JP6848787B2 - Light emitting element - Google Patents

Description

The present invention relates to a light emitting device.

Light emitting devices such as organic electroluminescence devices can be suitably used for display and lighting applications, and research and development are being carried out. For example, Patent Document 1 describes a light emitting element having an organic layer containing a polymer compound (HT-1) and a light emitting layer containing a light emitting material having a triazine skeleton and a carbazole skeleton.

International Publication No. 2014/163083

However, the above-mentioned light emitting device does not always have sufficient external quantum efficiency.
Therefore, an object of the present invention is to provide a light emitting device having excellent external quantum efficiency.

The present invention provides the following [1] to [12].
[1]
A light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.
The first organic layer contains a compound (T) in which the absolute value of the difference between the energy level in the lowest triplet excited state and the energy level in the lowest singlet excited state is 0.5 eV or less, and A layer that does not contain a phosphorescent metal complex.
The second organic layer is a layer containing a crosslinked body of a crosslinking material.
The cross-linking material is a low molecular weight compound having at least one cross-linking group selected from the cross-linking group A group, or a high-molecular compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. There is a light emitting element.
(Crosslinking group A group)

［式中、Ｒ^XLは、メチレン基、酸素原子又は硫黄原子を表し、ｎ^XLは、０〜５の整数を表す。Ｒ^XLが複数存在する場合、それらは同一でも異なっていてもよく、ｎ^XLが複数存在する場合、それらは同一でも異なっていてもよい。＊１は結合位置を表す。これらの架橋基は置換基を有していてもよい。］
［２］
前記架橋材料が、架橋基Ａ群から選ばれる少なくとも１種の架橋基を有する架橋構成単位を含む高分子化合物であり、且つ、前記架橋構成単位が、式（２）で表される構成単位又は式（２’）で表される構成単位である、［１］に記載の発光素子。

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer from 0 to 5. If there are multiple R ^XLs , they may be the same or different, and ^{if there are multiple n XLs} , they may be the same or different. * 1 represents the bonding position. These cross-linking groups may have substituents. ]
[2]
The cross-linking material is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group, and the cross-linking structural unit is a structural unit represented by the formula (2) or The light emitting element according to [1], which is a structural unit represented by the formula (2').

［式中、
ｎＡは０〜５の整数を表し、ｎは１又は２を表す。ｎＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ³は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘは、架橋基Ａ群から選ばれる架橋基を表す。Ｘが複数存在する場合、それらは同一でも異なっていてもよい。］

[During the ceremony,
nA represents an integer from 0 to 5, and n represents 1 or 2. When there are a plurality of nA, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a cross-linking group selected from the cross-linking group A group. When there are a plurality of X's, they may be the same or different. ]

［式中、
ｍＡは０〜５の整数を表し、ｍは１〜４の整数を表し、ｃは０又は１を表す。ｍＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ⁵は、芳香族炭化水素基、複素環基、又は、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ⁴及びＡｒ⁶は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ⁴、Ａｒ⁵及びＡｒ⁶はそれぞれ、該基が結合している窒素原子に結合している該基以外の基と、直接結合して、又は、酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。
Ｋ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、前記と同じ意味を表す。Ｋ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’は、架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｘ’が複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも１つのＸ’は、架橋基Ａ群から選ばれる架橋基である。］
［３］
前記架橋材料が、架橋基Ａ群から選ばれる少なくとも１種の架橋基を有する低分子化合物であり、且つ、前記低分子化合物が式（３）で表される低分子化合物である、［１］に記載の発光素子。

[During the ceremony,
mA represents an integer from 0 to 5, m represents an integer from 1 to 4, and c represents 0 or 1. If there are multiple mAs, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ are each directly bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, or bonded via an oxygen atom or a sulfur atom. , May form a ring.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents the same meaning as described above. If K ^A there are a plurality, they may be the same or different.
X'represents a cross-linking group selected from the cross-linking group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple X's, they may be the same or different. However, at least one X'is a cross-linking group selected from the cross-linking group A group. ]
[3]
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from the cross-linking group A group, and the low-molecular-weight compound is a low-molecular-weight compound represented by the formula (3) [1]. The light emitting element according to.

［式中、
ｍ^B1及びｍ^B2は、それぞれ独立に、０以上の整数を表す。ｍ^B3は、０以上５以下の整数を表す。複数存在するｍ^B1は、同一でも異なっていてもよい。ｍ^B3が複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ⁷は、芳香族炭化水素基、複素環基、又は、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。Ａｒ⁷が複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^B1は、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−Ｎ(Ｒ’’’)−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’’’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^B1が複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’’は、架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＸ’’は、同一でも異なっていてもよい。但し、複数存在するＸ’’のうち、少なくとも１つは、架橋基Ａ群から選ばれる架橋基である。］
［４］
前記化合物（Ｔ）が式（Ｔ−１）で表される化合物である、［１］〜［３］のいずれかに記載の発光素子。

[During the ceremony,
m ^B1 and m ^B2 each independently represent an integer of 0 or more. m ^B3 represents an integer of 0 or more and 5 or less. A plurality of m ^B1s may be the same or different. If there are multiple m ^B3s , they may be the same or different.
Ar ⁷ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be. If there are multiple Ar ⁷ , they may be the same or different.
^LB1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N (R''')-, an oxygen atom or a sulfur atom, and these groups are substituents. May have. R'''represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of LB1s} exist, they may be the same or different.
X'' represents a cross-linking group selected from the cross-linking group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. .. A plurality of X''s may be the same or different. However, at least one of the plurality of X''s present is a cross-linking group selected from the cross-linking group A group. ]
[4]
The light emitting device according to any one of [1] to [3], wherein the compound (T) is a compound represented by the formula (T-1).

［式中、
ｎ^T1は、０以上５以下の整数を表す。ｎ^T1が複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^T1は、アリール基、置換アミノ基、又は、１価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^T1が複数存在する場合、それらは同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、Ａｒ^T1の少なくとも１つは、置換アミノ基であるか、或いは、環内に二重結合を有さない窒素原子を含み、且つ、環内に＝Ｎ−で表される基、ホウ素原子、−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基、及び、式（Ｐ）：

[During the ceremony,
n ^T1 represents an integer of 0 or more and 5 or less. When a ^{plurality of n T1s} exist, they may be the same or different.
Ar ^T1 represents an aryl group, a substituted amino group, or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of Ar T1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, ^{at least one of Ar T1} is a substituted amino group or contains a nitrogen atom having no double bond in the ring, and a group represented by = N− in the ring, a boron atom. , -C (= Z ^T1 )-represented by-, -S (= O)-represented by-, -S (= O) _2- represented by, and formula (P) :.

で表される基を含まない、１価の複素環基である。Ｚ^T1は、酸素原子、硫黄原子又は＝ＮＲ^ZT1で表される基を表す。Ｒ^ZT1は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^T1は、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ^T1'−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ^T1'は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^T1が複数存在する場合、それらは同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。
Ａｒ^T2は、ホウ素原子、−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基、前記式（Ｐ）で表される基、電子求引性基を有する芳香族炭化水素基、又は、環内に＝Ｎ−で表される基を含む複素環基であり、これらの基は置換基を有していてもよい。
ｎ^T2は、１以上１５以下の整数を表す。但し、Ａｒ^T2がホウ素原子又は前記式（Ｐ）で表される基である場合、ｎ^T2は３である。Ａｒ^T2が−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、又は、−Ｓ（＝Ｏ）₂−で表される基である場合、ｎ^T2は２である。
Ａｒ^T1とＬ^T1とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。Ａｒ^T2とＬ^T1とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。Ａｒ^T1とＡｒ^T2とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。］
［５］
前記Ａｒ^T1の少なくとも１つが、式（T１−１）で表される基である、［４］に記載の発光素子。

It is a monovalent heterocyclic group containing no group represented by. Z ^T1 represents an oxygen atom, a group represented by a sulfur atom or = NR ^ZT1. R ^ZT1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
L ^T1 is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR ^T1 '- represents a group represented by an oxygen atom or a sulfur atom in these groups have a substituent You may. ^{RT1'represents} a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of LT1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.
Ar ^T2 is a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, the above formula. It is a group represented by (P), an aromatic hydrocarbon group having an electron-attracting group, or a heterocyclic group containing a group represented by = N- in the ring, and these groups have a substituent. You may have.
n ^T2 represents an integer of 1 or more and 15 or less. However, when Ar ^T2 is a boron atom or a group represented by the above formula (P), n ^T2 is 3. If Ar ^T2 is a group represented by −C (= Z ^T1 ) −, a group represented by −S (= O) −, or a group represented by −S (= O) ₂ −, n ^T2 is 2.
Ar ^T1 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T2 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T1 and Ar ^T2 may be directly bonded or bonded via a divalent group to form a ring. ]
[5]
The light emitting device according to [4], wherein ^{at least one of the Ar T1} is a group represented by the formula (T1-1).

［式中、
環Ｒ^T1及び環Ｒ^T2は、それぞれ独立に、環内に−Ｃ（＝Ｚ^T1）−で表される基を含まない芳香族炭化水素環、又は、環内に＝Ｎ−で表される基、ホウ素原子、−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基、及び、前記式（Ｐ）で表される基を含まない複素環を表し、これらの環は置換基を有していてもよい。Ｚ^T1は前記と同じ意味を表す。
Ｘ^T1は、単結合、酸素原子、硫黄原子、−Ｎ(Ｒ^XT1)−で表される基、又は、−Ｃ(Ｒ^XT1')₂−で表される基を表す。Ｒ^XT1及びＲ^XT1'は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^XT1'は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^XT1と環Ｒ^T1が有していてもよい置換基、Ｒ^XT1と環Ｒ^T2が有していてもよい置換基、Ｒ^XT1'と環Ｒ^T1が有していてもよい置換基、及び、Ｒ^XT1'と環Ｒ^T2が有していてもよい置換基は、それぞれ直接結合して、又は、２価の基を介して結合して、それぞれが結合する原子とともに環を形成していてもよい。］
［６］
前記式（T１−１）で表される基が、式（T１−１Ａ）で表される基、式（T１−１Ｂ）で表される基、式（T１−１Ｃ）で表される基又は式（T１−１Ｄ）で表される基である、［５］に記載の発光素子。

[During the ceremony,
Rings R ^T1 and Ring R ^T2 are independently represented by an aromatic hydrocarbon ring containing no group represented by -C (= Z ^T1 )-in the ring, or by = N- in the ring. A group, a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, and the above formula. It represents a heterocycle containing no group represented by (P), and these rings may have a substituent. Z ^T1 has the same meaning as described above.
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, ^{a group represented by −N (R XT1} ) −, or a group represented by −C (R ^XT1 ′) ₂ −. R ^XT1 and R ^XT1'are independent of hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or Representing a cyano group, these groups may have substituents. The plurality of R ^XT1's present may be the same or different, and may be bonded to each other to form a ring with the carbon atom to which each is bonded.
Substituents that R ^XT1 and ring R ^T1 may have, Substituents that R ^XT1 and ring R ^T2 may have, Substituents that R ^XT1'and ring R ^T1 may have, and , R ^{XT1'and the} substituents that ring R ^T2 may have are each directly bonded or bonded via a divalent group to form a ring with the atoms to which they are bonded. May be good. ]
[6]
The group represented by the formula (T1-1) is a group represented by the formula (T1-1A), a group represented by the formula (T1-1B), a group represented by the formula (T1-1C), or a group represented by the formula (T1-1C). The light emitting device according to [5], which is a group represented by the formula (T1-1D).

［式中、
Ｘ^T1は、前記と同じ意味を表す。
Ｘ^T2及びＸ^T3は、それぞれ独立に、単結合、酸素原子、硫黄原子、−Ｎ(Ｒ^XT2)−で表される基、又は、−Ｃ(Ｒ^XT2')₂−で表される基を表す。Ｒ^XT2及びＲ^XT2'は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^XT2'は、同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^T1、Ｒ^T2、Ｒ^T3、Ｒ^T4、Ｒ^T5、Ｒ^T6、Ｒ^T7、Ｒ^T8、Ｒ^T9、Ｒ^T10、Ｒ^T11及びＲ^T12は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。
Ｒ^T1とＲ^T2、Ｒ^T2とＲ^T3、Ｒ^T3とＲ^T4、Ｒ^T5とＲ^T6、Ｒ^T6とＲ^T7、Ｒ^T7とＲ^T8、Ｒ^T9とＲ^T10、Ｒ^T10とＲ^T11、及び、Ｒ^T11とＲ^T12は、それぞれ直接結合して、又は、２価の基を介して結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］
［７］
前記Ａｒ^T2が、環内に＝Ｎ−で表される基を含む複素環基（該基は置換基を有していてもよい。）である、［４］〜［６］のいずれかに記載の発光素子。
［８］
前記Ａｒ^T2が、ジアゾール環、トリアゾール環、オキサジアゾール環、チアジアゾール環、チアゾール環、オキサゾール環、イソチアゾール環、イソオキサゾール環、ベンゾジアゾール環、ベンゾトリアゾール環、ベンゾオキサジアゾール環、ベンゾチアジアゾール環、ベンゾチアゾール環、ベンゾオキサゾール環、アザカルバゾール環、ジアザカルバゾール環、ピリジン環、ジアザベンゼン環、トリアジン環、アザナフタレン環、ジアザナフタレン環、トリアザナフタレン環、テトラアザナフタレン環、アザアントラセン環、ジアザアントラセン環、トリアザアントラセン環、テトラアザアントラセン環、アザフェナントレン環、ジアザフェナントレン環、トリアザフェナントレン環又はテトラアザフェナントレン環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子１個以上を除いた基（該基は置換基を有していてもよい）である、［７］に記載の発光素子。
［９］
前記化合物（Ｔ）の振動子強度が０．０００１以上である、［１］〜［８］のいずれかに記載の発光素子。
［１０］
前記第１の有機層が、ホスト材料、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、蛍光発光材料及び酸化防止剤からなる群より選ばれる少なくとも１種を更に含有する、［１］〜［９］のいずれかに記載の発光素子。
［１１］
前記第１の有機層と、前記第２の有機層とが、隣接している、［１］〜［１０］のいずれかに記載の発光素子。
［１２］
前記第２の有機層が、前記陽極及び前記第１の有機層との間に設けられた層である、［１］〜［１１］のいずれかに記載の発光素子。

[During the ceremony,
X ^T1 has the same meaning as described above.
X ^T2 and X ^T3 independently form a single bond, an oxygen atom, a sulfur atom, ^{a group represented by −N (R XT2} ) −, or a group represented by −C (R ^XT2 ′) ₂ −. Represent. R ^XT2 and R ^XT2'are independent of hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or Representing a cyano group, these groups may have substituents. The plurality of R ^XT2's present may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring together with the carbon atom to which each is bonded.
^{R T1, R T2, R T3} , R T4, R T5, R T6, R T7, R T8, R T9, R T10, R T11 and R ^T12 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group , Alkyl group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or cyano group, and these groups may have a substituent.
R ^T1 and R ^T2, R ^T2 and R ^T3, R ^T3 and R ^T4, R ^T5 and R ^T6, R ^T6 and R ^T7, R ^T7 and R ^T8, R ^T9 and R ^T10, R ^T10 and R ^T11 and, R ^T11 and R ^T12 may be directly bonded to each other or bonded via a divalent group to form a ring together with the carbon atom to which each is bonded. ]
[7]
Ar ^T2 is any of [4] to [6], which is a heterocyclic group containing a group represented by = N- in the ring (the group may have a substituent). The light emitting element described.
[8]
The Ar ^T2 is a diazole ring, a triazole ring, an oxaziazole ring, a thiazizole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazol ring, a benzotriazole ring, a benzoxaziazole ring, a benzothiazol ring. Ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthrene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthrene ring, azaanthracene ring , Diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring, hydrogen directly bonded to the carbon atom or hetero atom constituting the ring. The light emitting element according to [7], which is a group excluding one or more atoms (the group may have a substituent).
[9]
The light emitting device according to any one of [1] to [8], wherein the oscillator strength of the compound (T) is 0.0001 or more.
[10]
The first organic layer further contains at least one selected from the group consisting of host materials, hole transport materials, hole injection materials, electron transport materials, electron injection materials, fluorescent materials and antioxidants. The light emitting element according to any one of [1] to [9].
[11]
The light emitting device according to any one of [1] to [10], wherein the first organic layer and the second organic layer are adjacent to each other.
[12]
The light emitting device according to any one of [1] to [11], wherein the second organic layer is a layer provided between the anode and the first organic layer.

According to the present invention, it is possible to provide a light emitting device having excellent external quantum efficiency.

Hereinafter, preferred embodiments of the present invention will be described in detail.

<Explanation of common terms>
Unless otherwise specified, the terms commonly used in the present specification have the following meanings.

Me stands for methyl group, Et stands for ethyl group, Bu stands for butyl group, i-Pr stands for isopropyl group, and t-Bu stands for tert-butyl group.

The hydrogen atom may be a deuterium atom or a light hydrogen atom.
In the formula representing the metal complex, the solid line representing the bond with the central metal means a covalent bond or a coordination bond.

The “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ .
The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or any other embodiment.
The terminal group of the polymer compound is preferably a stable group because if the polymerization active group remains as it is, the light emission characteristics or the luminance life may decrease when the polymer compound is used for manufacturing a light emitting element. Is. The terminal group of the polymer compound is preferably a group conjugated to the main chain, for example, an aryl group or a monovalent heterocyclic group bonded to the main chain of the polymer compound via a carbon-carbon bond. Examples include groups that are bound to.

By "low molecular compound" does not have a molecular weight distribution, molecular weight means a 1 × 10 ⁴ or less of the compound.

The “constituent unit” means a unit existing in one or more in a polymer compound.

The "alkyl group" may be either linear or branched. The number of carbon atoms of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkyl group may have a substituent, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, 2-Ethylbutyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group. , And a group in which the hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like (for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group). , Perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3,5-di-hexylphenyl) propyl group, 6-ethyloxyhexyl group) Can be mentioned.
The number of carbon atoms of the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

"Aryl group" means the remaining atomic group excluding one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10, not including the number of carbon atoms of the substituent.
The aryl group may have a substituent, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthrasenyl group, a 2-anthrasenyl group, a 9-anthrasenyl group, a 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups. However, examples thereof include groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom and the like.

The "alkoxy group" may be either linear or branched. The number of carbon atoms of the linear alkoxy group is usually 1 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The alkoxy group may have a substituent, for example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, and the like. Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is cycloalkyl group, alkoxy group, Examples thereof include a cycloalkoxy group, an aryl group, a group substituted with a fluorine atom and the like.
The number of carbon atoms of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

The number of carbon atoms of the "aryloxy group" is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
The aryloxy group may have a substituent, for example, a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthrasenyloxy group, a 9-anthrasenyloxy group, 1-. Examples thereof include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom or the like.

A "p-valent heterocyclic group" (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. It means the remaining atomic group excluding the hydrogen atom of. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group" is preferred.
The "aromatic heterocyclic compound" is a heterocyclic compound such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphor, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, and dibenzophosphol. Even if the compound whose ring itself exhibits aromaticity and the heterocycle itself such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran do not exhibit aromaticity, the aromatic ring is fused to the heterocycle. Means a compound.

The number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
The monovalent heterocyclic group may have a substituent, for example, a thienyl group, a pyrrolyl group, a furyl group, a pyridinyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and these. Examples thereof include a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or the like.

The "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The "amino group" may have a substituent, and a substituted amino group is preferable. As the substituent contained in the amino group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable.
Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group and a diarylamino group.
Examples of the amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis (4-methylphenyl) amino group, a bis (4-tert-butylphenyl) amino group, and a bis (3,5-di-tert-). Butylphenyl) amino groups can be mentioned.

The "alkenyl group" may be either linear or branched. The number of carbon atoms of the linear alkenyl group is usually 2 to 30, preferably 3 to 20, excluding the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
The number of carbon atoms of the "cycloalkenyl group" is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4- Examples thereof include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and a group in which these groups have a substituent.

The "alkynyl group" may be either linear or branched. The number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The number of carbon atoms of the "cycloalkynyl group" is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4- Examples thereof include a pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and a group in which these groups have a substituent.

The "arylene group" means the remaining atomic group excluding the two hydrogen atoms directly bonded to the carbon atoms constituting the ring from the aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent.
The arylene group may have a substituent, for example, a phenylene group, a naphthalenediyl group, an anthracendiyl group, a phenanthrenidyl group, a dihydrophenantrenyl group, a naphthacendyl group, a full orangeyl group, a pyrenyl group, a perylene diyl group, Examples thereof include a chrysendiyl group and a group in which these groups have a substituent, and the groups represented by the formulas (A-1) to (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

［式中、Ｒ及びＲ^aは、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表す。複数存在するＲ及びＲ^aは、各々、同一でも異なっていてもよく、Ｒ^a同士は互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Wherein, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. A plurality of R and ^Ra may be the same or different from ^{each other, and R a} may be bonded to each other to form a ring together with the atoms to which each is bonded. ]

The number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, not including the number of carbon atoms of the substituent.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acrydin, A divalent group obtained by removing two hydrogen atoms from dihydroaclysin, furan, thiophene, azole, diazole, and triazole from among the hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the ring is preferable. Is a group represented by the formulas (AA-1) to (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

［式中、Ｒ及びＲ^aは、前記と同じ意味を表す。］

[In the formula, R and ^Ra have the same meanings as described above. ]

The "crosslinked group" is a group capable of forming a new bond by being subjected to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc., and is preferably a crosslinked group. It is a cross-linking group represented by the formulas (XL-1) to (XL-15) of Group A.

The "substituent" is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group and an alkenyl group. , Cycloalkenyl group, alkynyl group or cycloalkynyl group. The substituent may be a cross-linking group.

<Light emitting element>
The light emitting element of the present invention is a light emitting element having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode, wherein the first organic layer is Contains a compound (T) in which the absolute value of the difference between the energy level in the lowest triplet excited state and the energy level in the lowest singlet excited state (hereinafter, _{also referred to as “ΔE ST”) is 0.5 eV or less.} However, the layer does not contain a phosphorescent metal complex, the second organic layer is a layer containing a crosslinked product of a cross-linking material, and the cross-linking material is at least one selected from the cross-linking group A group. A light emitting element which is a low molecular weight compound having a kind of cross-linking group or a polymer compound containing a cross-linking structural unit having at least one kind of cross-linking group selected from the bridging group A group. The phosphorescent metal complex is a metal complex that emits light from a triplet excited state at room temperature (25 ° C.).

Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum vapor deposition method and a wet method such as a spin coating method and an inkjet printing method, and the wet method is preferable.

When the first organic layer is formed by a wet method, it is preferable to use the first ink described later.

When the second organic layer is formed by a wet method, it is preferable to use a second ink described later. After forming the second organic layer, the cross-linked material contained in the second organic layer can be crosslinked by heating or irradiating with light, and by heating, the cross-linked material contained in the second organic layer can be crosslinked. It is preferable to crosslink the material. When the crosslinked material is contained in the second organic layer in a state of being crosslinked (crosslinked body of the crosslinked material), the second organic layer is substantially insoluble in the solvent. Therefore, the second organic layer can be suitably used for laminating light emitting elements.

The heating temperature for crosslinking is usually 25 ° C. to 300 ° C., preferably 50 ° C. to 260 ° C., more preferably 130 ° C. to 230 ° C., and even more preferably 180 ° C. to 210 ° C. ..
The heating time is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1 to 120 minutes, and even more preferably 10 to 60 minutes.

The types of light used for light irradiation are, for example, ultraviolet light, near-ultraviolet light, and visible light.

Examples of the method for analyzing the components contained in the first organic layer or the second organic layer include chemical separation analysis such as extraction, infrared spectroscopy (IR), and nuclear magnetic resonance spectroscopy (NMR). An instrumental analysis method such as mass spectrometry (MS), and an analysis method combining a chemical separation analysis method and an instrumental analysis method can be mentioned.

By performing solid-liquid extraction of the first organic layer or the second organic layer using an organic solvent such as toluene, xylene, chloroform, or tetrahydrofuran, a component (insoluble) that is substantially insoluble in the organic solvent (insoluble). It is possible to separate a component) and a component that dissolves in an organic solvent (dissolving component). The insoluble component can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and the dissolved component can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.

<First organic layer>
[Compound (T)]
Compound (T) is preferably a Thermally Activated Delayed Fluorescence (TADF) material.

Delta] E _ST of the compound (T) is preferably not more than 0.45 eV, more preferably not more than 0.40 eV, more preferably less 0.30 eV, particularly preferably not more than 0.20 eV, especially preferably Is 0.13 eV or less, and more preferably 0.11 eV or less. Delta] E _ST of the compound (T) is preferably not less than 0.0001EV, more preferably not less than 0.001EV, more preferably not less than 0.01 eV. Delta] E _ST of the compound (T), since the external quantum efficiency of the light emitting element is excellent in the present invention, preferably, not more than more 0.0001EV 0.45 eV, more preferably, be less than 0.0001EV 0.20 eV , More preferably 0.001 eV or more and 0.13 eV or less, and further preferably 0.01 eV or more and 0.11 eV or less.

The oscillator strength of compound (T) is preferably 0.0001 or more, more preferably 0.001 or more, still more preferably 0.005 or more, particularly preferably 0.05 or more, and in particular. It is preferably 0.1 or more. The oscillator strength of compound (T) is preferably 1 or less, more preferably 0.8 or less, still more preferably 0.6 or less, and particularly preferably 0.3 or less. The oscillator strength of compound (T) is preferably 0.0001 or more and 1 or less, more preferably 0.001 or more and 0.8 or less, still more preferably, because the external quantum efficiency of the light emitting device of the present invention is excellent. Is 0.005 or more and 0.6 or less, particularly preferably 0.05 or more and 0.6 or less, and particularly preferably 0.1 or more and 0.3 or less.

Calculation of the values of Delta] E _ST and the oscillator strength of the compound, the density of the B3LYP level functional method, the ground state of the compound and structure optimization, the time, as the basis function, using 6-31G *. Then, using a Gaussian09 as a quantum chemistry calculation program, the time-dependent density functional method B3LYP level, calculates a Delta] E _ST and the oscillator strength of the compound. However, when 6-31G * contains an atom that cannot be used, LANL2DZ is used for the atom.

The molecular weight of compound (T) is preferably 1 × 10 ² to 1 × 10 ⁴ , more preferably 2 × 10 ^{2 to} 5 × 10 ³ , and even ^{more preferably 3 × 10 2 to} 3 ×. It is 10 ³ , and particularly preferably 5 × 10 ^{2 to} 1.5 × 10 ³ .

The compound (T) is preferably a compound represented by the formula (T-1) because the external quantum efficiency of the light emitting device of the present invention is excellent.

Since n ^T1 is excellent in the external quantum efficiency of the light emitting device of the present invention, it is preferably an integer of 0 or more and 3 or less, more preferably an integer of 0 or more and 2 or less, and further preferably 0 or 1.

n ^T2 is preferably an integer of 1 or more and 10 or less, more preferably an integer of 1 or more and 7 or less, and further preferably 1 or more and 5 or less because the external quantum efficiency of the light emitting device of the present invention is excellent. Is an integer of, and is particularly preferably 2 or 3.

Examples of the aryl group in Ar ^T1 include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, an inden ring, a pyrene ring, a perylene ring, a chrysen ring, or a chrysen ring. , A group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a ring obtained by condensing these rings, preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a dihydrophenanthrene ring. , Naphthalene ring, fluorene ring, spirobifluorene ring, inden ring, pyrene ring, perylene ring, or chrysen ring, from which one hydrogen atom directly bonded to the carbon atom constituting the ring is removed, which is more preferable. Is a phenyl group, a naphthyl group, an anthrasenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group or a spirobifluorenyl group, and more preferably a phenyl group, a naphthyl group, a fluorenyl group or a spirobifluole. It is an enyl group, particularly preferably a phenyl group, and these groups may have a substituent.

Examples of the monovalent heterocyclic group in Ar ^T1 include a monovalent donor type heterocyclic group described later and a monovalent heterocyclic group other than the monovalent donor type heterocyclic group described later, and a monovalent heterocyclic group other than the monovalent donor type heterocyclic group described later is preferable. Carbazole ring, 9,10-dihydroaclydin ring, 5,10-dihydrophenazine ring, phenoxazine ring, phenothiazine ring, indolocarbazole ring, indenocarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diah Directly from the zanaphthalene ring, azaanthracene ring, diazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, dibenzofuran ring, dibenzothiophene ring, azacarbazole ring or diazacarbazole ring to the carbon atom or heteroatom constituting the ring. It is a group excluding one hydrogen atom to be bonded, and more preferably constitutes a ring from a carbazole ring, an indolocarbazole ring, an indenocarbazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a dibenzofuran ring or a dibenzothiophene ring. It is a group excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom, and more preferably hydrogen directly bonded to a carbon atom or a hetero atom constituting the ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring. It is a group excluding one atom, and these groups may have a substituent.

Among ^{the substituted amino groups in Ar T1, as} the substituent contained in the amino group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable, an aryl group or a monovalent heterocyclic group is more preferable, and an aryl group is preferable. Groups are more preferred, and these groups may further have substituents. The example and preferred range of the aryl group in the substituent of the amino group is the same as the example and preferred range of the aryl group in ^{Ar T1.} The example and preferred range of the monovalent heterocyclic group in the substituent of the amino group is the same as the example and preferred range of the monovalent heterocyclic group in ^{Ar T1.}

"Nitrogen atom without double bond" means a nitrogen atom having only a single bond between the nitrogen atom and all the atoms bonded to the nitrogen atom.
By "in the ring containing a nitrogen atom having no double bond", -N in the ring (-R ^N) - (. Wherein, R ^N represents a hydrogen atom or a substituent), or formula :

で表される基を含むことを意味する。

It means that it contains a group represented by.

A group containing a nitrogen atom having no double bond in the ring and represented by = N-, a boron atom, a group represented by -C (= Z ^T1 )-, -S (= A monovalent heterocyclic group (in the present specification) that does not include a group represented by O) −, a group represented by −S (= O) _{2 −, and a group represented by the above formula (P).} , Also referred to as “monovalent donor heterocyclic group”), the number of nitrogen atoms having no double bond constituting the ring is usually 1 to 10, preferably 1 to 5. It is more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.

The number of carbon atoms of the monovalent donor heterocyclic group is usually 2 to 60, preferably 3 to 20, excluding the number of carbon atoms of the substituent.

Examples of the monovalent donor-type heterocyclic group include a pyrrole ring, an indole ring, an isoindole ring, a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, an acridone ring, a phenoxazine ring, and a phenothiazine. From a ring, an indolocarbazole ring, an indenocarbazole ring, or a ring obtained by condensing an aromatic hydrocarbon ring and / or a heterocycle on these heterocycles, a hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring. Examples include groups excluding one, and these groups may have substituents. However, the aromatic hydrocarbon ring that may be condensed into a heterocycle is an aromatic hydrocarbon ring that does not contain a group represented by ^{−C (= Z T1) − in the ring described later.} Heterocycles that may be condensed into a heterocycle include a group represented by = N-, a boron atom, a group represented by -C (= Z ^T1 )-, and -S (= O)-in the ring described later. It is a heterocycle containing no group represented by, a group represented by −S (= O) ₂ −, and a group represented by the above formula (P).

The monovalent donor type heterocyclic group is preferably a pyrrole ring, an indole ring, an isoindole ring, a carbazole ring, a 9,10-dihydroacrine ring, a 5,10-dihydrophenazine ring, an acridone ring, a phenoxazine ring, or a phenothiazine. It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the ring, the indolocarbazole ring or the indenocarbazole ring, and more preferably the carbazole ring, 9,10-dihydroaclysine. A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the ring, 5,10-dihydrophenazine ring, phenoxazine ring, phenothiazine ring, indolocarbazole ring or indenocarbazole ring. Yes, more preferably, it is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the carbazole ring, the indolocarbazole ring or the indenocarbazole ring, and particularly preferably the carbazole ring. It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom forming a ring from the above, and these groups may have a substituent.

The number of carbon atoms of the monovalent heterocyclic group other than the monovalent donor type heterocyclic group is usually 2 to 60, preferably 3 to 20, excluding the number of carbon atoms of the substituent.

Examples of the monovalent heterocyclic group other than the monovalent donor type heterocyclic group include a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiazazole ring, a pyridine ring, a diazabenzene ring, and a triazine ring. Azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring, dibenzofuran ring, dibenzothiophene ring, dibenzo A carbon atom constituting a ring from a silol ring, a dibenzophosphor ring, an azacarbazole ring, a diazacarbazole ring, a ring obtained by condensing these heterocycles, and a ring obtained by condensing these heterocycles with an aromatic hydrocarbon ring. Alternatively, a group excluding one hydrogen atom directly bonded to a hetero atom can be mentioned, preferably a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiazazole ring, a pyridine ring, a diazabenzene ring, or a triazine ring. , Azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenantren ring, triazaphenanthrene ring, dibenzofuran ring, dibenzothiophene ring, A group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring from the dibenzosilol ring, dibenzophosphor ring, azacarbazole ring or diazacarbazole ring, and more preferably the pyridine ring. From the diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, azaanthracene ring, diazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, dibenzofuran ring, dibenzothiophene ring, azacarbazole ring or diazacarbazole ring. It is a group excluding one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring, and more preferably, the ring is composed of a pyridine ring, a diazabenzene ring, a triazine ring, a dibenzofuran ring or a dibenzothiophene ring. It is a group excluding one hydrogen atom directly bonded to a carbon atom, and particularly preferably a group excluding one hydrogen atom directly bonded to a carbon atom constituting the ring from a dibenzofuran ring or a dibenzothiophene ring. These groups may have substituents.

The ^{substituents that Ar T1} may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group. Groups are preferred, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, monovalent heterocyclic groups, substituted amino groups or cyano groups are more preferred, alkyl groups, cycloalkyl groups, aryl groups and monovalent groups. Is more preferably a heterocyclic group or a substituted amino group, particularly preferably an alkyl group, an aryl group or a substituted amino group, and these groups may further have a substituent.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that Ar ^T1 may have are aryl groups, monovalent heterocyclic groups and substituted amino groups in Ar ^{T1, respectively.} It is the same as the example and the preferable range of.

The ^{substituent that Ar T1} may have may further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent group. Is a heterocyclic group, a substituted amino group, a halogen atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group or a substituted amino group. More preferably, it is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and particularly preferably an alkyl group or a cycloalkyl group, and these groups further contain a substituent. You may have.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that the substituents that Ar ^T1 may have may further include the aryl groups in ^{Ar T1, respectively.} It is the same as the example and preferable range of monovalent heterocyclic group and substituted amino group.

At ^{least one of Ar T1} is preferably a monovalent donor-type heterocyclic group because the external quantum efficiency of the light emitting device of the present invention is excellent, and more preferably a group represented by the formula (T1-1). These groups may have substituents.
That is, the monovalent donor-type heterocyclic group is preferably a group represented by the formula (T1-1).

When Ar ^T1 is not a substituted amino group and a monovalent donor type heterocyclic group, Ar ^T1 is preferably an aryl group or a monovalent donor type complex because it has excellent external quantum efficiency of the light emitting element of the present invention. It is a monovalent heterocyclic group other than the ring group, more preferably an aryl group, and these groups may have a substituent.

Ar ^T1 is preferably an aryl group or a monovalent donor-type heterocyclic group because the external quantum efficiency of the light emitting element of the present invention is more excellent, and more preferably an aryl group or the formula (T1-1). These groups may have substituents.

When a ^{plurality of Ar T1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring, but do not form a ring. Is preferable.

Examples of the "divalent group" include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, ^{a group represented by -N (R ArT1} )-, and a group represented by -B (R ^ArT1 )-. Group represented by -P (R ^ArT1 )-, group represented by-(O =) P (R ^ArT1 )-, group represented by -Si (R ^ArT1 ') _2- Examples thereof include a group represented by S (= O)-, a group represented by -S (= O) ₂ , a group represented by -C (= Z ^T1 )-, an oxygen atom or a sulfur atom, and preferably. , Alkylene group, cycloalkylene group, arylene group, divalent heterocyclic group, ^{group represented by -N (R ArT1} )-, group represented by -P (R ^ArT1 )-, -Si (R ^ArT1 ' ) _{A group represented by 2} −, an oxygen atom or a sulfur atom, more preferably an alkylene group, a cycloalkylene group, ^{a group represented by −N (R ArT1} ) −, and a group represented by −P (R ^ArT1 ) −. A group to be ^{represented, a group represented by −Si (R ArT1} ′) ₂ −, an oxygen atom or a sulfur atom, more preferably an alkylene group, ^{a group represented by −N (R ArT1} ) −, an oxygen atom or a group. It is a sulfur atom, particularly preferably an oxygen atom or a sulfur atom, and these groups may have a substituent.

The examples and preferred ranges of substituents that the divalent group may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have.

Examples and preferred ranges of substituents that the divalent group may have may further include substitutions that the Ar ^T1 may have further substituents. It is the same as the example of the group and the preferable range.

Examples of the alkylene group and preferable range of the divalent groups are the same as examples and preferred ranges of the alkylene group represented by the below-mentioned L ^A. Examples and preferred ranges cycloalkylene group in the divalent group are the same as examples and preferred ranges of cycloalkylene groups represented by the below-mentioned L ^A.

Examples of the arylene group and the preferable range of the divalent groups are the same as examples and preferred ranges of the arylene group represented by the below-mentioned L ^T1. The example and preferable range of the divalent heterocyclic group in the divalent group are the same as the example and preferable range of the divalent heterocyclic group represented by ^{LT1 described later.}

R ^ArT1 and R ^ArT1'are independent of hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or Representing a cyano group, these groups may have substituents.

The examples and preferred ranges of R ^ArT1 are the same as the examples and preferred ranges of R ^XT1 described below.
R ^ART1 'examples and preferable range is below the R ^XT1' is the same as the examples and preferable range.

-The number of carbon atoms of the group represented by the formula (T1-1) " ^{aromatic hydrocarbon ring containing no group represented by -C (= Z T1} )-in the ring" is the number of carbon atoms of the substituent. Is not included, it is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.

Examples of the aromatic hydrocarbon ring containing no group represented by -C (= Z ^T1 )-in the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthalene ring, and a fluorene ring. , Spirobifluorene ring, inden ring, pyrene ring, perylene ring, chrysen ring and a ring obtained by condensing these rings, preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthalene ring. , Fluorene ring, spirobifluorene ring, inden ring, pyrene ring, perylene ring or chrysen ring, more preferably benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring or spirobifluorene ring. It is more preferably a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, particularly preferably a benzene ring or a fluorene ring, and particularly preferably a benzene ring, and these rings are substituents. May have.

"In the ring, a group represented by = N-, a boron atom, a group represented by -C (= Z ^T1 )-, a group represented by -S (= O)-, -S (= O) ₂ The number of carbon atoms of the "group not containing the group represented by-and the group represented by the above formula (P)" is usually 2 to 60, preferably 2 to 60, not including the number of carbon atoms of the substituent. Is 3 to 30, more preferably 4 to 15.

In the ring, a group represented by = N-, a boron atom, a group represented by -C (= Z ^T1 )-, a group represented by -S (= O)-, a group represented by -S (= O) _2- Examples of the heterocycle containing no group represented by the above formula (P) and the group represented by the above formula (P) include a pyrrole ring, a furan ring, a thiophene ring, a silol ring, a phosphor ring, an indole ring, a benzofuran ring, and a benzo. Thiophene ring, benzocilol ring, benzophosphor ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzocilol ring, dibenzophosphor ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacrine ring, 5,10-dihydro Examples thereof include a phenazine ring, a ring in which these rings are condensed, and a ring in which an aromatic hydrocarbon ring containing no group represented by ^{−C (= Z T1) − is condensed in the ring.} Preferably, a pyrrole ring, a furan ring, a thiophene ring, a silol ring, a phosphor ring, an indole ring, a benzofuran ring, a benzothiophene ring, a benzocilol ring, a benzophosphor ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzocilol ring, A dibenzophosphor ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacrine ring or a 5,10-dihydrophenazine ring, more preferably an indole ring, a benzofuran ring, a benzothiophene ring, a carbazole ring, a dibenzofuran ring, A dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacrine ring or a 5,10-dihydrophenazine ring, more preferably a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, It is a 9,10-dihydroaclydin ring or a 5,10-dihydrophenazine ring, particularly preferably a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and particularly preferably a carbazole ring, and these rings have a substituent. You may be doing it.

^{The examples and preferred ranges of substituents that ring RT1} and ring ^RT2 may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have.

Examples and preferred ranges of substituents that may be further possessed by the substituents that ring R ^T1 and ring R ^{T2 may have are further contained in the substituents that Ar T1} may have. It is the same as the example of a good substituent and the preferable range.

At least one of the ring ^RT1 and the ring ^{RT2 is preferably an aromatic hydrocarbon ring containing no group represented by −C (= Z T1} ) − in the ring, and is preferably a benzene ring. More preferably, these rings may have a substituent.

^{It is preferable that both the ring RT1} and the ring ^RT2 are aromatic hydrocarbon rings containing no group represented by −C (= Z ^T1 ) − in the ring, and more preferably a benzene ring. The ring of may have a substituent.

X ^T1 is preferably a single bond, an oxygen atom, a sulfur atom or -C (R ^XT1 ') ₂ - In a group represented, more preferably a single bond, an oxygen atom or a sulfur atom, more preferably It is a single bond.

R ^XT1 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably. It is an aryl group, and these groups may have a substituent.

R ^XT1'is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and even more preferably an alkyl group or an alkyl group or a monovalent heterocyclic group. It is a cycloalkyl group, and these groups may have a substituent.

The plurality of R ^XT1's present may be the same or different, and may be bonded to each other to form a ring with the carbon atom to which each bond is formed, but it is preferable not to form a ring.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in R ^XT1 and R ^{XT1'are examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in Ar T1, respectively.} Is the same as.

The examples and preferred ranges of substituents that R ^XT1 and R ^XT1'may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have. Is.

Substituents that R ^XT1 and ring R ^T1 may have, Substituents that R ^XT1 and ring R ^T2 may have, Substituents that R ^XT1'and ring R ^T1 may have, and , R ^{XT1'and the} substituents that ring R ^T2 may have are each directly bonded or bonded via a divalent group to form a ring with the atoms to which they are bonded. It may be possible, but it is preferable not to form a ring.

The group represented by the formula (T1-1) is preferably a group represented by the formula (T1-1A), a group represented by the formula (T1-1B), and a group represented by the formula (T1-1C). A group or a group represented by the formula (T1-1D), more preferably a group represented by the formula (T1-1A), a group represented by the formula (T1-1B) or a group represented by the formula (T1-1C). It is a group represented by, more preferably a group represented by the formula (T1-1A) or a group represented by the formula (T1-1C), and particularly preferably a group represented by the formula (T1-1A). It is a basic expression.

X ^T2 and XT ³ are preferably single bonds, ^{groups represented by −N (R XT2} ) −, or groups represented by −C (R ^XT2 ′) ₂ −, and more preferably simple. A bond or a group represented by ^{-N (R XT2)-.}
At least one of ^XT2 and ^XT3 is preferably single-bonded, and more preferably ^{XT3 is single-bonded.}

Among X ^T2 and X ^T3, when at least one is a single bond and the other oxygen atom, a sulfur atom, -N (R ^XT2) -, a group represented by _{^{or, -C (R XT2 ') 2}} - It is preferably a group represented by −N (R ^XT2 ) −, or a group represented by −C (R ^XT2 ′) ₂ −, more preferably −N ( It is more preferable that the group is represented by R ^{XT2) −.}

The example and preferred range of the R ^XT2 are the same as the example and preferred range of the R ^XT1 .
R ^XT2 'examples and preferred ranges, R ^XT1' is the same as the examples and preferable range.
The examples and preferred ranges of substituents that R ^XT2 and R ^XT2'may have are the same as the examples and preferred ranges of substituents that R ^XT1 and R ^XT1'may have.

^{R T1, R T2, R T3} , R T4, R T5, R T6, R T7, R T8, R T9, R T10, R T11 and R ^T12 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, It is preferably a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a cyano group, and is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group or a substituted amino group. More preferably, these groups may further have substituents.

In the group represented by the formula ^{(T1-1A), R T1, R} T2, R T4, R T5, R T7 and R ^T8 represents a hydrogen atom, an alkyl group, an aryl group, monovalent heterocyclic group or a substituted amino It is preferably a group, more preferably a hydrogen atom or an alkyl group, even more preferably a hydrogen atom, and these groups may further have a substituent.

In the group represented by the formula (T1-1A), R ^T3 and R ^T6 are alkyl group, aryl group, monovalent preferably a heterocyclic group or a substituted amino group, an aryl group, a monovalent heterocyclic It is more preferably a group or a substituted amino group, further preferably a substituted amino group, and these groups may further have a substituent.

In the group represented by the formula (T1-1B), formula (T1-1C) and formula ^{(T1-1D), R T1, R} T2, R T3, R T4, R T5, R T6, R T7, R T8 , ^RT9 , ^RT10 , ^RT11 and ^RT12 are preferably hydrogen atoms, alkyl groups, aryl groups, monovalent heterocyclic groups or substituted amino groups, more preferably hydrogen atoms or alkyl groups. , Hydrogen atoms are more preferred, and these groups may further have substituents.

^{R T1, R T2, R T3} , R T4, R T5, R T6, R T7, R T8, R T9, the aryl group in R ^T10, R ^T11 and R ^T12, monovalent heterocyclic group and substituted amino group The examples and preferred ranges are the same as the examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in ^{Ar T1, respectively.}

^{R T1, R T2, R T3} , R T4, R T5, R T6, R T7, R T8, R T9, R T10, examples of R ^T11 and the substituent which may be R ^T12 is had and preferred ranges , Ar ^T1 may have the same substituents as the examples and preferred ranges of the substituents which may be further present.

R ^T1 and R ^T2, R ^T2 and R ^T3, R ^T3 and R ^T4, R ^T5 and R ^T6, R ^T6 and R ^T7, R ^T7 and R ^T8, R ^T9 and R ^T10, R ^T10 and R ^T11 and, R ^T11 and R ^T12 may be directly bonded to each other or bonded via a divalent group to form a ring together with the carbon atom to which each is bonded, but it is preferable not to form a ring. ..

^LT1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group, and even more preferably an arylene group. , These groups may have substituents.

The arylene group represented by L ^T1, preferably a phenylene group, a naphthalene-diyl group, a fluorenediyl group, phenanthrenediyl group or dihydro phenanthrenediyl group, more preferably, the formula (A-1) ~ formula ( A-9), a group represented by the formula (A-19) or the formula (A-20), and more preferably a group represented by the formulas (A-1) to (A-3). Particularly preferably, it is a group represented by the formula (A-1) or (A-2), and particularly preferably, it is a group represented by the formula (A-1), and these groups have a substituent. You may have.

The divalent heterocyclic group represented by L ^T1, preferably, a group represented by the formula (AA-1) ~ formula (AA-34), more preferably formula (AA-1) ~ It is a group represented by the formula (AA-6), the formula (AA-10) to the formula (AA-21) or the formula (AA-24) to the formula (AA-34), and more preferably the formula (AA-). 1) -formula (AA-4), formula (AA-10) -formula (AA-15) or formula (AA-29) -formula (AA-34), and particularly preferably the formula. (AA-2), formula (AA-4), formula (AA-10), formula (AA-12) or formula (AA-14).

The examples and preferred ranges of substituents that L ^T1 may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have.

Examples and preferred ranges of the substituents that the substituents that L ^T1 may have may further include the substituents that the substituents that Ar ^T1 may have further. Same as for example and preferred range.

^RT1'is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

Examples of the aryl group and monovalent heterocyclic group in R ^T1 'and preferred ranges are respectively the same as examples of the aryl group and monovalent heterocyclic group, and preferable range of Ar ^T1.

The examples and preferred ranges of substituents that R ^T1'may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have.

When a ^{plurality of LT1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring, but do not form a ring. Is preferable.

Ar ^T2 is preferably a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) ₂ , and a group represented by −S (= O) 2. It is a group represented by the formula (P), an aromatic hydrocarbon group having an electron-attracting group, or a heterocyclic group containing a group represented by = N- in the ring, and more preferably boron. An atom, a group represented by -C (= Z ^T1 )-, a group represented by -S (= O) ₂ , an aromatic hydrocarbon group having an electron-attracting group, or = N- in the ring. It is a heterocyclic group containing a group represented by, more preferably _{a group represented by −S (= O) 2} , an aromatic hydrocarbon group having an electron-withdrawing group, or = N in the ring. It is a heterocyclic group containing a group represented by −, and particularly preferably an aromatic hydrocarbon group having an electron-attracting group or a heterocyclic group containing a group represented by = N− in the ring. Yes, and particularly preferably, it is a heterocyclic group containing a group represented by = N− in the ring, and these groups may have a substituent.

Z ^T1 is preferably an oxygen atom.
R ^ZT1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group. These groups may have substituents.

The examples and preferred ranges of aryl groups and monovalent heterocyclic groups in R ^ZT1 are the same as the examples and preferred ranges of aryl groups and monovalent heterocyclic groups in ^{Ar T1, respectively.}

The examples and preferred ranges of substituents that R ^{Z T1} may have are the same as the examples and preferred ranges of substituents that Ar T1 may have.

In an aromatic hydrocarbon group having an electron-attracting group, the number of carbon atoms of the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 30, excluding the number of carbon atoms of the substituent. , More preferably 6-18.

Examples of the aromatic hydrocarbon group in the aromatic hydrocarbon group having an electron-attracting group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, and a spirobifluorene ring. Examples thereof include an inden ring, a pyrene ring, a perylene ring, a chrysene ring, and a ring obtained by condensing these rings from which one or more hydrogen atoms directly bonded to carbon atoms constituting the ring are removed, and a benzene ring is preferable. Hydrogen atom 1 directly bonded to a carbon atom constituting a ring from a naphthalene ring, an anthracene ring, a phenylene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, an inden ring, a pyrene ring, a perylene ring or a chrysen ring. It is a group excluding one or more, and more preferably, a hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring or a spirobifluorene ring. It is a group excluding one or more, and more preferably, it is a group excluding one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring. Particularly preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the benzene ring or fluorene ring, and particularly preferably, directly from the benzene ring to the carbon atoms constituting the ring. It is a group excluding one or more hydrogen atoms to be bonded, and these groups may have a substituent.

Examples of the electron-attracting group include an alkyl group having a fluorine atom as a substituent, a fluorine atom, a cyano group and a nitro group, and preferably an alkyl group having a fluorine atom as a substituent, a fluorine atom or a cyano group. And more preferably a cyano group.

The alkyl group having a fluorine atom as a substituent is preferably a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, or a perfluorooctyl group.

Among the aromatic hydrocarbon groups having an electron-attracting group, the number of electron-attracting groups contained in the aromatic hydrocarbon group is usually 1 to 10, preferably 1 to 5, and more. The number is preferably 1 to 3, and more preferably 1 or 2.

In a heterocyclic group containing a group represented by = N- in the ring, the number of nitrogen atoms having a double bond constituting the ring is usually 1 to 10, preferably 1 to 7, and more. It is preferably 1 to 5, more preferably 1 to 3, and particularly preferably 3.

In a heterocyclic group containing a group represented by = N- in the ring, the number of carbon atoms constituting the ring is usually 1 to 60, preferably 2 to 30, and more preferably 3 to 15. Yes, especially preferably 3-5.

Examples of the heterocyclic group containing a group represented by = N- in the ring include a diazole ring, a triazole ring, an oxaziazole ring, a thiazazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, and a benzo. Diazol ring, benzotriazole ring, benzoxaziazole ring, benzothiazol ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diaza Naphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring, tetraazaanthracene ring Or, a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring from a ring in which an aromatic ring is fused to these heterocycles can be mentioned, preferably a diazole ring or a triazole. Ring, oxaziazole ring, thiazizol ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzodiazol ring, benzotriazole ring, benzoxaziazole ring, benzothiazol ring, benzothiazole ring, benzoxazole ring , Azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene A group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring from a ring, a tetraazaanthracene ring, an azaphenanthracene ring, a diazaphenanthrene ring, a triazaphenanthracene ring, or a tetraazaphenanthracene ring. Yes, more preferably, a triazole ring, an oxaziazole ring, a thiadiazole ring, an azacarbazole ring, a diazacarbazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an anthracene ring, a diazanaphthalene ring, a triazanaphthalene ring, a tetra. A ring is composed of an azanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, a tetraazaanthracene ring, an azaphenanthracene ring, a diazaphenanthrene ring, a triazaanthracene ring or a tetraazaanthracene ring. It is a group excluding one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom, and more preferably, a triazole ring, an oxadiazole ring, a thiadiazol ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, or a diah. It is a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from the zanaphthalene ring, the azaanthracene ring, the diazaanthracene ring, the azaphenanthrene ring, or the diazaphenanthrene ring, which is particularly preferable. Excludes one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the pyridine ring, diazabenzene ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, aclydin ring, phenazine ring or phenanthroline ring. It is a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a pyridine ring, a diazabenzene ring, and a triazine ring, and these groups have a substituent. May be.

The ^{substituents that Ar T2} may have (different from the group represented by the formula (1T') described later; the same applies hereinafter) include an alkyl group, a cycloalkyl group, an alkoxy group, and a cycloalkoxy. A group, a halogen atom or a cyano group is preferable, an alkyl group, a cycloalkyl group, a fluorine atom or a cyano group is more preferable, an alkyl group or a cycloalkyl group is further preferable, and these groups may have a substituent.

Examples and preferred ranges of substituents that Ar ^T2 may have may further include substituents that Ar ^T1 may further possess. Same as the example and preferred range.

It is preferable that Ar ^T1 and L ^T1 are directly bonded or bonded via a divalent group so as not to form a ring. It is preferable that Ar ^T2 and L ^T1 are directly bonded or bonded via a divalent group so as not to form a ring. It is preferable that Ar ^T1 and Ar ^T2 are directly bonded or bonded via a divalent group so as not to form a ring.

In the compound represented by the formula (T-1), when Ar ^T2 is a heterocyclic group containing a group represented by = N- in the ring, the compound represented by the formula (T-1) is the present compound. Since the external quantum efficiency of the light emitting element of the present invention is excellent, it is preferably a compound represented by the formulas (T'-1) to (T'-14), and more preferably the compounds represented by the formulas (T'-1) to (T'-1) to. It is a compound represented by the formula (T'-8) or the formulas (T'-12) to (T'-14), and more preferably the formulas (T'-1) to (T'-4). Alternatively, it is a compound represented by a compound represented by the formulas (T'-12) to (T'-14), and particularly preferably represented by the formulas (T'-1) to (T'-4). It is a compound to be used, and particularly preferably a compound represented by the formula (T'-4).

In the compound represented by the formula (T-1), when Ar ^T2 is an aromatic hydrocarbon group having an electron-attracting group, the compound represented by the formula (T-1) is the light emitting element of the present invention. Since the external quantum efficiency of the compound is excellent, it is preferably a compound represented by the formulas (T'-15) to (T'-18), and more preferably the formulas (T'-15) and the formula (T'. It is a compound represented by -17) or the formula (T'-18), and more preferably a compound represented by the compound represented by the formula (T'-15).

In the compound represented by the formula (T-1), Ar ^T2 is a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) −, and −S (=). O) When the _{group is represented by 2} − or the group represented by the formula (P), the compound represented by the formula (T-1) is excellent in the external quantum efficiency of the light emitting device of the present invention. A compound represented by the formulas (T'-18) to (T'-22) is preferable, and a compound represented by the formulas (T'-19) to (T'-22) is more preferable. It is more preferably a compound represented by the formula (T'-20) or the formula (T'-21), and particularly preferably a compound represented by the formula (T'-21). It is a compound.

Since the compound represented by the formula (T-1) is more excellent in the external quantum efficiency of the light emitting element of the present invention, the formulas (T'-1) to (T'-4) and the formula (T') are preferable. -12) to the compound represented by the formula (T'-15) or the formula (T'-17) to the formula (T'-21), more preferably the formula (T'-1) to the formula (T'. '-4), formula (T'-12) to formula (T'-15), formula (T'-17), formula (T'-18), formula (T'-20) or formula (T'- It is a compound represented by the formula (21), more preferably a compound represented by the formulas (T'-1) to (T'-4), the formula (T'-15) or the formula (T'-21). Yes, it is particularly preferably a compound represented by the formulas (T'-1) to (T'-4), and particularly preferably a compound represented by the formula (T'-4).

［式中、
Ｒ^1Tは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、ハロゲン原子、シアノ基又は式（１T’）で表される基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^1Tは、同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、複数存在するＲ^1Tのうち、少なくとも１個は式（１T’）で表される基である。
Ｒ^1T'は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、電子求引性基又は式（１T’）で表される基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^1T'は、同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、複数存在するＲ^1T'のうち、少なくとも１個は式（１T’）で表される基であり、且つ、少なくとも１個は電子求引性基である。］

[During the ceremony,
R ^1T represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, a cyano group or a group represented by the formula (1T'), and these groups have a substituent. You may. The plurality of R ^1Ts present may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, at least one of the plurality of R ^1Ts is a group represented by the formula (1T').
R ^{1T'represents} a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron-attracting group or a group represented by the formula (1T'), and these groups have a substituent. May be. The plurality of R ^1T's present may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, of the plurality of R ^1T'existing , at least one is a group represented by the formula (1T'), and at least one is an electron-attracting group. ]

Of the plurality of R ^1Ts existing, 2 n ^Ts are preferably groups represented by the formula (1T').
Of the plurality of R ^{1 T'existing,} two n T are preferably groups represented by the formula (1 T').

Of the plurality of R ^1T'existing , 1 to 5 are preferably electron-attracting groups, 1 to 3 are more preferably electron-attracting groups, and 1 or 2 are electron-seeking. It is more preferably an attracting group.

［式中、Ｌ^T1、ｎ^T1及びＡｒ^T1は、前記と同じ意味を表す。］

[In the formula, L ^T1 , n ^T1 and Ar ^{T 1} have the same meanings as described above. ]

R ^1T is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, a cyano group or a group represented by the formula (1T'), and more preferably a hydrogen atom. It is an alkyl group, a cycloalkyl group or a group represented by the formula (1T'), more preferably a hydrogen atom, an alkyl group or a group represented by the formula (1T'), and particularly preferably a hydrogen atom or a group represented by the formula (1T'). It is a group represented by the formula (1T'), and these groups may have a substituent.

R ^1T'is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron-attracting group or a group represented by the formula (1T'), and more preferably a hydrogen atom. , An alkyl group, a cycloalkyl group, an electron-attracting group or a group represented by the formula (1T'), more preferably a hydrogen atom, an alkyl group, an electron-attracting group or a group represented by the formula (1T'). The group is particularly preferably a hydrogen atom, an electron-attracting group or a group represented by the formula (1T'), and these groups may have a substituent.

The examples and preferred ranges of substituents that R ^1T and R ^1T'may have are the same as the examples and preferred ranges of substituents that Ar ^T1 may have. Is.

Examples of the compound (T) include a compound represented by the following formula. In the formula, Z ¹ represents a group represented by −N = or a group represented by −CH =. Z ² represents an oxygen atom or a sulfur atom. A plurality of Z ¹ and Z ² may be the same or different from each other.

Z ¹ is preferably a group represented by −N =. Z ² is preferably an oxygen atom.

Compound (T) is described in Aldrich, Luminesis Technology Corp. It is available from etc. In addition, for example, International Publication No. 2007/063754, International Publication No. 2008/056746, International Publication No. 2011/0326886, International Publication No. 2012/0962363, Japanese Patent Application Laid-Open No. 2009-227663, Japanese Patent Application Laid-Open No. 2010- It can be synthesized according to the method described in 275255, Advanced Materials (Adv. Matter), Vol. 26, pp. 7931-7985, 2014.

[Host material]
Since the external quantum efficiency of the light emitting device of the present invention is excellent, the first organic layer has a function of at least one of the compound (T) and the hole injecting property, the hole transporting property, the electron injecting property and the electron transporting property. It is preferable that the layer contains the host material having. When the first organic layer is a layer containing the compound (T) and the host material, the host material may be contained alone or in combination of two or more. However, the compound (T) and the host material are different.

When the first organic layer is a layer containing the compound (T) and the host material, the compound (T) is preferably a light emitting material.

The host material means a material that plays a role in transferring electrical energy to a light emitting material. Since electrical energy can be efficiently transferred from the host material to the light emitting material and the light emitting material can emit light more efficiently, the lowest excited triplet state of the host material is the lowest excited triplet of the light emitting material. It is preferable that the energy level is higher than the state and the lowest excited singlet state of the host material is higher than the lowest excited singlet state of the light emitting material.

When the first organic layer is a layer containing the compound (T) and the host material, the content of the compound (T) is 100 parts by mass when the total of the compound (T) and the host material is 100 parts by mass. It is usually 0.1 to 50 parts by mass, preferably 1 to 45 parts by mass, more preferably 5 to 40 parts by mass, and further preferably 10 to 20 parts by mass.

As the host material, since the light emitting element of the present invention can be produced by a solution coating process, it exhibits solubility in a solvent capable of dissolving the compound (T) contained in the first organic layer. Is preferable.

The host material is classified into a low molecular weight compound and a high molecular weight compound, and is preferably a high molecular weight compound.

[Small molecule host]
A preferable low-molecular-weight compound (hereinafter referred to as “low-molecular-weight host”) as a host material is preferably a compound represented by the formula (H-1) or a compound represented by the formula (H-2). More preferably, it is a compound represented by the formula (H-1). However, the compound represented by the formula (H-1) and the compound represented by the formula (H-2) are different from the compound (T). The compound represented by the formula (H-1) and the compound represented by the formula (H-2) are different.

［式中、
ｎ^H1は、０以上１０以下の整数を表す。
Ａｒ^H1及びＡｒ^H2は、それぞれ独立に、環内に−Ｃ（＝Ｚ^T1）−で表される基を含まない芳香族炭化水素環から、環を構成する炭素原子に直接結合する水素原子１個を除いた基（該基は電子求引基以外の置換基を有していてもよい）、又は、環内に＝Ｎ−で表される基、ホウ素原子、−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基、及び、前記式（Ｐ）で表される基を含まない複素環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子１個を除いた基（該基は置換基を有していてもよい）である。
Ｌ^H1は、置換基を有していてもよいアルキレン基又は置換基を有していてもよいシクロアルキレン基であるか、環内に−Ｃ（＝Ｚ^T1）−で表される基を含まない芳香族炭化水素環から、環を構成する炭素原子に直接結合する水素原子２個を除いた基（該基は電子求引基以外の置換基を有していてもよい）であるか、環内に＝Ｎ−で表される基、ホウ素原子、−Ｃ（＝Ｚ^T1）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基、及び、前記式（Ｐ）で表される基を含まない複素環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子２個を除いた基（該基は置換基を有していてもよい）である。Ｌ^H1が複数存在する場合、それらは同一でも異なっていてもよい。
Ｚ^T1は前記と同じ意味を表す。］

[During the ceremony,
n ^H1 represents an integer of 0 or more and 10 or less.
Ar ^H1 and Ar ^H2 are independently bonded to the carbon atoms constituting the ring from the aromatic hydrocarbon ring containing no group represented by -C (= Z ^{T1)-in the ring.} A group excluding the number (the group may have a substituent other than an electron-withdrawing group), or a group represented by = N- in the ring, a boron atom, -C (= Z ^T1 ). A complex that does not include a group represented by −, a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, and a group represented by the above formula (P). It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring from the ring (the group may have a substituent).
L ^H1 is an alkylene group which may have a substituent or a cycloalkylene group which may have a substituent, or contains a group represented by ^{−C (= Z T1) − in the ring.} Is it a group obtained by removing two hydrogen atoms that are directly bonded to the carbon atoms constituting the ring from a non-aromatic hydrocarbon ring (the group may have a substituent other than an electron-withdrawing group)? In the ring, a group represented by = N-, a boron atom, a group represented by -C (= Z ^T1 )-, a group represented by -S (= O)-, a group represented by -S (= O) _2- A group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring from a heterocycle containing no group represented by the above formula (P) and the group represented by the above formula (P) (the group is the group). It may have a substituent). When ^{there are a plurality of L H1} , they may be the same or different.
Z ^T1 has the same meaning as described above. ]

n ^H1 is preferably an integer of 0 or more and 5 or less, more preferably an integer of 0 or more and 3 or less, still more preferably 1 or 2, and particularly preferably 1.

Ar ^H1 and Ar ^H2 are preferably benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, inden ring, pyrene ring, perylene ring, chrysen ring, pyrrole. Ring, furan ring, thiophene ring, silol ring, phosphor ring, indole ring, benzofuran ring, benzothiophene ring, benzosilol ring, benzophosphor ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilol ring, dibenzophosphor ring , Phenanthazine ring, phenothyazine ring, 9,10-dihydroaclydin ring, 5,10-dihydrophenanthrene ring and a ring in which these rings are fused, directly bonded to a carbon atom or a hetero atom constituting the ring. It is a group excluding one hydrogen atom, and more preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, an inden ring, a pyrene ring, and a perylene ring. , Chrysen ring, pyrrole ring, furan ring, thiophene ring, silol ring, phosphor ring, indole ring, benzofuran ring, benzothiophene ring, benzosilol ring, benzophosphor ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilol ring , Dibenzophosphor ring, phenanthazine ring, phenanthrene ring, 9,10-dihydroacrine ring or 5,10-dihydrophenazine ring, hydrogen atom 1 directly bonded to the carbon atom or heteroatom constituting the ring. It is a group excluding the benzene ring, more preferably a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring, a phenanthrene ring, a 9,10-dihydroacrine ring or 5, It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring constituting the ring from the 10-dihydrophenanthrene ring, and particularly preferably, a benzene ring, a fluorene ring, a spirobifluorene ring, and the like. It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring constituting the ring from the carbazole ring, the dibenzofuran ring or the dibenzothiophene ring, and particularly preferably the carbazole ring, the dibenzofuran ring or the dibenzo. Directly binds from the thiophene ring to the carbon atom or heteroatom that constitutes the ring. It is a group excluding one matching hydrogen atom, and these groups may have a substituent.

L ^H1 is preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, an inden ring, a pyrene ring, a perylene ring, a chrysen ring, a pyrrole ring, and a furan. Ring, thiophene ring, silol ring, phosphor ring, indol ring, benzofuran ring, benzothiophene ring, benzosilol ring, benzophosphor ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilol ring, dibenzophosphor ring, phenoxazine From a ring, a phenanthidine ring, a 9,10-dihydroaclydin ring, a 5,10-dihydrophenazine ring and a ring obtained by condensing these rings, a hydrogen atom 2 directly bonded to a carbon atom or a heteroatom constituting the ring constituting the ring. It is a group excluding the number of groups, more preferably a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, an inden ring, a pyrene ring, a perylene ring, and a chrysene ring. , Pyrol ring, furan ring, thiophene ring, silol ring, phosphor ring, indole ring, benzofuran ring, benzothiophene ring, benzosilol ring, benzophosphor ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilol ring, dibenzophos From the whole ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacrine ring or 5,10-dihydrophenazine ring, two hydrogen atoms directly bonded to the carbon atom or heteroatom constituting the ring are excluded. Group, more preferably a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacrine ring or a 5,10-dihydro. It is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring constituting the ring from the phenanthrene ring, and particularly preferably, a benzene ring, a fluorene ring, a spirobifluorene ring, a carbazole ring, and the like. It is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting the ring constituting the ring from the dibenzofuran ring or the dibenzothiophene ring, and particularly preferably from the carbazole ring, the dibenzofuran ring or the dibenzothiophene ring. , A hydrogen atom directly bonded to a carbon atom or a heteroatom forming a ring 2 It is a group excluding the number, and these groups may have a substituent.

The ^{substituents that Ar H1} , Ar ^H2 and L ^H1 may have are preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group. , More preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and even more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. It is particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent. However, the aryl group in the substituent that ^{Ar H1} , Ar ^H2 and L ^H1 may have is from an aromatic hydrocarbon ring that does not contain a group represented by ^{−C (= Z T1) − in the ring.} It is a group excluding one hydrogen atom directly bonded to a carbon atom constituting a ring (the group may have a substituent other than an electron-withdrawing group). The ^{monovalent heterocyclic group in the substituent that Ar H1} , Ar ^H2 and L ^H1 may have is a group represented by = N-, a boron atom, -C (= Z ^T1 )-in the ring. From a heterocycle that does not contain a group represented by a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, and a group represented by the above formula (P). , A group excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring (the group may have a substituent).

Substituents that may be further contained in Ar ^H1 , Ar ^H2 and L ^H1 are preferably alkyl groups, cycloalkyl groups, alkoxy groups or cycloalkoxy groups, and more. It is preferably an alkyl group or a cycloalkyl group.

［式中、
ｎ^H2は、１以上１０以下の整数を表す。
Ａｒ^H3及びＡｒ^H4は、それぞれ独立に、環内に＝Ｎ−で表される基を含む１価の複素環基、水素原子、ハロゲン原子、シアノ基、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリールオキシ基又はアリール基を表し、これらの基は置換基を有していてもよい。
Ｌ^H2は、環内に＝Ｎ−で表される基を含む２価の複素環基、アルキレン基、シクロアルキレン基又はアリーレン基を表し、これらの基は置換基を有していてもよい。Ｌ^H2が複数存在する場合、それらは同一でも異なっていてもよい。但し、Ｌ^H2のうち、少なくとも１つは環内に＝Ｎ−で表される基を含む２価の複素環基である。］

[During the ceremony,
n ^H2 represents an integer of 1 or more and 10 or less.
Ar ^H3 and Ar ^H4 are independently monovalent heterocyclic groups containing a group represented by = N- in the ring, hydrogen atom, halogen atom, cyano group, alkyl group, cycloalkyl group, alkoxy group, respectively. It represents a cycloalkoxy group, an aryloxy group or an aryl group, and these groups may have a substituent.
L ^H2 represents a divalent heterocyclic group, an alkylene group, a cycloalkylene group or an arylene group containing a group represented by = N− in the ring, and these groups may have a substituent. When ^{there are a plurality of L H2s} , they may be the same or different. However, ^{at least one of L H2} is a divalent heterocyclic group containing a group represented by = N− in the ring. ]

Ar ^H3 and Ar ^H4 are preferably monovalent heterocyclic groups, hydrogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups or aryl groups containing a group represented by = N− in the ring. Yes, more preferably a monovalent heterocyclic group, an alkyl group, a cycloalkyl group or an aryl group containing a group represented by = N− in the ring, and even more preferably represented by = N− in the ring. It is a monovalent heterocyclic group or an aryl group containing the group to be used, particularly preferably an aryl group, and these groups may have a substituent.

The examples and preferred ranges of aryl groups in Ar ^H3 and Ar ^H4 are the same as the examples and preferred ranges of aryl groups in ^{Ar T1.}

A monovalent heterocyclic group containing a group represented by = N- in the ring is a carbon atom or a hetero atom constituting the ring among the heterocyclic groups containing a group represented by = N- in the ring. It is a group excluding one hydrogen atom directly bonded to.

n ^H2 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, still more preferably 1 or 2, and particularly preferably 1.

L ^H2 is preferably a divalent heterocyclic group or an arylene group containing a group represented by = N- in the ring, and more preferably a divalent group containing a group represented by = N- in the ring. It is a heterocyclic group of, and these groups may have a substituent.

The example and preferred range of the arylene group in L ^H2 is the same as the example and preferred range of the arylene group represented by LT ^1.

A divalent heterocyclic group containing a group represented by = N- in the ring is a carbon atom or a hetero atom constituting the ring among the heterocyclic groups containing a group represented by = N- in the ring. It is a group excluding two hydrogen atoms that are directly bonded to.

The ^{substituents that L H2} , Ar ^H3 and Ar ^H4 may have include a monovalent heterocyclic group including a group represented by = N−, an alkyl group, a cycloalkyl group, an alkoxy group and a cycloalkoxy group. Alternatively, it is an aryl group, more preferably a monovalent heterocyclic group containing a group represented by = N−, an alkyl group, a cycloalkyl group or an aryl group, and further preferably an alkyl group, a cycloalkyl group or an aryl group. It is a group, and these groups may further have a substituent.

The examples and preferred ranges of aryl groups in the substituents that L ^H2 , Ar ^H3 and Ar ^H4 may have are the same as the examples and preferred ranges of aryl groups in ^{Ar T1.}

Substituents that may be further contained in L ^H2 , Ar ^H3 and Ar ^H4 are preferably alkyl groups, cycloalkyl groups, alkoxy groups or cycloalkoxy groups, and more. It is preferably an alkyl group or a cycloalkyl group.

Examples of the compound represented by the formula (H-1) include compounds represented by formulas (H-101) to (H-106) and formulas (H-113) to (H-118). .. Examples of the compound represented by the formula (H-2) include compounds represented by the formulas (H-107) to (H-112).

Examples of the polymer compound used as the host material include a polymer compound which is a hole transporting material described later and a polymer compound which is an electron transporting material described later.

[Polymer host]
A preferable polymer compound as a host compound (hereinafter, referred to as “polymer host”) is preferably a polymer compound containing a structural unit represented by the formula (Y).

The ^{arylene group represented by Ar Y1} is more preferably the formula (A-1), the formula (A-2), the formula (A-6)-the formula (A-10), the formula (A-19) or the formula. It is a group represented by (A-20), and more preferably, the formula (A-1), the formula (A-2), the formula (A-7), the formula (A-9) or the formula (A-19). ), And these groups may have a substituent.

The ^{divalent heterocyclic group represented by Ar Y1} is more preferably the formula (AA-1)-formula (AA-4), the formula (AA-10) -formula (AA-15), the formula (AA-). 18)-A group represented by formula (AA-21), formula (AA-33) or formula (AA-34), more preferably formula (AA-4), formula (AA-10), formula. It is a group represented by the formula (AA-12), the formula (AA-14) or the formula (AA-33), and these groups may have a substituent.

A more preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ^{Y1 and at least one divalent heterocyclic group are directly bonded, further preferable.} The range is the same as the more preferable range and the more preferable range of the arylene group and the divalent heterocyclic group represented by ^{Ar Y1, respectively.}

Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include a group represented by the following formula, which have a substituent. You may be doing it.

［式中、Ｒ^XXは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, R ^XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

R ^XX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

The ^{substituent that the group represented by Ar Y1} may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

Examples of the structural unit represented by the formula (Y) include the structural unit represented by the formula (Y-1)-formula (Y-10), from the viewpoint of the external quantum efficiency of the light emitting device of the present invention. Is preferably a structural unit represented by the formula (Y-1)-formula (Y-3), and from the viewpoint of electron transportability of the light emitting device of the present invention, the formula (Y-4)-formula is preferable. It is a structural unit represented by (Y-7), and is preferably a structural unit represented by the formulas (Y-8)-formula (Y-10) from the viewpoint of hole transportability of the light emitting device of the present invention. Is.

［式中、Ｒ^Y1は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y1は、同一でも異なっていてもよく、隣接するＲ^Y1同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, ^RY1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. .. A plurality of ^RY1s existing may be the same or different, and adjacent ^RY1s may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

^RY1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

The structural unit represented by the formula (Y-1) is preferably the structural unit represented by the formula (Y-1').

［式中、Ｒ^Y11は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y11は、同一でも異なっていてもよい。］

[In the formula, ^RY11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY11s may be the same or different. ]

^RY11 is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

［式中、Ｒ^Y1は前記と同じ意味を表す。Ｘ^Y1は、−Ｃ(Ｒ^Y2)₂−、−Ｃ(Ｒ^Y2)＝Ｃ(Ｒ^Y2)−又は−Ｃ(Ｒ^Y2)₂−Ｃ(Ｒ^Y2)₂−で表される基を表す。Ｒ^Y2は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y2は、同一でも異なっていてもよく、Ｒ^Y2同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, ^RY1 has the same meaning as described above. X ^{Y1 _{is, -C (R Y2) 2 -}} , - represents a group represented by ^{- C (R Y2) = C} (R Y2) - , or _{^{-C (R Y2) 2 -C (}} R Y2) 2. ^RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY2s existing may be the same or different, and the ^RY2s may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

^RY2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. You may be doing it.

In ^{X Y1, -C (R Y2)} 2 - 2 pieces of combinations of R ^Y2 in the group represented by is preferably both an alkyl group or a cycloalkyl group, both an aryl group, both monovalent heterocyclic A ring group, or one of which is an alkyl or cycloalkyl group and the other of which is an aryl or monovalent heterocyclic group, more preferably one of which is an alkyl or cycloalkyl group and the other of which is an aryl group. May have a substituent. The two existing ^RY2s may be bonded to each other to form a ring with the atoms to which they are bonded, and when ^RY2 forms a ring, as a group represented by ^{−C (RY2} ) _{2 −.} Is preferably a group represented by the formula (Y-A1)-formula (Y-A5), more preferably a group represented by the formula (Y-A4), and these groups have a substituent. You may be doing it.

In ^{X Y1, -C (R Y2)} = C (R Y2) - 2 pieces of combinations of R ^Y2 in the group represented by is preferably both an alkyl group or a cycloalkyl group, or, one is an alkyl group Alternatively, it may be a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In ^{X Y1, -C (R Y2)} 2 -C (R Y2) 2 - 4 pieces of R ^Y2 in the group represented by is preferably an optionally substituted alkyl group or a cycloalkyl group Is. A plurality of ^{RY 2s} may be bonded to each other to form a ring together with the atoms to which each bond is formed. When ^{RY 2} forms a ring, −C ( ^RY2 ) ₂ −C ( ^RY2 ) ₂ − The group represented is preferably a group represented by the formula (Y-B1)-(Y-B5), more preferably a group represented by the formula (Y-B3), and these groups are substituted. It may have a group.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

[In the formula, ^RY2 has the same meaning as described above. ]

The structural unit represented by the formula (Y-2) is preferably the structural unit represented by the formula (Y-2').

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

[In the formula, ^RY1 and ^XY1 have the same meanings as described above. ]

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

[In the formula, ^RY1 and ^XY1 have the same meanings as described above. ]

The structural unit represented by the formula (Y-3) is preferably the structural unit represented by the formula (Y-3').

［式中、Ｒ^Y11及びＸ^Y1は前記と同じ意味を表す。］

[In the formula, ^RY11 and ^XY1 have the same meanings as described above. ]

［式中、Ｒ^Y1は前記と同じ意味を表す。Ｒ^Y3は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RY1 has the same meaning as described above. ^RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

^RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. You may.

The structural unit represented by the formula (Y-4) is preferably the structural unit represented by the formula (Y-4'), and the structural unit represented by the formula (Y-6) is the structural unit represented by the formula (Y-6). It is preferably a structural unit represented by -6').

［式中、Ｒ^Y1及びＲ^Y3は前記と同じ意味を表す。］

[In the formula, ^RY1 and ^RY3 have the same meanings as described above. ]

［式中、Ｒ^Y1は前記を同じ意味を表す。Ｒ^Y4は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RY1 has the same meaning as above. ^RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

^RY4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. You may.

Examples of the structural unit represented by the formula (Y) include a structural unit consisting of an arylene group represented by the formula (Y-101) -formula (Y-121) and the formula (Y-201) -formula (Y-121). A structural unit consisting of a divalent heterocyclic group represented by 206), at least one arylene group represented by the formula (Y-300) -formula (Y-304), and at least one divalent heterocycle. Examples thereof include a structural unit composed of a divalent group in which a group is directly bonded.

The structural unit represented by the formula (Y) in which Ar ^Y1 is an arylene group has excellent external quantum efficiency of the light emitting element of the present invention, and therefore is included in the total amount of the structural units contained in the polymer host. On the other hand, it is preferably 0.5 to 90 mol%, and more preferably 30 to 80 mol%.

A structural unit represented by the formula (Y), in which Ar ^Y1 is a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. Since the structural unit which is the basis of the above is excellent in charge transportability of the light emitting element of the present invention, it is preferably 0.5 to 40 mol%, more preferably 3 with respect to the total amount of the structural units contained in the polymer host. ~ 30 mol%.

The structural unit represented by the formula (Y) may contain only one type or two or more types in the polymer host.

Since the polymer host has excellent hole transportability, it is preferable that the polymer host further contains a structural unit represented by the following formula (X).

［式中、
ａ^X1及びａ^X2は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1及びＡｒ^X3は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^X2及びＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2及びＡｒ^X4が複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^X1、Ｒ^X2及びＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^X2及びＲ^X3が複数存在する場合、それらは同一でも異なっていてもよい。］

[During the ceremony,
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 each independently form an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. Representing, these groups may have substituents. If there are multiple Ar ^X2 and Ar ^X4 , they may be the same or different.
R ^X1 , R ^{X 2} and R ^{X 3} independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple R ^X2 and R ^{X 3} , they may be the same or different. ]

Since the external quantum efficiency of the light emitting device of the present invention is more excellent, ^{a X1 is preferably 2 or less, and more preferably 1.}
Since the external quantum efficiency of the light emitting device of the present invention is more excellent, ^{a X2 is preferably 2 or less, and more preferably 0.}

R ^X1 , R ^{X 2} and R ^{X 3} are preferably alkyl groups, cycloalkyl groups, aryl groups or monovalent heterocyclic groups, more preferably aryl groups, and these groups have substituents. May be good.

The ^{arylene group represented by Ar X1} and Ar ^X3 is more preferably a group represented by the formula (A-1) or the formula (A-9), and further preferably represented by the formula (A-1). It is a group, and these groups may have a substituent.

The ^{divalent heterocyclic group represented by Ar X1} and Ar ^X3 is more preferably represented by the formula (AA-1), the formula (AA-2) or the formula (AA-7) -formula (AA-26). These groups may have substituents.

Ar ^X1 and Ar ^X3 are preferably arylene groups which may have a substituent.

The ^{arylene group represented by Ar X2} and Ar ^X4 is more preferably the formula (A-1), the formula (A-6), the formula (A-7), the formula (A-9)-the formula (A-11). ) Or a group represented by the formula (A-19), and these groups may have a substituent.

The more preferred range of the divalent heterocyclic groups represented by Ar ^X2 and Ar ^X4 is the same as the more preferred range of the divalent heterocyclic groups represented by ^{Ar X1} and Ar ^X3.

A more preferable range of an arylene group and a divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^{X4 and at least one divalent heterocyclic group are directly bonded.} The more preferable range is the same as the more preferable range of the arylene group represented by ^{Ar X1} and Ar ^X3 and the divalent heterocyclic group, respectively, and the further preferable range.

The divalent group in which at least one arylene group represented by ^{Ar X2} and Ar ^X4 and at least one divalent heterocyclic group are directly bonded is at least represented by ^{Ar Y1 of the formula (Y).} Examples thereof include those similar to a divalent group in which one arylene group and at least one divalent heterocyclic group are directly bonded.

Ar ^X2 and Ar ^X4 are preferably arylene groups which may have a substituent.

The ^{substituents that the groups represented by Ar X1 to} Ar ^X4 and R ^{X1 to} R ^X3 may have are preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups further have a substituent. You may be doing it.

The structural unit represented by the formula (X) is preferably the structural unit represented by the formula (X-1) -formula (X-7), and more preferably the formula (X-1)-formula (X-). It is a structural unit represented by 6), and more preferably a structural unit represented by equations (X-3)-(X-6).

［式中、Ｒ^X4及びＲ^X5は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、ハロゲン原子、１価の複素環基又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^X4は、同一でも異なっていてもよい。複数存在するＲ^X5は、同一でも異なっていてもよく、隣接するＲ^X5同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, ^RX4 and ^RX5 are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, halogen atom, monovalent heterocyclic group or cyano. Representing groups, these groups may have substituents. A plurality of R ^X4s may be the same or different. A plurality of R ^X5s existing may be the same or different, and adjacent R ^X5s may be bonded to each other to form a ring with carbon atoms to which each is bonded. ]

Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably 1 to 1 to the total amount of the structural units contained in the polymer host. It is 40 mol%, more preferably 5 to 30 mol%.

Examples of the structural unit represented by the formula (X) include the structural unit represented by the formula (X1-1) -formula (X1-11), preferably the formula (X1-3)-formula (X1). It is a structural unit represented by -10).

In the polymer host, the structural unit represented by the formula (X) may contain only one type or two or more types.

Examples of the polymer host include polymer compounds P-1 to P-6.

［表中、ｐ、ｑ、ｒ、ｓ及びｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝100であり、かつ、100≧ｐ＋ｑ＋ｒ＋ｓ≧70である。その他の構成単位とは、式(Ｙ)で表される構成単位、式(Ｘ)で表される構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s and t indicate the molar ratio of each structural unit. p + q + r + s + t = 100, and 100 ≧ p + q + r + s ≧ 70. The other structural unit means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X). ]

The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, and other embodiments, but a plurality of kinds of raw material monomers are used together. It is preferably a polymerized copolymer.

The polystyrene-equivalent number average molecular weight of the polymer host is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ⁵ , and more preferably 1.5 × 10 ^{4 to 1.5.} × 10 ⁵

[Manufacturing method of polymer host]
The polymer host can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and can be produced by Suzuki reaction, Yamamoto reaction, Buchwald, etc. Examples thereof include a method of polymerizing by a coupling reaction using a transition metal catalyst such as a reaction, a Stille reaction, a Negishi reaction and a Kumada reaction.

In the above-mentioned polymerization method, as a method of charging the monomer, a method of charging the entire amount of the monomer in a batch, a method of charging a part of the monomer and reacting, and then collectively charging the remaining monomer. Examples thereof include a method in which the monomer is continuously or dividedly charged, a method in which the monomer is continuously or dividedly charged, and the like.

Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.

The post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, a reaction solution after the polymerization reaction is added to a lower alcohol such as methanol, the precipitated precipitate is filtered, and then dried. The method of making the mixture is used alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, or column chromatography.

[First composition]
The first organic layer is at least selected from the group consisting of the compound (T) and the above-mentioned host material, hole transport material, hole injection material, electron transport material, electron injection material, fluorescent material and antioxidant. It may be a layer containing a composition containing one kind of material (hereinafter, also referred to as "first composition"). However, the hole transport material, the hole injection material, the electron transport material, the electron injection material, and the fluorescent light emitting material are different from the compound (T).

[Hole transport material]
The hole transporting material is classified into a low molecular weight compound and a high molecular weight compound, and is preferably a high molecular weight compound. The hole transport material may have a cross-linking group.

Examples of the polymer compound include polyvinylcarbazole and its derivatives; polyarylene having an aromatic amine structure in its side chain or main chain and its derivatives. The polymer compound may be a compound to which an electron accepting site is bound. Examples of the electron-accepting site include fullerenes, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like, and fullerenes are preferable.

In the first composition, when the compound (T) is 100 parts by mass, the amount of the hole transporting material is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, more preferably. Is 5 to 150 parts by mass.
The hole transporting material may be used alone or in combination of two or more.

[Electronic transport material]
Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds. The electron transport material may have a cross-linking group.

Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinone dimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinone dimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone. , And these derivatives.

Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymeric compound may be metal-doped.

In the first composition, the blending amount of the electron transporting material is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, more preferably 1 part by mass, when the compound (T) is 100 parts by mass. 5 to 150 parts by mass.
The electron transport material may be used alone or in combination of two or more.

[Hole injection material and electron injection material]
Hole injection materials and electron injection materials are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a cross-linking group.

Examples of the low molecular weight compound include metal phthalocyanines such as copper phthalocyanines; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride and potassium fluoride.

Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductivity of polymers containing an aromatic amine structure in the main chain or side chain. Examples include polypolymers.

In the first composition, the compounding amount of the hole injection material and the electron injection material is usually 0.1 to 1000 parts by mass, preferably 1 to 400 parts by mass, respectively, when the compound (T) is 100 parts by mass. Parts, more preferably 5 to 150 parts by mass.
The electron injection material and the hole injection material may be used alone or in combination of two or more.

[Ion dope]
When the hole injection material or the electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10 ^-5 S / cm to 1 × 10 ^{3 S / cm.} In order to keep the electric conductivity of the conductive polymer within such a range, an appropriate amount of ions can be doped into the conductive polymer.

The type of ion to be doped is an anion in the case of a hole injection material and a cation in the case of an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and cerebral sulfonic acid ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

The type of ion to be doped may be used alone or in combination of two or more.

[Fluorescent luminescent material]
Fluorescent materials are classified into low molecular weight compounds and high molecular weight compounds. The fluorescent material may have a cross-linking group.

Examples of low molecular weight compounds include naphthalene and its derivatives, anthracene and its derivatives, and perylene and its derivatives.

Examples of the polymer compound include a phenylene group, a naphthalenediyl group, an anthracendiyl group, a fluorinatedyl group, a phenanthrendiyl group, a dihydrophenanthrenyl group, a group represented by the formula (X), a carbazolediyl group and a phenoxazidinediyl. Examples thereof include high molecular compounds containing a group, a phenothiazinediyl group, a pyrenedyl group and the like.

In the first composition, the blending amount of the fluorescent light emitting material is usually 0.1 to 1000 parts by mass, preferably 0.1 to 400 parts by mass, and more preferably 0.1 to 1000 parts by mass when the compound (T) is 100 parts by mass. 5 to 150 parts by mass.

When the first composition is a composition containing the compound (T) and a fluorescent light emitting material, the compound (T) is preferably a host material.

When the first composition is a composition containing the compound (T) and the fluorescent light emitting material and the compound (T) is the host material, the content of the fluorescent light emitting material is the compound (T) and the fluorescent light emitting material. When the total with the material is 100 parts by mass, it is usually 0.1 to 50 parts by mass, preferably 1 to 45 parts by mass, more preferably 5 to 40 parts by mass, and further preferably 10 to 30 parts by mass. It is a department.

The fluorescent light emitting material may be used alone or in combination of two or more.

[Antioxidant]
The antioxidant may be a compound that is soluble in the same solvent as compound (T) and does not inhibit light emission and charge transport, and examples thereof include phenolic antioxidants and phosphorus-based antioxidants.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the compound (T) is 100 parts by mass.
The antioxidant may be used alone or in combination of two or more.

[First ink]
The composition containing the compound (T) and the solvent (hereinafter, also referred to as “first ink”) includes a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, and a roll coating. Suitable for application methods such as method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. it can.

The viscosity of the first ink may be adjusted according to the type of coating method, but when a solution such as an inkjet printing method is applied to a printing method via an ejection device, clogging and flight bending occur during ejection. Since it is difficult, it is preferably 1 to 20 mPa · s at 25 ° C.

The solvent contained in the first ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptan, n-octane, n-nonan, n- Aliper hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellsolve acetate, methyl benzoate and phenyl acetate System solvent: Polyhydric alcohol solvent such as ethylene glycol, glycerin, 1,2-hexanediol; Alcohol solvent such as isopropyl alcohol and cyclohexanol; Sulfoxide solvent such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , N-Dimethylformamide and other amide-based solvents can be mentioned. The solvent may be used alone or in combination of two or more.

In the first ink, when the compound (T) is 100 parts by mass, the amount of the solvent is usually 10000 to 10000 parts by mass, preferably 2000 to 20000 parts by mass.

<Second organic layer>
The crosslinked body of the crosslinked material can be obtained by bringing the crosslinked material into a state of being crosslinked by the above-mentioned method, conditions and the like.

The cross-linking material is selected from a low molecular weight compound having at least one kind of cross-linking group selected from the cross-linking group A group (hereinafter, also referred to as "low molecular weight compound of the second organic layer") or the cross-linking group A group. It is a polymer compound containing a cross-linking structural unit having at least one kind of cross-linking group (hereinafter, also referred to as “polymer compound of the second organic layer”), and the external quantum efficiency of the light emitting element of the present invention is more excellent. , A polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the group A of cross-linking groups is preferable.

As the cross-linking group selected from the cross-linking group A group, since the external quantum efficiency of the light emitting element of the present invention is more excellent, the formula (XL-1), the formula (XL-9) or the formula (XL-10) is preferable. It is a cross-linking group represented, and more preferably a cross-linking group represented by the formula (XL-1).

[Polymer compound of the second organic layer]
The structural unit having at least one cross-linking group selected from the cross-linking group A group contained in the polymer compound of the second organic layer is a structural unit represented by the formula (2) or the formula (2') described later. It is preferably a structural unit represented by the following formula, but it may be a structural unit represented by the following formula.

The structural unit nA represented by the equation (2) is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, because the external quantum efficiency of the light emitting element of the present invention is more excellent. It is preferably 0 or 1, and particularly preferably 0.

n is preferably 2 because the external quantum efficiency of the light emitting device of the present invention is more excellent.

Ar ³ is an aromatic hydrocarbon group which may have a substituent because the external quantum efficiency of the light emitting device of the present invention is more excellent.

The ^{number of carbon atoms of the aromatic hydrocarbon group represented by Ar 3} is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.
The ^{arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by Ar 3} is preferably a group represented by the formulas (A-1) to (A-20). More preferably, the group represented by the formula (A-1), the formula (A-2), the formula (A-6) to the formula (A-10), the formula (A-19) or the formula (A-20). , And more preferably, a group represented by the formula (A-1), the formula (A-2), the formula (A-7), the formula (A-9) or the formula (A-19). The group of may have a substituent.

The ^{number of carbon atoms of the heterocyclic group represented by Ar 3} is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, not including the number of carbon atoms of the substituent.
The ^{divalent heterocyclic group portion excluding the n substituents of the heterocyclic group represented by Ar 3} is preferably a group represented by the formulas (AA-1) to (AA-34). is there.

The ^{aromatic hydrocarbon group and heterocyclic group represented by Ar 3} may have a substituent, and the substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group and an aryloxy group. Groups, halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

L ^A number of carbon atoms of the alkylene group represented by the not including the carbon atom number of substituent is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10. The number of carbon atoms a cycloalkylene group represented by L ^A is not including the carbon atom number of substituent is usually 3 to 20.
The alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group and an octylene group.

Alkylene group and cycloalkylene group represented by L ^A may have a substituent. As the substituent which the alkylene group and the cycloalkylene group may have, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group are preferable, and these groups further have a substituent. You may be.

Arylene group represented by L ^A may have a substituent. As the arylene group, a phenylene group or a fluoreneyl group is preferable, and an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, and a fluorene-9,9-diyl group are more preferable. Examples of the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group or a bridging group A. Bridging groups selected from the group are preferred, and these groups may further have substituents.

The divalent heterocyclic group represented by L ^A, is preferably a group represented by the formula (AA-1) ~ formula (AA-34).

L ^A, since the preparation of the polymer compound of the second organic layer becomes easier, preferably, an arylene group or an alkylene group, more preferably a phenylene group, fluorenediyl group or an alkylene group, these The group of may have a substituent.

As the cross-linking group represented by X, since the external quantum efficiency of the light emitting element of the present invention is more excellent, it is preferably represented by the formula (XL-1), the formula (XL-9) or the formula (XL-10). It is a cross-linking group, more preferably a cross-linking group represented by the formula (XL-1).

Since the structural unit represented by the formula (2) is excellent in stability and crosslinkability of the polymer compound of the second organic layer, it is relative to the total amount of the structural units contained in the polymer compound of the second organic layer. It is preferably 0.5 to 80 mol%, more preferably 3 to 50 mol%, and further preferably 5 to 20 mol%.
The structural unit represented by the formula (2) may contain only one type or two or more types in the polymer compound of the second organic layer.

The structural unit mA represented by the equation (2') is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, because the external quantum efficiency of the light emitting element of the present invention is more excellent. It is more preferably 0 or 1, and particularly preferably 0.

m is preferably 1 or 2, and more preferably 2 because the external quantum efficiency of the light emitting device of the present invention is more excellent.

c is preferably 0 because it facilitates the production of the polymer compound of the second organic layer and the external quantum efficiency of the light emitting device of the present invention is more excellent.

Ar ⁵ is an aromatic hydrocarbon group which may have a substituent because the external quantum efficiency of the light emitting device of the present invention is more excellent.

The definition and example of the arylene group portion excluding the m substituents of the aromatic hydrocarbon group represented by Ar ⁵ are the same as the definition and example of the arylene group represented by ^{Ar X 2 in the formula (X).} ..

The definition and example of the divalent heterocyclic group portion excluding the m substituents of the heterocyclic group represented by Ar ⁵ are the divalent heterocyclic group portion represented by ^{Ar X 2 in the formula (X).} Same as definition and example.

The definition and example of a divalent group excluding the m substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar ^{5 and at least one heterocycle are directly bonded are given by the formula (X).} It is the same as the definition and example of a divalent group in which at least one arylene group represented by Ar ^{X2 and at least one divalent heterocyclic group are directly bonded.}

Ar ⁴ and Ar ⁶ are arylene groups which may have a substituent because the external quantum efficiency of the light emitting device of the present invention is more excellent.

The definitions and examples of the arylene groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the arylene groups represented by ^{Ar X 1} and Ar ^{X 3 in the formula (X).}

The definitions and examples of the divalent heterocyclic groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the divalent heterocyclic groups represented by ^{Ar X 1} and Ar ^{X 3 in the formula (X).}

The ^{groups represented by Ar 4} , Ar ⁵ and Ar ⁶ may have a substituent, and the substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group and an aryloxy group. Halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

Alkylene group represented by K ^A, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by L ^A, a cycloalkylene group, an arylene group, a divalent heterocyclic It is the same as the definition and example of the ring group.

K ^A, since production of the polymer compound of the second organic layer becomes easy, it is preferable that a phenylene group or a methylene group.

The definition and example of the cross-linking group represented by X'are the same as the definition and example of the cross-linking group represented by X described above.

The structural unit represented by the formula (2') has excellent stability of the polymer compound of the second organic layer and excellent crosslinkability of the polymer compound of the second organic layer, so that the second organic It is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, and further preferably 5 to 20 mol% with respect to the total amount of the constituent units contained in the polymer compound of the layer.
The structural unit represented by the formula (2') may contain only one type or two or more types in the polymer compound of the second organic layer.

-Preferable mode of the structural unit represented by the formula (2) or (2') The structural unit represented by the formula (2) is represented by, for example, the formulas (2-1) to (2-19). Examples of the structural unit represented by the equation (2') include the structural units represented by the equations (2'-2) to (2'-9). Among these, since the external quantum efficiency of the light emitting device of the present invention is more excellent, equations (2-1) to (2-8), equations (2-13), equations (2-16), and equations (2-16) are preferable. It is a structural unit represented by 2-18), equation (2-19) or equations (2-2') to equations (2-9').

-Other Structural Units Since the polymer compound of the second organic layer has excellent hole transportability, it is preferable to further contain a structural unit represented by the formula (X). Further, since the polymer compound of the second organic layer has more excellent external quantum efficiency of the light emitting device of the present invention, it is preferable that the polymer compound further contains a structural unit represented by the formula (Y).

Since the polymer compound of the second organic layer has excellent hole transportability and more excellent external quantum efficiency of the light emitting device of the present invention, the structural unit represented by the formula (X) and the formula (Y) are further excellent. ) Is preferably included.

Definitions and examples of structural units represented by the formula (X) which may be contained in the polymer compound of the second organic layer are represented by the formula (X) which may be contained in the polymer host described above. It is the same as the definition and example of the structural unit. Definitions and examples of structural units represented by the formula (Y) which may be contained in the polymer compound of the second organic layer are represented by the formula (Y) which may be contained in the polymer host described above. It is the same as the definition and example of the structural unit.

The structural unit represented by the formula (X) may contain only one type or two or more types in the polymer compound of the second organic layer. The structural unit represented by the formula (Y) may contain only one type or two or more types in the polymer compound of the second organic layer.

When the polymer compound of the second organic layer contains a structural unit represented by the formula (X), the structural unit represented by the formula (X) has excellent hole transportability, so that the structural unit of the second organic layer has excellent hole transportability. It is preferably 0.1 to 90 mol%, more preferably 1 to 70 mol%, and further preferably 10 to 50 mol% with respect to the total amount of the structural units contained in the polymer compound.

When the polymer compound of the second organic layer contains a structural unit represented by the formula (Y) and Ar ^Y1 is a structural unit of an arylene group, the external quantum efficiency of the light emitting element of the present invention is more excellent. Therefore, it is preferably 0.5 to 90 mol%, more preferably 30 to 60 mol%, based on the total amount of the structural units contained in the polymer compound of the second organic layer.

The polymer compound of the second organic layer contains a structural unit represented by the formula (Y), and Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent. When it is a structural unit which is a divalent group directly bonded to the heterocyclic group of the above, it is included in the polymer compound of the second organic layer because the charge transportability of the polymer compound of the second organic layer is excellent. It is preferably 0.1 to 90 mol%, more preferably 1 to 70 mol%, still more preferably 10 to 50 mol%, based on the total amount of the constituent units.

Examples of the polymer compound of the second organic layer include polymer compounds P-7 to P-14. Here, the “other structural unit” means a structural unit other than the structural unit represented by the equation (2), the equation (2'), the equation (X), and the equation (Y).

［表中、ｐ’、ｑ’、ｒ’、ｓ’及びｔ’は、各構成単位のモル比率を表す。ｐ’＋ｑ’＋ｒ’＋ｓ’＋ｔ’＝100であり、かつ、70≦ｐ’＋ｑ’＋ｒ’＋ｓ’≦100である。］

[In the table, p', q', r', s'and t'represent the molar ratio of each structural unit. p'+ q'+ r'+ s'+ t'= 100, and 70 ≦ p'+ q'+ r'+ s'≦ 100. ]

The polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other embodiments, but may be plural. It is preferably a copolymer in which the seed raw material monomer is copolymerized.

The number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably ^{5 × 10 3 ~1 × 10 6} , more preferably from ^{1 × 10 4 ~5 × 10 5} , more preferably It is 1.5 × 10 ⁴ to 1 × 10 ⁵ .

[Method for Producing Polymer Compound in Second Organic Layer]
The polymer compound of the second organic layer can be produced by the same method as the above-mentioned method for producing a polymer host.

[Low molecular weight compound in the second organic layer]
The low molecular weight compound of the second organic layer is preferably a low molecular weight compound represented by the formula (3).

m ^B1 is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0, because it facilitates the synthesis of the crosslinked material. ..

m ^B2 is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, because it facilitates the synthesis of the crosslinked material and the external quantum efficiency of the light emitting device of the present invention is more excellent. It is preferably 1 or 2, and particularly preferably 1.

m ^B3 is preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and even more preferably 0, because it facilitates the synthesis of the crosslinked material.

Definition and examples of the arylene group part excluding the m ^B3 substituents of the aromatic hydrocarbon group represented by Ar ⁷ has a definition and examples of the arylene group represented by Ar ^X2 in the formula (X) described above It is the same.

The definition and example of the divalent heterocyclic group portion excluding the ^MB3 substituents of the heterocyclic group represented by Ar ⁷ are the divalent heterocycle represented by ^{Ar X 2 in the above formula (X).} It is the same as the definition and example of the base part.

The definition and example of a divalent group excluding the ^mb3 substituent of the group in which at least one aromatic hydrocarbon ring represented by Ar ^{7 and at least one heterocycle are directly bonded are described in the above formula.} It is the same as the definition and the example of the divalent group in which at least one arylene group represented by ^{Ar X2} and at least one divalent heterocyclic group are directly bonded in (X).

The definitions and examples of the substituents that the group represented by Ar ⁷ may have are the same as the definitions and examples of the substituents that the group represented by ^{Ar X 2 may have in the above formula (X).} is there.

Ar ⁷ is preferably an aromatic hydrocarbon group because the external quantum efficiency of the light emitting element of the present invention is excellent, and this aromatic hydrocarbon group may have a substituent.

Alkylene group represented by L ^B1, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by the above-mentioned L ^A, a cycloalkylene group, an arylene group, a divalent It is the same as the definition and example of the heterocyclic group in.

Since ^LB1 facilitates the synthesis of a cross-linking material, it is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, and further preferably a phenylene group, a fluoreneyl group or It is an alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups may have a substituent.

X ″ is preferably a bridging group represented by the formulas (XL-1) to (XL-15), an aryl group or a monovalent heterocyclic group, and more preferably the formula (XL-1). , A cross-linking group represented by the formula (XL-9) or the formula (XL-10), or an aryl group, more preferably the formula (XL-1), the formula (XL-9) or the formula (XL-). It is a cross-linking group represented by 10), a phenyl group, a naphthyl group or a fluorenyl group, and particularly preferably a cross-linking group represented by the formula (XL-1), a phenyl group or a naphthyl group, and these groups are substituted. It may have a group.

Examples of the cross-linking material include low molecular weight compounds represented by formulas (3-1), formulas (3-2) or formulas (3-11) to (3-15).

The low molecular weight compounds of the second organic layer are described in Aldrich, Luminescience Technology Corp. , American Day Source, etc. In addition, for example, it can be synthesized according to the methods described in International Publication No. 1997/033193, International Publication No. 2005/0352221, and International Publication No. 2005/049548.

In the second organic layer, the crosslinked body of the crosslinking material may be contained alone or in combination of two or more.

[Second composition]
The second organic layer comprises a crosslinked body of a crosslinked material and at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant. It may be a layer containing a composition containing (hereinafter, also referred to as “second composition”).

Examples and preferred ranges of the hole-transporting material, the electron-transporting material, the hole-injecting material and the electron-injecting material contained in the second composition are the hole-transporting material and the electron-transporting material contained in the first composition. , The same as the examples and preferred ranges of hole-injected materials and electron-injected materials.

Examples of the luminescent material contained in the second composition include a fluorescent luminescent material which may be contained in the first composition and a phosphorescent metal complex containing iridium, platinum or europium as a central metal. Can be mentioned. The luminescent material may be used alone or in combination of two or more.

In the second composition, the blending amounts of the hole transporting material, the electron transporting material, the hole injecting material, the electron injecting material and the light emitting material are usually 1 when the crosslinked body of the crosslinked material is 100 parts by mass. It is ~ 400 parts by mass, preferably 5 to 150 parts by mass.

The examples and preferred ranges of the antioxidants contained in the second composition are the same as the examples and preferred ranges of the antioxidants contained in the first composition. In the second composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the crosslinked body of the crosslinked material is 100 parts by mass.

[Second ink]
The composition containing the cross-linking material and the solvent (hereinafter, also referred to as “second ink”) can be suitably used for the wet method described in the section of the first ink. The preferred range of the viscosity of the second ink is the same as the preferred range of the viscosity of the first ink. The examples and preferred ranges of the solvent contained in the second ink are the same as the examples and preferred ranges of the solvent contained in the first ink.

In the second ink, when the crosslinked material is 100 parts by mass, the amount of the solvent is usually 10000 to 10000 parts by mass, preferably 2000 to 20000 parts by mass.

<Layer structure of light emitting element>
The light emitting device of the present invention may have a layer other than the anode, the cathode, the first organic layer and the second organic layer.

In the light emitting device of the present invention, the first organic layer is usually a light emitting layer (hereinafter, referred to as "first light emitting layer").

In the light emitting device of the present invention, the second organic layer is usually a hole transport layer, a second light emitting layer or an electron transport layer, preferably a hole transport layer or a second light emitting layer, and more preferably. Is a hole transport layer.

In the light emitting device of the present invention, the first organic layer and the second organic layer are preferably adjacent to each other because the external quantum efficiency of the light emitting device of the present invention is more excellent.
In the light emitting device of the present invention, the second organic layer is preferably a layer provided between the anode and the first organic layer because the external quantum efficiency of the light emitting device of the present invention is more excellent. It is more preferably a hole transport layer or a second light emitting layer provided between the first organic layers, and further preferably a hole transport layer provided between the anode and the first organic layer. preferable.

In the first organic layer of the light emitting device of the present invention, the compound (T) may be contained alone or in combination of two or more. In the second organic layer of the light emitting device of the present invention, the crosslinked body of the crosslinking material may be contained alone or in combination of two or more.

In the light emitting device of the present invention, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the anode and the light emitting device It is preferable to further have a hole injection layer between the second organic layer and the second organic layer. When the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the first organic layer are separated from each other. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer in between.

In the light emitting device of the present invention, when the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the anode It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the surface and the second organic layer. When the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the first organic layer are used. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer between the two.

In the light emitting device of the present invention, when the second organic layer is the second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, and thus the anode. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the first organic layer and the first organic layer. When the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the second organic layer are used. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer between the two.

In the light emitting device of the present invention, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that the anode and the first It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the organic layer and the hole 1. When the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is more excellent, so that between the cathode and the second organic layer. It is preferable to further have an electron injection layer.

Specific layer configurations of the light emitting device of the present invention include, for example, the layer configurations represented by (D1) to (D15). The light emitting device of the present invention usually has a substrate, but may be laminated on the substrate from the anode, or may be laminated on the substrate from the cathode.

(D1) Electron / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D2) anode / hole transport layer (second organic layer) / second 1 light emitting layer (first organic layer) / cathode (D3) anode / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D4) Electron / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / cathode (D5) anode / hole injection layer / Second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D6) anode / hole injection layer / second light emitting layer (second (Organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D7) anode / hole injection layer / hole transport layer (second organic layer) / second 1 light emitting layer (first organic layer) / cathode (D8) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron transport Layer / cathode (D9) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D10) anode / hole Injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D11) anode / hole injection layer / hole transport Layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D12) anode / hole injection layer / hole transport Layer (second organic layer) / first light emitting layer (first organic layer) / second light emitting layer / electron transport layer / electron injection layer / cathode (D13) anode / hole injection layer / hole transport Layer / first light emitting layer (first organic layer) / second light emitting layer (second organic layer) / electron transport layer / electron injection layer / cathode (D14) anode / hole injection layer / hole transport Layer / first light emitting layer (first organic layer) / electron transport layer (second organic layer) / electron injection layer / cathode (D15) anode / hole injection layer / hole transport layer (second organic) Layer) / second light emitting layer / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

In (D1) to (D15), "/" means that the layers before and after the layer are adjacent to each other and laminated. Specifically, the "second light emitting layer (second organic layer) / first light emitting layer (first organic layer)" refers to the second light emitting layer (second organic layer) and the first. It means that the light emitting layer (first organic layer) of No. 1 is adjacent to each other and laminated.

Since the external quantum efficiency of the light emitting device of the present invention is more excellent, the layer structure represented by (D3) to (D12) is preferable, and the layer structure represented by (D7) to (D10) is more preferable.

In the light emitting device of the present invention, the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer and the cathode are each provided with two or more layers, if necessary. May be good.
When a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers and cathodes are present, they may be the same or different from each other.

The thickness of the anode, the hole injection layer, the hole transport layer, the first light emitting layer, the second light emitting layer, the electron transport layer, the electron injection layer and the cathode is usually 1 nm to 1 μm, preferably 2 nm to 2 nm. It is 500 nm, more preferably 5 nm to 150 nm.

In the light emitting device of the present invention, the order, number, and thickness of the layers to be laminated may be adjusted in consideration of the luminous efficiency, driving voltage, and element life of the light emitting device.

[Second light emitting layer]
The second light emitting layer is usually a second organic layer or a layer containing a light emitting material, and is preferably a layer containing a light emitting material. When the second light emitting layer is a layer containing a light emitting material, examples of the light emitting material contained in the second light emitting layer include a light emitting material that may be contained in the above-mentioned second composition. Be done. The light emitting material contained in the second light emitting layer may be contained alone or in combination of two or more.
When the light emitting device of the present invention has a second light emitting layer, and the hole transport layer and the electron transport layer described later are not the second organic layer, the second light emitting layer is the second organic layer. Is preferable.

[Hole transport layer]
The hole transport layer is usually a second organic layer or a layer containing a hole transport material, preferably a second organic layer. When the hole transporting layer is a layer containing a hole transporting material, examples of the hole transporting material include a hole transporting material that may be contained in the first composition described above. The hole transport material contained in the hole transport layer may be contained alone or in combination of two or more.
When the light emitting device of the present invention has a hole transport layer, and the second light emitting layer described above and the electron transport layer described later are not the second organic layer, the hole transport layer is the second organic layer. It is preferable to have.

[Electron transport layer]
The electron transport layer is usually a second organic layer or a layer containing an electron transport material, preferably a layer containing an electron transport material. When the electron transport layer is a layer containing an electron transport material, examples of the electron transport material contained in the electron transport layer include an electron transport material that may be contained in the above-mentioned first composition. .. The electron transport material contained in the electron transport layer may be contained alone or in combination of two or more.
When the light emitting device of the present invention has an electron transport layer and the above-mentioned second light emitting layer and the above hole transport layer are not the second organic layer, the electron transport layer is the second organic layer. Is preferable.

[Hole injection layer and electron injection layer]
The hole injection layer is a layer containing a hole injection material. Examples of the hole injection material contained in the hole injection layer include a hole injection material that may be contained in the above-mentioned first composition. The hole injection material contained in the hole injection layer may be contained alone or in combination of two or more.
The electron injection layer is a layer containing an electron injection material. Examples of the electron-injecting material contained in the electron-injecting layer include an electron-injecting material that may be contained in the above-mentioned first composition. The electron injection material contained in the electron injection layer may be contained alone or in combination of two or more.

[Substrate / Electrode]
The substrate in the light emitting element may be a substrate that can form electrodes and does not chemically change when the organic layer is formed, and is, for example, a substrate made of a material such as glass, plastic, or silicon. When using an opaque substrate, it is preferable that the electrode farthest from the substrate is transparent or translucent.

Examples of the material of the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide and the like. Conductive compounds; composites of silver, palladium and copper (APC); NESA, gold, platinum, silver, copper.

Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc and indium; two or more alloys thereof; one of them. Alloys of more than one species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten and tin; and graphite and graphite interlayer compounds. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.

In the light emitting device of the present invention, at least one of the anode and the cathode is usually transparent or translucent, but it is preferable that the anode is transparent or translucent.
Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method and a laminating method.

[Manufacturing method of light emitting element]
In the light emitting element of the present invention, a low molecular weight compound is used as a method for forming each layer such as the first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer. In the case, for example, a vacuum vapor deposition method from powder, a method by forming a film from a solution or a molten state can be mentioned, and when a polymer compound is used, for example, a method by forming a film from a solution or a molten state can be mentioned.
The first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer and the electron injection layer are the first ink, the second ink, and the above-mentioned light emitting material and holes. It can be formed by a coating method such as a spin coating method or an inkjet printing method using inks containing a transport material, an electron transport material, a hole injection material, and an electron injection material, respectively.

[Use of light emitting element]
In order to obtain planar light emission using the light emitting element, the planar anode and cathode may be arranged so as to overlap each other. In order to obtain patterned light emission, a method of installing a mask having a patterned window on the surface of the planar light emitting element, or forming an extremely thick layer to be a non-light emitting portion to make it substantially non-light emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any of these methods and arranging several electrodes so that they can be turned ON / OFF independently, a segment type display device capable of displaying numbers, characters, etc. can be obtained. In order to use the dot matrix display device, both the anode and the cathode may be formed in a striped shape and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method of using a color filter or a fluorescence conversion filter. The dot matrix display device can be passively driven, or can be actively driven in combination with a TFT or the like. These display devices can be used for displays such as computers, televisions, and mobile terminals. The planar light emitting element can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can also be used as a curved light source and display device.

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

In the examples, the polystyrene-equivalent number average molecular weight (Mn) and the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. The measurement conditions of SEC are as follows.

The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. The mobile phase was flowed at a flow rate of 2.0 mL / min. PLgel MIXED-B (manufactured by Polymer Laboratories) was used as a column. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

LC-MS was measured by the following method.
The measurement sample was dissolved in chloroform or tetrahydrofuran so as to have a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (manufactured by Agilent, trade name: 1100LCMSD). For the mobile phase of LC-MS, the ratio of acetonitrile and tetrahydrofuran was changed, and the mixture was flowed at a flow rate of 0.2 mL / min. As the column, L-column 2 ODS (3 μm) (manufactured by Chemical Substances Evaluation and Research Organization, inner diameter: 2.1 mm, length: 100 mm, particle size 3 μm) was used.

NMR was measured by the following method.
About 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethylsulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol Alternatively, it was dissolved in methylene bicarbonate and measured using an NMR apparatus (manufactured by Agent, trade name: INOVA300 or MERCURY 400VX).

A value of high performance liquid chromatography (HPLC) area percentage was used as an index of the purity of the compound. Unless otherwise specified, this value is a value at UV = 254 nm by HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into HPLC depending on the concentration. For the mobile phase of HPLC, the ratio of acetonitrile / tetrahydrofuran was changed from 100/0 to 0/100 (volume ratio), and the mixture was flowed at a flow rate of 1.0 mL / min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance was used. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

Calculation of the values of Delta] E _ST and the oscillator strength of the compound, the density of the B3LYP level function method, and the structure optimization of the ground state of the compound, where, as a basis function, using 6-31G *. Then, using a Gaussian09 as a quantum chemistry calculation program, the time-dependent density functional method B3LYP level was calculated Delta] E _ST and the oscillator strength of the compound.

<Synthesis Examples T1, T2> Synthesis of Compounds T1 and T2 Compound T1 was synthesized according to the method described in International Publication No. 2010/136109.
Compound T2 was synthesized according to the method described in WO 2007/063754.

The ΔE _ST and oscillator strengths of compound T1 were 0.1295 eV and 0.0011, respectively. Delta] E _ST and the oscillator strength of the compound T2, respectively, were 0.1072eV and 0.0062.

<Synthesis Example T3> Synthesis of compound T3

(Synthesis of compound T3-3)
After setting the inside of the reaction vessel to an argon gas atmosphere, compound T3-1 (2.5 g), compound T3-2 (2.8 g), tris (dibenzylideneacetone) dipalladium (0) (0.25 g), tri-tert-butyl Phosphonium tetrafluoroborate (0.13 g), sodium-tert-butoxide (1.3 g) and toluene (75 mL) were added, and the mixture was stirred at room temperature for 1 hour. Hexane and silica gel were added thereto, and the mixture was stirred at 50 ° C. and then filtered through a filter covered with silica gel. The obtained filtrate was concentrated under reduced pressure to give a solid. This solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and then dried under reduced pressure at 50 ° C. to obtain a crude product of compound T3-3 (3.1 g, brown oil). Hexane and activated carbon were added to the obtained crude product, and the mixture was stirred at room temperature and then filtered under reduced pressure. The obtained filtrate was concentrated under reduced pressure to give compound T3-3 (2.7 g, yellow solid). The HPLC area percentage value of compound T3-3 was 98.5%.

_{^{1 H-NMR (CDCl 3,}} 400MHz): δ (ppm) = 8.20-8.11 (m, 2H), 7.74-6.85 (m, 26H), 2.50-2.30 (m, 7H), 1.53-0.82 (m, 22H ).

(Synthesis of compound T3-4)
After setting the inside of the reaction vessel to a nitrogen atmosphere, compound T3-3 (2.6 g), tetrahydrofuran (26 mL), dimethyl sulfoxide (16 mL) and 33 mass% potassium hydroxide aqueous solution (5.4 g) were added, and the mixture was stirred under reflux for 6.5 hours. did. Then, after cooling to room temperature, extraction was performed using ion-exchanged water and toluene, and the obtained organic layer was washed with ion-exchanged water. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and dried under reduced pressure at 50 ° C. to obtain compound T3-4 (2.1 g, brown oil). The HPLC area percentage value of compound T3-4 was 97.6%.

(Synthesis of compound T3)
After setting the inside of the reaction vessel to a nitrogen atmosphere, compound T3-4 (2.1 g), compound T3-5 (1.3 g), palladium acetate (0.071 g), tri-tert-butylphosphonium tetrafluoroborate (0.096 g) and Xylene (84 mL) was added. Sodium-tert-butoxide (0.76 g) was added thereto, and the mixture was stirred at 100 ° C. for 1 hour. Then, after cooling to room temperature, hexane and silica gel were added thereto, the mixture was stirred at room temperature, and then filtered through a filter covered with silica gel. A crude product was obtained by concentrating the obtained filtrate under reduced pressure. This crude product was crystallized from a mixed solvent of hexane and ethanol to obtain a solid. The obtained solid is purified by silica gel column chromatography (mixed solvent of hexane and toluene), further crystallized from a mixed solvent of toluene, ethyl acetate and acetonitrile, and dried under reduced pressure at 50 ° C. to obtain compound T3. (1.2 g, yellow solid) was obtained. The HPLC area percentage value of compound T3 was 99.5% or more.

LC-MS (APCI, positive): m / z = 977.5 [M + H] ^{+
_{1 H-NMR (CDCl 3,}} 400MHz): δ (ppm) = 9.06-8.98 (m, 2H), 8.82-8.80 (m, 4H), 7.90-6.80 (m, 32H), 2.54-2.43 (m, 4H ), 1.53-1.49 (m, 4H), 1.25 (m, 12H), 0.85-0.83 (m, 6H).

The ΔE _ST and oscillator strengths of compound T3 were 0.1088 eV and 0.1848, respectively.

<Compounds T4 to T12> Synthesis or acquisition of compounds T4 to T12 Compounds T4, T5, T6, T7 and T10 were purchased from Luminesse Technology.
Compound T8 was synthesized according to the method described in WO 2008/056746.
Compound T9 was synthesized according to the method described in WO 2006/114966.
Compound T11 was synthesized according to the method described in WO 2015/102118.
Compound T12 was synthesized according to the method described in JP-A-2010-254676.

The ΔE _ST and oscillator strengths of compound T4 were 0.1563 eV and 0.0069, respectively.
The ΔE _ST and oscillator strengths of compound T5 were 0.0265 eV and 0.0323, respectively.
The ΔE _ST and oscillator strengths of compound T6 were 0.0065 eV and 0, respectively.
Delta] E _ST and the oscillator strength of the compound T7, respectively, were 0.1185eV and 0.0574.
Delta] E _ST and the oscillator strength of the compound T8, respectively, were 0.0659eV and 0.0007.
Delta] E _ST and the oscillator strength of the compound T9, respectively, were 0.3215eV and 0.0448.
The ΔE _ST and oscillator strengths of compound T10 were 0.0102 eV and 0, respectively.
The ΔE _ST and oscillator strengths of compound T11 were 0.4464 eV and 0.4672, respectively.
The ΔE _ST and oscillator strengths of compound T12 were 0.5762 eV and 0.3640, respectively.

<Compounds HM-1 and E1> Synthesis or acquisition of compounds HM-1 and E1 Compound E1 was synthesized according to the method described in WO 2007/058368.
Compound HM-1 was purchased from Luminescience Technology.

Delta] E _ST and oscillator strength of Compound HM-1, respectively, were 0.2966eV and 0.0082.
The ΔE _ST and oscillator strengths of compound E1 were 0.7881 eV and 0.1353, respectively.

<Synthesis Example M1> Synthesis of Compounds M1 to M25 Compounds M1 and M3 were synthesized according to the method described in JP-A-2010-189630.
Compound M2 was synthesized according to the method described in International Publication No. 2012/086671.
Compound M4, Compound M5, Compound M20 and Compound M21 were synthesized according to the method described in WO 2013/191088.
Compound M6 and Compound M7 were synthesized according to the method described in WO 2002/045184.
Compound M8 was synthesized according to the method described in WO 2011/049241.
Compound M9 and Compound M10 were synthesized according to the method described in WO 2013/146806.
Compound M11 was synthesized according to the method described in WO 2005/049546.
Compound M12 was synthesized according to the method described in WO 2015/145871.
Compound M13 was synthesized according to the method described in JP-A-2010-215886.
Compound M14 was synthesized according to the method described in JP-A-2008-106241.
Compound M15 was synthesized according to the method described in JP-A-2010-215886.
Compound M16 and Compound M24 were synthesized according to the method described in International Publication No. 2016/031639.
Compound M17 and compound M19 were synthesized according to the method described in JP2011-174062.
Compound M18 was synthesized according to the method described in WO 2016/031639.
Compound M22 and compound M23 were synthesized according to the method described in WO 2016/031639.
Compound M25 was synthesized according to the method described in WO 2002/045184.

<Synthesis Example HP1> Synthesis of Polymer Compound HP-1 Polymer compound HP-1 was synthesized by using Compound M1, Compound M2 and Compound M3 according to the method described in JP2012-036388. Mn of the polymer compound HP-1 is 9.6 × 10 ^4, Mw was 2.2 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HP-1 has a structural unit derived from the compound M1, a structural unit derived from the compound M2, and a structural unit derived from the compound M3. It is a copolymer composed of a molar ratio of 50:40:10.

<Synthesis Example HP2> Synthesis of Polymer Compound HP-2 Polymer compound HP-2 was synthesized by using Compound M1, Compound M4 and Compound M5 according to the method described in International Publication No. 2015/008851. Mn of the polymer compound HP-2 is 8.5 × 10 ^4, Mw was 2.2 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HP-2 has a structural unit derived from the compound M1, a structural unit derived from the compound M4, and a structural unit derived from the compound M5. It is a copolymer composed of a molar ratio of 50:26:24.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 Polymer compound HTL-1 was synthesized by using Compound M6 and Compound M7 according to the method described in JP2012-36381A. Mn of the polymer compound HTL-1 is 8.1 × 10 ^4, Mw was 3.4 × 10 ^5.
According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-1 was composed of the structural unit derived from the compound M6 and the structural unit derived from the compound M7 in a molar ratio of 50:50. It is a copolymer.

<Synthetic Example HTL2> Synthesis of Polymer Compound HTL-2 The polymer compound HTL-2 uses compound M19, compound M11, compound M25 and compound M15 according to the method described in JP2012-144722. Synthesized. Mn of the polymer compound HTL-2 is 5.0 × 10 ^4, Mw is of 2.5 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-2 has a structural unit derived from compound M19, a structural unit derived from compound M11, a structural unit derived from compound M25, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50: 30: 12.5: 7.5.

<Synthesis Example HTL3> Synthesis of Polymer Compound HTL-3 Polymer Compound HTL-3 was synthesized using Compound M1 and Compound M11 according to the method described in International Publication No. 2015/194448. The Mn of the polymer compound HTL-3 was 4.5 × 10 ⁴ , and the Mw was 1.5 × 10 ⁵ .
According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-3 was composed of a structural unit derived from the compound M1 and a structural unit derived from the compound M11 in a molar ratio of 50:50. It is a copolymer.

<Synthesis Example HTL4> Synthesis of Polymer Compound HTL-4 Polymer Compound HTL-4 was synthesized by using Compound M1, Compound M11 and Compound M8 according to the method described in International Publication No. 2013/146806. Mn of the polymer compound HTL-4 is 1.9 × 10 ^4, Mw was 9.9 × 10 ^4.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-4 has a structural unit derived from the compound M1, a structural unit derived from the compound M11, and a structural unit derived from the compound M8. It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

<Synthesis Example HTL5> Synthesis of polymer compound HTL-5 After setting the inside of the reaction vessel to an inert gas atmosphere, compound M9 (1.07 g), compound M10 (0.198 g), compound M7 (0.919 g), dichlorobis [Tris (2-methoxyphenyl) phosphine] Palladium (1.8 mg) and toluene (50 ml) were added and heated to 100 ° C. A 20 mass% tetraethylammonium hydroxide aqueous solution (8.7 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 6 hours. Then, 2-ethylphenylboronic acid (60.0 mg), 20 mass% tetraethylammonium hydroxide aqueous solution (8.7 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) were added thereto. , 16 hours reflux. Then, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling the obtained reaction solution, the mixture was washed twice with 3.6% by mass hydrochloric acid, twice with a 2.5% by mass aqueous ammonia solution, and 6 times with water, and the obtained solution was added dropwise to methanol to cause precipitation. occured. The obtained precipitate was dissolved in toluene and purified by passing the solution in the order of an alumina column and a silica gel column. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The obtained precipitate was collected by filtration and dried to obtain 1.14 g of the polymer compound HTL-5. Mn of the polymer compound HTL-5 is 3.6 × 10 ^4, Mw was 2.0 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-5 has a structural unit derived from the compound M9, a structural unit derived from the compound M10, and a structural unit derived from the compound M7. It is a copolymer composed of a molar ratio of 40:10:50.

<Synthesis Example HTL6> Synthesis of Polymer Compound HTL-6 Polymer Compound HTL-6 is synthesized using Compound M12, Compound M10, and Compound M24 according to the method described in International Publication No. 2015/145871. did. Mn of the polymer compound HTL-6 is 2.8 × 10 ^4, Mw was 1.1 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-6 has a structural unit derived from the compound M12, a structural unit derived from the compound M10, and a structural unit derived from the compound M24. It is a copolymer composed of a molar ratio of 40:10:50.

<Synthetic Example HTL7> Synthesis of Polymer Compound HTL-7 The polymer compound HTL-7 is prepared by using Compound M1, Compound M13, Compound M14, and Compound M15 according to the method described in International Publication No. 2016/031639. It was synthesized according to the above. Mn of the polymer compound HTL-7 is 2.4 × 10 ^4, Mw was 1.7 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-7 has a structural unit derived from the compound M1, a structural unit derived from the compound M13, a structural unit derived from the compound M14, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthesis Example HTL8> Synthesis of polymer compound HTL-8 After setting the inside of the reaction vessel to an inert gas atmosphere, compound M1 (0.995 g), compound M7 (0.736 g), compound M14 (0.106 g), compound M15 (0.0924 g), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) and toluene (50 ml) were added, and the mixture was heated to 105 ° C. A 20 mass% tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 5.5 hours. Then, phenylboronic acid (24.4 mg), 20 mass% tetraethylammonium hydroxide aqueous solution (6.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) were added thereto for 14 hours. It was refluxed. Then, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling the obtained reaction solution, it was washed twice with water, twice with a 3 mass% acetic acid aqueous solution, and twice with water, and the obtained solution was added dropwise to methanol to cause precipitation. The obtained precipitate was dissolved in toluene and purified by passing the solution in the order of an alumina column and a silica gel column. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The obtained precipitate was collected by filtration and dried to obtain 0.91 g of the polymer compound HTL-8. Mn of the polymer compound HTL-8 is 5.2 × 10 ^4, Mw is of 2.5 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-8 has a structural unit derived from compound M1, a structural unit derived from compound M7, a structural unit derived from compound M14, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthetic Example HTL9> Synthesis of Polymer Compound HTL-9 The polymer compound HTL-9 can be prepared by using Compound M16, Compound M17, Compound M14, and Compound M15 according to the method described in International Publication No. 2016/125560. It was synthesized according to the above. Mn of the polymer compound HTL-9 is 3.5 × 10 ^4, Mw was 1.6 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-9 has a structural unit derived from the compound M16, a structural unit derived from the compound M17, a structural unit derived from the compound M14, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthetic Example HTL10> Synthesis of Polymer Compound HTL-10 Polymer Compound HTL-10 is prepared by using Compound M18, Compound M17, Compound M14, and Compound M15 according to the method described in International Publication No. 2016/031639. Synthesized. Mn of the polymer compound HTL-10 is 5.3 × 10 ^4, Mw was 2.0 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-10 has a structural unit derived from the compound M18, a structural unit derived from the compound M17, a structural unit derived from the compound M14, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthetic Example HTL11> Synthesis of Polymer Compound HTL-11 The polymer compound HTL-11 uses the compound M19, the compound M20, the compound M21, and the compound M22 according to the method described in International Publication No. 2016/031639. Synthesized. Mn of the polymer compound HTL-11 is 5.1 × 10 ^4, Mw was 2.0 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-11 has a structural unit derived from the compound M19, a structural unit derived from the compound M20, a structural unit derived from the compound M21, and a compound. The structural unit derived from M22 is a copolymer composed of a molar ratio of 40: 5: 5: 50.

<Synthetic Example HTL12> Synthesis of Polymer Compound HTL-12 The polymer compound HTL-12 uses the compound M23, the compound M17, the compound M14, and the compound M15 according to the method described in International Publication No. 2016/125560. Synthesized. Mn of the polymer compound HTL-12 is 5.2 × 10 ^4, Mw was 2.2 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-12 has a structural unit derived from the compound M23, a structural unit derived from the compound M17, a structural unit derived from the compound M14, and a compound. The structural unit derived from M15 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthesis Example HTL13> Synthesis of Polymer Compound HTL-13 Polymer Compound HTL-13 was synthesized using Compound M12, Compound M10, and Compound M11 according to the method described in International Publication No. 2015/145871. Mn of the polymer compound HTL-13 is 2.3 × 10 ^4, Mw was 1.2 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-13 has a structural unit derived from the compound M12, a structural unit derived from the compound M10, and a structural unit derived from the compound M11. It is a copolymer composed of a molar ratio of 45: 5: 50.

<Synthesis Example HTL14> Synthesis of Polymer Compound HTL-14 Polymer Compound HTL-14 was synthesized using Compound M6, Compound M7 and Compound M8 according to the method described in International Publication No. 2011/049241. The Mn of the polymer compound HTL-14 was 8.9 × 10 ⁴ , and the Mw was 4.2 × 10 ⁵ .
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-14 has a structural unit derived from the compound M6, a structural unit derived from the compound M7, and a structural unit derived from the compound M8. It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

<Synthesis Example HTL15> Synthesis of Polymer Compound HTL-15 Polymer Compound HTL-15 was synthesized by using Compound M19, Compound M11, Compound M25 and Compound M14 according to the method described in JP2012-144722. .. Mn of the polymer compound HTL-15 is 7.8 × 10 ^4, Mw was 2.6 × 10 ^5.
In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-15 has a structural unit derived from the compound M19, a structural unit derived from the compound M11, a structural unit derived from the compound M25, and a compound. The structural unit derived from M14 is a copolymer composed of a molar ratio of 50: 30: 12.5: 7.5.

<Example D1> Fabrication and evaluation of light emitting device D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film to a glass substrate with a thickness of 45 nm by a sputtering method. ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed on the anode to a thickness of 50 nm by a spin coating method. A hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes in an air atmosphere.

(Formation of second organic layer)
The polymer compound HTL-14 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film was formed on the hole injection layer to a thickness of 20 nm by a spin coating method, and heated on a hot plate at 200 ° C. for 30 minutes in a nitrogen gas atmosphere. Formed an organic layer. By this heating, the polymer compound HTL-14 became a crosslinked product.

(Formation of the first organic layer)
Compound HM-1 and compound T3 (Compound HM-1 / Compound T3 = 85% by mass / 15% by mass) were dissolved in toluene at a concentration of 2% by mass. Using the obtained toluene solution, a film was formed on the second organic layer by a spin coating method to a thickness of 70 nm, and the first organic layer was heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. Was formed.

(Cathode formation)
The substrate on which the first organic layer was formed ^{was decompressed to 1.0 × 10 -4} Pa or less in the vapor deposition machine, and then sodium fluoride was placed on the first organic layer as a cathode at about 4 nm, and then, huff. About 80 nm of aluminum was deposited on the sodium fluoride layer. After the vapor deposition, the light emitting element D1 was manufactured by sealing with a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D1. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 3.

<Example D2> Fabrication and evaluation of light emitting element D2 In the (formation of the second organic layer) of Example D1, "polymer compound HTL-4" was used instead of "polymer compound HTL-14". The light emitting element D2 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element D2. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 3.

<Comparative Example CD1> Fabrication and Evaluation of Light Emitting Element CD1 In Example D1 (formation of the second organic layer), "polymer compound HTL-1" was used instead of "polymer compound HTL-14". The light emitting element CD1 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD1. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 3.

<Comparative Example CD2> Fabrication and Evaluation of Light Emitting Element CD2 In Example D1 (formation of the second organic layer), "polymer compound HTL-3" was used instead of "polymer compound HTL-14". The light emitting element CD2 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD2. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 3.

The results of Example D1, Example D2, Comparative Example CD1 and Comparative Example CD2 are shown in Table 3. The relative value of the external quantum efficiency at ² mA / cm 2 of each light emitting element is shown when the external quantum efficiency at ² mA / cm 2 of the light emitting element CD2 is 1.0.

<Example D3> Preparation and evaluation of light emitting element D3 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Xylene, polymer compound HP-1 and compound T1 (polymer compound HP-1 / compound T1 = 85% by mass / 15) Mass%) was dissolved at a concentration of 1.8 mass%. ”In addition, in place of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ high A light emitting element D3 was produced in the same manner as in Example D1 except that the molecular compound HTL-15 was used. EL light emission was observed by applying a voltage to the light emitting element D3. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 4.

<Comparative Example CD3> Preparation and Evaluation of Light Emitting Element CD3 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene). / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ In xylene, polymer compound HP-1 and compound T1 (polymer compound HP-1 / compound T1 = 85% by mass / 15) Mass%) was dissolved at a concentration of 1.8 mass%. ”In addition, in place of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ high A light emitting element CD3 was produced in the same manner as in Example D1 except that the molecular compound HTL-2 was used. EL light emission was observed by applying a voltage to the light emitting element CD3. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 4.

The results of Example D3 and Comparative Example CD3 are shown in Table 4. The relative value of the external quantum efficiency at ² mA / cm 2 of the light emitting element D3 is shown when the external quantum efficiency at ² mA / cm 2 of the light emitting element CD3 is 1.0.

<Example D4> Preparation and evaluation of light emitting element D4 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, polymer compound HP-2 and compound T2 (polymer compound HP-2 / compound T2 = 85% by mass / 15) The light emitting element D4 was produced in the same manner as in Example D1 except that "% by mass) was dissolved at a concentration of 1.4% by mass." EL light emission was observed by applying a voltage to the light emitting element D4. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 5.

<Comparative Example CD4> Preparation and Evaluation of Light Emitting Element CD4 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, polymer compound HP-2 and compound T2 (polymer compound HP-2 / compound T2 = 85% by mass / 15) Mass%) was dissolved at a concentration of 1.4 mass%. ”In addition, in place of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ high A light emitting element CD4 was produced in the same manner as in Example D1 except that the molecular compound HTL-1 was used. EL light emission was observed by applying a voltage to the light emitting element CD4. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 5.

The results of Example D4 and Comparative Example CD4 are shown in Table 5. The relative value of the external quantum efficiency at ² mA / cm 2 of the light emitting element D4 is shown when the external quantum efficiency at ² mA / cm 2 of the light emitting element CD4 is 1.0.

<Example D5> Fabrication and evaluation of light emitting device D5 In the case of Example D1 (formation of the second organic layer), "polymer compound HTL-6" was used instead of "polymer compound HTL-14". The light emitting element D5 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element D5. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D6> Fabrication and evaluation of light emitting element D6 In Example D5 (formation of the second organic layer), "polymer compound HTL-7" was used instead of "polymer compound HTL-6". A light emitting element D6 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D6. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D7> Fabrication and evaluation of light emitting element D7 In place of "polymer compound HTL-6" in (formation of the second organic layer) of Example D5, "polymer compound HTL-5" was used. A light emitting element D7 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D7. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D8> Fabrication and evaluation of light emitting device D8 In place of "polymer compound HTL-6" in Example D5 (formation of the second organic layer), "polymer compound HTL-8" was used. A light emitting element D8 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D8. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D9> Fabrication and evaluation of light emitting device D9 "Polymer compound HTL-9" was used instead of "polymer compound HTL-6" in (formation of a second organic layer) of Example D5. A light emitting element D9 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D9. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D10> Fabrication and evaluation of light emitting device D10 "Polymer compound HTL-10" was used instead of "polymer compound HTL-6" in (formation of a second organic layer) of Example D5. The light emitting element D10 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D10. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D11> Fabrication and evaluation of light emitting device D11 In the case of Example D5 (formation of the second organic layer), "polymer compound HTL-4" was used instead of "polymer compound HTL-6". The light emitting element D11 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D11. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D12> Fabrication and evaluation of light emitting device D12 In the case of Example D5 (formation of the second organic layer), "polymer compound HTL-11" was used instead of "polymer compound HTL-6". A light emitting element D12 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D12. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Example D13> Fabrication and evaluation of light emitting device D13 “Polymer compound HTL-12” was used instead of “polymer compound HTL-6” in (formation of the second organic layer) of Example D5. The light emitting element D13 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element D13. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

<Comparative Example CD5> Fabrication and Evaluation of Light Emitting Element CD5 In Example D5 (formation of the second organic layer), "polymer compound HTL-2" was used instead of "polymer compound HTL-6". A light emitting element CD5 was produced in the same manner as in Example D5 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD5. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 6.

The results of Examples D5 to D13 and Comparative Example CD5 are shown in Table 6. The relative value of the external quantum efficiency at ^{0.5 mA / cm 2} of the light emitting elements D5 to D13 is shown when the external quantum efficiency of the light emitting element CD5 at 0.5 mA / cm ^{2 is 1.0.}

<Example D14> Preparation and evaluation of light emitting element D14 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, compound HM-1, compound T1 and compound E1 (compound HM-1 / compound T1 / compound E1 = 75% by mass) / 15% by mass / 10% by mass) was dissolved at a concentration of 2.6% by mass. ”Instead of“ polymer compound HTL-14 ”in (formation of the second organic layer) of Example D1. Therefore, the light emitting element D14 was produced in the same manner as in Example D1 except that "polymer compound HTL-13" was used. EL light emission was observed by applying a voltage to the light emitting element D14. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D15> Preparation and evaluation of light emitting element D15 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, compound HM-1, compound T1 and compound E1 (compound HM-1 / compound T1 / compound E1 = 75% by mass) / 15% by mass / 10% by mass) was dissolved at a concentration of 2.6% by mass. ”Instead of“ polymer compound HTL-14 ”in (formation of the second organic layer) of Example D1. Therefore, the light emitting element D15 was produced in the same manner as in Example D1 except that "polymer compound HTL-4" was used. EL light emission was observed by applying a voltage to the light emitting element D15. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D16> Fabrication and evaluation of light emitting element D16 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T2 and Compound E1 (Compound HM-1 / Compound T2 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was used, and the light emitting element D16 was produced in the same manner as in Example D14. EL light emission was observed by applying a voltage to the light emitting element D16. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D17> Preparation and evaluation of light emitting element D17 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T2 and Compound E1 (Compound HM-1 / Compound T2 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was used, and the light emitting element D17 was produced in the same manner as in Example D15. EL light emission was observed by applying a voltage to the light emitting element D17. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D18> Preparation and evaluation of light emitting element D18 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T4 and Compound E1 (Compound HM-1 / Compound T4 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was used, and the light emitting element D18 was produced in the same manner as in Example D14. EL light emission was observed by applying a voltage to the light emitting element D18. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D19> Fabrication and evaluation of light emitting element D19 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T4 and Compound E1 (Compound HM-1 / Compound T4 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D15, except that the light emitting element D19 was produced. EL light emission was observed by applying a voltage to the light emitting element D19. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D20> Fabrication and evaluation of light emitting element D20 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was used, and the light emitting element D20 was produced in the same manner as in Example D14. EL light emission was observed by applying a voltage to the light emitting element D20. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D21> Preparation and evaluation of light emitting element D21 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D15, except that the light emitting element D21 was produced. EL light emission was observed by applying a voltage to the light emitting element D21. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D22> Fabrication and evaluation of light emitting element D22 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 82% by mass / 15% by mass / 3% by mass)" %) ”Was used, and the light emitting element D22 was produced in the same manner as in Example D14. EL light emission was observed by applying a voltage to the light emitting element D22. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D23> Fabrication and evaluation of light emitting element D23 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 84% by mass / 15% by mass / 1% by mass)" %) ”Was produced in the same manner as in Example D14, except that the light emitting element D23 was produced. EL light emission was observed by applying a voltage to the light emitting element D23. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D24> Fabrication and evaluation of light emitting element D24 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 84% by mass / 15% by mass / 1% by mass)" %) ”Was produced in the same manner as in Example D15, except that the light emitting element D24 was produced. EL light emission was observed by applying a voltage to the light emitting element D24. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D25> Preparation and evaluation of light emitting element D25 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 84% by mass / 15% by mass / 1% by mass)" %) ”, And in Example D14 (formation of the second organic layer), with the exception of Example D14 except that“ polymer compound HTL-5 ”was used instead of“ polymer compound HTL-13 ”. Similarly, the light emitting element D25 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D25. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D26> Fabrication and evaluation of light emitting element D26 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T3 and Compound E1 (Compound HM-1 / Compound T3 / Compound E1 = 84% by mass / 15% by mass / 1% by mass)" %) ”, And in Example D14 (formation of the second organic layer), with the exception of Example D14 except that“ polymer compound HTL-6 ”was used instead of“ polymer compound HTL-13 ”. Similarly, the light emitting element D26 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D26. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D27> Preparation and evaluation of light emitting element D27 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T5 and Compound E1 (Compound HM-1 / Compound T5 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D14, except that the light emitting element D27 was produced. EL light emission was observed by applying a voltage to the light emitting element D27. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D28> Preparation and evaluation of light emitting element D28 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T5 and Compound E1 (Compound HM-1 / Compound T5 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D15, except that the light emitting element D28 was produced. EL light emission was observed by applying a voltage to the light emitting element D28. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D29> Preparation and evaluation of light emitting element D29 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T8 and Compound E1 (Compound HM-1 / Compound T8 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D14, except that the light emitting element D29 was produced. EL light emission was observed by applying a voltage to the light emitting element D29. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D30> Fabrication and evaluation of light emitting element D30 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T6 and Compound E1 (Compound HM-1 / Compound T6 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D14, except that the light emitting element D30 was produced. EL light emission was observed by applying a voltage to the light emitting element D30. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Example D31> Preparation and evaluation of light emitting element D31 In Example D15 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T6 and Compound E1 (Compound HM-1 / Compound T6 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”Was produced in the same manner as in Example D15, except that the light emitting element D31 was produced. EL light emission was observed by applying a voltage to the light emitting element D31. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

<Comparative Example CD6> Preparation and Evaluation of Light Emitting Element CD6 In Example D14 (formation of the first organic layer), "Compound HM-1, Compound T1 and Compound E1 (Compound HM-1 / Compound T1 / Compound E1 =" Instead of "75% by mass / 15% by mass / 10% by mass", "Compound HM-1, Compound T6 and Compound E1 (Compound HM-1 / Compound T6 / Compound E1 = 75% by mass / 15% by mass / 10% by mass)" %) ”, And in Example D14 (formation of the second organic layer), with the exception of Example D14 except that“ polymer compound HTL-3 ”was used instead of“ polymer compound HTL-13 ”. Similarly, the light emitting element CD6 was produced. EL light emission was observed by applying a voltage to the light emitting element CD6. The external quantum efficiency at 0.15 mA / cm ^{2 was measured.} The results are shown in Table 7.

The results of Examples D14 to D31 and Comparative Example CD6 are shown in Table 7. The relative value of the external quantum efficiency at ^{0.15 mA / cm 2} of the light emitting elements D14 to D31 ^{is shown when the external quantum efficiency at 0.15 mA / cm 2} of the light emitting element CD6 is 1.0.

<Example D32> Fabrication and evaluation of light emitting element D32 In Example D1 (formation of the first organic layer), "compound HM-1 and compound T3 (compound HM-1 / compound T3 = 85% by mass) were added to toluene. / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Compound HM-1 and Compound T7 (Compound HM-1 / Compound T7 = 85% by mass / 15% by mass) were added to chlorobenzene. It was dissolved at a concentration of 2% by mass. ”Instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ polymer compound HTL-5 ”was used. The light emitting element D32 was produced in the same manner as in Example D1 except that the light emitting element D32. EL light emission was observed by applying a voltage to the light emitting element D32. The external quantum efficiency at 0.25 mA / cm ^{2 was measured.} The results are shown in Table 8.

<Comparative Example CD7> Fabrication and Evaluation of Light Emitting Device CD7 In Example D32 (formation of the second organic layer), "polymer compound HTL-2" was used instead of "polymer compound HTL-5". A light emitting element CD7 was produced in the same manner as in Example D32 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD7. The external quantum efficiency at 0.25 mA / cm ^{2 was measured.} The results are shown in Table 8.

The results of Example D32 and Comparative Example CD7 are shown in Table 8. The relative value of the external quantum efficiency at ^{0.25 mA / cm 2} of the light emitting element D32 when the external quantum efficiency at ^{0.25 mA / cm 2} of the light emitting element CD7 is 1.0 is shown.

<Example D33> Fabrication and evaluation of light emitting element D33 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Xylene, polymer compound HP-2 and compound T9 (polymer compound HP-2 / compound T9 = 85% by mass / 15) (Mass%) was dissolved at a concentration of 1.8% by mass. ”Instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ polymer compound A light emitting element D33 was produced in the same manner as in Example D1 except that "HTL-5" was used. EL light emission was observed by applying a voltage to the light emitting element D33. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D34> Fabrication and evaluation of light emitting element D34 In Example D33 (formation of the first organic layer), "Polymer compound HP-2 and compound T9 (Polymer compound HP-2 / Compound T9 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T10 (polymer compound HP-2 / compound T10 = 85% by mass / 15% by mass) ”was used as Example D33. Similarly, the light emitting element D34 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D34. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D35> Fabrication and evaluation of light emitting element D35 In Example D33 (formation of the first organic layer), "Polymer compound HP-2 and compound T9 (Polymer compound HP-2 / Compound T9 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T6 (polymer compound HP-2 / compound T6 = 85% by mass / 15% by mass) ”was used as Example D33. Similarly, the light emitting element D35 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D35. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D36> Fabrication and evaluation of light emitting element D36 In Example D33 (formation of the first organic layer), "Polymer compound HP-2 and compound T9 (Polymer compound HP-2 / Compound T9 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T1 (polymer compound HP-2 / compound T1 = 85% by mass / 15% by mass) ”was used as Example D33. Similarly, the light emitting element D36 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D36. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D37> Fabrication and evaluation of light emitting element D37 In Example D33 (formation of the first organic layer), "Polymer compound HP-2 and compound T9 (Polymer compound HP-2 / Compound T9 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T11 (polymer compound HP-2 / compound T11 = 85% by mass / 15% by mass) ”was used as Example D33. Similarly, the light emitting element D37 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D37. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D38> Fabrication and evaluation of light emitting element D38 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass / 15 mass). %) ”In place of“ Compound HM-1 and Compound T9 (Compound HM-1 / Compound T9 = 85% by mass / 15% by mass) ”in Example D1 (formation of the second organic layer). , The light emitting element D38 was produced in the same manner as in Example D1 except that "Polymer compound HTL-5" was used instead of "Polymer compound HTL-14". EL light emission was observed by applying a voltage to the light emitting element D38. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D39> Fabrication and evaluation of light emitting element D39 In Example D38 (formation of the first organic layer), "Compound HM-1 and Compound T9 (Compound HM-1 / Compound T9 = 85% by mass / 15 mass). %) ”Was replaced with“ Compound HM-1 and Compound T1 (Compound HM-1 / Compound T1 = 85% by mass / 15% by mass) ”, except that the light emitting element D39 was used in the same manner as in Example D38. Made. EL light emission was observed by applying a voltage to the light emitting element D39. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D40> Fabrication and evaluation of light emitting element D40 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Compound HM-1 and Compound T2 (Compound HM-1 / Compound T2 = 85% by mass / 15% by mass) were added to chlorobenzene. It was dissolved at a concentration of 1.8% by mass. ”Instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ polymer compound HTL-5 ”was used. The light emitting element D40 was produced in the same manner as in Example D1 except that the above was used. EL light emission was observed by applying a voltage to the light emitting element D40. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Example D41> Fabrication and evaluation of light emitting element D41 In Example D38 (formation of the first organic layer), "Compound HM-1 and Compound T9 (Compound HM-1 / Compound T9 = 85% by mass / 15 mass). %) ”In place of“ Compound HM-1 and Compound T11 (Compound HM-1 / Compound T11 = 85% by mass / 15% by mass) ”, but the light emitting element D41 was used in the same manner as in Example D38. Made. EL light emission was observed by applying a voltage to the light emitting element D41. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Comparative Example CD8> Fabrication and Evaluation of Light Emitting Element CD8 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass / 15 mass). %) ”In place of“ Compound HM-1 and Compound T1 (Compound HM-1 / Compound T1 = 85% by mass / 15% by mass) ”in Example D1 (formation of the second organic layer). , The light emitting element CD8 was produced in the same manner as in Example D1 except that "polymer compound HTL-2" was used instead of "polymer compound HTL-14". EL light emission was observed by applying a voltage to the light emitting element CD8. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Comparative Example CD9> Fabrication and Evaluation of Light Emitting Element CD9 In Comparative Example CD8 (formation of the second organic layer), "polymer compound HTL-3" was used instead of "polymer compound HTL-2". A light emitting element CD9 was produced in the same manner as in Comparative Example CD8 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD9. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

<Comparative Example CD10> Fabrication and Evaluation of Light Emitting Element CD10 In Example D33 (formation of the first organic layer), "Polymer compound HP-2 and compound T9 (Polymer compound HP-2 / Compound T9 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T12 (polymer compound HP-2 / compound T12 = 85% by mass / 15% by mass) ”was used as Example D33. In the same manner, the light emitting element CD10 was produced. EL light emission was observed by applying a voltage to the light emitting element CD10. The external quantum efficiency at 0.75 mA / cm ^{2 was measured.} The results are shown in Table 9.

The results of Examples D33 to D41 and Comparative Examples CD8 to CD10 are shown in Table 9. The relative values of the external quantum efficiencies of the light emitting elements D33 to D41, CD8 and CD9 at 0.75 mA / cm ^{2 when} the external quantum efficiency of the light emitting element CD10 at 0.75 mA / cm ^{2 is shown are shown.}

<Example D42> Fabrication and evaluation of light emitting element D42 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ 2.6% by mass of compound T1 and compound E1 (compound T1 / compound E1 = 70% by mass / 30% by mass) in chlorobenzene. Was dissolved at a concentration of%. ”, Except that“ polymer compound HTL-13 ”was used instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer). Made a light emitting element D42 in the same manner as in Example D1. EL light emission was observed by applying a voltage to the light emitting element D42. The external quantum efficiency at 1 mA / cm ^{2 was measured.} The results are shown in Table 10.

<Example D43> Fabrication and evaluation of light emitting device D43 In Example D42 (formation of the second organic layer), "polymer compound HTL-4" was used instead of "polymer compound HTL-13". A light emitting element D43 was produced in the same manner as in Example D42 except for the above. EL light emission was observed by applying a voltage to the light emitting element D43. The external quantum efficiency at 1 mA / cm ^{2 was measured.} The results are shown in Table 10.

<Comparative Example CD11> Fabrication and Evaluation of Light Emitting Element CD11 In Example D42 (formation of the second organic layer), "polymer compound HTL-3" was used instead of "polymer compound HTL-13". The light emitting element CD11 was produced in the same manner as in Example D42 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD11. The external quantum efficiency at 1 mA / cm ^{2 was measured.} The results are shown in Table 10.

The results of Example D42, Example D43 and Comparative Example CD11 are shown in Table 10. The relative value of the external quantum efficiency at ^{1 mA / cm 2} of the light emitting elements D42 and D43 ^{is shown when the external quantum efficiency at 1 mA / cm 2} of the light emitting element CD11 is 1.0.

<Example D44> Fabrication and evaluation of light emitting element D44 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass / 15 mass). %) ”Was replaced with“ Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15% by mass) ”, except that the light emitting element D44 was used in the same manner as in Example D1. Made. EL light emission was observed by applying a voltage to the light emitting element D44. The external quantum efficiency at ^2.5 mA / cm 2 was measured. The results are shown in Table 11.

<Example D45> Preparation and evaluation of light emitting element D45 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Xylene, polymer compound HP-2 and compound T4 (polymer compound HP-2 / compound T4 = 85% by mass / 15) The light emitting element D45 was produced in the same manner as in Example D1 except that "% by mass) was dissolved at a concentration of 1.8% by mass." EL light emission was observed by applying a voltage to the light emitting element D45. The external quantum efficiency at ^2.5 mA / cm 2 was measured. The results are shown in Table 11.

<Comparative Example CD12> Preparation and evaluation of light emitting element CD12 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass / 15 mass). %) ”In place of“ Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15% by mass) ”in Example D1 (formation of the second organic layer). , The light emitting element CD12 was produced in the same manner as in Example D1 except that "polymer compound HTL-1" was used instead of "polymer compound HTL-14". EL light emission was observed by applying a voltage to the light emitting element CD12. The external quantum efficiency at ^2.5 mA / cm 2 was measured. The results are shown in Table 11.

The results of Example D44, Example D45 and Comparative Example CD12 are shown in Table 11. The relative values of the external quantum efficiencies of ^{the light emitting elements D44 and D45 at 2.5} mA / cm 2 are shown when the external quantum efficiency of the light emitting element CD12 at ^2.5 mA / cm 2 is 1.0.

<Example D46> Fabrication and evaluation of light emitting element D46 In Example D44 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”Was replaced with“ Compound HM-1 and Compound T9 (Compound HM-1 / Compound T9 = 85% by mass / 15% by mass) ”, except that the light emitting element D46 was used in the same manner as in Example D44. Made. EL light emission was observed by applying a voltage to the light emitting element D46. The external quantum efficiency at 5 mA / cm ^{2 was measured.} The results are shown in Table 12.

<Example D47> Fabrication and evaluation of light emitting element D47 In Example D45 (formation of the first organic layer), "Polymer compound HP-2 and compound T4 (Polymer compound HP-2 / Compound T4 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T9 (polymer compound HP-2 / compound T9 = 85% by mass / 15% by mass) ”was used as Example D45. Similarly, the light emitting element D47 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D47. The external quantum efficiency at 5 mA / cm ^{2 was measured.} The results are shown in Table 12.

<Comparative Example CD13> Fabrication and Evaluation of Light Emitting Element CD13 In Comparative Example CD12 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”, The light emitting element CD13 was used in the same manner as in Comparative Example CD12 except that“ Compound HM-1 and Compound T9 (Compound HM-1 / Compound T9 = 85% by mass / 15% by mass) ”was used. Made. EL light emission was observed by applying a voltage to the light emitting element CD13. The external quantum efficiency at 5 mA / cm ^{2 was measured.} The results are shown in Table 12.

The results of Example D46, Example D47 and Comparative Example CD13 are shown in Table 12. The relative values of the external quantum efficiencies of the light emitting elements D46 and D47 at 5 mA / cm ^{2 when} the external quantum efficiency of the light emitting element CD13 at 5 mA / cm ^{2 is 1.0 are shown.}

<Example D48> Fabrication and evaluation of light emitting element D48 In Example D45 (formation of the first organic layer), "Polymer compound HP-2 and compound T4 (Polymer compound HP-2 / Compound T4 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-1 and compound T5 (polymer compound HP-1 / compound T5 = 85% by mass / 15% by mass) ”was used as Example D45. Similarly, the light emitting element D48 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D48. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 13.

<Comparative Example CD14> Preparation and evaluation of light emitting element CD14 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ Xylene, polymer compound HP-1 and compound T5 (polymer compound HP-1 / compound T5 = 85% by mass / 15) (Mass%) was dissolved at a concentration of 1.8% by mass. ”Instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ polymer compound A light emitting element CD14 was produced in the same manner as in Example D1 except that "HTL-1" was used. EL light emission was observed by applying a voltage to the light emitting element CD14. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 13.

The results of Example D48 and Comparative Example CD14 are shown in Table 13. The relative value of the external quantum efficiency at ² mA / cm 2 of the light emitting element D48 is shown when the external quantum efficiency at ² mA / cm 2 of the light emitting element CD14 is 1.0.

<Example D49> Fabrication and evaluation of light emitting element D49 In Example D44 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”Was replaced with“ Compound HM-1 and Compound T6 (Compound HM-1 / Compound T6 = 85% by mass / 15% by mass) ”, except that the light emitting element D49 was used in the same manner as in Example D44. Made. EL light emission was observed by applying a voltage to the light emitting element D49. The external quantum efficiency at 1 mA / cm ^{2 was measured.} The results are shown in Table 14.

<Comparative Example CD15> Fabrication and Evaluation of Light Emitting Element CD15 In Comparative Example CD12 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”, The light emitting element CD15 was used in the same manner as in Comparative Example CD12 except that“ Compound HM-1 and Compound T6 (Compound HM-1 / Compound T6 = 85% by mass / 15% by mass) ”was used. Made. EL light emission was observed by applying a voltage to the light emitting element CD15. The external quantum efficiency at 1 mA / cm ^{2 was measured.} The results are shown in Table 14.

The results of Example D49 and Comparative Example CD15 are shown in Table 14. The relative value of the external quantum efficiency at ^{1 mA / cm 2} of the light emitting element D49 is shown when the external quantum efficiency at ^{1 mA / cm 2} of the light emitting element CD15 is 1.0.

<Example D50> Fabrication and evaluation of light emitting element D50 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, compound HM-1, compound T3 and compound E1 (compound HM-1 / compound T3 / compound E1 = 84% by mass) A light emitting element D50 was produced in the same manner as in Example D1 except that "/ 15% by mass / 1% by mass) was dissolved at a concentration of 2.6% by mass." EL light emission was observed by applying a voltage to the light emitting element D50. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 15.

<Comparative Example CD16> Fabrication and Evaluation of Light Emitting Element CD16 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass) were added to toluene. / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ in chlorobenzene, compound HM-1, compound T3 and compound E1 (compound HM-1 / compound T3 / compound E1 = 84% by mass) / 15% by mass / 1% by mass) was dissolved at a concentration of 2.6% by mass. ”Instead of“ polymer compound HTL-14 ”in (formation of the second organic layer) of Example D1. Therefore, the light emitting element CD16 was produced in the same manner as in Example D1 except that "polymer compound HTL-1" was used. EL light emission was observed by applying a voltage to the light emitting element CD16. The external quantum efficiency at 0.5 mA / cm ^{2 was measured.} The results are shown in Table 15.

The results of Example D50 and Comparative Example CD16 are shown in Table 15. The relative value of the external quantum efficiency at ^{0.5 mA / cm 2} of the light emitting element D50 when the external quantum efficiency at ^{0.5 mA / cm 2} of the light emitting element CD16 is 1.0 is shown.

<Example D51> Fabrication and evaluation of light emitting element D51 In Example D44 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”In place of“ Compound HM-1 and Compound T11 (Compound HM-1 / Compound T11 = 85% by mass / 15% by mass) ”, but the light emitting element D51 was used in the same manner as in Example D44. Made. EL light emission was observed by applying a voltage to the light emitting element D51. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 16.

<Example D52> Fabrication and evaluation of light emitting element D52 In Example D45 (formation of the first organic layer), "polymer compound HP-2 and compound T4 (polymer compound HP-2 / compound T4 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T11 (polymer compound HP-2 / compound T11 = 85% by mass / 15% by mass) ”was used as Example D45. Similarly, the light emitting element D52 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D52. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 16.

<Comparative Example CD17> Fabrication and Evaluation of Light Emitting Element CD17 In Comparative Example CD12 (formation of the first organic layer), "Compound HM-1 and Compound T4 (Compound HM-1 / Compound T4 = 85% by mass / 15 mass). %) ”, The light emitting element CD17 was used in the same manner as in Comparative Example CD12 except that“ Compound HM-1 and Compound T11 (Compound HM-1 / Compound T11 = 85% by mass / 15% by mass) ”was used. Made. EL light emission was observed by applying a voltage to the light emitting element CD17. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 16.

The results of Example D51, Example D52 and Comparative Example CD17 are shown in Table 16. The relative value of the external quantum efficiency at ² mA / cm 2 of the light emitting elements D51 and D52 ^{is shown when the external quantum efficiency at 2} mA / cm 2 of the light emitting element CD17 is 1.0.

<Example D53> Fabrication and evaluation of light emitting element D53 In Example D45 (formation of the first organic layer), "Polymer compound HP-2 and compound T4 (Polymer compound HP-2 / Compound T4 = 85 mass). % / 15% by mass) ”, except that“ polymer compound HP-2 and compound T10 (polymer compound HP-2 / compound T10 = 85% by mass / 15% by mass) ”was used as Example D45. Similarly, the light emitting element D53 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D53. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 17.

<Comparative Example CD18> Preparation and evaluation of light emitting element CD18 In Example D1 (formation of the first organic layer), "Compound HM-1 and Compound T3 (Compound HM-1 / Compound T3 = 85% by mass in toluene)". / 15% by mass) was dissolved at a concentration of 2% by mass. ”Instead of“ In xylene, the polymer compound HP-2 and the compound T10 (polymer compound HP-2 / compound T10 = 85% by mass / 15) (Mass%) was dissolved at a concentration of 1.8% by mass. ”Instead of“ polymer compound HTL-14 ”in Example D1 (formation of the second organic layer),“ polymer compound A light emitting element CD18 was produced in the same manner as in Example D1 except that "HTL-1" was used. EL light emission was observed by applying a voltage to the light emitting element CD18. The external quantum efficiency at ² mA / cm 2 was measured. The results are shown in Table 17.

The results of Example D53 and Comparative Example CD18 are shown in Table 17. The relative value of the external quantum efficiency at ² mA / cm 2 of the light emitting element D53 is shown when the external quantum efficiency at ² mA / cm 2 of the light emitting element CD18 is 1.0.

<Example D54> Fabrication and evaluation of light emitting device D54 "Polymer compound HTL-15" was used instead of "polymer compound HTL-14" in (formation of a second organic layer) of Example D1. A light emitting element D54 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element D54. The external quantum efficiency at 5 mA / cm ^{2 was measured.} The results are shown in Table 18.

<Comparative Example CD19> Fabrication and Evaluation of Light Emitting Device CD19 In place of "Polymer Compound HTL-6" in Example D1 (Formation of Second Organic Layer), "Polymer Compound HTL-2" was used. A light emitting element CD19 was produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting element CD19. The external quantum efficiency at 5 mA / cm ^{2 was measured.} The results are shown in Table 18.

The results of Example D54 and Comparative Example CD19 are shown in Table 18. The relative value of the external quantum efficiency at ^{5 mA / cm 2} of the light emitting element D54 is shown when the external quantum efficiency at ^{5 mA / cm 2} of the light emitting element CD19 is 1.0.

Claims (11)

A light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.
The first organic layer contains a compound (T) in which the absolute value of the difference between the energy level in the lowest triplet excited state and the energy level in the lowest singlet excited state is 0.5 eV or less, and A layer that does not contain a phosphorescent metal complex.
The second organic layer is a layer containing a crosslinked body of a crosslinking material.
The cross-linking material is a low molecular weight compound having at least one cross-linking group selected from the cross-linking group A group, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. Oh it is,
The second organic layer, Ru layers der disposed between the anode and the first organic layer, the light emitting element.
(Crosslinking group A group)

[In the formula , * 1 represents the bond position. The bridging group may have a substituent. ] The cross-linking material is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group, and the cross-linking structural unit is a structural unit represented by the formula (2) or The light emitting element according to claim 1, which is a structural unit represented by the formula (2').

[During the ceremony,
nA represents an integer from 0 to 5, and n represents 1 or 2. When there are a plurality of nA, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a cross-linking group selected from the cross-linking group A group. When there are a plurality of X's, they may be the same or different. ]

[During the ceremony,
mA represents an integer from 0 to 5, m represents an integer from 1 to 4, and c represents 0 or 1. If there are multiple mAs, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ are each directly bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, or bonded via an oxygen atom or a sulfur atom. , May form a ring.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents the same meaning as described above. If K ^A there are a plurality, they may be the same or different.
X'represents a cross-linking group selected from the cross-linking group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple X's, they may be the same or different. However, at least one X'is a cross-linking group selected from the cross-linking group A group. ] Claim 1 that the cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from the cross-linking group A group, and the low-molecular-weight compound is a low-molecular-weight compound represented by the formula (3). The light emitting element according to.

[During the ceremony,
m ^B1 and m ^B2 each independently represent an integer of 0 or more. m ^B3 represents an integer of 0 or more and 5 or less. A plurality of m ^B1s may be the same or different. If there are multiple m ^B3s , they may be the same or different.
Ar ⁷ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be. If there are multiple Ar ⁷ , they may be the same or different.
^LB1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N (R''')-, an oxygen atom or a sulfur atom, and these groups are substituents. May have. R'''represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of LB1s} exist, they may be the same or different.
X'' represents a cross-linking group selected from the cross-linking group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. .. A plurality of X''s may be the same or different. However, at least one of the plurality of X''s present is a cross-linking group selected from the cross-linking group A group. ] The light emitting device according to any one of claims 1 to 3, wherein the compound (T) is a compound represented by the formula (T-1).

[During the ceremony,
n ^T1 represents an integer of 0 or more and 5 or less. When a ^{plurality of n T1s} exist, they may be the same or different.
Ar ^T1 represents an aryl group, a substituted amino group, or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of Ar T1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, ^{at least one of Ar T1} is a substituted amino group or contains a nitrogen atom having no double bond in the ring, and a group represented by = N− in the ring, a boron atom. , -C (= Z ^T1 )-represented by-, -S (= O)-represented by-, -S (= O) _2- represented by, and formula (P) :.

It is a monovalent heterocyclic group containing no group represented by. Z ^T1 represents an oxygen atom, a group represented by a sulfur atom or = NR ^ZT1. R ^ZT1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
L ^T1 is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR ^T1 '- represents a group represented by an oxygen atom or a sulfur atom in these groups have a substituent You may. ^{RT1'represents} a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a ^{plurality of LT1s} are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.
Ar ^T2 is a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, the above formula. It is a group represented by (P), an aromatic hydrocarbon group having an electron-attracting group, or a heterocyclic group containing a group represented by = N- in the ring, and these groups have a substituent. You may have.
n ^T2 represents an integer of 1 or more and 15 or less. However, when Ar ^T2 is a boron atom or a group represented by the above formula (P), n ^T2 is 3. If Ar ^T2 is a group represented by −C (= Z ^T1 ) −, a group represented by −S (= O) −, or a group represented by −S (= O) ₂ −, n ^T2 is 2.
Ar ^T1 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T2 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T1 and Ar ^T2 may be directly bonded or bonded via a divalent group to form a ring. ] The light emitting device according to claim 4, wherein ^{at least one of the Ar T1} is a group represented by the formula (T1-1).

[During the ceremony,
Rings R ^T1 and Ring R ^T2 are independently represented by an aromatic hydrocarbon ring containing no group represented by -C (= Z ^T1 )-in the ring, or by = N- in the ring. A group, a boron atom, ^{a group represented by −C (= Z T1} ) −, a group represented by −S (= O) −, a group represented by −S (= O) ₂ −, and the above formula. It represents a heterocycle containing no group represented by (P), and these rings may have a substituent. Z ^T1 has the same meaning as described above.
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, ^{a group represented by −N (R XT1} ) −, or a group represented by −C (R ^XT1 ′) ₂ −. R ^XT1 and R ^XT1'are independent of hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or Representing a cyano group, these groups may have substituents. The plurality of R ^XT1's present may be the same or different, and may be bonded to each other to form a ring with the carbon atom to which each is bonded.
Substituents that R ^XT1 and ring R ^T1 may have, Substituents that R ^XT1 and ring R ^T2 may have, Substituents that R ^XT1'and ring R ^T1 may have, and , R ^{XT1'and the} substituents that ring R ^T2 may have are each directly bonded or bonded via a divalent group to form a ring with the atoms to which they are bonded. May be good. ] The group represented by the formula (T1-1) is a group represented by the formula (T1-1A), a group represented by the formula (T1-1B), a group represented by the formula (T1-1C), or a group represented by the formula (T1-1C). The light emitting device according to claim 5, which is a group represented by the formula (T1-1D).

[During the ceremony,
X ^T1 has the same meaning as described above.
X ^T2 and X ^T3 independently form a single bond, an oxygen atom, a sulfur atom, ^{a group represented by −N (R XT2} ) −, or a group represented by −C (R ^XT2 ′) ₂ −. Represent. R ^XT2 and R ^XT2'are independent of hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or Representing a cyano group, these groups may have substituents. The plurality of R ^XT2's present may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring together with the carbon atom to which each is bonded.
^{R T1, R T2, R T3} , R T4, R T5, R T6, R T7, R T8, R T9, R T10, R T11 and R ^T12 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group , Alkyl group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group, halogen atom or cyano group, and these groups may have a substituent.
R ^T1 and R ^T2, R ^T2 and R ^T3, R ^T3 and R ^T4, R ^T5 and R ^T6, R ^T6 and R ^T7, R ^T7 and R ^T8, R ^T9 and R ^T10, R ^T10 and R ^T11 and, R ^T11 and R ^T12 may be directly bonded to each other or bonded via a divalent group to form a ring together with the carbon atom to which each is bonded. ] According to ^{any one of claims 4 to 6, the Ar T2} is a heterocyclic group containing a group represented by = N- in the ring (the group may have a substituent). The light emitting element described. The Ar ^T2 is a diazole ring, a triazole ring, an oxaziazole ring, a thiazidol ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, a benzodiazol ring, a benzotriazole ring, a benzoxaziazole ring, a benzothiazol ring. Ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring , Diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring, hydrogen directly bonded to the carbon atom or hetero atom constituting the ring. The light emitting element according to claim 7, which is a group excluding one or more atoms (the group may have a substituent). The light emitting device according to any one of claims 1 to 8, wherein the oscillator strength of the compound (T) is 0.0001 or more. The first organic layer further contains at least one selected from the group consisting of host materials, hole transport materials, hole injection materials, electron transport materials, electron injection materials, fluorescent materials and antioxidants. The light emitting element according to any one of claims 1 to 9. The light emitting device according to any one of claims 1 to 10, wherein the first organic layer and the second organic layer are adjacent to each other.