is one. ~ 5),
Q ¹¹ ~ Q ¹³ are each independently a single bond or -CH ₂ -,
R ²¹ and R ²² are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
R ²³ to R ²⁶ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (provided that the total number of perfluoroalkyl groups substituted with ring X substituted with m Ls). Is 1 or more and less than 2 mn),
Q ²¹ is a single bond or -CH _2-
L is a linking group composed of one aromatic ring.
m is an integer greater than or equal to 1 and
n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
p and q are independently the maximum number (existence) that can be replaced with 0 (absence) or L, respectively.
R ³¹ , R ³⁵ , and R ³⁹ are independently monovalent aromatic ring groups, respectively.
R ³² to R ³⁴ , R ³⁶ to R ³⁸ , and R ⁴⁰ to R ⁴⁸ are independently hydrogen atoms, perfluoroalkyl groups, or electron donating groups (provided that they are replaced with 6 rings X). The total number of perfluoroalkyl groups to be produced is 1 to 8),
Q ³¹ ~ Q ³³ and Q ⁴¹ ~ Q ⁴³ are each independently a single bond or -CH ₂ - is preferably a compound represented by any one of a.

In the formula (1), the R ¹⁰ is preferably an aryl group, more preferably a phenyl group or a naphthyl group, and even more preferably a phenyl group. These may have one or more substituents, and examples of the substituent include an alkyl group, a perfluoroalkyl group, and a cyano group.

As a combination of ^{R 11} to R ^20,
R ¹¹ and R ¹² are perfluoroalkyl groups and
R ¹³ , R ¹⁴ , R ¹⁷ and R ¹⁸ are hydrogen atoms, perfluoroalkyl groups, or electron donating groups.
A combination in which R ¹⁵ , R ¹⁶ , R ¹⁹ and R ²⁰ are hydrogen atoms or electron donating groups is preferable.
R ¹¹ and R ¹² are perfluoroalkyl groups and
A ^{combination in which R 13} to R ²⁰ are hydrogen atoms, or R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are perfluoroalkyl groups.
A ^{combination in which R 15} to R ²⁰ are hydrogen atoms is more preferable.

The total number of perfluoroalkyl groups substituted with 3 rings X is preferably 2-4.

In the formula (2), as the alkyl group represented by ^{R 21} and R ²² _{, a C 1-4} alkyl group is preferable, a C _1-3 alkyl group is more preferable, and a methyl group or an ethyl group is further preferable.

Examples of the monovalent aromatic ring group represented by R ²¹ and R ^{22 include the same group as R 10,} and an aryl group or a heteroaryl group which may have one or more phenyl groups. Is preferable, or a pyridyl group, a pyridazil group, a pyrimidyl group, a pyrazil group, or a triazil group which may have one or more phenyl groups is more preferable.

R ²¹ and R ²² are particularly preferably hydrogen atoms, methyl groups, phenyl groups, or 4,6-diphenyl-1,3,5-triazine-2-yl groups.

As a combination of ^{R 23} and R ^24,
R ²³ and R ²⁴ are hydrogen atoms or electron donating groups,
Combinations in which R ²⁵ and R ²⁶ are perfluoroalkyl groups are also preferred,
R ²³ and R ²⁴ are perfluoroalkyl groups and
A combination in which R ²⁵ and R ²⁶ are hydrogen atoms or electron donating groups is more preferable.
It is preferable that all of R ²³ to R ^{26 are not perfluoroalkyl groups.}

Examples of L include a group exemplified as a linking group composed of one aromatic ring in the description of the π-conjugated linking group. L is preferably a linking group composed of a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a 1,3,5-triazine ring.

N is preferably 2, 3, 4, or 5 depending on the type of L.

M is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, and even more preferably 1 or 2.

For p and q, the maximum number that can be replaced with 0 or L can be selected depending on L, n, and m.
(Example 1) When m is 1, L is a pyridine ring, and n is 5, p and q are 0.
(Example 2) When m is 1, L is a benzene ring, and n is 5, the sum of p and q is 1.
(Example 3) When m is 1, L is a benzene ring, and n is 4, the sum of p and q is 2.
(Example 4) When m is 1, L is a benzene ring, and n is 3, the sum of p and q is 3.
(Example 5) m is 2, each L is a benzene ring, the number n of rings X substituted with L to which ^{R 21} is bonded is 4, and the number of rings X substituted with L to which ^{R 22 is bonded.} When n is 2, p is 1 and q is 3.
(Example 6) m is 2, ^{L to which R 21} is bonded is a benzene ring, L to which R ²² is bonded is a 1,3,5-triazine ring, and a ring substituted with L to which ^{R 21 is bonded.} When the number n of X is 4 and the number n of ^{the ring X substituted with L to which R 22} binds is 2, p is 1 and q is 0.

In the formula (3), examples of the monovalent aromatic ring group represented by ^{R 31} , R ³⁵ , and R ^{39 include the same group as R 10} , preferably an aryl group, and a phenyl group or a naphthyl group. Is more preferable, and a phenyl group is further preferable.

As a combination of R ³² to R ³⁴ , R ³⁶ to R ³⁸ , and R ⁴⁰ to R ⁴⁸ ,
R ³² and R ³³ are perfluoroalkyl groups
A combination in which R ³⁴ , R ³⁶ to R ³⁸ , and R ⁴⁰ to R ⁴⁸ are hydrogen atoms is preferable.
R ³² , R ³³ , R ³⁶ , and R ³⁷ are perfluoroalkyl groups,
Combinations in which R ³⁴ , R ³⁸ , and R ⁴⁰ to R ⁴⁸ are hydrogen atoms are also preferred,
A combination in which R ³² , R ³³ , R ³⁶ , R ³⁷ , R ⁴⁰ , and R ⁴¹ are perfluoroalkyl groups and R ³⁴ , R ³⁸ , and R ⁴² to R ⁴⁸ are hydrogen atoms is more preferred.

In one embodiment, the compound of the present invention is preferably a compound selected from the compound group shown in Table 1 below.

In one embodiment, the compound of the present invention preferably satisfies the following formula (a).
W ₁ > W ₀ (a)
_{[W 1 in} equation (a) is the following equation (b):
W = 863.2-0.4440 x SMR_VSA9 [Å ² ] + 2.109 x fr_para_hydroxylation [-] -115.4 x HOMO-LUMO Gap [eV] (b)
W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the compound in
_{W 0 in the} formula (a) is the total number of perfluoroalkyl groups substituted with N rings X, where N is the total number of rings X contained in the compound in the formula (b). W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the comparative compound having the same structure as the compound except that the number is 2N].

In formula (b), the descriptor "SMR_VSA9" is the total surface area (unit: Å ² ) of the carbon having a triple bond and the aromatic carbon bonded to the oxygen atom and the aromatic ring. More specifically, SMR_VSA9 is one of the VSA-type descriptors created by LABUTE to predict the physicochemical properties of molecules such as free dissolution energy and boiling point (LABUTE, Paul. A widely applicable set of). descriptors. Journal of Molecular Graphics and Modeling, 2000, 18.4-5: 464-477).

で表される。ここで、V_iは各原子のファンデルワールス表面積(van der Waals surface area; VSA)であり、原子のファンデルワールス半径と標準的な結合距離から近似的に計算された値である。δ(A)は条件式Aが真のとき1、偽のとき0を返す関数である。 The VSA type descriptor is defined as the sum of the surface areas having the property P within a certain range, assuming that each atom in the molecule has an arbitrary property (numerical value) P _i.

It is represented by. Here, V _i is the van der Waals surface area (VS A) of each atom, which is a value approximately calculated from the van der Waals radius of the atom and the standard bond length. δ (A) is a function that returns 1 when the conditional expression A is true and 0 when it is false.

で表される。MRとは、分子のモル屈折率(molar refractivity)を原子寄与法（下記式(S3)）：

により予測する際の原子毎の係数P_iであり、Crippenらによって3412分子の実験データから決定されたものである。MRの値は68個の原子タイプ毎に定められている。そのうち、SMR_VSA9に対応する範囲[3.80, 4.00]にある原子タイプは、下表に示す3タイプのみである。

　例えば、アンピロンの場合、ピラゾール環に結合する芳香族炭素がC20に該当し、フェノールの場合、ヒドロキシ基に隣接する芳香族炭素がC23に該当する。 The VSA type descriptor "P_VSAk" is _{the sum of V i} δ (A) for all atoms except the hydrogen atom. When the P _{i of the} conditional expression A is MR (described later), this VSA type descriptor is called SMR_VSAk. SMR_VSAk mainly describes the polarizability. The range boundary {a _k } for SMR_VS Ak is given by the following equation (S2):

It is represented by. MR is an atomic contribution method (the following formula (S3)):

It is the coefficient P _i of each atom in predicting by, those determined from the experimental data of 3412 molecules by Crippen et al. MR values are defined for each of the 68 atomic types. Of these, only the three atomic types shown in the table below are in the range [3.80, 4.00] corresponding to SMR_VSA9.

For example, in the case of ampyrone, the aromatic carbon bonded to the pyrazole ring corresponds to C20, and in the case of phenol, the aromatic carbon adjacent to the hydroxy group corresponds to C23.

That is, SMR_VSA9 can be said to be the sum of the van der Waals surface areas of atoms belonging to the atomic type in the corresponding range [3.80, 4.00].

In formula (b), the descriptor "fr_para_hydroxylation" indicates the number of reaction sites on the aromatic ring that can undergo para-hydroxylation. The definition of the reaction site on the aromatic ring that can undergo hydroxylation in the descriptor satisfies both (b1) and (b2) below.
(B1) An oxygen atom or a nitrogen atom is bonded to an aromatic ring composed of 6 carbon atoms. The aromatic ring may be a partial structure of a polycyclic aromatic compound, and the oxygen atom and the nitrogen atom may be a part constituting another ring structure condensed with the aromatic ring. The nitrogen atom must be covalently bonded to three arbitrary atoms or covalently bonded to two hydrogen or carbon atoms.
(B2) A hydrogen atom is bonded to a carbon atom at the para-position and a meta-position with reference to a carbon atom to which an oxygen atom or a nitrogen atom is bonded.
When the above definition is shown in SMARTS notation, it is described by the following logical formula.
[$ ([cH] 1 [cH] cc (c [cH] 1) ~ [$ ([# 8, $ ([# 8] ~ [H, c, C])])]), $ ([cH] ] 1 [cH] cc (c [cH] 1) ~ [$ ([# 7X3, $ ([# 7] (~ [H, c, C]) ~ [H, c, C])])]) , $ ([cH] 1 [cH] cc (c [cH] 1)-!: [$ ([NX3H, $ (NC (= O) [H, c, C])])])]

In equation (b), the descriptor "HOMO-LUMO Gap" is a value obtained by calculating the HOMO and LUMO energy levels of the compound by quantum chemistry calculation and subtracting the HOMO level from the calculated LUMO level. The quantum chemistry calculation was performed by the density functional theory, and B3LYP was used for the functional and 6-31g (d, p) was used for the basis set. For the energy level, the value calculated when the structure was optimized by the functional and the basis function was used as a representative value. The software for quantum chemistry calculation is not particularly limited and can be obtained in the same manner by using any of them, but Gaussian 09 Rev. D is used in the present invention.

Equation (b) is preferably a prediction equation (or regression equation) for the maximum emission wavelength, which is created by machine learning.
(I) The step of extracting the descriptor related to the emission maximum wavelength from the structure of the learning compound, and (ii) the prediction formula of the emission maximum wavelength expressed as a function of the descriptor extracted by step (i). It is preferable that the formula is a prediction formula for the maximum emission wavelength, which is prepared by a method including a step of making.

Step (i)
The learning compound is not particularly limited as long as the emission maximum wavelength is known or the compound is measured by the following method.
(Measurement method of maximum emission wavelength)
Excitation light of 280 nm was applied to a thin film (thickness 50 nm) adjusted so that the learning compound was 10% by mass with respect to the host material (2,8-Bis (diphenylphosphoryl) dibenzo [b, d] thiophene (PPT)). The peak top of the emission spectrum when irradiated is measured.

From the viewpoint of expanding the prediction range, the learning compound preferably includes both a compound having a measured maximum emission wavelength of 400 nm or less and a compound having a maximum emission wavelength of 500 nm or more.

From the viewpoint of considering the influence of the number of perfluoroalkyl groups substituted on the ring X, the learning compounds include a compound in which two perfluoroalkyl groups are substituted on all rings X and a perfluoroalkyl group on all rings X. It preferably contains both compounds in which the alkyl group has not been substituted at all.

In one embodiment, the learning compound preferably comprises a compound selected from the compound group shown in Table 3 below.

The lower limit of the number of learning compounds is not particularly limited, but from the viewpoint of improving prediction accuracy, 5 or more is preferable, 10 or more is more preferable, 15 or more is further preferable, and 20 or more is particularly preferable. The upper limit of the learning compound is not particularly limited, but from the viewpoint of data collectability, 50 or less is preferable, 40 or less is more preferable, and 30 or less is further preferable.

The type of descriptor related to the maximum emission wavelength is not particularly limited. The descriptor associated with the emission maximum wavelength is preferably at least one selected from 0-4D descriptors. Examples of the 0-dimensional descriptor include the number of atoms such as C, H, O, N, and halogen, the number of bonds, and the molecular weight. The one-dimensional descriptor includes, for example, the number of functional groups such as an alkyl group, an aryl group, an arylalkyl group, a hydroxy group, an ester group, and an amino group, the number of aromatic rings, and on an aromatic ring capable of undergoing para-hydroxylation. The number of reaction points and the like can be mentioned. Examples of the two-dimensional descriptor include those characterized by structural formulas such as SMR_VSA1 to 10, PEOE_VSA1 to 14, SlogP_VSA1 to 12, Estate_VSA1 to 11. Examples of the three-dimensional descriptor include geometrically characterized ones such as 3D-MoRSE, WHIM, and GETAWAY, and HOMO-LUMO Gap and the like. Examples of the four-dimensional descriptor include those calculated by GRID, CoMFA, Volsurf, etc. and characterized by the interaction energy.

The descriptors related to the emission maximum wavelength include, for example, 80% or more, preferably 90% or more, more preferably 95% or more, and particularly preferably 100% of the total number of learning compounds. Preferably do not contain descriptors that have the same value in common.

The number of descriptors related to the maximum emission wavelength is not particularly limited. From the viewpoint of overfitting, the number of descriptors related to the emission maximum wavelength is preferably smaller than the number of learning compounds. Also, the number of descriptors associated with the emission maximum wavelength may be adjusted using regularization to control the coefficients of the descriptors.

The method for extracting the descriptor related to the emission maximum wavelength from the structure of the learning compound is not particularly limited, but (i-1) a step of generating a group of descriptor values from the structure of the learning compound, and (i). -2) It is preferable that the method includes a step of extracting a descriptor related to the emission maximum wavelength from the group. The method further preferably includes a step of normalizing and transforming the values of the set of descriptors generated in step (i-1). Examples of the normalization conversion method include standardization conversion and Yeo-Johnson conversion. In one embodiment, it is more preferred to perform the normalization transformation using Scikit-learn, a Python library for machine learning.

Examples of the extraction method in step (i-2) include a method of extracting by sparse modeling, a method of selecting by the correlation coefficient with the prediction target, and a method of recursively adding or deleting descriptors based on the prediction accuracy. Be done. Of these, the method of extraction by sparse modeling is preferable.

Examples of sparse modeling include greedy method, convex relaxation method, and stochastic reasoning. Examples of the greedy algorithm include orthogonal matching tracking (OMP), matching tracking (MP), weak matching tracking (Weak MP), and threshold algorithm. Examples of the convex relaxation method include a basis tracking method, an iterative reweighting least squares method (IRLS), and a homotopy method. Probabilistic inference includes approximate message propagation method (AMP). In one embodiment, the sparse modeling is preferably orthogonal matching tracking.

Step (ii)
In step (ii), it is preferable to create a prediction formula by machine learning. Machine learning includes, for example, multiple regression, Ridge regression, LASSO regression, Elastic Net, support vector regression, random forest regression, neural network and the like. These may be used alone or in combination of two or more. When the number of data is small, it is preferable to adopt the method of adopting a linear model from the viewpoint of prevention of overfitting and high interpretability. In one embodiment, machine learning is preferably Ridge regression, Lasso regression, Elastic Net. Also, in one embodiment, machine learning includes LibSVM, TensorFlowTM, Chainer ™, Jubatus ™, Caffe, Theano, Torch, neonTM, MXNet, The Microsoft Cognitive Toolkit, R (C), MATLAB ™, Using computer software such as Mathematica ™, SAS ™, RapidMiner ™, KNIME ™, WeKa, shogun-toolbox / shogun, Orange, Apache MahoutTM, scikit-learn, mlpy, XGBoost, Deeplearning4j It is preferable to carry out.

In one embodiment, the compound of the present invention preferably satisfies the following formula (c):
W ₁ > W ₂ (c)
_{[W 1 in} equation (c) is the same _{as W 1 in} equation (a),
W ₂ of the formula (c) has the total number of perfluoroalkyl groups substituted with N rings X, where N is the total number of rings X contained in the compound in the formula (b). W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the comparative compound having the same structure as the compound except that the number is 0].

The compound of the present invention is useful as a delayed fluorescent material. Further, the compound of the present invention is useful as a light emitting material for an organic light emitting device, and can be suitably used as a material for a light emitting layer of an organic light emitting device.

The emission maximum wavelength (λmax) of the compound of the present invention is preferably 450 nm or more or 455 nm or more, or 520 nm or less or 510 nm or less. For the maximum emission wavelength, the peak top of the emission spectrum when a thin film (thickness 50 nm) adjusted so that the compound of the present invention is 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm is measured. It is required by doing.

The HOMO level of the compound of the present invention may preferably be -5.0 eV or less or -5.5 eV or less, and is -7.0 eV or more, -6.5 eV or more, or -6.4 eV or more. You may. As the total number of perfluoroalkyl groups substituted with N rings X increases, the HOMO level tends to decrease. Due to such a HOMO level, compatibility with peripheral materials such as host materials is excellent. The HOMO level can be measured using an atmospheric photoelectron spectrometer (for example, AC-3 manufactured by RIKEN Keiki Co., Ltd.).

The absolute value of the difference between the lowest excited singlet energy (S ₁₎ and the lowest excited triplet energy of the compound of the present invention (T ₁₎ (ΔE _ST) is preferably not more than 0.3eV or less, or 0.2 eV, Usually, it is 0.001 eV or more. When ΔE _ST is in such a range, triplet excitons can be efficiently up-converted to singlet excitons, which leads to improvement in device efficiency and durability. ΔE _ST can be measured by the same method as the method for measuring λmax, and the fluorescence spectrum (room temperature) and the phosphorescence spectrum (77K) can be measured and calculated from the difference between the rising wavelengths of the respective rising wavelengths.

The compound of the present invention is characterized in that the total number of perfluoroalkyl groups substituted with N carbazole rings is 0 or 2N (particularly, each carbazole ring is substituted with 2 perfluoroalkyl groups). Except for this, it is preferable that the emission intensity is higher than that of a compound having the same structure as the compound of the present invention (comparative compound). The emission intensity of the compound of the present invention is preferably 110 or more or 120 or more when the emission intensity of the comparative compound is 100. When the light emission intensity is in such a range, the light emission efficiency is high and the power consumption of the device can be reduced. The emission intensity is determined by the following formula from the ratio of peak emission intensity when a thin film (thickness 50 nm) adjusted so that the light emitting material is 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm. I asked.
Emission intensity = (Peak emission intensity of the compound of the invention) / (Peak emission intensity of the compound having a carbazole ring in which the perfluoroalkyl group is not substituted) × 100
The peak emission intensity can be measured by a conventional device (for example, "PMA12" manufactured by Hamamatsu Photonics Co., Ltd.).

The delayed fluorescence lifetime of the compound of the present invention is preferably 10 μs or less or 5 μs or less, and usually 10 ns or more. When the fluorescence lifetime is in such a range, the triplet exciton concentration is lowered, and the durability of the device can be improved. The delayed fluorescence lifetime can be measured by a conventional device (for example, "Quantaurus-Tau" manufactured by Hamamatsu Photonics Co., Ltd.).

The excited state stability of the compound of the present invention is preferably 0.5 hours or more or 1 hour or more. When the excited state stability is in such a range, the durability of the device can be improved. For excited state stability, a toluene solution (concentration 1.0 x ^10-5 M) of the compound of the present invention was used, degassed by argon bubbling, and then excited light (Xenon light source MAX-303 manufactured by Asahi Spectroscopy Co., Ltd.) with stirring. It is obtained by irradiating a wavelength of 300 to 400 nm, 5 mW / cm ² ) and measuring the time from the initial emission to the reduction of the emission intensity by half.

<Compound manufacturing method>
In one embodiment, the compound of the present invention is a reaction in which, for example, two rings X are linked by either (A) direct linking, (B) linking via a π-conjugated linking group, or (C) condensation linking. Can be repeatedly manufactured.

(A) The reaction linked by direct linking is not particularly limited as long as it is a reaction in which a direct bond is formed between an arbitrary atom of one ring X and an arbitrary atom of the other ring X. For example, it may be a reaction between a halogen atom substituting for one ring X and an NH site of the other ring X (hereinafter referred to as reaction A).

One reaction component of the reaction A is preferably compound A1 having a ring X substituted with one or more halogen atoms, and the other reaction component is a compound A2 having a ring X in which the halogen atom is not substituted. Is preferable.

In compound A1, the halogen atom substituted for ring X is preferably a fluorine atom, a chlorine atom, or a bromine atom. The number of halogen atoms substituted on the ring X is, for example, one or two, preferably two. Further, the substitution position of the halogen atom may be the 2-position, 3-position, 6-position, 7-position or the like of the acridine ring or the carbazole ring.

It is preferable that one or more (preferably two) perfluoroalkyl groups are substituted on the ring X of either one of the compound A1 and the compound A2, and one or more (preferably) the ring X of the compound A1 is substituted. It is more preferable that (2) perfluoroalkyl groups are substituted. The substitution position of the perfluoroalkyl group may be the 2-position, 3-position, 6-position, 7-position or the like of the acridine ring or the carbazole ring.

［式中、
Ｒ^1aは、１価の芳香環基であり、
Ｒ^1c及びＲ^1hが、パーフルオロアルキル基であり、Ｒ^1b、Ｒ^1d、Ｒ^1e、Ｒ^1f、Ｒ^1g、及びＲ¹ⁱのうち、１又は２個が臭素原子であり、残りが水素原子又は電子供与性基であるか、又は
Ｒ^1d及びＲ^1gが、パーフルオロアルキル基であり、Ｒ^1b、Ｒ^1c、Ｒ^1e、Ｒ^1f、Ｒ^1h、及びＲ¹ⁱのうち、１又は２個が臭素原子であり、残りが水素原子又は電子供与性基であり、Ｑ^1aは、単結合又は－ＣＨ₂－である］
で表される化合物が好ましい。 The compound A1 has the following formula (4):

[During the ceremony,
R ^1a is a monovalent aromatic ring group and
R ^1c and R ^1h are perfluoroalkyl groups, and ^{one or two of R 1b} , R ^1d , R ^1e , R ^1f , R ^1g , and R ¹ⁱ are bromine atoms, and the rest are hydrogen atoms or An electron donating group, or R ^1d and R ^1g are perfluoroalkyl groups, and one or two of ^{R 1b} , R ^1c , R ^1e , R ^1f , R ^1h , and R ^{1i are bromine.} It is an atom, the rest is a hydrogen atom or an electron donating group, and Q ^1a is a single bond or -CH _2- ].
The compound represented by is preferable.

The total number of moles of halogen atoms substituted for the ring X of the compound A1 is 0.5 mol or more, 0.6 mol or more, 0.7 mol with respect to 1 mol of the NH site of the ring X of the compound A2. It is preferable to use the above or 0.8 mol or more, and it is also preferable to use it so as to be 2.5 mol or less, 2 mol or less, 1.5 mol or less, or 1.2 mol or less.

Reaction A is preferably carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction component can be dissolved, and is, for example, an amine (eg, a chain amine such as triethylamine, a cyclic amine such as N-methylpyrrolidone), an amide (eg, dimethylformamide), a sulfoxide. (Example: dimethyl sulfoxide) and the like. As the solvent, one type can be used alone or two or more types can be mixed and used.

Reaction A is preferably carried out in the presence of a base. Examples of the base include n-butyllithium, NaH, K ₂ CO ₃ , Cs ₂ CO ₃ , t-butoxy sodium, t-butoxy potassium, and a combination of two or more of these. When using n-butyllithium, refer to International Publication No. 2008/1178226, Chemistry of Materials, 2010, 22 (7), 2403-2410, etc. When using NaH, Korean Patent Application Publication No. 2018-063708 You can refer to the publications and the like.

Reaction A is preferably carried out in the presence of a catalyst. Examples of the catalyst include a palladium catalyst and the like. When a palladium catalyst is used, International Publication No. 2011/08902, International Publication No. 2015/137472, and the like can be referred to.

(B) In the case of connection via a π-conjugated linking group, as long as the reaction is such that a bond is formed between an arbitrary atom of one ring X and an arbitrary atom of the other ring X via a π-conjugated linking group. There are no particular restrictions. For example, it may be a reaction (hereinafter, referred to as reaction B) between each halogen atom of the π-conjugated compound having two or more halogen atoms and the NH site of the ring X.

One reaction component of reaction B is preferably a π-conjugated compound B1 having two or more halogen atoms. The π-conjugated compound B1 is not particularly limited as long as it is a compound that reacts with two or more rings X to form a π-conjugated linking group. In the π-conjugated compound, the halogen atom is preferably a fluorine atom, a chlorine atom, or a bromine atom, and the number of halogen atoms is 2, 3, 4, 5, or 6. preferable.

The π-conjugated compound B1 is preferably an aromatic compound having two or more halogen atoms. As the aromatic ring constituting the aromatic compound, for example, in the description of the π-conjugated linking group, a linking group composed of one aromatic ring or a linking group composed of two or more aromatic rings directly bonded to each other. In the above, a ring exemplified as an aromatic ring can be mentioned.

［式中、
Ｘは、ハロゲン原子であり、
ａは、１以上ｎ未満の整数であり、
Ｒ²¹～Ｒ²⁶、Ｑ²¹、Ｌ、ｍ、ｎ、ｐ、及びｑは、前記と同じである］
で表される化合物が好ましい。 The π-conjugated compound B1 has the following formula (5):

[During the ceremony,
X is a halogen atom,
a is an integer of 1 or more and less than n,
R ²¹ to R ²⁶ , Q ²¹ , L, m, n, p, and q are the same as above]
The compound represented by is preferable.

In the formula (5), as X, a fluorine atom, a chlorine atom, or a bromine atom is preferable.

Of the m rings X substituted with L, in at least one ring X, at least one of R ²³ to R ²⁶ is preferably a perfluoroalkyl group, and R ²³ and R ²⁴ , or R ^25. And R ²⁶ are more preferably perfluoroalkyl groups, and R ²³ and R ²⁴ are even more preferably perfluoroalkyl groups.

The other reaction component of reaction B is preferably compound B2 having a ring X in which the halogen atom is not substituted.

In the π-conjugated compound B1, the total number of moles of halogen atoms in the compound is 0.5 mol or more, 0.6 mol or more, 0.7 mol or more, with respect to 1 mol of the NH site of the ring X of the compound B2. Alternatively, it is preferably used so as to be 0.8 mol or more, and it is also preferable to use it so as to be 2.5 mol or less, 2 mol or less, 1.5 mol or less, or 1.2 mol or less.

Reaction B is preferably carried out in the presence of a solvent, a base, a catalyst, etc., as in Reaction A, and the same components as those exemplified in Reaction A can be used.

In the case of (C) condensation connection, a condensate of two or more rings X can be used, for example, an indolo [3,2-a] carbazole ring, an indolo [3,2-b] carbazole ring, an indolo [ 2,3-a] carbazole ring, indolo [2,3-b] carbazole ring, indolo [2,3-c] carbazole ring, diindro [2,3-a: 2', 3'-c] carbazole ring, The diindro [3,2-a: 3', 2'-c] carbazole ring can be utilized.

[Organic light emitting device]
In one embodiment, the organic light emitting device of the present invention preferably contains the compound of the present invention, and more preferably contains the compound of the present invention as a light emitting material or an assist dopant compound.

Examples of the organic light emitting element include an organic photoluminescence element (organic PL element) and an organic electroluminescence element (organic EL element). The organic light emitting element is preferably an organic EL element.

The organic EL element preferably has an anode, a cathode, and an organic layer formed between the anode and the cathode.

The organic layer preferably contains at least a light emitting layer, and may be composed of only a light emitting layer, or may include one or more other organic layers in addition to the light emitting layer. Other organic layers include, for example, an injection layer (eg, a hole injection layer, an electron injection layer), a blocking layer (eg, an electron blocking layer, a hole blocking layer, an exciton blocking layer), a hole transport layer, and an electron. The transportation layer and the like can be mentioned. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

The organic EL element may be a bottom emission type that extracts the light generated in the light emitting layer from the substrate side, or may be a top emission type that extracts the light generated in the light emitting layer from the opposite side of the substrate. In any type, the electrode formed on the substrate side may be an anode or a cathode. The electrode on the side that extracts light is preferably transparent, and the electrode on the opposite side may or may not be transparent.

The organic EL element is preferably supported by a substrate. The substrate is not particularly limited as long as it is conventionally used for organic EL elements, and for example, a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.

As the anode in the organic EL element, a metal having a large work function (for example, 4 eV or more), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material are preferably used. Specific examples of such electrode materials include metals such as Au and transparent conductive materials such as _{CuI, indium tin oxide (ITO), SnO 2, and ZnO.} Further, a material such as IDIXO (In ₂ O _3- ZnO) capable of producing an amorphous transparent conductive film may be used. For the anode, a thin film may be formed by a method such as vapor deposition or sputtering of the electrode material to form a pattern having a desired shape by a photolithography method, or a pattern may be formed through a mask having a desired shape during vapor deposition or sputtering of the electrode material. May be formed. Alternatively, when a coatable material such as an organic conductive compound is used, a wet film forming method such as a printing method or a coating method can also be used. When the light emission is taken out from the anode, it is desirable to increase the transmittance to more than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. The film thickness of the anode depends on the material, but is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.

As the cathode, a metal having a small work function (for example, 4 eV or less) (electron-injectable metal), an alloy, an electrically conductive compound, or a mixture thereof as an electrode material is preferably used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al ₂ O). ₃ ) A mixture, lithium / aluminum mixture, aluminum, etc. are suitable. The cathode can be produced by forming a thin film of an electrode material by a method such as vapor deposition or sputtering. Further, the sheet resistance as a cathode is preferably several hundred Ω / □ or less. The film thickness of the cathode is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm. It is preferable that either the anode or the cathode of the organic EL element is transparent or translucent because the emission brightness is improved. Further, by using the transparent conductive material mentioned in the description of the anode for the cathode, a transparent or translucent cathode can be produced, and an element in which both the anode and the cathode have transparency can be produced.

The light emitting layer is a layer that emits light (eg, fluorescent light emission, delayed fluorescent light emission, or both) after excitons are generated by recombination of holes and electrons injected from each of the anode and cathode. Is preferable. The light emitting layer may be a layer containing a light emitting material alone, but is preferably a layer containing a light emitting material and a host material. As the luminescent material, the compound of the present invention (one type or two or more types) can be used. The host material is not particularly limited, but it is preferable to use an organic compound in which at least one of the excitation singlet energy and the excitation triplet energy has a value higher than that of the compound of the present invention. Further, the host material is preferably an organic compound having a hole transporting ability and an electron transporting ability, preventing a long wavelength of light emission, and having a high glass transition temperature.

Furthermore, if a compound exhibiting TADF properties is included in the light emitting layer as a third component (assist dopant compound) in the light emitting layer containing the host compound and the light emitting compound, it is effective in developing high luminous efficiency (H. Nakanоtani, et al). ., Nature Compound, 2014, 5, 4016-4022). By generating 25% singlet excitons and 75% triplet excitons on the assist dopant compound by electric field excitation, the triplet excitons generate singlet excitons with inverse intersystem crossing (RISC). can do. The energy of the singlet exciton is transferred to the luminescent compound, and the luminescent compound can emit light. Therefore, it is theoretically possible to make the luminescent compound emit light by using 100% exciton energy, and high luminous efficiency is exhibited.

The content of the compound of the present invention in the light emitting layer is preferably 0.1% by mass or more, more preferably 1% by mass or more, and preferably 50% by mass or less, preferably 20% by mass. It is more preferably 10% by mass or less, and further preferably 10% by mass or less.

The injection layer is preferably a layer provided between the electrode and the organic layer in order to reduce the driving voltage or improve the emission brightness. The injection layer includes a hole injection layer and an electron injection layer. The injection layer may be provided between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.

The blocking layer is preferably a layer capable of blocking the diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer. The electron blocking layer can be arranged between the light emitting layer and the hole transporting layer, and can prevent electrons from passing through the light emitting layer toward the hole transporting layer. Similarly, the hole blocking layer can be placed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer towards the electron transporting layer. The electron blocking layer and the hole blocking layer can also function as exciton blocking layers, respectively. The electron blocking layer or exciton blocking layer referred to in the present specification is used in the sense that one layer includes a layer having the functions of an electron blocking layer and an exciton blocking layer.

The hole blocking layer has the function of an electron transport layer in a broad sense. The hole blocking layer has a role of blocking the holes from reaching the electron transporting layer while transporting electrons, which can improve the recombination probability of electrons and holes in the light emitting layer. As the material of the hole blocking layer, a material of the electron transport layer described later can be used as needed.

The electron blocking layer has a function of transporting holes in a broad sense. The electron blocking layer has a role of blocking electrons from reaching the hole transporting layer while transporting holes, which can improve the probability that electrons and holes are recombined in the light emitting layer. ..

The exciton blocking layer is preferably a layer for blocking excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. By inserting the exciton blocking layer, excitons can be efficiently confined in the light emitting layer, and the luminous efficiency of the device can be improved. The exciton blocking layer can be inserted into either the anode side or the cathode side adjacent to the light emitting layer, and both can be inserted at the same time. That is, when the exciton blocking layer is provided on the anode side, the layer can be inserted between the hole transport layer and the light emitting layer adjacent to the light emitting layer, and when inserted on the cathode side, the light emitting layer and the light emitting layer can be inserted. The layer can be inserted adjacent to the light emitting layer between the cathode and the light emitting layer. Further, a hole injection layer, an electron blocking layer and the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer. An electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided between the cathode and the exciton blocking layer adjacent to the cathode side of the light emitting layer. When the blocking layer is arranged, it is preferable that at least one of the excited singlet energy and the excited triplet energy of the material used as the blocking layer is higher than the excited singlet energy and the excited triplet energy of the light emitting material.

The hole transport layer is preferably made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers. As the hole transporting material, a material having either injection or transport of holes or an electron barrier property is preferable, and it may be either an organic substance or an inorganic substance. Examples of the hole transporting material that can be used include triazole derivative, oxadiazole derivative, imidazole derivative, carbazole derivative, indolocarbazole derivative, polyarylalkane derivative, pyrazoline derivative and pyrazolone derivative, phenylenediamine derivative, arylamine derivative, and amino. Examples thereof include substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilben derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers. As the hole transport material, it is preferable to use a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound, and it is more preferable to use an aromatic tertiary amine compound. Inorganic semiconductors such as molybdenum oxide can also be used as the hole transport material.

The electron transport layer is preferably made of a material having a function of transporting electrons, and the electron transport layer can be provided with a single layer or a plurality of layers. The electron transporting material (which may also serve as a hole blocking material) preferably has a function of transferring electrons injected from the cathode to the light emitting layer. Examples of the electron transporting layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, freolenidenemethane derivatives, anthracinodimethane and anthrone derivatives, and oxadiazole derivatives. Further, among the above oxadiazole derivatives, a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is replaced with a sulfur atom, and a quinoxalin derivative having a quinoxalin ring known as an electron attractant can also be used as an electron transport material. .. Further, a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used. Further, an inorganic semiconductor such as zinc oxide can also be used as an electron transport material.

When producing an organic EL device, the compound of the present invention may be used not only for the light emitting layer but also for a layer other than the light emitting layer. At that time, the compound of the present invention used for the light emitting layer and the compound of the present invention used for the layer other than the light emitting layer may be the same or different. For example, the compound of the present invention may be used for the above-mentioned injection layer, blocking layer (eg, hole blocking layer, electron blocking layer, exciton blocking layer), hole transport layer, electron transport layer and the like.

The film forming method for these layers is not particularly limited, and may be formed by either a dry process or a wet process.

Hereinafter, preferable materials that can be used for the organic electroluminescence device will be specifically exemplified. However, the materials that can be used in the present invention are not limitedly interpreted by the following exemplary compounds. Further, even a compound exemplified as a material having a specific function can be diverted as a material having another function. In addition, R, R', and R ₁ to R ₁₀ in the structural formulas of the following exemplified compounds independently represent hydrogen atoms or substituents. X represents a carbon atom or a complex atom forming a ring skeleton, n represents an integer of 3 to 5, Y represents a substituent, and m represents an integer of 0 or more.

Preferred compounds that can also be used as host material for the light emitting layer are listed. In order to match the HOMO / LUMO level of the luminescent material to be used, the HOMO / LUMO level of the host material can be adjusted by appropriately introducing a substituent into the basic skeleton of the following exemplified compound. For example, by introducing a cyano group or a perfluoroalkyl group into the basic skeleton of the following exemplified compound, a compound having a deepened HOMO / LUMO level can be obtained, and this can be used as a host material or a peripheral compound. As the host material, it is also a bipolar character (flow good both holes and electrons) may be a unipolar resistance, but high excited triplet energy level E _T1 than the light emitting material Is preferable. A more preferred host material has bipolarity and has a higher excited triplet energy level E _T1 than the light emitting material.

Next, examples of preferable compounds that can be used as the hole injection material will be given.

Next, examples of preferable compounds that can be used as an electron injection material will be given.

Next, examples of preferable compounds that can be used as a hole blocking material are given.

Next, examples of preferable compounds that can be used as an electron blocking material are given.

Next, examples of preferable compounds that can be used as hole transport materials will be given.

Next, examples of preferable compounds that can be used as an electron transport material will be given.

Examples of preferable compounds as materials that can be further added are given. For example, it can be added as a stabilizing material.

The organic EL element of the present invention can be applied to any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix. The organic light emitting device such as the organic EL device of the present invention can be further applied to various applications. For example, it is possible to manufacture an organic electroluminescence display device using the organic EL element of the present invention. For details, see "Organic EL Display" by Shizushi Tokito, Chihaya Adachi, and Hideyuki Murata (Ohmsha). Can be referred to. In particular, the organic EL device of the present invention can also be applied to organic electroluminescence lighting and backlight, which are in great demand. Further, the organic light emitting device of the present invention can be applied to an organic light emitting diode.

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

<Learning data>
As learning compounds, 25 compounds including the compounds S1 to S7 shown in Table 4 below were used.

The learning compounds S1 to S4 were synthesized according to the following documents.
S1: Nature, 2012, 482, 234
S2: Materials Horizons, 2016, 3 (2), 145 S3: Nature, 2012, 492, 234
S4: International Publication No. 2018/047948 In addition, the learning compounds S5 to S7 were synthesized as follows. For each of S1 to S7, the maximum emission wavelength (emission maximum wavelength) due to the peak top of the emission spectrum when a thin film (thickness 50 nm) adjusted to be 10% by mass with respect to the host material (PPT) is irradiated with excitation light of 280 nm. λmax) was measured.

(Synthesis of learning compound S5)
In a nitrogen atmosphere, in a 50 mL eggplant flask, 4-bromo 2,3,5,6-tetrafluorobenzonitrile (500 mg), dibenzofuran-4-boronic acid (626 mg), SPos (81 mg), potassium phosphate (836 mg), Tris (dibenzylideneacetone) (chloroform) dipalladium (0) (102 mg) was added and dissolved in toluene (20 mL). After degassing, the mixture was stirred at 110 ° C. for 16 hours and allowed to cool to room temperature. The reaction solution was filtered through Celite. The filtrate was concentrated and subjected to silica gel column chromatography (hexane: chloroform = 8: 1) for purification to obtain an intermediate (463 mg, yield 69%).
Under a nitrogen atmosphere, NaH (60 wt% oil dispersion, 106 mg) and carbazole (368 mg) were placed in a 50 mL eggplant flask and dissolved in THF (15 mL). After stirring at room temperature for 1 hour, an intermediate (135 mg) was added, and the mixture was stirred at 60 ° C. for 14 hours. The reaction solution was concentrated and then subjected to silica gel column chromatography (hexane: ethyl acetate = 3: 1) for purification to obtain learning compound S5 (135 mg, yield 37%). ^{The 1} H NMR spectra of the learning compound S5 are shown in FIGS. 1A and 1B.

(Synthesis of learning compound S6)
Under a nitrogen atmosphere, 2,7-bistrifluoromethylcarbazole (3.87 g) and NaH (60 wt% oil dispersion, 0.625 g) were placed in a 300 mL four-necked eggplant flask and dissolved in THF (75 mL). After stirring under ice-cooling for 1 hour, a THF solution (75 mL) of perfluorotoluene (3.04 g) was added. After stirring at room temperature for 3 hours, water (90 mL) and chloroform (100 mL) were added to the reaction solution. The precipitated white solid was collected by filtration to obtain an intermediate (2.84 g, yield 42%).
Under a nitrogen atmosphere, the reaction intermediate (1.50 g), carbazole (1.96 g) and cesium carbonate (4.51 g) were placed in a 100 mL four-necked eggplant flask and dissolved in DMSO (30 mL). After stirring at 120 ° C. for 16 hours, water (30 mL) and chloroform (10 mL) were added to the reaction solution, and the mixture was ice-cooled. The precipitated pale yellow crystals were collected by filtration and washed with chloroform to obtain learning compound S6 (2.56 g, yield 80%). ^{The 1} H NMR spectrum of the learning compound S6 is shown in FIG.

(Synthesis of learning compound S7)
Under a nitrogen atmosphere, 3,6-bistrifluoromethylcarbazole (3.87 g) and NaH (60 wt% oil dispersion, 0.625 g) were placed in a 300 mL four-necked eggplant flask and dissolved in THF (75 mL). After stirring under ice-cooling for 1 hour, a THF solution (75 mL) of perfluorotoluene (3.05 g) was added. After stirring at room temperature for 5 hours, water (90 mL) and chloroform (100 mL) were added to the reaction solution. The organic layer was concentrated and then subjected to silica gel column chromatography (hexane: chloroform = 9: 1) for purification to obtain an intermediate (3.36 g, yield 50%).
Under a nitrogen atmosphere, the reaction intermediate (1.51 g), carbazole (1.95 g), and cesium carbonate (4.51 g) were placed in a 100 mL four-necked eggplant flask and dissolved in DMSO (30 mL). After stirring at 100 ° C. for 6 hours, water (30 mL) and chloroform (10 mL) were added to the reaction solution, and the mixture was ice-cooled. The precipitated yellow-white crystals were collected by filtration and further washed with chloroform to obtain learning compound S7 (3.23 g, yield 99%). ^{The 1} H NMR spectrum and the ¹⁹ F NMR spectrum of the learning compound S7 are shown in FIGS. 3A and 3C, respectively.

<Creation of prediction model>
The prediction model of the emission maximum wavelength was created by two steps of (1) extraction of the descriptor related to the emission maximum wavelength and (2) creation of the regression equation using the learning data.

(1) Creation of descriptors Using Rdkit (Open-source cheminformatics; http://www.rdkit.org), 200 types of descriptor values are used for each compound of the training data based on the chemical structural formula. Was calculated and converted into a 200-dimensional vector. The 200 types of descriptors include descriptors representing the number of functional groups, topology, polarity, and the like. The descriptor also includes HOMO-LUMO Gap. HOMO-LUMO Gap is the value obtained by calculating the energy levels of HOMO and LUMO of the compound of the training data by quantum chemistry calculation using Gaussian 09 Rev.D, and subtracting the HOMO level from the calculated LUMO level. is there. Quantum chemistry calculations are performed by the density functional theory, B3LYP is used for the functionals, 6-31g (d, p) is used for the basis functions, and the structure is based on the functionals and basis functions for the calculation of energy levels. The molecular structure that was optimized for was used. In addition, since the basic and highly versatile descriptor is preferentially used, the 3D descriptor is excluded. In addition, descriptors with the same value in more than 80% of the compounds of the training data were excluded because they are not suitable for creating normalization and regression equations.

Before creating the regression equation, the values of the descriptors of a group of training data were standardized as shown in the equation below using Scikit-learn, a Python library for machine learning. Here, x _ij is the pre-conversion descriptor j _{of compound i, x'ij} is the post-conversion descriptor j of compound i, μ _j is the mean of the entire descriptor j, and σ _j is the standard deviation of the entire descriptor j. Represents.

(2) Creation of regression equations Only a few descriptors are required to predict the emission maximum wavelength of a compound of 25 types of learning data. Therefore, we created a regression equation by Lasso regression, which has the characteristic of selectively using a small number of descriptors. This process was performed using Scikit-learn (Machine Learning in Python, Pedregosa et al., JMLR 12, pp. 2825-2830, 2011), a Python library for machine learning. Regarding the regularization coefficient, which is a hyperparameter that affects the number of descriptors and the coefficient, alpha = 0.15 was set from the viewpoint of the number of descriptors.
By the above procedure, the following regression equation regarding the maximum emission wavelength was created.
W = 863.2-0.4440 x SMR_VSA9 [Å ² ] + 2.109 x fr_para_hydroxylation [-] -115.4 x HOMO-LUMO Gap [eV]

<Verification data>
As the verification compounds, 25 compounds used for learning including the compounds V1 to V7 shown in Table 5 below and 6 compounds not used for learning including V8 and V9 were used.

The verification compounds V8 and V9 were synthesized according to the following documents.
V8: Materials, Horizons, 2016, 3 (2), 145 V9: Nature, 2012, 492, 234

<Verification of prediction model>
The accuracy of the prediction model was evaluated using the verification data. The prediction accuracy of the emission maximum wavelength of the verification compound was 14.3 nm when evaluated by RMSE. The prediction accuracy of the verification compounds V8 and V9 was 15.4 nm when evaluated by RMSE. Here, RMSE is defined by the following formula. Note that n is the number of samples, y _obs is the observed value, and y _pred is the predicted value.

<Trial data>
As the test compounds, the compounds T1 to T36 shown in Table 6 below were used.

The test compounds T1, T4, T10, T13, T19, T19-2, T21, T22, T25, T28, T31, and T34 were synthesized as follows.

　窒素雰囲気下、１０ｍＬナスフラスコに、２，７-ビストリフルオロメチルカルバゾール（３０３ｍｇ）を入れ、THF（５ｍＬ）に溶解させた。０℃に冷却後、n-BuLi (1.6M ヘキサン溶液、０．６６ｍL) を滴下した。また、別の１０ｍLナスフラスコにシアヌル酸クロライド（９２．２ｍｇ）を入れ、THF(1ｍL)に溶解させ、０℃に冷却した。シアヌル酸クロライド溶液中に先に調製したカルバゾール溶液を滴下し、０℃で３０分撹拌した。反応液に水（５ｍL）を加え、析出物をろ取した。ろ取物を昇華精製し、中間体（１５０ｍｇ、収率４２％）を得た。中間体の¹H-NMRスペクトル,¹⁹F-NMR Rスペクトル、及びIRスペクトルをそれぞれ図４Ａ、図４Ｃ、及び図４Ｄに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

　反応の2段階目として、次の文献に基づいて、得られたアリールクロライドとアリールボロン酸の鈴木カップリング反応を行う。
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737.Chemical Reviews, 1995, 95(7), 2457.
　反応の3段階目として、次の文献に基づいて、塩基存在下、得られたフルオロアリールとカルバゾールの芳香族求核置換反応を行う。
Science Advances, 2018, 4(6), eaao6910.Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649. (Synthesis of test compound T1)

In a nitrogen atmosphere, 2,7-bistrifluoromethylcarbazole (303 mg) was placed in a 10 mL eggplant flask and dissolved in THF (5 mL). After cooling to 0 ° C., n-BuLi (1.6M hexane solution, 0.66 mL) was added dropwise. Further, cyanuric acid chloride (92.2 mg) was placed in another 10 mL eggplant flask, dissolved in THF (1 mL), and cooled to 0 ° C. The previously prepared carbazole solution was added dropwise to the cyanuric acid chloride solution, and the mixture was stirred at 0 ° C. for 30 minutes. Water (5 mL) was added to the reaction solution, and the precipitate was collected by filtration. The filtrate was sublimated and purified to obtain an intermediate (150 mg, yield 42%). The ¹ H-NMR spectrum, ¹⁹ F-NMR R spectrum, and IR spectrum of the intermediate are shown in FIGS. 4A, 4C, and 4D, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

As the second step of the reaction, the Suzuki coupling reaction of the obtained aryl chloride and arylboronic acid is carried out based on the following literature.
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737. Chemical Reviews, 1995, 95 (7), 2457.
As the third step of the reaction, the aromatic nucleophilic substitution reaction of the obtained fluoroaryl and carbazole is carried out in the presence of a base based on the following literature.
Science Advances, 2018, 4 (6), eaao6910. Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649.

　反応の第1段階目として、窒素雰囲気下、１００ｍＬ　四つ口フラスコに、ジフェニルトリアジンブロミド（１．０１ｇ）、ペンタフルオロフェニルボロン酸（８３４ｍｇ）、リン酸カリウム（１．６４ｇ）、酸化銀（１．０６ｇ）、テトラキストリフェニルホスフィンパラジウム（２６３ｍｇ）を入れ、DMF（２７ｍＬ）に溶解させた。７０℃で２１時間撹拌した後、室温まで放冷した。反応溶液を濾過し、ろ液に水（１００ｍＬ）を加え、９０分間静置した。分液後、有機層を硫酸ナトリウムで脱湿した。濾過、濃縮を行った後、シリカゲルカラムクロマトグラフィーに供して精製し、中間体（８５ｍｇ、収率５％）を得た。中間体の¹H-NMRスペクトル及びIRスペクトルをそれぞれ図５Ａ及び図５Ｃに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

　反応の2、3段階目として、次の文献に基づいて、塩基存在下、得られたフルオロアリールとカルバゾール類縁体の芳香族求核置換反応を行う。
Science Advances, 2018, 4(6), eaao6910.Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649. (Synthesis of test compound T4)

As the first step of the reaction, diphenyltriazine bromide (1.01 g), pentafluorophenylboronic acid (834 mg), potassium phosphate (1.64 g), silver oxide (1) were placed in a 100 mL four-necked flask under a nitrogen atmosphere. .06 g) and tetrakistriphenylphosphine palladium (263 mg) were added and dissolved in DMF (27 mL). After stirring at 70 ° C. for 21 hours, the mixture was allowed to cool to room temperature. The reaction solution was filtered, water (100 mL) was added to the filtrate, and the mixture was allowed to stand for 90 minutes. After the liquid separation, the organic layer was dehumidified with sodium sulfate. After filtration and concentration, the mixture was purified by silica gel column chromatography to obtain an intermediate (85 mg, yield 5%). The ¹ H-NMR spectrum and IR spectrum of the intermediate are shown in FIGS. 5A and 5C, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

As the second and third steps of the reaction, the aromatic nucleophilic substitution reaction of the obtained fluoroaryl and carbazole analog is carried out in the presence of a base based on the following literature.
Science Advances, 2018, 4 (6), eaao6910. Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649.

　反応の1、2段階目として、次の文献に基づいて、塩基存在下、得られたフルオロアリールとカルバゾール類縁体の芳香族求核置換反応を行う。
Science Advances, 2018, 4(6), eaao6910.Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234. Organic letters, 2014, 16 (11), 3130.Tetrahedron letters, 2013, 54 (35), 4649. (Synthesis of test compound T10)

As the first and second steps of the reaction, the aromatic nucleophilic substitution reaction of the obtained fluoroaryl and carbazole analog is carried out in the presence of a base based on the following literature.
Science Advances, 2018, 4 (6), eaao6910. Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234. Organic letters, 2014, 16 (11), 3130. Tetrahedron letters, 2013, 54 (35), 4649.

　反応の1段階目として、次の文献に基づいて、塩基存在下、フルオロアリールとカルバゾール類縁体の芳香族求核置換反応を行う。
CN108101898
ACS Applied Materials & Interfaces, 2017, 9 (38), 32946.　反応の2段階目として、次の文献に基づいて、得られたアリールブロマイドとアリールボロン酸の鈴木カップリング反応を行う。
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737.Chemical Reviews, 1995, 95(7), 2457.
　反応の3段階目として、次の文献に基づいて、塩基存在下、得られたフルオロアリールとカルバゾール類縁体の芳香族求核置換反応を行う。
Science Advances, 2018, 4(6), eaao6910.Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649. (Synthesis of test compound T13)

As the first step of the reaction, an aromatic nucleophilic substitution reaction of fluoroaryl and carbazole analog is carried out in the presence of a base based on the following literature.
CN108101898
ACS Applied Materials & Interfaces, 2017, 9 (38), 32946. As the second step of the reaction, the Suzuki coupling reaction of the obtained aryl bromide and aryl boronic acid is carried out based on the following literature.
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737. Chemical Reviews, 1995, 95 (7), 2457.
As the third step of the reaction, the aromatic nucleophilic substitution reaction of the obtained fluoroaryl and carbazole analog is carried out in the presence of a base based on the following literature.
Science Advances, 2018, 4 (6), eaao6910. Advanced Functional Materials 2018, 28, 1706023.Chem. Mater. 2018, 30, 6389-6399.
Nature 2012, 492, 234.
Organic letters, 2014, 16 (11), 3130.
Tetrahedron letters, 2013, 54 (35), 4649.

　反応の１段階目として、ジフェニルクロロトリアジンとアリールボロン酸の鈴木カップリング反応を行う。反応は次の文献を参考に実施する。
Journal of Materials Chemistry C, 2018, 6, 5536-5541.Advanced Materials, 2015, 27(39), 5861-5867。　反応の2段階目として、窒素雰囲気下、30ｍＬナスフラスコに、中間体（５００ｍｇ）、２，７ービストリフルオロメチルカルバゾール（４４４ｍｇ）、炭酸セシウム（９６１ｍｇ）を入れ、DMSO（２０ｍＬ）に溶解させた。８５℃で３時間撹拌した後、室温まで放冷した。反応溶液に水（１２ｍＬ）、クロロホルム（１０ｍＬ）を加え、１０分間静置した。析出した灰色の結晶をろ取し、水（２ｍＬ）、クロロホルム（３ｍＬ）で洗浄することで、中間体（７６６ｍｇ、収率８６％）を得た。中間体の¹H-NMRスペクトル及びIRスペクトルをそれぞれ図６Ａ及び図６Ｃに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

　反応の3段階目として、窒素雰囲気下、30ｍＬナスフラスコに、中間体（４９９ｍｇ）、カルバゾール（２７４ｍｇ）、炭酸セシウム（１．１５８ｇ）を入れ、DMSO（２０ｍＬ）に溶解させた。１２０℃で１８時間撹拌した後、室温まで放冷した。次に、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した灰色の結晶をろ取し、冷クロロホルム（２ｍＬ）で洗浄することでT19（５１５ｍｇ、収率７１％）を得た。供試用化合物T19の¹H-NMRスペクトル及びIRスペクトルをそれぞれ図７Ａ及び図７Ｃに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

(Synthesis of test compound T19)

As the first step of the reaction, Suzuki coupling reaction of diphenylchlorotriazine and arylboronic acid is carried out. The reaction is carried out with reference to the following documents.
Journal of Materials Chemistry C, 2018, 6, 5536-5541. Advanced Materials, 2015, 27 (39), 5861-5867. As the second step of the reaction, an intermediate (500 mg), 2,7-bistrifluoromethylcarbazole (444 mg) and cesium carbonate (961 mg) were placed in a 30 mL eggplant flask under a nitrogen atmosphere and dissolved in DMSO (20 mL). .. After stirring at 85 ° C. for 3 hours, the mixture was allowed to cool to room temperature. Water (12 mL) and chloroform (10 mL) were added to the reaction solution, and the mixture was allowed to stand for 10 minutes. The precipitated gray crystals were collected by filtration and washed with water (2 mL) and chloroform (3 mL) to obtain an intermediate (766 mg, yield 86%). The ¹ H-NMR spectrum and IR spectrum of the intermediate are shown in FIGS. 6A and 6C, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

As the third step of the reaction, an intermediate (499 mg), carbazole (274 mg) and cesium carbonate (1.158 g) were placed in a 30 mL eggplant flask under a nitrogen atmosphere and dissolved in DMSO (20 mL). After stirring at 120 ° C. for 18 hours, the mixture was allowed to cool to room temperature. Next, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated gray crystals were collected by filtration and washed with cold chloroform (2 mL) to obtain T19 (515 mg, yield 71%). ^{The 1} H-NMR spectrum and IR spectrum of the test compound T19 are shown in FIGS. 7A and 7C, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

　窒素雰囲気下、30ｍＬナスフラスコに、中間体（６５ｍｇ）、３，６ジフェニルカルバゾール（８０ｍｇ）、炭酸セシウム（８２ｍｇ）を入れ、DMSO（３ｍＬ）に溶解させた。１００℃で１８時間撹拌した後、室温まで放冷した。次に、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した灰色の結晶をろ取し、IPA（２ｍＬ）で洗浄後、昇華することでT19－２（８５ｍｇ、収率６８％）を得た。供試用化合物T19-2の¹H-NMRスペクトル,¹⁹F-NMRスペクトル、及びIRスペクトルをそれぞれ図８Ａ、図８Ｃ、及び図８Ｄに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

(Synthesis of test compound T19-2)

The intermediate (65 mg), 3,6 diphenylcarbazole (80 mg) and cesium carbonate (82 mg) were placed in a 30 mL eggplant flask under a nitrogen atmosphere and dissolved in DMSO (3 mL). After stirring at 100 ° C. for 18 hours, the mixture was allowed to cool to room temperature. Next, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated gray crystals were collected by filtration, washed with IPA (2 mL), and sublimated to obtain T19-2 (85 mg, yield 68%). ^{The 1} H-NMR spectrum, ¹⁹ F-NMR spectrum, and IR spectrum of the test compound T19-2 are shown in FIGS. 8A, 8C, and 8D, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

　窒素雰囲気下、１００ｍＬナスフラスコに、２、７－ビストリフルオロメチルカルバゾール（１．５ｇ）をNMP（６０ｍL）に溶解させ、水素化ナトリウム（６０ｗｔ％オイルディスパージョン、２４０ｍｇ）を加えた。室温で1時間撹拌後、中間体（５１０ｍｇ）を加え１００℃で１６時間撹拌した後、室温まで放冷した。次に、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した灰色の結晶をろ取し、IPA（２ｍＬ）で洗浄後、昇華することでT２１（１．１８ｇ、収率６９％）を得た。供試用化合物T21の¹H-NMRスペクトルを図９に示す。 (Synthesis of test compound T21)

In a nitrogen atmosphere, 2,7-bistrifluoromethylcarbazole (1.5 g) was dissolved in NMP (60 mL) in a 100 mL eggplant flask, and sodium hydride (60 wt% oil dispersion, 240 mg) was added. After stirring at room temperature for 1 hour, an intermediate (510 mg) was added, and the mixture was stirred at 100 ° C. for 16 hours and then allowed to cool to room temperature. Next, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated gray crystals were collected by filtration, washed with IPA (2 mL), and sublimated to obtain T21 (1.18 g, yield 69%). ^{The 1} H-NMR spectrum of the test compound T21 is shown in FIG.

　反応の１段階目として、２、７－ビストリフルオロメチルカルバゾールの臭素化を行った。窒素雰囲気下、１０ｍＬナスフラスコに、２、７－ビストリフルオロメチルカルバゾール（１５１ｍｇ）をDMF（３ｍL）に溶解させた。室温下、N-ブロモスクシンイミド（８９ｍｇ）を加え、16時間撹拌した。チオ硫酸ナトリウム水溶液、酢酸エチルを加え分液後、有機層を濃縮した。得られた粗生成物をGPCカラム（溶媒：クロロホルム）により精製し、中間体（１９０ｍｇ、収率５０％）を得た。中間体の¹H-NMRスペクトル及び¹⁹F-NMRスペクトルをそれぞれ図１０Ａ及び図１０Ｃに示す。
　なお、反応の１段階目は、次の文献に記載の方法を用いてもよい。
　Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042.　反応の２段階目として、次の文献に基づいて、カルバゾールのNH部のフェニル化を行う。
RSC advances 2015, 5(77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116(15), 8699-8706.Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater. 15 (2014) 034202.
J.Org.Chem. 62(2) (2003) 452.
Chem.Eur.J.,2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743.　反応の３段階目として、次の文献に基づいて、得られた中間体と10,15-ジヒドロ-5H-ジインドロカルバゾールのカップリング反応を行う。
RSC advances 2015, 5(77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116(15), 8699-8706.Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater. 15 (2014) 034202.
J.Org.Chem. 62(2) (2003) 452.
Chem.Eur.J.,2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743. (Synthesis of test compound T22)

As the first step of the reaction, bromination of 2,7-bistrifluoromethylcarbazole was performed. 2,7-Bistrifluoromethylcarbazole (151 mg) was dissolved in DMF (3 mL) in a 10 mL eggplant flask under a nitrogen atmosphere. N-Bromosuccinimide (89 mg) was added at room temperature, and the mixture was stirred for 16 hours. An aqueous sodium thiosulfate solution and ethyl acetate were added to separate the liquids, and the organic layer was concentrated. The obtained crude product was purified by a GPC column (solvent: chloroform) to obtain an intermediate (190 mg, yield 50%). The ¹ H-NMR spectrum and the ¹⁹ F-NMR spectrum of the intermediate are shown in FIGS. 10A and 10C, respectively.
The method described in the following document may be used for the first step of the reaction.
Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042. As the second step of the reaction, the NH portion of carbazole is phenylated based on the following literature.
RSC advances 2015, 5 (77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater . 15 (2014) 034202.
J.Org.Chem. 62 (2) (2003) 452.
Chem.Eur.J., 2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743. As the third step of the reaction, based on the following literature, the obtained intermediate and a cup of 10,15-dihydro-5H-diindrocarbazole Perform a ring reaction.
RSC advances 2015, 5 (77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater . 15 (2014) 034202.
J.Org.Chem. 62 (2) (2003) 452.
Chem.Eur.J., 2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743.

　反応の１段階目として、２、７－ビストリフルオロメチルカルバゾールの臭素化を行った。窒素雰囲気下、１０ｍＬナスフラスコに、２、７－ビストリフルオロメチルカルバゾール（１５１ｍｇ）をDMF（３ｍL）に溶解させた。室温下、N-ブロモスクシンイミド（１７８ｍｇ）を加え、16時間撹拌した。チオ硫酸ナトリウム水溶液、酢酸エチルを加え分液後、有機層を濃縮した。得られた粗生成物をGPCカラム（溶媒：クロロホルム）により精製し、中間体（６９ｍｇ、収率３０％）を得た。中間体の¹H-NMRスペクトル及び¹⁹F-NMRスペクトルをそれぞれ図１１Ａ及び図１１Ｃに示す。
　なお、反応の１段階目は、次の文献に記載の方法を用いてもよい。
　Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042.　反応の２段階目として、次の文献に基づいて、カルバゾールのNH部のフェニル化を行う。
RSC advances 2015, 5(77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116(15), 8699-8706.Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater. 15 (2014) 034202.
J.Org.Chem. 62(2) (2003) 452.
Chem.Eur.J.,2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743.　反応の３段階目として、次の文献に基づいて、得られた中間体とカルバゾールのカップリング反応を行う。
RSC advances 2015, 5(77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116(15), 8699-8706.Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater. 15 (2014) 034202.
J.Org.Chem. 62(2) (2003) 452.
Chem.Eur.J.,2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743. (Synthesis of test compound T25)

As the first step of the reaction, bromination of 2,7-bistrifluoromethylcarbazole was performed. 2,7-Bistrifluoromethylcarbazole (151 mg) was dissolved in DMF (3 mL) in a 10 mL eggplant flask under a nitrogen atmosphere. N-Bromosuccinimide (178 mg) was added at room temperature, and the mixture was stirred for 16 hours. An aqueous sodium thiosulfate solution and ethyl acetate were added to separate the liquids, and the organic layer was concentrated. The obtained crude product was purified by a GPC column (solvent: chloroform) to obtain an intermediate (69 mg, yield 30%). The ¹ H-NMR spectrum and the ¹⁹ F-NMR spectrum of the intermediate are shown in FIGS. 11A and 11C, respectively.
The method described in the following document may be used for the first step of the reaction.
Chem. Rev. 2016, 116, 6837. Org. Lett. 2015, 17, 1042. As the second step of the reaction, the NH portion of carbazole is phenylated based on the following literature.
RSC advances 2015, 5 (77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater . 15 (2014) 034202.
J.Org.Chem. 62 (2) (2003) 452.
Chem.Eur.J., 2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743. As the third step of the reaction, a coupling reaction between the obtained intermediate and carbazole is carried out based on the following literature.
RSC advances 2015, 5 (77), 63130-63134.
Angew. Chem. Int. Ed., 2011, 50, 6722-6737.J. Phys. Chem. C. 2012, 116 (15), 8699-8706. Inorganica Chimica Acta 357 (2004) 4335-4340.Adv.Mater . 15 (2014) 034202.
J.Org.Chem. 62 (2) (2003) 452.
Chem.Eur.J., 2008,14,2443.
J. Am. Chem. Soc. 2006, 128, 8742-8743.

　反応の１段階目として、文献（Polymer, 2015, 70, 52-58.）を参考に合成を行い、中間体を得た。中間体の¹H-NMRスペクトル及び¹⁹F-NMRスペクトルをそれぞれ図１２Ａ及び図１２Ｃに示す。
　反応の２段階目として、窒素雰囲気下、30ｍＬナスフラスコに、中間体（１００ｍｇ）、２、７－ビストリフルオロメチルカルバゾール（９８ｍｇ）、炭酸セシウム（１２７ｍｇ）を入れ、NMP（２．５ｍＬ）に溶解させた。１５０℃で１８時間撹拌した後、室温まで放冷した。次に、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した白色の結晶をろ取し、クロロホルム（２ｍＬ）、アセトン（２ｍL）で洗浄後、昇華することで供試用化合物T28（９３ｍｇ、収率５３％）を得た。供試用化合物T28の¹H-NMRスペクトル,¹⁹F-NMRスペクトル、及びIRスペクトルをそれぞれ図１３Ａ、図１３Ｂ、及び図１３Ｃに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

(Synthesis of test compound T28)

As the first step of the reaction, an intermediate was obtained by synthesizing with reference to the literature (Polymer, 2015, 70, 52-58.). The ¹ H-NMR spectrum and the ¹⁹ F-NMR spectrum of the intermediate are shown in FIGS. 12A and 12C, respectively.
As the second step of the reaction, the intermediate (100 mg), 2,7-bistrifluoromethylcarbazole (98 mg) and cesium carbonate (127 mg) were placed in a 30 mL eggplant flask under a nitrogen atmosphere and dissolved in NMP (2.5 mL). I let you. After stirring at 150 ° C. for 18 hours, the mixture was allowed to cool to room temperature. Next, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated white crystals were collected by filtration, washed with chloroform (2 mL) and acetone (2 mL), and then sublimated to obtain test compound T28 (93 mg, yield 53%). ^{The 1} H-NMR spectrum, ¹⁹ F-NMR spectrum, and IR spectrum of the test compound T28 are shown in FIGS. 13A, 13B, and 13C, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

　反応の１段階目として、窒素雰囲気下、３０ｍＬナスフラスコに、ペンタフルオロヨードベンゼン（０．８ｍL）、２、７－ビストリフルオロメチルカルバゾール（９０９ｍｇ）、炭酸セシウム（１．１７ｇ）を入れ、DMSO（３０ｍＬ）に溶解させた。室温で１５時間撹拌した後、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した白色の結晶をろ取後、昇華することで中間体（１．１９ｇ、収率６９％）を得た。中間体の¹H-NMRスペクトル,¹⁹F-NMRスペクトル、及びIRスペクトルをそれぞれ図１４Ａ、図１４Ｃ、及び図１４Ｄに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

　反応の２段階目として、窒素雰囲気下、１０ｍＬナスフラスコに、中間体（２９ｍｇ）、カルバゾール（５０ｍｇ）、炭酸セシウム（３９０ｍｇ）を入れ、DMSO（２ｍＬ）に溶解させた。８５℃で１５時間撹拌した後、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した白色の結晶をろ取後、クロロホルム（５ｍL）で洗浄し、昇華することで中間体（３３ｍｇ、収率６０％）を得た。
　反応の３段階目として、次の文献に基づいて、ハロゲン化アリールとアリールボロン酸のカップリング反応を行う。
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737.Chemical Reviews, 1995, 95(7), 2457. (Synthesis of test compound T31)

As the first step of the reaction, pentafluoroiodobenzene (0.8 mL), 2,7-bistrifluoromethylcarbazole (909 mg) and cesium carbonate (1.17 g) were placed in a 30 mL eggplant flask under a nitrogen atmosphere, and DMSO (1.17 g) was added. It was dissolved in 30 mL). After stirring at room temperature for 15 hours, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated white crystals were collected by filtration and sublimated to obtain an intermediate (1.19 g, yield 69%). The ¹ H-NMR spectrum, ¹⁹ F-NMR spectrum, and IR spectrum of the intermediate are shown in FIGS. 14A, 14C, and 14D, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

As the second step of the reaction, an intermediate (29 mg), carbazole (50 mg) and cesium carbonate (390 mg) were placed in a 10 mL eggplant flask under a nitrogen atmosphere and dissolved in DMSO (2 mL). After stirring at 85 ° C. for 15 hours, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated white crystals were collected by filtration, washed with chloroform (5 mL), and sublimated to obtain an intermediate (33 mg, yield 60%).
As the third step of the reaction, a coupling reaction of aryl halide and arylboronic acid is carried out based on the following literature.
Journal of Organometalic Chemistry, 1999, 576, 147-168.Angew. Chem. Int. Ed., 2011, 50, 6722-6737. Chemical Reviews, 1995, 95 (7), 2457.

　窒素雰囲気下、１０ｍＬナスフラスコに、カルバゾール（２６０ｍｇ）をNMP（５ｍL）に溶解させ、水素化ナトリウム（６０ｗｔ％オイルディスパージョン、７５ｍｇ）を加えた。室温で1時間撹拌後、中間体（２６０ｍｇ）を加え１３０℃で１６時間撹拌した後、室温まで放冷した。次に、反応溶液に水（１５ｍＬ）を加え、４０分間静置した。析出した灰色の結晶をろ取し、クロロホルム（５ｍＬ）で洗浄後、昇華することで供試用化合物T34（２００ｍｇ、収率５６％）を得た。供試用化合物T34の¹H-NMRスペクトル,¹⁹F-NMRスペクトル、及びIRスペクトルをそれぞれ図１５Ａ、図１５Ｃ、及び図１５Ｄに示す。なお、IRスペクトルにおける主なピークの位置及び強度は、次のとおりである。

(Synthesis of test compound T34)

In a nitrogen atmosphere, carbazole (260 mg) was dissolved in NMP (5 mL) in a 10 mL eggplant flask, and sodium hydride (60 wt% oil dispersion, 75 mg) was added. After stirring at room temperature for 1 hour, an intermediate (260 mg) was added, and the mixture was stirred at 130 ° C. for 16 hours and then allowed to cool to room temperature. Next, water (15 mL) was added to the reaction solution, and the mixture was allowed to stand for 40 minutes. The precipitated gray crystals were collected by filtration, washed with chloroform (5 mL), and sublimated to obtain test compound T34 (200 mg, yield 56%). ^{The 1} H-NMR spectrum, ¹⁹ F-NMR spectrum, and IR spectrum of the test compound T34 are shown in FIGS. 15A, 15C, and 15D, respectively. The positions and intensities of the main peaks in the IR spectrum are as follows.

(Λmax (prediction))
^{SMR_VSA9 [Å 2} ], fr_para_hydroxylation, and HOMO-LUMO Gap [eV] were calculated from the structures of the test compounds T1 to T36, and the calculated values were substituted into the prediction model to obtain the predicted value of the emission maximum wavelength. .. For some compounds, in the calculation of HOMO-LUMO Gap, the energy level of the structure with the smallest total energy was adopted as the representative value among the 50-step optimization calculations.

(Λmax (actual measurement))
For the test compounds T19, T19-2, T20, T21, T37, and T38, a thin film (thickness 50 nm) adjusted to be 10% by mass with respect to the host material (PPT) was irradiated with excitation light of 280 nm. The maximum emission wavelength (λmax) was measured from the peak top of the emission spectrum.

(HOMO)
The HOMO levels of the test compounds T19, T19-2, T21, and T37-T39 were measured using a photoelectron yield spectrometer.

(ΔE _ST )
_{The ΔE ST} of the test compounds T19, T19-2, T21, and T37 to T39 can be measured by the same method as the measurement method of λmax (actual measurement), and the fluorescence spectrum (room temperature) and the phosphorescence spectrum (77K) can be measured. It was measured and calculated from the difference in wavelength at each rising edge.

(Relative emission intensity)
The relative emission intensities of the test compounds T37 to T39 were measured by a conventional device (for example, "PMA12" manufactured by Hamamatsu Photonics Co., Ltd.).

(Delayed fluorescent life)
The delayed fluorescence lifetimes of the test compounds T19, T19-2, T21, and T37 to T39 were measured by a conventional device (for example, "PMA12" manufactured by Hamamatsu Photonics Co., Ltd.).

(Excited state stability)
The excited state stability of the test compounds T37 and T38 was determined by using a toluene solution of the compound (concentration 1.0 × 10 ^-5 M), degassing by argon bubbling, and then stirring with excitation light (wavelength 300 to 400 nm,). It was evaluated by irradiating with 5 mW / cm ² ) and measuring the time from the initial emission to the reduction of the emission intensity by half.

The results are shown in Table 15.

Than compounds in which two each CF ₃ group to all of the carbazole ring modified, increased emission maximum wavelength portions modifying compound, preferably it is found. For the test compounds T19 to T21, the maximum emission wavelength was actually measured, and the measured values showed the same tendency as the predicted values. In addition, the test compound T19 has a lower HOMO, a _{smaller ΔE ST} , and a shorter delayed fluorescence lifetime than T20 or T21, and is therefore excellent in compatibility with peripheral materials and durability. Further, the test compounds T37 and T38 have a lower HOMO, a _{smaller ΔE ST} , a larger emission intensity, and a shorter delayed fluorescence lifetime than T39, and thus are excellent in compatibility with peripheral materials and durability.

Claims (15)

Expression (X) of N (N is an integer of 2 or more):

(In the equation, Q is a single bond or -CH _2- .)
A compound having a ring X represented by, in which two adjacent rings X are linked by either (A) direct linking, (B) linking via a π-conjugated linking group, or (C) condensation linking. Compounds in which the total number of perfluoroalkyl groups that are linked and substituted with N rings X is 1 or more and less than 2N [However, the following compounds:

(In the formula, Y is a cyano group or a perfluoromethyl group.)
except for]. (A) In the case of direct connection, the nitrogen atom of one ring X and the carbon atom at the para position with respect to the nitrogen atom bonded to the benzene ring contained in the other ring X are connected by a single bond.
(B) In the case of connection via a π-conjugated linking group, the nitrogen atoms of both rings X are linked via the π-conjugated linking group.
(C) In the case of condensation connection, both rings X are condensed and the formula:

(In the equation, Q ¹ and Q ² are independently single-bonded or -CH _2- .)
Connected by forming a ring represented by,
The compound according to claim 1. The compound according to claim 1 or 2, wherein the π-conjugated linking group is an aromatic ring group. The compound according to any one of claims 1 to 3, wherein the perfluoroalkyl group is substituted at the meta position with respect to the nitrogen atom bonded to the benzene ring contained in the ring X having 1 or more and less than N rings. The compound according to any one of claims 1 to 3, wherein the perfluoroalkyl group is substituted at the para position with respect to the nitrogen atom bonded to the benzene ring contained in the ring X having 1 or more and less than N rings. The compound according to any one of claims 1 to 5, wherein the perfluoroalkyl group is a perfluoroC _{1-4 alkyl group.} The compound according to any one of claims 1 to 6, wherein one or more rings X are substituted with an electron donating group. The compound according to any one of claims 1 to 7, wherein Q is a single bond. The following formulas (1) to (3):

[During the ceremony,
R ¹⁰ is a monovalent aromatic ring group and
R ¹¹ to R ²⁰ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (however, the total number of perfluoroalkyl groups substituted into three rings is one to one. 5),
Q ¹¹ ~ Q ¹³ are each independently a single bond or -CH ₂ -,
R ²¹ and R ²² are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
R ²³ to R ²⁶ are each independently a hydrogen atom, a perfluoroalkyl group, or an electron donating group (provided that the total number of perfluoroalkyl groups substituted with m rings substituted with L is the total number. 1 or more and less than 2 mn),
Q ²¹ is a single bond or -CH _2-
L is a linking group composed of one aromatic ring.
m is an integer greater than or equal to 1 and
n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
p and q are the maximum numbers that can be independently replaced with 0 or L, respectively.
R ³¹ , R ³⁵ , and R ³⁹ are independently monovalent aromatic ring groups, respectively.
R ³² to R ³⁴ , R ³⁶ to R ³⁸ , and R ⁴⁰ to R ⁴⁸ are independently hydrogen atoms, perfluoroalkyl groups, or electron donating groups (provided that they are replaced with 6 rings). The total number of perfluoroalkyl groups is 1-8),
The compound according to claim 1, wherein Q ³¹ to Q ³³ and Q ⁴¹ to Q ⁴³ are each independently represented by either a single bond or -CH _2-]. The compound according to any one of claims 1 to 9, which satisfies the following formula (a):
W ₁ > W ₀ (a)
_{[W 1 in} equation (a) is the following equation (b):
W = 863.2-0.4440 x SMR_VSA9 [Å ² ] + 2.109 x fr_para_hydroxylation [-] -115.4 x HOMO-LUMO Gap [eV] (b)
W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the compound in
_{W 0 in the} formula (a) is the total number of perfluoroalkyl groups substituted with N rings X, where N is the total number of rings X contained in the compound in the formula (b). W obtained by substituting the values of the descriptors SMR_VSA9, fr_para_hydroxylation, and HOMO-LUMO Gap of the comparative compound having the same structure as the compound except that the number is 2N]. A delayed fluorescent material containing the compound according to any one of claims 1 to 10. An organic light emitting device containing the compound according to any one of claims 1 to 10. The organic light emitting element according to claim 12, which is an organic EL element. The following formula (4):

[During the ceremony,
R ^1a is a monovalent aromatic ring group and
R ^1c and R ^1h are perfluoroalkyl groups, and ^{one or two of R 1b} , R ^1d , R ^1e , R ^1f , R ^1g , and R ¹ⁱ are bromine atoms, and the rest are hydrogen atoms or An electron donating group, or R ^1d and R ^1g are perfluoroalkyl groups, and one or two of ^{R 1b} , R ^1c , R ^1e , R ^1f , R ^1h , and R ^{1i are bromine.} It is an atom, the rest is a hydrogen atom or an electron donating group, and Q ^1a is a single bond or -CH _2- ].
The compound represented by. The following formula (5):

[During the ceremony,
R ²¹ and R ²² are independently hydrogen atoms, alkyl groups, or monovalent aromatic ring groups, respectively.
R ²³ to R ²⁶ are independently hydrogen atoms or perfluoroalkyl groups (provided that at least one of the m rings substituted with L has at least one of R ²³ to R ²⁶ . The individual is a perfluoroalkyl group, and ^{not all of R 23} to R ²⁶ are perfluoroalkyl groups),
Q ²¹ is a single bond or -CH _2-
L is a linking group composed of one aromatic ring.
X is a halogen atom,
m is an integer greater than or equal to 1 and
n is an integer of 2 or more and less than or equal to the maximum number that can be replaced with L.
p and q are the maximum numbers that can be independently replaced with 0 or L, respectively.
a is an integer greater than or equal to 1 and less than n]
The compound represented by.

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