Polycyclic aromatic compounds, materials for organic devices, organic electroluminescent devices, display devices and lighting devices

Abstract

Providing novel compounds as materials for organic devices such as organic electroluminescent devices. [Solution] A polycyclic aromatic compound represented by the following formula (1); TIFF2026071228000175.tif70170 In the formula, rings A and C are aryl rings having substituents such as halogens, and rings B and D are aryl rings, and at least one hydrogen atom in these rings may be substituted.

Description

[Technical Field]

[0001] This invention relates to polycyclic aromatic compounds. The invention also relates to green light-emitting materials containing the above-mentioned polycyclic aromatic compounds. Furthermore, the invention relates to organic devices such as organic field-effect light-emitting devices, organic field-effect transistors, and organic thin-film solar cells, as well as display devices and lighting devices, using the above-mentioned polycyclic aromatic compounds. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been studied extensively due to their potential for power saving and miniaturization. Furthermore, organic electroluminescent elements made from organic materials have been actively investigated because they are easily made lighter and larger. In particular, the development of organic materials with luminescence properties such as green, one of the three primary colors of light, and the development of organic materials with charge transport capabilities (potentially becoming semiconductors or superconductors) have been actively researched, regardless of whether they are polymer compounds or low molecular weight compounds.

[0003] An organic electroluminescent device has a structure consisting of a pair of electrodes, an anode and a cathode, and one or more layers containing an organic compound, disposed between the pair of electrodes. The layers containing the organic compound include light-emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] For example, benzofluorene compounds have been developed as materials for the light-emitting layer (Patent Document 1). For example, triphenylamine compounds have been developed as hole transport materials (Patent Document 2). For example, anthracene compounds have been developed as electron transport materials (Patent Document 3).

[0005] Furthermore, in recent years, improved triphenylamine derivatives have been reported as materials used in organic EL elements and organic thin-film solar cells (Patent Document 4). This material is characterized by its enhanced planarity, achieved by linking the aromatic rings constituting triphenylamine, based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which had already been put into practical use. In this document, for example, the charge transport properties of NO-linked compounds (compound 1 on page 63) are evaluated, but the manufacturing method of materials other than NO-linked compounds is not described, and since the electronic state of the entire compound differs depending on the linked elements, the properties obtained from materials other than NO-linked compounds are still unknown. Other examples of such compounds can be seen (Patent Document 5). For example, the lowest excited triplet energy level (E T1 Compounds with a large T1 conjugated structure can emit phosphorescence at shorter wavelengths, making them useful as materials for blue light-emitting layers. Furthermore, there is a demand for novel conjugated structures with a large T1 for use as electron transport materials and hole transport materials sandwiching the light-emitting layer.

[0006] The host materials for organic light-emitting diodes (OLEDs) are generally molecules in which multiple existing aromatic rings, such as benzene and carbazole, are linked by single bonds or phosphorus or silicon atoms. This is because linking many relatively small conjugated aromatic rings ensures the large HOMO-LUMO gap (band gap Eg in thin films) required for the host material. Furthermore, host materials for OLEDs using phosphorescent materials or thermally activated delayed fluorescence (TADF) materials have a high lowest excited triplet energy level (Eg). T1 Although this is also necessary, by linking donor or acceptor aromatic rings or substituents to the molecule, the triplet excited state (T1) SOMO1 and SOMO2 are localized, and the exchange interaction between the two orbitals is reduced, thereby lowering the lowest excited triplet energy level (E T1This makes it possible to improve the redox stability of small aromatic rings in conjugated systems. However, the redox stability of small aromatic rings in conjugated systems is not sufficient, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient lifespan. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but the HOMO-LUMO gap (band gap Eg in thin films) and the lowest excited triplet energy level (E) are not. T1 Because of its low ) ratio, it has been considered unsuitable as a host material.

[0007] Furthermore, in recent years, compounds in which multiple aromatic rings are fused with boron or other elements as the central atom have also been reported (Patent Document 6). In this document, an organic EL device is evaluated using such a compound with multiple aromatic rings fused as a dopant material for the light-emitting layer. However, a very large number of compounds are disclosed in this document, and it is beneficial to investigate compounds among them that have particularly excellent organic EL properties, such as light emission characteristics.

[0008] In addition to vacuum deposition, wet deposition is also used to form the organic layers that make up organic EL elements. Active efforts are being made to develop materials for wet deposition, particularly inks for forming hole injection layers, hole transport layers, and light-emitting layers. Regarding the inks for hole injection and hole transport layers, the properties of each layer formed by wet deposition using these inks have reached a practical level. [Prior art documents] [Patent Documents]

[0009] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] Japanese Patent Publication No. 2001-172232 [Patent Document 3] Japanese Patent Publication No. 2005-170911 [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 [Overview of the Initiative] [Problems that the invention aims to solve]

[0010] As mentioned above, various materials have been developed for use in organic EL devices, but in order to further improve organic EL properties such as luminescence characteristics and to increase the range of organic EL materials such as materials for the light-emitting layer, the development of compounds that were not previously known in concrete terms is desired. [Means for solving the problem]

[0011] The inventors of the present invention, after diligently studying to solve the above problems, discovered that an excellent organic EL element can be obtained by using a compound having a specific structure among polycyclic aromatic compounds in which multiple aromatic rings are linked by a boron atom and a nitrogen atom or oxygen atom, and thus completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and furthermore, organic device materials containing the following polycyclic aromatic compounds.

[0012] [1] Polycyclic aromatic compounds represented by the following formula (1); [ka]

[0013] In formula (1), Rings A and C are independently substituted aryl rings or substituted heteroaryl rings. Rings B and D are independently optionally substituted aryl rings or optionally substituted heteroaryl rings. X 1 , X 2 , X 3 and X 4is independently >O, >N-R, >CR2, >S or >Se, where R in >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl or optionally substituted alkyl, and R in >N-R may also be bonded to the A ring, B ring, C ring and / or D ring by a linking group or a single bond. R in >CR2 is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl or optionally substituted alkyl, and R in >CR2 may also be bonded to the A ring, B ring, C ring and / or D ring by a linking group or a single bond. R 1 and R 2 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), cyano, or halogen. In the compound represented by formula (1), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound represented by formula (1) may be substituted with deuterium.

[0014] [2] The A ring is an aryl ring having one substituent Z 1 or a heteroaryl ring having one substituent Z 1 or has a structure in which Z 1 in an aryl ring having one substituent Z 1 or a heteroaryl ring having one substituent Z 1 is bonded to the aryl ring or heteroaryl ring to which Z 1 is bonded by a single bond or a linking group. The C ring is an aryl ring having one substituent Z2 An aryl ring having or one substituent Z 2 A heteroaryl ring having one substituent Z 2 An aryl ring having or one substituent Z 2 Z in a heteroaryl ring having 2 Z is formed by a single bond or linking group. 2 It has a structure to which is bonded to an aryl ring or heteroaryl ring, Z 1 and Z 2 Each of these is independently one of the following bases: Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryl; Diarylaminos may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or halogen-substituted (the two aryls may be bonded to each other); Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted diheteroarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylheteroarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or alkyl which may be substituted with halogen; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted cycloalkyl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylthio; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroarylthio; Cyano; or halogen, Rings B and D are independently aryl rings or heteroaryl rings that may be substituted with alkyl, cyano, or halogen atoms. Rings A and B are B, X 1 and X 2 Formula (1) consists of a fused biring structure on the left and a five-membered or six-membered ring sharing a bond, with the C and D rings being B and X. 3 and X 4 Formula (1) consists of the fused two-ring structure on the right and has a five-membered or six-membered ring that shares a bond with it. R 1 and R 2 These are, independently, hydrogen, cyano, or halogen. [1] A polycyclic aromatic compound as described above.

[0015] [3] A polycyclic aromatic compound represented by the following formula (2) as described in [1]; [ka]

[0016] In formula (2), R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 Each of these is independently a hydrogen atom or a substituent selected from the substituent group X, and R 5 ~R 7 and R 10 ~R 12 Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the b ring and / or d ring. At least one hydrogen in the formed ring may be substituted with a substituent selected from the substituent group X; Substituent group X: Aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted aryls; Heteroaryls that may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Diarylaminos which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen (the two aryls may be bonded to each other); Diheteroarylaminos which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted arylheteroarylaminos; Alkyl, heteroaryl, cycloalkyl, cyano, or halogen-substituted alkyl; aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted cycloalkyl; Alkoxy that may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Aryloxys which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Heteroaryloxys which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Arylthio, which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Heteroarylthio, which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Alkyl-substituted silyls that may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Cyano; and halogen, X 1 , X 2 , X 3 and X 4 These are independently >O, >NR, >CR2, >S, or >Se, The R in the aforementioned >NR and >CR2 is independently one of the following groups: A C1-C6 alkyl, cyano, or halogen-substituted aryl atom with C6-C12; A heteroaryl molecule having 2 to 15 carbon atoms, which may be substituted with an alkyl, cyano, or halogen molecule having 1 to 6 carbon atoms; Cycloalkyl groups having 3 to 12 carbon atoms, which may be substituted with alkyl groups having 1 to 6 carbon atoms, cyano groups, or halogen groups; or A C1-C6 alkyl group which may be substituted with a cyano or halogen, The R in >NR and >CR2 may be linked to the a, b, c, and / or d rings by a linking group or a single bond. R1 and R 2 These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cyano group, or a halogen group. Z 1 and Z 2 Each of these is independently one of the following bases: Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted aryl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted heteroaryl; Diarylaminos that may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen; Diheteroarylaminos which may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylheteroarylamino; Aryl, heteroaryl, alkyl-substituted silyl, cyano, or halogen-substituted alkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted cycloalkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryloxy; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryloxy; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylthio; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroarylthio; Cyano; or halogen, Z 1 R3 and / or R 4 It may also be bonded to form a ring, in which case R 3 and / or R 4 This may represent boron, and may also represent two aryl groups of diarylamino bonded together. Z 2 R 8 and / or R 9 It may also be bonded to form a ring, in which case R 8 and / or R 9 This may represent boron, and may also represent two aryl groups of diarylamino bonded together. At least one hydrogen atom in the compound represented by formula (2) may be substituted with deuterium.

[0017] [4] X 1 , X 2 , X 3 and X 4 A polycyclic aromatic compound as described in [3], wherein at least one of the following is >NR. [5] The polycyclic aromatic compound according to [3] or [4], wherein R in NR is a C1-C6 alkyl, a C6-C10 aryl which may be substituted with a cyano or halogen, or a C1-C4 alkyl which may be substituted with a cyano or halogen. [6] R 1 and R 2 A polycyclic aromatic compound as described in any of [3] to [5], wherein all of the atoms are hydrogen. [7] R 3 , R 4 , R 8 , and R 9 A polycyclic aromatic compound as described in any of [3] to [6], wherein all of the atoms are hydrogen.

[0018] [8] X 1 , X 2 , X 3 and X 4 All of them are >NR, >The R in NR is an aryl atom having 6 to 10 carbon atoms, which may be substituted with an alkyl, cyano, or halogen atom having 1 to 6 carbon atoms. Z 1 and Z 2 are each a diarylamino optionally substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano or halogen, Z 1 and X 1 or X 2 the R in >N-R in either is bonded to the a ring with boron as a linking group being R 3 or R 4 and is a polycyclic aromatic compound as described in any one of [3] to [6] that is bonded to the c ring with boron as a linking group being R Z 2 and X 3 or X 4 the R in >N-R in either is bonded to the c ring with boron as a linking group being R 8 or R 9 and is a polycyclic aromatic compound as described in any one of [3] to [6]. [9] R 5 , R 6 , R 7 , R 10 , R 11 and R 12 are each independently aryl having 6 to 10 carbon atoms optionally substituted with hydrogen, cyano or halogen, cycloalkyl having 3 to 12 carbon atoms optionally substituted with cyano or halogen, or alkyl having 1 to 6 carbon atoms optionally substituted with cyano or halogen, and is a polycyclic aromatic compound as described in any one of [3] to [8].

[0019]

[10] The polycyclic aromatic compound as described in [1], represented by formula (1-307), formula (1-313), formula (1-321), or formula (1-331); [Chemical formula] In the formula, Me is methyl and tBu is t-butyl.

[0020]

[11] A green light-emitting material containing the polycyclic aromatic compound as described in any one of [1] to

[10] .

[12] A material for an organic device containing the polycyclic aromatic compound as described in any one of [1] to

[10] .

[13] The organic device material is the organic device material according to

[12] , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

[14] A light-emitting layer material for forming a light-emitting layer of an organic electroluminescent element, containing a polycyclic aromatic compound according to any one of [1] to

[10] .

[15] An organic electroluminescent element having a pair of electrodes composed of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and containing the light-emitting layer material according to

[14] .

[0021]

[16] The organic electroluminescent element according to

[15] , wherein the light-emitting layer further contains one or more compounds selected from the group consisting of a compound represented by the following formula (3), a compound represented by the following formula (4), and a compound represented by the following formula (5);

Chemical formula

[0022]

[17] The organic electroluminescent element according to

[15] or

[16] , further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives.

[18] The organic electroluminescent element according to

[17] , wherein the electron transport layer and / or electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. A display device equipped with an organic electroluminescent element as described in any of

[19]

[15] to

[18] . A lighting device equipped with an organic electroluminescent element as described in any of

[20]

[15] to

[18] . [Effects of the Invention]

[0023] The present invention provides novel polycyclic aromatic compounds. These compounds can provide green light-emitting materials with high color purity. Furthermore, the compounds of the present invention are useful as materials for organic devices such as organic electroluminescent devices. [Brief explanation of the drawing]

[0024] [Figure 1] This is a schematic cross-sectional view showing an organic EL element according to this embodiment. [Figure 2] This diagram illustrates a method for fabricating organic EL elements on a substrate with a bank using an inkjet method. [Figure 3]This is the absorption and fluorescence spectrum of compound (1-307). [Figure 4] This is the absorption and fluorescence spectrum of compound (1-313). [Figure 5] This is the absorption and fluorescence spectrum of compound (1-321). [Modes for carrying out the invention]

[0025] The present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, numerical ranges represented by "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, in this specification, "hydrogen" in the description of structural formulas means "hydrogen atom (H)". In this specification, an organic electroluminescent element may be referred to as an organic EL element.

[0026] In this specification, chemical structures and substituents are sometimes expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B.

[0027] 1. Polycyclic aromatic compounds represented by formula (1) Three types of light-emitting materials are used for organic EL displays: fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. However, fluorescent materials have low luminous efficiency, ranging from approximately 25% to 62.5%. On the other hand, phosphorescent and TADF materials can reach 100% luminous efficiency in some cases, but both suffer from low color purity (wide emission spectrum). Displays express various colors by mixing the emission of the three primary colors of light: red, green, and blue. If the color purity of each is low, some colors cannot be reproduced, significantly degrading the image quality of the display. Therefore, commercially available displays use optical filters to remove unnecessary colors from the emission spectrum, thereby increasing color purity (narrowing the spectral width) before use. Consequently, if the original spectral width is wide, the proportion of colors removed increases, so even if the luminous efficiency is high, the actual efficiency decreases significantly. For example, the half-width at half maximum (FWHM) of the blue emission spectrum of commercially available smartphones is approximately 20-25 nm, while the FWHM of typical fluorescent materials is around 40-60 nm, phosphorescent materials around 60-90 nm, and TADF materials around 70-100 nm. When using fluorescent materials, the FWHM is relatively narrow, so it is sufficient to remove only a portion of the unwanted color, but when using phosphorescent or TADF materials, it is necessary to remove more than half. Against this backdrop, there has been a desire for the development of light-emitting materials that combine both luminescence efficiency and color purity.

[0028] Generally, phosphorescent materials are used as green light-emitting materials for organic EL displays. Green phosphorescent materials are coordination compounds that have a heavy metal atom such as Ir at the center. Although green phosphorescent materials have a very high luminescence efficiency of nearly 100%, their emission spectrum has a very broad half-width of 60-90 nm, which is disadvantageous in terms of practical efficiency when used in organic EL displays.

[0029] Therefore, Patent Document 6 (International Publication No. 2015 / 102118) proposes a new molecular design that dramatically improves the color purity of organic EL materials. For example, in the compound (1-401) disclosed in this document, by utilizing the multiple resonance effect of boron (electron-withdrawing) and nitrogen (electron-donating), it has been successful in localizing the HOMO on three carbons (black circles) on the benzene ring consisting of six carbons and the LUMO on the remaining three carbons (white circles). Due to this efficient inverse intersystem crossing, the luminescence efficiency of this compound reaches up to 100% at maximum. Furthermore, boron and nitrogen in the compound (1-401) not only localize the HOMO and LUMO, but also play a role in maintaining a rigid planar structure by condensing three benzene rings and suppressing structural relaxation in the excited state. As a result, it has also been successful in obtaining a luminescence spectrum with a small Stokes shift of the absorption and emission peaks and high color purity. The full width at half maximum of its luminescence spectrum is 28 nm, showing a level of color purity that exceeds even highly color-pure fluorescent materials that have been put into practical use.

[0030] [Chemical formula]

[0031] On the other hand, in the case of a dimer compound such as formula (1-421), due to the induction of intermolecular stacking because of its high planarity, there has also arisen a problem that the efficiency in a light-emitting device is not sufficiently satisfactory. Also, in Patent Document 6, the wavelength of the emission peak has not been clarified for all the disclosed compounds.

[0032] As a result of intensive research, the present inventors have achieved adjustment of the peak wavelength of light emission and high device efficiency by introducing substituents. Specifically, it has been found that a polycyclic aromatic compound represented by formula (1) in which a specific ring has an aromatic ring having a substituent in a skeleton similar to the above dimer compound gives a light emission spectrum with high color purity. The present inventors have also found that the polycyclic aromatic compound represented by formula (1) exhibits green light emission. It is considered that the light emission spectrum with high color purity was realized because the introduction of substituents reduced the ratio of the structure existing on the same plane in the whole molecule, thereby reducing intermolecular stacking. However, the effect of the polycyclic aromatic compound of the present invention is not restricted by the above principle. The polycyclic aromatic compound represented by formula (1) is preferably a polycyclic aromatic compound represented by the following formula (2).

[0033]

Chemical formula

[0034] Ring A and ring C in formula (1) are each independently an aryl ring having a substituent or a heteroaryl ring having a substituent. Ring B and ring D are each independently an aryl ring which may have a substituent or a heteroaryl ring which may have a substituent. The substituents on ring A and ring C and on ring B and ring D are preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (the two aryls may be bonded), substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, alkyl-substituted silyl, cyano, or halogen. Examples of the substituents when these groups have substituents include aryl, heteroaryl or alkyl.

[0035] Furthermore, rings A and B are "B (boron)" and "X 1 " and "X 2 Formula (1) consists of the fused biring structure on the left and has a 5-membered or 6-membered ring that shares a bond with the C ring and D ring, and the C ring and D ring are "B (boron)" and "X 3 " and "X 4 Formula (1) is composed of the above, and it is preferable that it has a 5-membered ring or a 6-membered ring that shares a bond with the condensed two-ring structure on the right.

[0036] Here, the "condensed two-ring structure" refers to the left-hand part of equation (1) where "B (boron)" and "X" are located. 1 " and "X 2 This refers to a structure formed by the condensation of two saturated hydrocarbon rings, including the 'A' ring. The same applies to the condensed biring structure in the right-hand part of formula (1). Furthermore, 'a six-membered ring sharing a bond with a condensed biring structure' means, for example, an a-ring (benzene ring (six-membered ring)) condensed into a condensed biring structure, as shown in formula (2) above. Also, 'an aryl ring or heteroaryl ring (which is the A ring) has this six-membered ring' means that the A ring is formed by this six-membered ring alone, or that other rings are further condensed onto this six-membered ring to form the A ring. In other words, 'an aryl ring or heteroaryl ring (which is the A ring) having a six-membered ring' here means that a six-membered ring constituting all or part of the A ring is condensed into a condensed biring structure. The same explanation applies to 'B ring (b-ring)', 'C ring (c-ring)', 'D ring (d-ring)', and 'five-membered ring'.

[0037] In formula (1), the A ring and the C ring are each independently a substituted aryl ring or a substituted heteroaryl ring. The number of substituents is not particularly limited and can be any number possible depending on the type of aryl ring or heteroaryl ring, but it is preferable to have one substituent. The one substituent may recombine with the ring to which it is attached to form another ring. In this specification, the one substituent in the A ring is referred to as Z 1 , one substituent in ring A is Z 2 That happens.

[0038] In other words, ring A has one substituent Z 1 An aryl ring having one substituent Z 1 A heteroaryl ring having one substituent Z 1 An aryl ring having one substituent Z 1 Z in a heteroaryl ring having 1 Z is formed by a single bond or linking group. 1 It is preferable that the C ring has a structure bonded to an aryl ring or heteroaryl ring. 2 An aryl ring having one substituent Z 2 A heteroaryl ring having one substituent Z 2 An aryl ring having one substituent Z 2 Z in a heteroaryl ring having 2 Z is formed by a single bond or linking group. 2 It is preferable that the structure is bonded to an aryl ring or heteroaryl ring to which the compound is bonded. It is more preferable that both the A ring and the C ring are in one of the preferred embodiments. Preferred bonding positions for substituents will be discussed later.

[0039] In formula (1), the A ring (or B ring, C ring, D ring) corresponds to the a ring and its substituent Z in formula (2). 1 , R 3 and R 4 (or the b-ring and its substituent R) 5 ~R 7 , the c ring and its substituent Z 2 ,R 8 and R 9 , the d-ring and its substituent R 10 ~R 12 This corresponds to equation (2). In other words, equation (2) corresponds to the equation in equation (1) in which "rings A to D having 6-membered rings" are selected as rings A to D. For this reason, each ring in equation (2) is represented by lowercase letters a to d.

[0040] R in equation (2) 3 , R 4 , R 5 , R 6, R 7 , R 8 , R 9 , R 10 , R 11 and R 12 Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, alkyl-substituted silyl, cyano, or halogen. In this case, at least one hydrogen in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, or alkyl-substituted silyl may be substituted with aryl, heteroaryl, alkyl, cyano, or halogen.

[0041] In equation (2), the substituent R of the b ring 5 ~R 7 and / or substituent R of the d-ring 10 ~R 12Adjacent groups among them may bond to each other to form an aryl ring or heteroaryl ring together with the b ring and / or d ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, alkyl-substituted silyl, cyano, or halogen. At least one hydrogen in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, or heteroarylthio may be substituted with aryl, heteroaryl, alkyl, cyano, or halogen. Therefore, the ring structure of the compound represented by formula (2) changes depending on the bonding configuration of the substituents in the b ring and d ring, as shown in formula (2-1) below. The B' ring and D' ring in formula (2-1) correspond to the B ring and D ring in formula (1), respectively. Also, the definition of each sign in formula (2-1) is the same as the sign in formula (2).

[0042] [ka]

[0043] The B' and D' rings in formula (2-1) are, as explained in formula (2), substituent R 5 ~R 7 and R 10 ~R 12 Adjacent groups among them bond together, forming aryl rings or heteroaryl rings with the b-ring and d-ring, respectively (they can also be described as fused rings formed by the fusion of other ring structures with the b-ring or d-ring). Also, as can be seen from formula (2-1), the R of the b-ring 7 and the R of the d ring 12 These do not fall under the category of "adjacent groups," and therefore they do not bond. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring. Note that Z 1Z may be bonded to the A ring (a ring) by a linking group or a single bond, and Z 2 The C ring (c ring) may be bonded to the C ring (or C ring) by a linking group or a single bond, and if bonded, the ring structure will change in the same way as the B' ring and D' ring described above.

[0044] For example, a compound having a B' ring (or D' ring) formed by the condensation of a benzene ring (or B ring) with a benzene ring, an indan ring (including dimethyl-substituted compounds), an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, a cyclopentane ring, or a cyclohexane ring, where the resulting condensed ring B' (or D') is a naphthalene ring, a fluorene ring (including dimethyl-substituted compounds), a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a dihydroindene ring, or a tetrahydronaphthalene ring, respectively.

[0045] X in equations (1) and (2) 1 , X 2 , X 3 and X 4 Each of these is independently >O, >NR, >CR2, >S, or >Se. The R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, or optionally substituted alkyl, and the R in >NR may be bonded to the A, B, C, and / or D rings by a linking group or a single bond. The R in >CR2 is hydrogen, an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl, or optionally substituted alkyl, and the R in >CR2 may be bonded to the A, B, C, and / or D rings by a linking group or a single bond.

[0046] X 1 , X 2 , X 3 and X 4Each of these is preferably >O or >NR independently, more preferably at least one is >NR and the others are >O, and even more preferably all are >NR.

[0047] X 1 , X 2 , X 3 and X 4 In >NR, R is preferably an optionally substituted aryl or optionally substituted cycloalkyl, more preferably an optionally substituted phenyl, even more preferably an optionally substituted phenyl with a C1-C6 alkyl group, even more preferably an unsubstituted phenyl or a phenyl in which at least one meta position or at least one ortho position is substituted with a C1-C4 alkyl group, and particularly preferably an unsubstituted phenyl or a phenyl in which two meta positions are substituted with methyl groups.

[0048] When the R in NR and the R in CR2 are bonded to the A, B, C, and / or D rings, respectively, the linking groups are preferably -O-, -S-, -C(-R)2-, or boron, as described later. The R in "-C(-R)2-" is hydrogen or alkyl. Examples of alkyl groups described later are given below. C1-C6 alkyl groups, and even more preferably C1-C4 alkyl groups (e.g., methyl, ethyl, etc.), are preferred.

[0049] Here, the provision in formula (1) that "R in >NR is bonded to the A, B, C, and / or D rings by a linking group or a single bond" corresponds to the provision in formula (2) that "R in >NR is bonded to the a, b, c, and / or d rings by a linking group or a single bond."

[0050] This provision is represented by the following formula (2-3), X 1 Ya X 3 This can be represented by compounds having a ring structure in which X is incorporated into fused rings B' and D'. That is, for example, for the benzene ring which is the b ring (or d ring) in formula (2), X1 (or X 3 ) is a compound having a B' ring (or D' ring) formed by the condensation of other rings so as to incorporate it. The formed condensed ring B' (or condensed ring D') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, an acridine ring, or the like. These rings may have substituents. Examples of the substituents at this time include alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), cyano, or halogen. In addition, the definitions of the respective symbols in formula (2-3) are the same as those of the symbols in formula (2).

[0051]

Chemical formula

[0052] In formula (2-3), X 1 and X 3 show the ring structures incorporated into the condensed ring B' and the condensed ring D'. However, R of >N-R as X 2 and X 4 can also be bonded to the a ring and the c ring in the same way, and when bonded, the ring structure will change in the same way as the above B' ring and D' ring.

[0053] In addition, the substitution positions of the substituents Z 1 and Z 2 in formula (2) are limited to the para positions of the positions where boron is bonded in the a ring and the c ring. The A ring and the C ring in formula (1) are not limited to benzene rings, and are various aryl rings and heteroaryl rings. The substitution positions of the substituents on these rings are not limited, but it is preferable to substitute at a position relatively far from the position where boron is bonded, and it is more preferable to substitute at the most distant position. For example, when the A ring is a naphthalene ring, a fluorene ring, or the like, the substituent (Z 1The following are examples of preferred substitution positions for the following structures. The signs in each structure have the same definition as the signs in formula (2). In the following formulas, A is >CR2, >NR2, >O, or >S, and R is hydrogen, alkyl (preferably an alkyl having 1 to 4 carbon atoms), or phenyl.

[0054] [ka]

[0055] R in equation (1) or equation (2) 1 and R 2 Each of these is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (where the aryl group has 6 to 12 carbon atoms), a cyano group, or a halogen group. 1 and R 2 It is preferably hydrogen, methyl, cyano, or halogen, more preferably hydrogen, cyano, or halogen, and even more preferably hydrogen.

[0056] Substituents for the aryl or heteroaryl rings in the A and C rings of formula (1) include optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino (the two aryls may be bonded to each other), optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio, optionally substituted heteroarylthio, cyano, or Halogens are preferred. The following are more preferred substituents on the aryl or heteroaryl rings in the A and C rings of formula (1):

[0057] Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryl; Diarylaminos may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or halogen-substituted (the two aryls may be bonded to each other); Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted diheteroarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylheteroarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or alkyl which may be substituted with halogen; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted cycloalkyl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylthio; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroarylthio; Cyano; or halogen.

[0058] Z in equation (2) 1 and Z 2 Each of these is independently one of the following groups: Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted aryl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted heteroaryl; Diarylaminos which may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen (the two aryls may be bonded to each other); Diheteroarylaminos which may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylheteroarylamino; Aryl, heteroaryl, alkyl-substituted silyl, cyano, or halogen-substituted alkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted cycloalkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryloxy; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryloxy; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylthio; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroarylthio; Cyano; or halogen.

[0059] Z 1 or Z 2 The two aryl groups in the diarylamino may be bonded to each other. In this case, the two aryl groups in the diarylamino may be bonded together, for example, with a >SiR2, >CR2 (where R is hydrogen and alkyl (preferably an alkyl group having 1 to 4 carbon atoms)) as a linking group.

[0060] In equation (2), Z 1 R 3 and / or R 4 It may also be bonded to form a ring, in which case R 3 and / or R 4 This may represent boron. Also, Z 2 R 8 and / or R 9 It may also be bonded to form a ring, in which case R 8 and / or R 9 This may represent boron.

[0061] Z in equation (1) or equation (2) 1 and Z 2For aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, aryloxy, heteroaryloxy, arylthio, heteroarylthio, cyano, or halogen, and for aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or halogen as substituents thereon, refer to the descriptions of "aryl," "heteroaryl," "diarylamino," "diheteroarylamino," "arylheteroarylamino," "aryloxy," "heteroaryloxy," "arylthio," "heteroarylthio," "alkyl," "cycloalkyl," "alkoxy," "alkyl-substituted silyl," or "halogen" below. 1 and Z 2 Preferably, these are diarylamino, alkyl, cycloalkyl, aryloxy, heteroaryl such as N-carbazolyl, or halogen. Z 1 and Z 2 These may be the same or different, but from the viewpoint of ease of synthesis, they are preferably the same.

[0062] Examples of "aryl rings" which are rings A, B, C, and D in formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. Note that this "aryl ring" is defined as "R" in formula (2). 5 ~R 7 and R 10 ~R 12 This corresponds to an aryl ring formed by the bonding of adjacent groups together with the b-ring and / or d-ring, and since the b-ring (or d-ring) is already composed of a benzene ring with 6 carbon atoms, the lower limit of carbon numbers is 9, which is the total number of carbon atoms in the fused ring formed by the fusion of a 5-membered ring with it. Also, Z 1 An aryl ring formed by a linking group or single bond with the A ring (a ring), or Z 2The same applies to aryl rings formed by a linking group or single bond connecting to a C ring (c ring).

[0063] Specific examples of "aryl rings" include the monocyclic benzene ring, the bicyclic biphenyl ring, the condensed bicyclic naphthalene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, the condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, and the condensed pentacyclic perylene ring, pentacene ring, etc.

[0064] Examples of heteroaryl rings, which are rings A, B, C, and D in formula (1), include heteroaryl rings having 2 to 30 carbon atoms, with heteroaryl rings having 2 to 25 carbon atoms being preferred, heteroaryl rings having 2 to 20 carbon atoms being more preferred, heteroaryl rings having 2 to 15 carbon atoms being even more preferred, and heteroaryl rings having 2 to 10 carbon atoms being particularly preferred. Furthermore, examples of heteroaryl rings include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. Note that this heteroaryl ring is defined as "R" in formula (2). 5 ~R 7 and R 10 ~R 12 This corresponds to a heteroaryl ring formed by the bonding of adjacent groups with the b-ring and / or d-ring, and since the b-ring (or d-ring) is already composed of a benzene ring with 6 carbon atoms, the lower limit of carbon numbers is 6 for the fused ring formed by the fusion of this ring and a 5-membered ring. 1 A heteroaryl ring or Z is formed when it is bonded to the A ring (a ring) by a linking group or single bond. 2 The same applies to heteroaryl rings formed by a linking group or single bond connecting to a C ring (c ring).

[0065] Specific examples of "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, and 1H-benzo Examples include triazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, quinoxaline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, indoridine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazan rings, and thiantrene rings.

[0066] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted or unsubstituted "heteroaryloxy", a substituted or unsubstituted "arylthio", a substituted or unsubstituted "heteroarylthio", an alkyl-substituted silyl, a cyano, or a halogen. In particular, the "aryl ring" or "heteroaryl ring" in ring A and ring C is substituted with any of the above. Examples of the monovalent groups of the aforementioned "aryl ring" or "heteroaryl ring" as this first substituent include the aryl group of "aryl," the aryl group of "diarylamino," the heteroaryl group of "diheteroarylamino," the aryl group of "arylheteroarylamino," the aryl group of "aryloxy," the heteroaryl group of "heteroaryloxy," the aryl group of "arylthio," and the heteroaryl group of "heteroarylthio."

[0067] Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenyl, condensed bicyclic naphthyl (1-naphthyl or 2-naphthyl), tricyclic terpheniryl (m-terpheniryl, o-terpheniryl or p-terpheniryl), condensed tricyclic acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic perilenyl, pentacenyl, etc.

[0068] Examples of the "heteroaryl" (first substituent) include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Examples of the "heteroaryl" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0069] Specific examples of "heteroaryls" include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, Examples include synnorinyl, quinazolinil, quinoxalinil, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxadinyl, phenothiazinyl, phenadinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphtobenzofuranil, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphtobenzothienyl, flazanil, and thianthrenyl.

[0070] Furthermore, the "alkyl" as the first substituent may be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A alkyl having 1 to 18 carbon atoms (a branched alkyl having 3 to 18 carbon atoms) is preferred, a alkyl having 1 to 12 carbon atoms (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a alkyl having 1 to 6 carbon atoms (a branched alkyl having 3 to 6 carbon atoms) is even more preferred, and a alkyl having 1 to 4 carbon atoms (a branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0071] Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples include -ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0072] Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0073] Examples of the "cycloalkyl" as the first substituent include cycloalkyls having 3 to 12 carbon atoms. Preferred cycloalkyls are those having 3 to 10 carbon atoms. More preferred cycloalkyls are those having 3 to 8 carbon atoms. Even more preferred cycloalkyls are those having 3 to 6 carbon atoms.

[0074] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 5 carbon atoms, as well as norbornel, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazlenyl.

[0075] Examples of the first substituent, "alkoxy," include linear alkoxys with 1 to 24 carbon atoms or branched alkoxys with 3 to 24 carbon atoms. Alkoxys with 1 to 18 carbon atoms (branched alkoxys with 3 to 18 carbon atoms) are preferred, alkoxys with 1 to 12 carbon atoms (branched alkoxys with 3 to 12 carbon atoms) are more preferred, alkoxys with 1 to 6 carbon atoms (branched alkoxys with 3 to 6 carbon atoms) are even more preferred, and alkoxys with 1 to 4 carbon atoms (branched alkoxys with 3 to 4 carbon atoms) are particularly preferred.

[0076] Specific examples of alkoxys include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0077] As the first substituent, trialkylsilyl is preferred. For the alkyl to be substituted, refer to the description of the first substituent, "alkyl," above. Preferred alkyls for substitution are C1 to C5 alkyls, specifically methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0078] Specific examples of trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, buty Examples include diethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0079] Examples of halogens as the first substituent include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I). Preferably, fluorine, chlorine, or bromine, more preferably chlorine.

[0080] The first substituents, which are substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "heteroaryloxy", substituted or unsubstituted "arylthio", and substituted or unsubstituted "heteroarylthio", may have at least one hydrogen substituted with the second substituent, as described as substituted or unsubstituted. Examples of this second substituent include aryl, heteroaryl, alkyl, cyano, or halogen, and specific examples thereof can be found in the descriptions of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" and "halogen" as first substituents described above. Furthermore, aryl and heteroaryl groups as second substituents also include groups in which at least one hydrogen atom is substituted with an aryl group such as phenyl (specific examples are the groups mentioned above), an alkyl group such as methyl (specific examples are the groups mentioned above), a cyano group, or a halogen group. For example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is substituted with an aryl group such as phenyl or an alkyl group such as methyl is also included as a heteroaryl group as a second substituent.

[0081] R in equation (2) 3 ~R 12 In this context, aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of aryloxy, heteroaryloxy, aryl of arylthio, and heteroarylthio include the monovalent groups of the "aryl ring" or "heteroaryl ring" described in formula (1). Also, R 3 ~R 12For alkyl, cycloalkyl, alkoxy, alkyl-substituted silyl, or halogen in formula (1) above, refer to the descriptions of "alkyl," "cycloalkyl," "alkoxy," "alkyl-substituted silyl," or "halogen" as the first substituent in the description of formula (1) above. Furthermore, the same applies to aryl, heteroaryl, or alkyl as substituents to these groups. 5 ~R 7 and R 10 ~R 12 The same applies to substituents on rings when adjacent groups among them are bonded together with the b-ring or d-ring to form an aryl ring or heteroaryl ring, such as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, alkyl-substituted silyl, cyano, or halogen, and further substituents such as aryl, heteroaryl, alkyl, cyano, or halogen.

[0082] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the structure of the first substituent. Substituents of aryl rings or heteroaryl rings in rings A, B, C, and D (Z 1 and Z 2Preferred specific examples of (including) include the group represented by the following structural formula, cyano and halogen. More preferably are methyl, t-butyl, t-pentyl(t-amyl), phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and even more preferably methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and chlorine. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis. Specifically, t-butyl, t-pentyl(t-amyl), o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and chlorine are preferred.

[0083] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bond position. [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] [ka]

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[0096] In the aryl or heteroaryl rings in rings A and C of formula (1), Z 1 and Z 2 Each of these is independently one of the preferred substituents described above, and Z1 and Z 2 It is preferable that it does not have substituents other than R in formula (2). For example, R 3 , R 4 , R 8 , and R 9 Preferably, all of these are hydrogen. Z 1 and Z 2 The substituents may be the same or different, but it is preferable that they be the same from the viewpoint of facilitating synthesis.

[0097] In formula (1), it is preferable that the aryl ring or heteroaryl ring in the B ring and D ring each have one substituent or no substituent. Preferred substituents are alkyl groups having 1 to 6 carbon atoms, and more preferably methyl or t-butyl. For example, in formula (2), R 5 , R 7 , R 10 , R 12 Both are hydrogen, and R 6 and R 11 It is preferable that each of these is independently methyl or t-butyl.

[0098] X in equation (1) 1 , X 2 , X 3 and X 4 In >NR, R is an aryl, heteroaryl, cycloalkyl, or alkyl group, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, alkyl-substituted silyl, cyano, or halogen. Examples of these groups and their substituents are given above. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl), and alkyl groups with 1 to 4 carbon atoms (e.g., methyl, ethyl). This explanation is based on X in formula (2). 1 , X2 , X 3 and X 4 But it's the same.

[0099] X in equation (1) 1 , X 2 , X 3 and X 4 In formula (2), R in >CR2 is hydrogen, aryl, heteroaryl, cycloalkyl, or alkyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio, alkyl-substituted silyl, cyano, or halogen. Examples of these groups and the substituents that substitute for them are listed above. C1-C4 alkyls (e.g., methyl, ethyl, etc.) are particularly preferred. This explanation is for X in formula (2). 1 , X 2 , X 3 and X 4 But it's the same.

[0100] R in equation (1) or equation (2) 1 and R 2 For a more detailed explanation of alkyls with 1 to 6 carbon atoms, aryls with 6 to 12 carbon atoms, heteroaryls or diarylaminos with 2 to 15 carbon atoms (where aryl refers to aryls with 6 to 12 carbon atoms), please refer to the above-mentioned explanations of "alkyl," "aryl," "heteroaryl," or "diarylamino."

[0101] At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (1) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0102] Examples of "cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0103] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0104] Among these, a structure in which at least one hydrogen is substituted at the α-carbon of the cycloalkane (in a cycloalkyl condensed to an aryl ring or heteroaryl ring, the carbon adjacent to the carbon at the condensation site) is preferred, a structure in which two hydrogens are substituted at the α-carbon is more preferred, and a structure in which a total of four hydrogens are substituted at two α-carbons is even more preferred. Examples of substituents include alkyl (especially methyl) substituted compounds having 1 to 5 carbon atoms, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. In particular, a structure in which a substructure represented by the following formula (B10) or formula (B11) is bonded to an adjacent carbon atom in an aryl ring or heteroaryl ring is preferred.

[0105] [ka] In the formula, Me represents a methyl group, and * indicates the bond position.

[0106] Furthermore, all or part of the hydrogen atoms in the compound represented by formula (1) or (2) may be substituted with deuterium. For example, in formula (1), ring A, ring B, ring C, ring D (rings A to D are aryl rings or heteroaryl rings), substituents on rings A to D, X 1 ~X 4 In NR, R (=aryl, heteroaryl, alkyl), R 1 , R 2 , Z 1 and Z 2 Hydrogen in these compounds can be substituted with deuterium, and among these, examples include cases in which all or some of the hydrogen in aryl or heteroaryl compounds is substituted with deuterium.

[0107] As described above, X in equation (1) 1 , X 2 , X 3 and X 4 The R in >NR and the R in >CR2 may be linked to the A, B, C, and / or D rings by a linking group or a single bond, and the linking group in this case may be the same as the linking group to which the substituents in the A, B, C, and / or D rings are linked to the aryl or heteroaryl ring. Boron is an example of such a linking group, and for example, the following configuration can be seen in formula (2). (1)Z 1 is X 1 R is B (boron) along with R of NR as >NR 4 It is bonded to the a-ring via: (2)Z 2 is X 3 R is B (boron) along with R of NR as >NR 9 It is bonded to the c ring via a rifle. (3)Z 1 is X 2 R is B (boron) along with R of NR as >NR 3 It is bonded to the α ring via [a]. (4)Z 2 is X 4 R is B (boron) along with R of NR as >NR 8 It is bonded to the c-ring via a rifle.

[0108] Examples of structures that satisfy any of the above conditions (1) to (4) include compounds represented by any of the following formulas: (1-X-1), (1-X-2), (1-X-3), and (1-X-4). Formula (1-X-1) satisfies (1) and (2) above, formula (1-X-2) satisfies (1) and (4) above, formula (1-X-3) satisfies (3) and (2) above, and formula (1-X-4) satisfies (3) and (4) above.

[0109] [ka]

[0110] Other specific examples of polycyclic aromatic compounds represented by formula (1) include, for example, the compounds represented by the following formula. In the following formula, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium.

[0111] [ka]

[0112] [ka]

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[0146] 2. Method for producing polycyclic aromatic compounds Polycyclic aromatic compounds represented by formula (1), preferably formula (2), can basically be processed by first bonding the ring structures together to produce an intermediate (first reaction), and then by bonding the ring structures together with boron atoms to produce the final product (second reaction). In the first reaction, common etherification reactions such as nucleophilic substitution reactions and Ullmann reactions, or common amination reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (a series of electrophilic aromatic substitution reactions, the same applies below) can be used. The signs in the structural formulas in each of the following schemes have the same definition as those in formula (1) or formula (2).

[0147] The second reaction is a reaction that introduces boron atoms to bond each ring structure, as shown in scheme (1) below. First, X 1 and X 2 between and X 3 and X 4 The hydrogen atoms between the two atoms are orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium. Then, boron trichloride or boron tribromide is added to perform a lithium-boron metal exchange, and a Brønsted base such as N,N-diisopropylethylamine is added to carry out a tandem bora-Friedel-Crafts reaction to obtain the desired product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction.

[0148] [ka]

[0149] In scheme (1), lithium was introduced to the desired position by orthometallation. However, as shown in scheme (2) below, a halogen atom (Hal) can be introduced beforehand at the position where lithium is to be introduced, and then lithium can be introduced to the desired position by halogen-metal exchange. This method is useful because it allows the synthesis of the target product even in cases where orthometallation is not possible due to the influence of substituents.

[0150] [ka]

[0151] By appropriately selecting the above synthesis method and the raw materials used, it is possible to obtain X with substituents at the desired positions. 1 , X 2 , X 3 and X 4 However, each of these can be used independently to synthesize polycyclic aromatic compounds that are >O, >NR, >CR2, >S, or >Se.

[0152] Furthermore, because the location of the tandem Bora-Friedel-Crafts reaction may differ depending on the rotation of, for example, an amino acid in the intermediate, by-products may be generated. In such cases, the target polycyclic aromatic compound can be isolated from these mixtures by chromatography, recrystallization, or other methods.

[0153] Examples of orthometalation reagents used in the above scheme include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, as well as organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0154] Examples of metal-boron metal exchange reagents used in the above scheme include boron halides such as boron trifluoride, trichloride, tribromide, and triiodide, boron amination halides such as CIPN(NEt2)2, boron alkoxyides, and boron aryl oxyides.

[0155] Examples of Brønsted bases used in the above scheme include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (where Ar is an aryl such as phenyl).

[0156] Examples of Lewis acids used in the above scheme include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0157] In the above scheme, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, when boron halides such as boron trifluoride, trichloride, tribromide, and triiodide are used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction progresses, so the use of a Brønsted base to capture the acids is effective. On the other hand, when boron amination halides or boron alkoxyides are used, amines and alcohols are generated as the aromatic electrophilic substitution reaction progresses, so in most cases, it is not necessary to use a Brønsted base. However, because the leaving ability of aminos and alkoxys is low, the use of a Lewis acid to promote their elimination is effective.

[0158] Polycyclic aromatic compounds represented by formula (1), which have a cyano or halogen in their structure, can be synthesized in the same manner as described above by using starting materials in which the desired sites are cyanated, halogenated, or deuterated. Furthermore, compounds in which at least some hydrogen atoms are substituted with deuterium can be synthesized in the same manner as described above by using starting materials in which the desired sites are deuterated.

[0159] 3. Organic devices The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells.

[0160] 3-1. Organic electroluminescent element The polycyclic aromatic compounds according to the present invention can be used, for example, as materials for organic electroluminescent devices. Below, an organic EL element according to this embodiment will be described in detail with reference to the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

[0161] <Structure of Organic Field-Emitting Light> The organic electroluminescent element 100 shown in Figure 1 comprises a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0162] The organic electroluminescent element 100 may also be configured by reversing the manufacturing order, for example, by having a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0163] Not all of the above layers are necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0164] In addition to the above-mentioned configurations of "substrate / anodote / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", other configurations of layers constituting an organic electroluminescent element include "substrate / anodote / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodote / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodote / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anodote / hole injection layer / hole transport layer / emissive layer / electron The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

[0165] <Substrates for organic electroluminescent devices> The substrate 101 is a support for the organic electroluminescent element 100, and is typically made of quartz, glass, metal, or plastic. The substrate 101 is formed in the form of a plate, film, or sheet depending on the purpose, and can be made of glass, metal, metal foil, plastic film, or plastic sheet, for example. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a dense gas barrier film, such as a silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0166] <Anode in an organic electroluminescent element> The anode 102 plays the role of injecting holes into the light-emitting layer 105. If a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes will be injected into the light-emitting layer 105 via these layers.

[0167] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and NESA glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline. In addition, other materials used as anodes in organic electroluminescent devices can be appropriately selected and used.

[0168] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0169] <Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 plays the role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays the role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0170] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0171] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in the hole injection layer and hole transport layer of organic electroluminescent devices.

[0172] Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), and triarylamine derivatives (polymers having aromatic tertiary amino acids in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’Triphenylamine derivatives such as -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc., stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples include conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the monomers in their side chains are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for fabricating a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0173] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes through an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD), starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175). Alternatively, conductive polymers known as PEDOT / PSS, as shown in the examples, may be used as hole injection and transport materials.

[0174] Crosslinkable polymer materials: Compounds represented by formula (XLP-1) The hole injection layer and hole transport layer may also preferably contain a compound represented by formula (XLP-1). Note that the compound represented by formula (XLP-1) may also be included in other organic layers in the organic electroluminescent device. In particular, when the organic layer is formed by a wet deposition method of the organic layer-forming composition, it is preferable that the organic layer-forming composition contains a compound represented by formula (XLP-1).

[0175] [ka] In equation (XLP-1), Each MUx is a divalent group obtained by removing two hydrogen atoms from either the above-mentioned MU or an aromatic compound having a crosslinking substituent (PG), and each ECx is a monovalent group obtained by removing one hydrogen atom from either the above-mentioned EC or an aromatic compound having a crosslinking substituent (PG), provided that the content of the monovalent and divalent aromatic compounds having a crosslinking substituent (PG) is 0.1 to 80 wt% in the molecule, and k is an integer from 2 to 50000.

[0176] More specifically, The divalent groups obtained by removing any two hydrogens from the aromatic compound having a crosslinkable substituent (PG) in MUx are, independently, arylene, heteroarylene, dialylenearylamino, dialylenearylboryl, oxavorin-diyl, or azavorin-diyl, and at least one hydrogen in these divalent groups is substituted with a crosslinkable substituent (PG), and at least one hydrogen in these divalent groups may be further substituted with one or more substituents selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl. If there are two or more crosslinkable substituents (PG) in MUx, they may be the same or different, but it is preferable that they be the same.

[0177] The monovalent groups obtained by removing one hydrogen from any of the aromatic compounds having a crosslinkable substituent (PG) in ECx are, independently, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, where at least one hydrogen in these monovalent groups is substituted with a crosslinkable substituent (PG), and at least one hydrogen in these monovalent groups may be further substituted with one or more substituents selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl. If there are two or more crosslinkable substituents (PG) in ECx, they may be the same or different, but it is preferable that they be the same.

[0178] The content of divalent groups obtained by removing any two hydrogen atoms from an aromatic compound having a crosslinkable substituent (PG), and monovalent groups obtained by removing any one hydrogen atom from an aromatic compound, is 0.1 to 80 wt% of the molecule, preferably 0.5 to 50 wt%, and more preferably 1 to 20 wt%.

[0179] k is an integer between 2 and 50000, preferably between 20 and 50000, and more preferably between 100 and 50000. If k MUx consist of two or more divalent groups, these groups may be randomly bonded or identical divalent groups may form blocks, but the latter is preferred.

[0180] Examples of crosslinkable substituents (PGs) include monovalent groups in which a monovalent crosslinkable substructure, represented by the following formulas (PG-1) to (PG-18), is bonded to L in a divalent substructure.

[0181] [ka]

[0182] In the above formulas (PG-1) to (PG-18), R PG n represents a methylene atom, an oxygen atom, or a sulfur atom. PG This represents integers from 0 to 5, and R PG If there are multiple instances, they may be the same or different, n PG If multiple such groups exist, they may be identical or different, *G represents the bonding position (bonding position with L), and each of the bridging groups represented by the formula may have substituents. Examples of L in the above-mentioned divalent substructure of the crosslinkable substituent (PG) include single bonds, -O-, >C=O, -OC(=O)-, alkylenes having 1 to 12 carbon atoms, oxyalkylenes having 1 to 12 carbon atoms, and polyoxyalkylenes having 1 to 12 carbon atoms. Preferred crosslinkable substituents (PG) are formulas (PG-1), (PG-2), (PG-3), (PG-9), (PG-10), or (PG-18), with formulas (PG-1), (PG-3), or (PG-18) being more preferred.

[0183] If multiple crosslinkable substituents (PGs) are present in formula (XLP-1), they may be identical or different. Examples of divalent groups obtained by removing any two hydrogen atoms from an aromatic compound having a crosslinkable substituent (PG) include the following divalent groups:

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] <Emitting layer in organic electroluminescent element> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 can be any compound that emits light when excited by the recombination of holes and electrons (luminescent compound), and it is preferable that the compound can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. In the present invention, it is preferable to use a polycyclic aromatic compound represented by the above formula (1) as the material for the light-emitting layer.

[0188] The light-emitting layer may consist of a single layer or multiple layers, each formed from a light-emitting layer material (host material, dopant material). The host material and dopant material may each be of one type or a combination of multiple types. The dopant material may be contained throughout the host material or partially contained within it. As for doping methods, it can be formed by co-evaporation with the host material, but it may also be pre-mixed with the host material and then deposited simultaneously, or pre-mixed with an organic solvent and the host material and then deposited by a wet deposition method.

[0189] The amount of host material used varies depending on the type of host material and should be determined according to the characteristics of that host material. The guideline for the amount of host material used is preferably 50 to 99.999% by mass of the total material for the light-emitting layer, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass.

[0190] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant used is preferably 0.001 to 50% by mass of the total material for the light-emitting layer, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0191] On the other hand, in organic electroluminescent devices using thermally activated delayed fluorescence dopant materials, a lower concentration of dopant material is preferable in that it can prevent concentration quenching, but a higher concentration of dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in organic electroluminescent devices using thermally activated delayed fluorescence assisting dopant materials, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant material, it is preferable that the amount of dopant material (emittering dopant) used is lower than the amount of assisting dopant material used.

[0192] When assisting dopant materials are used, the approximate amounts of host material, assisting dopant material, and dopant material used are 40-99.999% by mass, 59-1% by mass, and 20-0.001% by mass, respectively, preferably 60-99.99% by mass, 39-5% by mass, and 10-0.01% by mass, respectively, and more preferably 70-99.95% by mass, 29-10% by mass, and 5-0.05% by mass. The compounds and polymer compounds according to the present invention can also be used as assisting dopant materials.

[0193] [Host Materials] Examples of host materials include condensed ring derivatives such as anthracene and pyrene, which have been known as light-emitting materials for some time; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; and benzofluorene derivatives.

[0194] From the viewpoint of promoting rather than inhibiting the generation of TADF within the light-emitting layer, the T1 energy of the host material is preferably higher than the T1 energy of the dopant or assist dopant having the highest T1 energy in the light-emitting layer. Specifically, the T1 energy of the host is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. In addition, a TADF-active compound may be used as the host material.

[0195] Examples of host materials include compounds represented by the following formulas (3), (4), or (5). [ka]

[0196] In formula (3), L 1The group is an arylene having 6 to 24 carbon atoms, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms. Specifically, examples include divalent groups such as benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, triphenylene rings, pyrene rings, naphthacene rings, perylene rings, and pentacene rings.

[0197] In formula (4), L 2 and L 3Each of these is independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. Preferably, the aryl group has 6 to 24 carbon atoms, more preferably aryl groups having 6 to 16 carbon atoms, even more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms. Specifically, examples include monovalent groups such as benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, triphenylene rings, pyrene rings, naphthacene rings, perylene rings, and pentacene rings. As for heteroaryls, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. Specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzo Examples of monovalent groups include the imidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indidine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, and thiantrene ring.

[0198] In formula (5), L 4 , L 5 and L 6Each of these is independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. Preferably, the aryl group has 6 to 24 carbon atoms, more preferably aryl groups having 6 to 16 carbon atoms, even more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms. Specifically, examples include monovalent groups such as benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, triphenylene rings, pyrene rings, naphthacene rings, perylene rings, and pentacene rings. As for heteroaryls, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. Specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzo Examples of monovalent groups include the imidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indidine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, and thiantrene ring.

[0199] At least one hydrogen atom in the compound represented by formula (3), formula (4), or formula (5) may be substituted with an alkyl, cyano, halogen, or deuterium atom having 1 to 6 carbon atoms.

[0200] As the host compound, it is preferable to use a compound having at least one structure selected from the substructure (HA) group represented by the following formulas. This compound may be a compound represented by formula (3), formula (4), or formula (5), or any other compound. At least one hydrogen atom in each structure in the substructure (HA) group may be substituted with any structure in the substructure (HA) group or the substructure (HB) group, and at least one hydrogen in these structures may be substituted with deuterium, halogen, cyano, C1-C4 alkyl (e.g., methyl or t-butyl), trimethylsilyl, or phenyl.

[0201] [ka]

[0202] [ka]

[0203] The host compound is preferably a compound represented by any of the structural formulas listed below, more preferably a compound having 1 to 3 structures selected from the above substructure (HA) group and 1 structure selected from the above substructure (HB) group, even more preferably a compound having carbazole as part of the above substructure (HA) group, and particularly preferably a compound represented by the following formulas (3-201), (3-202), (3-203), (3-204), (3-212), (3-221), (3-222), (3-261), or (3-262). In the structural formulas listed below, at least one hydrogen atom may be substituted with a halogen, cyano, a C1-C4 alkyl (e.g., methyl or t-butyl), phenyl, or naphthyl. In the following formulas, Me represents methyl.

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] [ka]

[0209] The following polymer host materials can also be used as host materials. [ka] In formula (SPH-1), each MU is independently selected from the group consisting of divalent groups of compounds represented by formulas (B-1) to (B-4), where two hydrogens in MU are substituted with EC or MU, and each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, where at least one hydrogen may be further substituted with aryl, heteroaryl, or diarylamino, and k is an integer from 2 to 50000. k is preferably an integer from 100 to 40000, and more preferably an integer from 500 to 25000.

[0210] Here, the compounds represented by formulas (B-1) to (B-4) are the following compounds. [ka]

[0211] In formulas (B-1) to (B-4), Ar is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, or diarylamino. Adjacent groups of Ar may bond together to form an aryl or heteroaryl ring with the parent skeleton of an anthracene ring, pyrene ring, fluorene ring, or carbazole ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy. A specific description of each group can be found by referring to the descriptions of polycyclic aromatic compounds in formulas (1) and (2) above. In each formula, n is an integer from 1 to 6, preferably from 1 to 4, more preferably from 1 to 2, and particularly preferably 1.

[0212] In equations (B-1) to (B-4), specific examples of "Ar" include, for example, the monovalent group in the following structural formulas, or the group in the following combination of structures.

[0213] [ka]

[0214] At least one hydrogen atom in the compounds represented by formulas (B-1) to (B-4) may be substituted with a group represented by formula (FG-1) described later, a group represented by formula (FG-2) described later, or an alkyl group having 1 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-, any -CH2- in the alkyl group other than the -CH2- directly attached to the compounds represented by formulas (B-1) to (B-4) may be substituted with an arylene group having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl group may be substituted with fluorine.

[0215] At least one hydrogen atom in EC in formula (SPH-1) may be substituted with a group represented by the following formula (FG-1), a group represented by the following formula (FG-2), an alkyl group having 1 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-, any -CH2- in the alkyl group other than the -CH2- directly connected to EC in formula (B-6) may be substituted with an arylene group having 6 to 24 carbon atoms, and any hydrogen atom in the alkyl group may be substituted with fluorine.

[0216] [ka]

[0217] (In equation (FG-1), R is independently fluorine, trimethylsilyl, trifluoromethyl, a C1-C24 alkyl group, or a C3-C24 cycloalkyl group, wherein any -CH2- in the alkyl group may be substituted with -O-, any -CH2- in the alkyl group except for those directly bonded to phenyl or phenylene may be substituted with a C6-C24 arylene group, and at least one hydrogen atom in the cycloalkyl group may be substituted with a C1-C24 alkyl group or a C6-C12 aryl group. When two adjacent Rs are alkyl or cycloalkyl, they may be bonded together to form a ring. m is an independent integer between 0 and 4, n is an integer between 0 and 5, p is an integer between 1 and 5, and * indicates the joining position.

[0218] [ka]

[0219] (In equation (FG-2), R is independently fluorine, trimethylsilyl, trifluoromethyl, a C1-C24 alkyl group, a C3-C24 cycloalkyl group, or a C6-C12 aryl group, wherein any -CH2- in the alkyl group may be substituted with -O-, any -CH2- in the alkyl group except for those directly bonded to phenyl or phenylene may be substituted with a C6-C24 arylene group, at least one hydrogen in the cycloalkyl group may be substituted with a C1-C24 alkyl group or a C6-C12 aryl group, and at least one hydrogen in the aryl group may be substituted with a C1-C24 alkyl group. When two adjacent Rs are alkyl or cycloalkyl, they may be bonded together to form a ring. m is an integer between 0 and 4, n are independent integers between 0 and 5, and * indicates the joining position.

[0220] Examples of MU include the divalent groups represented by the following formulas (MU-1-1) to (MU-1-12), (MU-2-1) to (MU-2-202), (MU-3-1) to (MU-3-201), and (MU-4-1) to (MU-4-122). Examples of EC include the groups represented by the following formulas (EC-1) to (EC-29). In these, MU bonds with MU or EC at *, and EC bonds with MU at *.

[0221] Furthermore, from the viewpoint of charge transport, the compound represented by formula (SPH-1) preferably has at least one divalent group represented by formula (B-5-X1) in its molecule, and more preferably has 10% or more of the divalent group represented by formula (B-5-X1) relative to the molecular weight of the compound represented by formula (SPH-1). Here, the divalent group represented by formula (B-5-X1) is bonded to MU or EC at *.

[0222] [ka]

[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] [ka]

[0228] From the viewpoint of solubility and coating film formation properties, the compound represented by formula (SPH-1) preferably has 10 to 100% of the total number of MUs (n) in the molecule being alkyl groups with 1 to 24 carbon atoms, more preferably has 30 to 100% of the total number of MUs (n) in the molecule being alkyl groups with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms), and even more preferably has 50 to 100% of the total number of MUs (n) in the molecule being alkyl groups with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (n) in the molecule be alkyl groups with 7 to 24 carbon atoms, and more preferably has 30 to 100% of the total number of MUs (n) in the molecule being alkyl groups with 7 to 24 carbon atoms (branched alkyl groups with 7 to 24 carbon atoms).

[0229] [TADF material (assisting dopant)] It is also preferable that the light-emitting layer contains TADF material. In this specification, TADF material refers to a material that is a "thermally activated delayed phosphor." In a "thermally activated delayed phosphor," by reducing the energy difference between the excited singlet state and the excited triplet state, the reverse energy transfer from the excited triplet state to the excited singlet state, which normally has a low transition probability, is generated with high efficiency, and emission from the singlet state (thermally activated delayed fluorescence, TADF) is produced. In normal fluorescence emission, 75% of the triplet excitons generated by electric excitation pass through the thermal deactivation pathway and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling the realization of highly efficient organic EL devices.

[0230] Preferably, the TADF material is a donor-acceptor type TADF compound (DA type TADF compound) designed to enable efficient reverse intersystem crossing by localizing the intramolecular HOMO and LUMO using electron-donating substituents called donors and electron-accepting substituents called acceptors.

[0231] Herein, in this specification, "electron-donating substituent" (donor) means substituents and substructures in which the HOMO orbital is localized in the TADF compound molecule, and "electron-accepting substituent" (acceptor) means substituents and substructures in which the LUMO orbital is localized in the TADF compound molecule.

[0232] Generally, TADF compounds using donors and acceptors have large spin-orbit coupling (SOC) and small exchange interaction between the HOMO and LUMO due to their structure, resulting in a ΔE S1T1 Because of its small size, a very fast reverse intersystem crossover rate can be obtained. On the other hand, TADF compounds using donors and acceptors exhibit greater structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when a conversion from the ground state to the excited state occurs due to an external stimulus, the structure subsequently changes to the stable structure in the excited state), resulting in a broad emission spectrum. Therefore, using them as luminescent materials may reduce color purity.

[0233] However, by using the polycyclic aromatic compound of the present invention simultaneously, the polycyclic aromatic compound of the present invention functions as an emitting dopant and the TADF material functions as an assisting dopant, thereby providing high color purity. The TADF material only needs to be a compound whose emission spectrum overlaps at least partially with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound of the present invention and the TADF material may be contained in the same layer or in adjacent layers.

[0234] Examples of TADF materials that can be used for this purpose include compounds represented by the following formula (H7), or compounds having the following formula (H7) as a substructure.

[0235] [ka]

[0236] In formula (H7), ED is an electron-donating group, Ln is a linking group, and EA is an electron-accepting group, and the lowest excited singlet energy level (E) of the compound represented by formula (H7) is S1 ) and the lowest excited triplet energy level (E T1 The energy difference (ΔE) S1T1 The energy difference (ΔE) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). S1T1 The voltage is preferably 0.15 eV or less, more preferably 0.10 eV or less, and even more preferably 0.08 eV or less.

[0237] For electron-donating groups (donor structures) and electron-accepting groups (acceptor structures) used in TADF materials, for example, structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. As for ED, for example, sp 3 Examples of nitrogen-containing functional groups include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(4-(tert-butyl)phenyl)amine, N 1 -(4-(diphenylamino)phenyl)-N 4 ,N 4 Examples of groups derived from -diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazacillin are also included. Furthermore, as EA, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings containing ketones, and cyano compounds, more specifically sulfonyl dibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazaphenalene, thioxanthonedioxy Examples of groups derived from dinitrates, dimethylanthracenone, anthracendione, pyridine, cycloheptabipyridine, benzenetricarbonitrate, fluoroorangecarbonitrate, pyrazinedicarbonitrate, pyridinedicarbonitrate, dibenzoquinoxalinedicarbonitrate, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthenedioxide, thianthurenetetraoxide, and tris(dimethylphenyl)borane are examples. Examples of Ln include single bonds and arylenes, more specifically phenylene, biphenylene, and naphthylene. Furthermore, hydrogen may be substituted with alkyl, cycloalkyl, and aryl groups in any of the structures. In particular, it is preferable that the compound has at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a substructure. In equation (H7), the linking group Ln functions as a spacer structure that separates the donor substructure from the acceptor substructure.

[0238] More specifically, the compound represented by formula (H7) can be any compound represented by formula (H7-1), formula (H7-2), or formula (H7-3). [ka]

[0239] In equations (H7-1), (H7-2), and (H7-3), M is independently a single bond, -O-, >N-Ar, or >C(-Ar)2, and is preferably a single bond, -O-, or >N-Ar in terms of the depth of the HOMO of the substructure formed and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. J is a linking group corresponding to Ln in formula (H7), and each is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation leaching from the donor substructure and the acceptor substructure, arylenes having 6 to 12 carbon atoms are preferred, and more specifically, phenylene, methylphenylene, and dimethylphenylene are examples. Q is independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the formed substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level, it is preferably =N-. Ar is independently hydrogen, a C6-C24 aryl, a C2-C24 heteroaryl, a C1-C12 alkyl, or a C3-C18 cycloalkyl, and from the viewpoint of the depth of the HOMO of the formed substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level, it is preferably hydrogen, a C6-C12 aryl, a C2-C14 heteroaryl, a C1-C4 alkyl, or a C6-C10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazol, di-tert-butylcarbazol, benzimidazole, or phenylbenzimidazole, and even more preferably hydrogen, phenyl, or carbazolyl. m is either 1 or 2. n is an integer between 2 and (6-m), and is preferably an integer between 4 and (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen atom in each of the above formulas may be substituted with a halogen or deuterium.

[0240] Examples of compounds represented by formula (H7) include those represented by any of the following structural formulas. In the structural formulas, * indicates a bond position, "Me" indicates methyl, and "tBu" indicates t-butyl.

[0241] [ka]

[0242] [ka]

[0243] [ka]

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] [ka] TIFF2026071228000097.tif113170

[0250] Among the specific compounds listed above, the compounds represented by formula (H7) are preferably PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz, and in particular PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, and ACRD SO2, DTC-DBT, DTAO, 4CzBN (AD4), 4CzIPN (AD3), PXZ-TRZ (AD5), AD1, AD2, AD6, AD7, and AD8 are preferred.

[0251] [Dopant material] The dopant material is not particularly limited and can be any known compound, and can be selected from a variety of materials depending on the desired emission color.Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. Derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Publication No. 1-245087), bisstyrylarylene derivatives (Japanese Patent Publication No. 2-247278), diazindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran, and other isobenzofuran derivatives. Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. Examples include conductors, fluorescein derivatives, pyririum derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, phlopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives. Alternatively, polycyclic aromatic compounds described in International Publication No. 2015 / 102118, etc., can also be used.

[0252] Examples of dopant materials for each color light include blue to blue-green compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene, aromatic hydrocarbon compounds and their derivatives, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, and pyrrolopy Examples include aromatic heterocyclic compounds such as lysine and thioxanthenes and their derivatives, distylylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and their metal complexes, as well as aromatic amine derivatives represented by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0253] Furthermore, examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. In addition, compounds obtained by introducing substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, into the compounds exemplified above as blue to blue-green dopant materials are also suitable examples.

[0254] Furthermore, examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes with ligands such as acetylacetone or benzoylacetone and phenanthroline, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. In addition, compounds to which substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, are introduced into the compounds exemplified above as blue to blue-green and green to yellow dopant materials are also suitable examples.

[0255] In addition, dopants can be appropriately selected and used from compounds listed on page 13 of the June 2004 issue of Chemical Industry and the references cited therein.

[0256] Among the dopant materials described above, amines, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives having a stilbene structure are particularly preferred.

[0257] Amines having a stilbene structure can be represented, for example, by the following formula. [ka] In the said formula, Ar 1 It is an m-valent group derived from aryls with 6 to 30 carbon atoms, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms, but Ar 1 ~Ar 3 At least one of them has a stilbene structure, Ar1 ~Ar 3 m may be substituted with an aryl, heteroaryl, alkyl, trisubstituted silyl (a silyl trisubstituted with an aryl and / or alkyl) or cyano, and m is an integer from 1 to 4.

[0258] Among amines having a stilbene structure, diaminostilbene represented by the following formula is more preferred. [ka] In the said formula, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms, and Ar 2 and Ar 3 It may be substituted with an aryl, heteroaryl, alkyl, trisubstituted silyl (a silyl trisubstituted with an aryl and / or alkyl) or cyano.

[0259] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0260] Specific examples of amines having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl Examples include nyl-4,4'-diaminostilbene, 4,4'-bis[4”-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, and 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. Alternatively, amines having a stilbene structure as described in Japanese Patent Publication No. 2003-347056 and Japanese Patent Publication No. 2001-307884 may be used.

[0261] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)peryleneyl). Furthermore, perylene derivatives described in Japanese Patent Publication No. 11-97178, Japanese Patent Publication No. 2000-133457, Japanese Patent Publication No. 2000-26324, Japanese Patent Publication No. 2001-267079, Japanese Patent Publication No. 2001-267078, Japanese Patent Publication No. 2001-267076, Japanese Patent Publication No. 2000-34234, Japanese Patent Publication No. 2001-267075, and Japanese Patent Publication No. 2001-217077 may also be used.

[0262] Examples of borane derivatives include 1,8-diphenyl-10-(dimethylboryl)anthracene, 9-phenyl-10-(dimethylboryl)anthracene, 4-(9'-anthryl)dimethylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimethylborylnaphthalene, 9-(dimethylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimethylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimethylboryl)anthracene. Alternatively, borane derivatives described in International Publication No. 2000 / 40586, etc., may be used.

[0263] Aromatic amine derivatives can be represented, for example, by the following formula. [ka] In the said formula, Ar 4 Ar is an n-valent group derived from aryl atoms with 6 to 30 carbon atoms, 5 and Ar 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 n may be substituted with an aryl, heteroaryl, alkyl, trisubstituted silyl (a silyl trisubstituted with an aryl and / or alkyl) or cyano, and n is an integer from 1 to 4.

[0264] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 Aromatic amine derivatives are more preferred, where n may be substituted with an aryl, heteroaryl, alkyl, trisubstituted silyl (trisubstituted silyl with aryl and / or alkyl) or cyano, and n is 2.

[0265] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, and pentacenyl.

[0266] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalene-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl Examples include -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

[0267] Furthermore, pyrene-based compounds include, for example, N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 Examples include -bis-(4-trimethylsilanylphenyl)-1H,8H-pyrene-1,6-diamine.

[0268] Furthermore, anthracene-based compounds include, for example, N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, and N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -Diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine N,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples include anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0269] Other examples include [4-(4-diphenylaminophenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylaminophenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4”-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4”-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl. Alternatively, aromatic amine derivatives described in Japanese Patent Publication No. 2006-156888, etc., may be used.

[0270] Examples of coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, coumarin derivatives described in Japanese Patent Publication No. 2004-43646, Japanese Patent Publication No. 2001-76876, and Japanese Patent Publication No. Hei 6-298758 may also be used.

[0271] Examples of pyran derivatives include DCM and DCJTB, listed below. [ka] Furthermore, pyran derivatives described in Japanese Patent Publication No. 2005-126399, Japanese Patent Publication No. 2005-097283, Japanese Patent Publication No. 2002-234892, Japanese Patent Publication No. 2001-220577, Japanese Patent Publication No. 2001-081090, and Japanese Patent Publication No. 2001-052869 may also be used.

[0272] <Composition for forming a light-emitting layer> The polycyclic aromatic compound represented by formula (1) can also be used as a composition for forming an emissive layer together with an organic solvent. The composition contains at least one polycyclic aromatic compound as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emissive layer obtained from the composition, and the second component functions as a host component of the emissive layer. The third component functions as a solvent that dissolves the first and second components in the composition, and during application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface shape.

[0273] [organic solvent] The above-mentioned composition for forming the light-emitting layer contains at least one organic solvent as a third component. By controlling the evaporation rate of the organic solvent during film formation, the film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness can be controlled and improved. Furthermore, when forming the film using an inkjet method, the meniscus stability at the pinholes of the inkjet head can be controlled, thereby controlling and improving the ejection performance. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL element having a light-emitting layer obtained from the light-emitting layer-forming composition can be improved.

[0274] (1) Physical properties of organic solvents In the third component, the boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferable from the viewpoint of inkjet ejection performance. A boiling point lower than 300°C is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. The third component is more preferably composed of two or more organic solvents from the viewpoint of good inkjet ejection performance, film formation, smoothness, and low residual solvent. On the other hand, depending on the circumstances, the composition may be in a solid state by removing the solvent from the light-emitting layer forming composition, taking into consideration transportability, etc.

[0275] Furthermore, the third component contains a good solvent (GS) and a poor solvent (PS) for the host material of the second component, and the boiling point (BP) of the good solvent (GS) GS ) is the boiling point (BP) of a poor solvent (PS) PS A configuration that is lower than ) is particularly preferable. By adding a high-boiling-point poor solvent, the low-boiling-point good solvent evaporates first during film formation, increasing the concentration of the constituents in the composition and the concentration of the poor solvent, thus promoting rapid film formation. As a result, a coating film with fewer defects, low surface roughness, and high smoothness can be obtained.

[0276] Difference in solubility (S GS -S PS The difference in boiling points (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS The temperature is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0277] The organic solvent is removed from the coating film after film formation by drying processes such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to do so at a temperature of 30°C or lower than the glass transition temperature (Tg) of the first component from the viewpoint of improving coating film formation. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature of 30°C or higher than the glass transition temperature (Tg) of the first component. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. In addition, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0278] (2) Specific examples of organic solvents Organic solvents used in compositions for forming the light-emitting layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptane-2-ol, octan-2-ol, decane-2-ol, dodecane-2-ol, and cyclohexanol. Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzo trifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenethole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1- Examples of solvents include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-vitrill, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene benzyl butyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, and benzyloctyl ether. Furthermore, the solvent may be used individually or in mixtures.

[0279] [Optional ingredients] The composition for forming the light-emitting layer may contain optional components as long as they do not impair its properties. Examples of optional components include binders and surfactants.

[0280] (1) Binder The light-emitting layer forming composition may contain a binder. The binder forms a film during film formation and also bonds the resulting film to the substrate. It also plays a role in dissolving, dispersing, and binding other components in the light-emitting layer forming composition.

[0281] Examples of binders used in compositions for forming a light-emitting layer include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0282] The binder used in the composition for forming the light-emitting layer may be of one type only, or it may be a mixture of multiple types.

[0283] (2) Surfactants The light-emitting layer-forming composition may contain surfactants, for example, to control the uniformity of the film surface, the solvent-hydrophilicity and liquid-repellent properties of the film surface. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic groups, and further classified into alkyl, silicon, and fluorine based on the structure of their hydrophobic groups. They are also classified into monomolecular systems with relatively small molecular weights and simple structures, and polymeric systems with large molecular weights and side chains or branching, based on their molecular structure. Furthermore, they are classified into single systems and mixed systems containing two or more surfactants and a substrate, based on their composition. All types of surfactants can be used in the light-emitting layer-forming composition.

[0284] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (product name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, and BYK. 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (product name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (product name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (product name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futergent 251, FTX-218 (product name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis(fluoroalkyl polyoxyethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene noni Examples include tetraphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate, and alkyldiphenyl ether disulfonate.

[0285] Furthermore, a single surfactant may be used, or two or more may be used in combination.

[0286] [Composition and physical properties of compositions for forming light-emitting layers] The content of each component in the light-emitting layer forming composition is preferably such that, from the viewpoint of good solubility, storage stability, and film-forming properties of each component in the light-emitting layer forming composition, as well as good film quality of the coating obtained from the light-emitting layer forming composition, good ejection properties when using an inkjet method, and good electrical properties, luminescence properties, efficiency, and lifespan of an organic EL element having a light-emitting layer made using the composition, the first component is 0.0001% to 2.0% by mass of the total mass of the light-emitting layer forming composition, the second component is 0.0999% to 8.0% by mass of the total mass of the light-emitting layer forming composition, and the third component is 90.0% to 99.9% by mass of the total mass of the light-emitting layer forming composition.

[0287] More preferably, the first component is present in an amount of 0.005% to 1.0% by mass relative to the total mass of the light-emitting layer forming composition, the second component in an amount of 0.095% to 4.0% by mass relative to the total mass of the light-emitting layer forming composition, and the third component in an amount of 95.0% to 99.9% by mass relative to the total mass of the light-emitting layer forming composition. Even more preferably, the first component is present in an amount of 0.05% to 0.5% by mass relative to the total mass of the light-emitting layer forming composition, the second component in an amount of 0.25% to 2.5% by mass relative to the total mass of the light-emitting layer forming composition, and the third component in an amount of 97.0% to 99.7% by mass relative to the total mass of the light-emitting layer forming composition.

[0288] The luminescent layer-forming composition can be produced by appropriately selecting and performing stirring, mixing, heating, cooling, dissolving, dispersion, etc., on the above-mentioned components using known methods. Furthermore, after preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / sealing treatment may be appropriately selected and performed.

[0289] Regarding the viscosity of the light-emitting layer-forming composition, a higher viscosity results in better film formation and good ejection when using an inkjet method. On the other hand, a lower viscosity makes it easier to create thin films. For this reason, the viscosity of the light-emitting layer-forming composition at 25°C is preferably 0.3 mPa·s to 3 mPa·s, and more preferably 1 mPa·s to 3 mPa·s. In this invention, viscosity is a value measured using a cone-plate type rotational viscometer.

[0290] A lower surface tension in the composition for forming the light-emitting layer results in better film formation and a defect-free coating. On the other hand, a higher surface tension results in better inkjet ejection performance. For this reason, the viscosity of the composition for forming the light-emitting layer is preferably 20 mN / m to 40 mN / m at 25°C, and more preferably 20 mN / m to 30 mN / m. In this invention, the surface tension is a value measured using the suspension drop method.

[0291] <Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 plays the role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays the role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0292] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and efficiently transport the injected electrons. Therefore, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a substance that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the primary role is to efficiently prevent holes from the anode from flowing to the cathode without recombining, then even if the electron transport capacity is not particularly high, the effect on improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that efficiently prevents hole movement.

[0293] The material used to form the electron transport layer 106 or electron injection layer 107 (electron transport material) can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0294] The materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their fused ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used individually or in combination with different materials.

[0295] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, and Examples include zoquinoline derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2”-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0296] Furthermore, metal complexes having electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0297] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0298] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0299] [Boran derivatives] Borane derivatives are compounds represented by the following formula (ETM-1), for example, and are disclosed in detail in Japanese Patent Application Publication No. 2007-27587. [ka] In formula (ETM-1), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of the following is independently an optionally substituted alkyl or optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or fewer carbon atoms, a substituted boryl or optionally substituted carbazolyl, and each of the following is independently an integer from 0 to 3.

[0300] Among the compounds represented by the above formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred. [ka]

[0301] In formula (ETM-1-1), R 11 and R 12Each is independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of these is independently an optionally substituted alkyl or an optionally substituted aryl, and R 21 and R 22 Each is independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, where n is an independent integer between 0 and 3, and where m is an independent integer between 0 and 4.

[0302] [ka]

[0303] In formula (ETM-1-2), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each is independently an optionally substituted alkyl or an optionally substituted aryl, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, and n is an independent integer between 0 and 3.

[0304] X 1 A specific example of this is the divalent group represented by the following equations (X-1) to (X-9). [ka] (In each formula, R a Each of these is independently an alkyl or optionally substituted phenyl compound, and * represents the bond position.

[0305] Specific examples of these borane derivatives include the following compounds. [ka]

[0306] This borane derivative can be produced using known raw materials and known synthesis methods.

[0307] [Pyridine derivatives] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0308] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[0309] In equation (ETM-2-1), R 11 ~R 18 Each of these is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms).

[0310] In equation (ETM-2-2), R 11 and R 12 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and R 11 and R 12 They may be joined together to form a ring.

[0311] In each formula, the "pyridine substituent" is one of the following formulas (Py-1) to (Py-15) (where * indicates the bond position), and each pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms. Furthermore, the pyridine substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via phenylene or naphthylene.

[0312] [ka]

[0313] The pyridine substituent is one of the above formulas (Py-1) to (Py-15), but among these, it is preferably one of the following formulas (Py-21) to (Py-44). [ka]

[0314] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine substituents" in formulas (ETM-2-1) and (ETM-2-2) may be substituted with an aryl atom.

[0315] R 11 ~R 18 The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms).

[0316] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0317] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, the above description of alkyl groups can be referenced.

[0318] R 11 ~R 18 Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyl" are cycloalkyls having 3 to 10 carbon atoms. More preferred "cycloalkyl" are cycloalkyls having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" are cycloalkyls having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0319] R 11 ~R 18 In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0320] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include the monocyclic aryl phenyl, the condensed bicyclic aryl (1-,2-)naphthyl, the condensed tricyclic aryls acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and the condensed pentacyclic aryls perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0321] Preferred "aryls having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, crisenyl, or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

[0322] In the above formula (ETM-2-2), R 11 and R 12 These may be bonded together to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene may be spirobonded to the five-membered ring of the fluorene skeleton.

[0323] Specific examples of pyridine derivatives include the following compounds. [ka]

[0324] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0325] [Fluorantene derivatives] Fluoranthene derivatives are compounds represented by formula (ETM-3) below, for example, and are disclosed in detail in International Publication No. 2010 / 134352. [ka]

[0326] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0327] Specific examples of fluorantene derivatives include the following compounds. [ka]

[0328] [BO derivatives] BO derivatives are, for example, polycyclic aromatic compounds represented by the following formula (ETM-4), or polymers of polycyclic aromatic compounds having multiple structures represented by the following formula (ETM-4). [ka]

[0329] R 1 ~R 11 Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, or aryloxy, where at least one hydrogen is substituted with aryl, heteroaryl, or alkyl.

[0330] Also, R 1 ~R 11Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, or alkyl.

[0331] Furthermore, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0332] For explanations of the substituents and ring formation in formula (ETM-4), as well as the polymers formed by the combination of multiple structures of formula (ETM-4), refer to the explanation of polymers in International Publication No. 2015 / 102118.

[0333] Specific examples of these BO derivatives include the following compounds. [ka]

[0334] This BO derivative can be produced using known raw materials and known synthesis methods.

[0335] [Anthracene derivatives] One example of anthracene derivatives is the compound represented by the following formula (ETM-5). [ka]

[0336] Ar 1 These are, independently, single-bonded, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0337] Ar 2Each of these is independently an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples of "aryls with 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6-,3,4-,3,5-)xylyl, mesityl(2,4,6-trimethylphenyl), (o-,m-,p-)cumenyl; bicyclic aryls such as (2-,3-,4-)biphenylyl; condensed bicyclic aryls such as (1-,2-)naphthyl; and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl Examples include nyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), the condensed tricyclic aryls anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl, and the condensed pentacyclic aryl perylene-(1-,2-,3-)yl. Specific examples of "aryl compounds with 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracerenyl, and perilenyl.

[0338] R 1 ~R 4 These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms. R 1 ~R4 The C1-C6 alkyl group in the formula may be either linear or branched. That is, it may be a linear alkyl group with C1-C6 or a branched alkyl group with C3-C6. More preferably, it may be an alkyl group with C1-C4 (a branched alkyl group with C3-C4). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, with methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl being preferred, and methyl, ethyl, or t-butyl being more preferred.

[0339] R 1 ~R 4 Specific examples of cycloalkyl compounds having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0340] R 1 ~R 4 Regarding the aryl compounds having 6 to 20 carbon atoms, aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred. Specific examples of "aryl compounds having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryls having 6 to 20 carbon atoms" can be cited. Preferred "aryls having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0341] Specific examples of these anthracene derivatives include the following compounds, for example. [ka]

[0342] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0343] [Benzofluorene derivatives] Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0344] Ar 1 Each of these is an aryl compound having 6 to 20 carbon atoms, and the same explanation as for "aryl compounds having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perilenyl.

[0345] Ar 2 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and two Ar 2 They may be joined together to form a ring.

[0346] Ar 2The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

[0347] Ar 2 Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyls" are those having 3 to 10 carbon atoms. More preferred "cycloalkyls" are those having 3 to 8 carbon atoms. Even more preferred "cycloalkyls" are those having 3 to 6 carbon atoms. Specific examples of "cycloalkyls" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0348] Ar 2 In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0349] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perilenyl, and pentacenyl.

[0350] Two Ar 2 These may be bonded together to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene may be spirobonded to the five-membered ring of the fluorene skeleton.

[0351] Specific examples of these benzofluorene derivatives include the following compounds. [ka]

[0352] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0353] [Phosphine oxide derivatives] Phosphine oxide derivatives are compounds represented by formula (ETM-7-1) below, for example. Further details are also described in International Publication Nos. 2013 / 079217 and 2013 / 079678. [ka] R 5 These are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, or heteroaryl groups having 5 to 20 carbon atoms. R 6 These are CN, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, or aryloxy groups having 6 to 20 carbon atoms. R 7 and R 8These are, independently, substituted or unsubstituted aryls with 6 to 20 carbon atoms or heteroaryls with 5 to 20 carbon atoms. R 9 It is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer between 0 and 4, and q is an integer between 1 and 3.

[0354] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0355] R 1 ~R 3 These may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, aryl ether group, arylthioether group, aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and condensed rings formed between adjacent substituents.

[0356] Ar 1 They may be the same or different, and are arylene or heteroarylene, Ar 2 They may be the same or different, and are aryl or heteroaryl. However, Ar 1 and Ar 2 At least one of them has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, when n is 0 there is no unsaturated structural part, and when n is 3 there is R 1 It does not exist.

[0357] Of these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted; for example, alkyl, aryl, and heterocyclic groups can be used, and this point is also common to the following description. Furthermore, the number of carbon atoms in alkyl is not particularly limited, but for reasons of availability and cost, it is usually in the range of 1 to 20.

[0358] Furthermore, cycloalkyl refers to saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but is usually in the range of 3 to 20.

[0359] Furthermore, aralkyl refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic and aromatic hydrocarbons may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0360] Furthermore, an alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in an alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0361] Furthermore, cycloalkenyl refers to unsaturated alicyclic hydrocarbon groups containing double bonds, such as cyclopentenyl, cyclopentadienyl, and cyclohexene, which may be unsubstituted or substituted.

[0362] Furthermore, alkynyl refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be unsubstituted or substituted. The number of carbon atoms in an alkynyl is not particularly limited, but is usually in the range of 2 to 20.

[0363] Furthermore, an alkoxy refers to an aliphatic hydrocarbon group mediated by an ether bond, such as methoxy, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in an alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0364] Furthermore, alkylthio is a group in which the oxygen atom in the ether bond of an alkoxy group is replaced by a sulfur atom.

[0365] Furthermore, an aryl ether group refers to an aromatic hydrocarbon group mediated by an ether bond, such as phenoxy, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in an aryl ether is not particularly limited, but is usually in the range of 6 to 40.

[0366] Furthermore, an arylthioether group is a group in which the oxygen atom in the ether bond of an aryl ether is replaced by a sulfur atom.

[0367] Furthermore, "aryl" refers to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, and pyrenyl. Aryl groups can be unsubstituted or substituted. The number of carbon atoms in an aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0368] Furthermore, heterocyclic groups refer to cyclic structural groups that have atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, and these can be unsubstituted or substituted. The number of carbon atoms in a heterocyclic group is not particularly limited, but it is usually in the range of 2 to 30.

[0369] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0370] Formyl, carbonyl, and amino groups can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic groups, etc.

[0371] Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons may be unsubstituted or substituted.

[0372] Silyl refers to a silicon compound group, such as trimethylsilyl, which can be unsubstituted or substituted. The number of carbon atoms in a silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually between 1 and 6.

[0373] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 Ar 1 and R 3 Ar 2 and R 2 Ar 2 and R 3 , R 2 and R 3 Ar 1 and Ar 2 These are conjugated or unconjugated fused rings formed between such as . Here, when n is 1, two R 1 These rings may form conjugated or non-conjugated fused rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, and may also be fused with other rings.

[0374] Specific examples of these phosphine oxide derivatives include the following compounds. [ka]

[0375] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0376] [Pyrimidine derivatives] The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Further details are also described in International Publication No. 2011 / 021689. [ka]

[0377] Each Ar is independently an optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0378] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0379] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0380] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0381] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0382] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0383] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

[0384] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0385] [Arylnitrile derivatives] Arylnitrile derivatives are compounds represented by formula (ETM-9) below, for example, or polymers formed by the linkage of multiple such compounds via single bonds or other means. Further details are described in U.S. Patent Application Publication No. 2014 / 0197386. [ka]

[0386] Ar ni From the viewpoint of fast electron transport, a high number of carbon atoms is preferable, and high E T1 From this viewpoint, a smaller number of carbon atoms is preferable. ni Specifically, it is not suitable for use in layers adjacent to the light-emitting layer due to its high E T1 It is preferable that the aryl group has 6 to 20 carbon atoms, preferably aryl group has 6 to 14 carbon atoms, and more preferably aryl group has 6 to 10 carbon atoms. Furthermore, the number of substituted nitrile groups n is high E T1 From this perspective, a large amount is preferable, and a high E S1 From this viewpoint, a small number is preferable. Specifically, the number of substituted nitrile groups n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 1.

[0387] Each Ar is independently an optionally substituted aryl or optionally substituted heteroaryl. High E S1 and high E T1 From this viewpoint, it is preferable that the compound is a donor heteroaryl, and it is preferable that the donor heteroaryl is few in number since it is used as an electron transport layer. From the viewpoint of charge transport, it is preferable that the compound is an aryl or heteroaryl with a large number of carbon atoms, and it is preferable that it has many substituents. Specifically, the number of Ar substitutions m is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 1 to 2.

[0388] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0389] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0390] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0391] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0392] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0393] The arylnitrile derivative may be a polymer in which multiple compounds represented by formula (ETM-9) are linked by single bonds or other means. In this case, in addition to single bonds, the linkage may also be by aryl rings (preferably polyvalent benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzofluorene rings, phenalene rings, phenanthrene rings, or triphenylene rings).

[0394] Specific examples of these arylnitrile derivatives include the following compounds. [ka]

[0395] This arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[0396] [Triadine derivatives] The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Further details are described in U.S. Patent Application No. 2011 / 0156013. [ka]

[0397] Each Ar is independently a substituted or substituted heteroaryl. n is an integer between 1 and 3, preferably 2 or 3.

[0398] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0399] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0400] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0401] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0402] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0403] Specific examples of these triazine derivatives include the following compounds. [ka]

[0404] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0405] [Benzimidazole derivatives] Benzimidazole derivatives are compounds represented by, for example, the following formula (ETM-11). [ka]

[0406] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "benzimidazole substituent" is a substituent in which pyridyl in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) above is replaced with benzimidazol, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium.

[0407] [ka]

[0408] R in the above benzimidazolyl 11 R is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in the above formulas (ETM-2-1) and (ETM-2-2) is... 11 You can quote the explanation.

[0409] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the explanation in formula (ETM-2-1) or formula (ETM-2-2) above, where R in each formula 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) above is explained in a form in which two pyridine substituents are bonded, when replacing these with benzimidazole substituents, both pyridine substituents may be replaced with benzimidazole substituents (i.e., n=2), or one of the pyridine substituents may be replaced with a benzimidazole substituent and the other pyridine substituent may be R 11 ~R 18 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) R 11 ~R 18Replace at least one of the "pyridine substituents" with a benzimidazole substituent and R 11 ~R 18 You can replace it with this.

[0410] Specific examples of these benzimidazole derivatives include, for example, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalene-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole Examples include 1-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, and 5-(9,10-di(naphthalene-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole.

[0411] [ka]

[0412] This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0413] [Phenanthroline derivatives] Phenanthroline derivatives are compounds represented, for example, by the following formulas (ETM-12) or (ETM-12-1). Further details are described in International Publication No. 2006 / 021982. [ka]

[0414] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[0415] R in each formula 11 ~R 18 Each of these is independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). Also, in the above formula (ETM-12-1), R 11 ~R 18 One of these forms a bond with the aryl ring φ.

[0416] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0417] R 11 ~R 18 The alkyl, cycloalkyl, and aryl in the above formula (ETM-2) are R 11 ~R 18 The explanation can be quoted. In addition to the examples above, φ can also be represented by the following structural formula. In the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * represents the bond position.

[0418] [ka]

[0419] Specific examples of phenanthroline derivatives include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluor-bis(1,10-phenanthroline-5-yl), basocuproine, and 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene.

[0420] [ka]

[0421] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0422] [Quinolinol-based metal complexes] Quinolinol-based metal complexes are compounds represented by, for example, the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 is a hydrogen atom or a substituent, M is Li, Al, Ga, Be, or Zn, and n is an integer from 1 to 3.

[0423] Specific examples of quinolinol-based metal complexes include 8-quinolinollithium, tris(8-quinolinolate)aluminum, tris(4-methyl-8-quinolinolate)aluminum, tris(5-methyl-8-quinolinolate)aluminum, tris(3,4-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,6-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum, and bis(2-methyl-8-quinolinolate) (2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -Dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate) (2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- Examples include aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, and bis(10-hydroxybenzo[h]quinoline)beryllium.

[0424] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0425] [Thiazole derivatives and benzothiazole derivatives] Thiazole derivatives are compounds represented by the following formula (ETM-14-1), for example. [ka] Benzothiazole derivatives are compounds represented by, for example, the following formula (ETM-14-2). [ka]

[0426] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4. The "thiazole substituent" and "benzothiazole substituent" are substituents in which pyridyl in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) above is replaced with thiazolyl or benzothiazol, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with deuterium.

[0427] [ka]

[0428] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the explanation in formula (ETM-2-1) or formula (ETM-2-2) above, where R in each formula 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) above is explained as a form in which two pyridine substituents are bonded, when replacing these with thiazole substituents (or benzothiazole substituents), both pyridine substituents may be replaced with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or one of the pyridine substituents may be replaced with a thiazole substituent (or benzothiazole substituent) and the other pyridine substituent may be R 11 ~R 18 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) R 11 ~R 18 Replace at least one of the "pyridine substituents" with a thiazole substituent (or benzothiazole substituent) 11 ~R 18You can replace it with this.

[0429] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0430] [Silole derivatives] Silole derivatives are compounds represented by the following formula (ETM-15), for example. Further details are described in Japanese Patent Publication No. 9-194487. [ka]

[0431] X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, and heteroaryl groups, which may be substituted. For details of these groups, refer to the explanations in formulas (1) and (2), and further to the explanation in formula (ETM-7-2). Alkenyloxy and alkynyloxy are groups in which the alkyl portion of an alkoxy is replaced by an alkenyl or alkynyl, respectively, and for details of these alkenyl and alkynyl groups, refer to the explanation in formula (ETM-7-2). Furthermore, X and Y, both alkyl groups, may be bonded together to form a ring.

[0432] R 1 ~R 4Each of these is independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl, or halogen, and may form a condensed ring with an adjacent substituent.

[0433] R 1 ~R 4 For details on halogens, alkyls, cycloalkyls, alkoxys, aryloxys, aminos, aryls, heteroaryls, alkenyls, and alkynyls in formulas (1) and (2), refer to the explanations provided.

[0434] R 1 ~R 4 Details regarding the alkyl, aryl, and alkoxy elements in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy can also be found by referring to the explanations in formulas (1) and (2).

[0435] Examples of silyls include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, alkyl, or cycloalkyl group. Trisubstituted silyls are preferred, and examples include triarylsilyls, trialkylsilyls, tricycloalkylsilyls, dialkylcycloalkylsilyls, and alkyldicycloalkylsilyls. Details of the aryl, alkyl, and cycloalkyl groups in these can be found in the explanations for formulas (1) and (2).

[0436] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These are conjugated or unconjugated fused rings formed between such rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, or they may be further fused with other rings.

[0437] However, preferably, R 1 and R 4 If is phenyl, then X and Y are not alkyl or phenyl. Also, preferably R 1 and R 4 If is thienyl, then X and Y are alkyl, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 It is a structure that does not simultaneously satisfy the requirement of a cycloalkyl group that is bonded to form a ring. Furthermore, preferably, R 1 and R 4 If R is a silyl group, 2 , R 3 X and Y are, independently, not hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, preferably, R 1 and R 2 In the case of a structure in which a benzene ring is fused, X and Y are not alkyl and phenyl.

[0438] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0439] [Azoline derivatives] Azoline derivatives are compounds represented by formula (ETM-16) below, for example. Further details are described in International Publication No. 2017 / 014226. [ka]

[0440] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl, R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, provided that Ar and R in >N-Ar are different. 1 ~R 5 One of these is a site that binds to L, L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

[0441] [ka]

[0442] In formula (L-1), X 1 ~X 6Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms. m is an integer from 1 to 4, and when m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0443] Specific azoline derivatives are compounds represented by the following formulas (ETM-16-1) or (ETM-16-2). [ka]

[0444] In equations (ETM-16-1) and (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen atom of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl. In formula (ETM-16-1), R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In formula (ETM-16-2), R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In equations (ETM-16-1) and (ETM-16-2), L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

[0445] [ka]

[0446] In formula (L-1), X 1 ~X 6 Each of them is independent of =CR 6 - or = N- and X1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms. m is an integer from 1 to 4, and when m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0447] Preferably, φ is selected from the group consisting of a monovalent group represented by formulas (φ1-1) to (φ1-18), a divalent group represented by formulas (φ2-1) to (φ2-34), a trivalent group represented by formulas (φ3-1) to (φ3-3), and a tetravalent group represented by formulas (φ4-1) to (φ4-2), and at least one hydrogen atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0448] [ka]

[0449] [ka]

[0450] [ka]

[0451] In the formulas, Z is >CR2, >N-Ar, >NL, -O-, or -S-, where R in >CR2 is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, where Ar in >N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and where L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). The asterisk (*) in the formulas indicates a bond position.

[0452] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, sinnoline, and pteridine, and at least one hydrogen of L may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C10 aryl, or a C2-C10 heteroaryl.

[0453] Preferably, in >N-Ar as Y or Z, Ar is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, synnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, or a C6-C10 aryl.

[0454] Preferably, R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, R 3 and R 4 They are identical, and R 1 ~R 4 Not all of them become hydrogen at the same time, and m is either 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0455] Specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents methyl. [ka]

[0456] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33), and (φ2-34), and at least one hydrogen atom of φ may be substituted with an aryl group having 6 to 18 carbon atoms. [ka]

[0457] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 14 carbon atoms. In >N-Ar as Y, Ar is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of said Ar may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, R 3 and R 4 They are identical, and R 1 ~R 4 Not all of them will turn into hydrogen at the same time, and, m is 2, and the group formed by the azoline ring and L is the same.

[0458] Other specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents methyl. [ka]

[0459] Details regarding the alkyl, cycloalkyl, aryl, or heteroaryl elements in each of the above formulas defining this azoline derivative can be found by reference to the explanations in formulas (1) and (2).

[0460] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0461] [Reducing substances, etc.] The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance having a certain reducing property; for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0462] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0463] <Cathode in an organic electroluminescent device> The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0464] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0465] Furthermore, preferred methods for electrode protection include laminating metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0466] <Binding agents that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0467] <Method for fabricating organic electroluminescent devices> Each layer constituting an organic electroluminescent device can be formed by thinning the material to be composed of each layer using methods such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular stacking, printing, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured using a quartz crystal oscillating film thickness measuring device.

[0468] When applying a DC voltage to the organic electroluminescent element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, this organic electroluminescent element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0469] Next, as an example of a method for fabricating an organic electroluminescent device, we will describe a method for fabricating an organic electroluminescent device consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode.

[0470] [Vapor deposition method] An anode is fabricated by forming a thin film of anode material on a suitable substrate using a vapor deposition method, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-deposited on this to form a thin film that serves as the light-emitting layer, and then an electron transport layer and an electron injection layer are formed on this light-emitting layer. Finally, a thin film made of cathode material is formed using a vapor deposition method to form the cathode, thereby obtaining the desired organic electroluminescent element. In addition, in the fabrication of the organic electroluminescent element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0471] When thin films are formed using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions involve heating the deposition crucible to a temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0472] [Wet film formation method] The wet film deposition method is carried out by preparing a liquid organic layer-forming composition containing low-molecular-weight compounds capable of forming each organic layer of an organic EL device. If a suitable organic solvent for dissolving these low-molecular-weight compounds is not available, the organic layer-forming composition may be prepared from polymer compounds obtained by polymerizing the low-molecular-weight compounds with other monomers or main-chain polymers that have solubility properties, by substituting reactive substituents on the low-molecular-weight compounds. The above-described composition for forming an emissive layer is an example of a composition for forming an organic layer, and the formation of an emissive layer using an organic layer-forming composition can also be carried out by a wet film deposition method. For organic solvents and optional components that can be used to prepare the organic layer-forming composition, and for the physical properties of the composition, please refer to the above-described description of the emissive layer-forming composition.

[0473] Wet film formation generally involves a coating step of applying an organic layer-forming composition to a substrate and a drying step of removing the solvent from the applied organic layer-forming composition to form a coating film. Depending on the coating step, methods using a spin coater are called spin coating, methods using a slit coater are called slit coating, methods using a printing plate are called gravure, offset, reverse offset, and flexographic printing, methods using an inkjet printer are called inkjet printing, and methods spraying in a mist are called spray printing. Drying methods include air drying, heating, and vacuum drying. The drying step may be performed only once, or multiple times using different methods and conditions. In addition, different methods may be used in combination, such as firing under reduced pressure.

[0474] Wet deposition is a method of forming thin films using a solution, such as certain printing methods (inkjet printing), spin coating or casting, and coating methods. Unlike vacuum deposition, wet deposition does not require expensive vacuum deposition equipment and can be performed under atmospheric pressure. In addition, wet deposition allows for large-area deposition and continuous production, leading to reduced manufacturing costs.

[0475] On the other hand, compared to vacuum deposition, wet deposition methods make it difficult to create multilayer films. When fabricating multilayer films using wet deposition, it is necessary to prevent the upper layer composition from dissolving the lower layer, and techniques such as controlled solubility of the composition, crosslinking of the lower layer, and orthogonal solvents (solvents that do not mix with each other) are employed. However, even with these techniques, it is sometimes difficult to use wet deposition for coating all films.

[0476] Therefore, a common approach is to fabricate organic EL elements using a wet deposition method for only a few layers, and a vacuum deposition method for the rest.

[0477] For example, the procedure for fabricating an organic EL element by partially applying a wet film deposition method is shown below. (Step 1) Film deposition by vacuum deposition of the anode (Step 2) Deposition of the hole injection layer by wet deposition method (Step 3) Deposition of the hole transport layer by wet deposition method (Step 4) Wet deposition of a light-emitting layer-forming composition containing a host material and a dopant material. (Step 5) Deposition of electron transport layer by vacuum deposition (Step 6) Deposition of electron injection layer by vacuum deposition (Step 7) Film deposition by vacuum deposition of cathode By following this procedure, an organic EL element is obtained consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. Of course, the electron transport layer and electron injection layer may also be formed by a wet deposition method using a layer-forming composition containing the electron transport layer material and the electron injection layer material, respectively. In this case, it is preferable to use means to prevent the dissolution of the lower light-emitting layer, or to deposit the film from the cathode side, in the opposite direction to the procedure described above.

[0478] [Other film deposition methods] Laser heating lithography (LITI) can be used to form the film of the light-emitting layer-forming composition. LITI is a method of heating and depositing a compound attached to a substrate with a laser, and the light-emitting layer-forming composition can be used as the material coated onto the substrate.

[0479] <Optional steps> Appropriate processing steps, cleaning steps, and drying steps may be appropriately inserted before and after each film formation step. Examples of processing steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for creating a bank may also be included.

[0480] Photolithography can be used to create the resist bank. Positive and negative resist materials can be used as the resist bank material for photolithography. Patternable printing methods such as inkjet, gravure offset printing, reverse offset printing, and screen printing can also be used. Permanent resist materials can also be used in these cases.

[0481] Materials used in the bank include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of ethylenic monomers having hydroxyls, biopolymers, polyacryloyl compounds, polyesters, polystyrene, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0482] Referring to Figure 2, a method for fabricating an organic EL element using an inkjet method on a substrate having banks will be explained. First, the banks (200) are provided on electrodes (120) on a substrate (110). In this case, ink droplets (310) are dropped from an inkjet head (300) between the banks (200) and dried to create a coating film (130). This process is repeated to create the next coating film (140), and then the light-emitting layer (150). By depositing electron transport layers, electron injection layers, and electrodes using a vacuum deposition method, an organic EL element with light-emitting areas separated by bank material can be fabricated.

[0483] <Application examples of organic electroluminescent devices> Furthermore, the present invention can also be applied to display devices equipped with organic electroluminescent elements or lighting devices equipped with organic electroluminescent elements. A display device or lighting device equipped with an organic electroluminescent element can be manufactured by known methods, such as connecting the organic electroluminescent element according to this embodiment with a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0484] Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include matrix and / or segment displays. Matrix and segment displays may coexist on the same panel.

[0485] In a matrix display, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed using a collection of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, while for large displays such as display panels, pixels with sides on the order of millimeters are used. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type displays. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

[0486] In segment-based displays, a pattern is formed to display predetermined information, causing a designated area to illuminate. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cooktops, and panel displays in automobiles.

[0487] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal displays, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal displays, especially backlights for personal computers where miniaturization is a challenge, conventional methods consist of fluorescent lamps and light guide plates, making miniaturization difficult. Therefore, the backlight using the light-emitting element according to this embodiment is characterized by being thin and lightweight.

[0488] 3-2. Other Organic Devices The polycyclic aromatic compounds according to the present invention can be used not only in the organic field-light-emitting device described above, but also in the fabrication of organic field-effect transistors or organic thin-film solar cells.

[0489] An organic field-effect transistor (OCT) is a type of transistor that controls current using an electric field generated by a voltage input. In addition to source and drain electrodes, it has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, allowing the current to be controlled by arbitrarily blocking the flow of electrons (or holes) between the source and drain electrodes. Compared to simple transistors (bipolar transistors), OTCs are easier to miniaturize and are frequently used as components in integrated circuits.

[0490] The structure of an organic field-effect transistor typically includes a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode further separated by an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following: (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode (4) Substrate / Source electrode / Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode Organic field-effect transistors configured in this way can be applied as pixel driving switching elements in active-matrix driven liquid crystal displays and organic electroluminescent displays.

[0491] Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. Organic thin-film solar cells can be appropriately selected and combined with known materials used in organic thin-film solar cells. [Examples]

[0492] The present invention will be described in detail below with reference to examples, but the present invention is not limited in any way by these examples. The following are compounds synthesized in the examples.

[0493] Synthesis example (1) Synthesis of compound (1-307): 7,17-dichloro-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene [ka]

[0494] [1st stage] 3,5-dimethylaniline (12.5 mL, 0.10 mol), 3-bromotoluene (14.0 mL, 0.11 mol), tert-leaf toxicodium (10.6 g, 0.11 mol), bis(dibenzylideneacetone)palladium(0) (456 mg, 0.50 mmol), and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos; 409 mg, 1.0 mmol) were added to toluene (500 mL) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 50 °C for 12 hours. After the reaction mixture cooled to room temperature, water (500 mL) was added, and extraction was performed twice with toluene (300 mL). The mixture was then washed with saturated saline solution (100 mL). The organic layer was recovered, the solvent was removed by vacuum distillation, and then 3,5-dimethyl-N-(m-tolyl)aniline (20.8 g, 99% yield) was obtained as a yellow liquid by silica gel column chromatography (eluent / hexane). The reaction mixture was washed with hexane and acetonitrile. The resulting crude product was stirred with hexane at 60°C for 3 hours to obtain 7,17-dichloro-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene (45.7 mg, yield 48%) as a red powder.

[0495] [ka]

[0496] The compound structure obtained by NMR spectroscopy was confirmed. 1H-NMR (δppm in CDCl3,500 MHz); 2.26 (s, 6H),2.30 (s 3H),5.54 (s, 1H),6.57 (s, 1H),6.32 (s, 2H),6.69 (s, 2H),6.72 (d, 1H),6.85 (s, 1H),6.86 (d, 1H),7.12 (t, 1H)

[0497] [Second stage] 1,3-Dibromo-5-chlorobenzene (21.6 g, 80 mmol), 3,5-dimethyl-N-(m-tolyl)aniline (16.9 g, 80 mmol), tert-leaf toxicodium (9.23 g, 96 mmol), bis(dibenzylideneacetone)palladium (0) (733 mg, 0.80 mmol), and 2,2'-bis(diphenylphosphin)-1,1'-binaphthyl (BINAP; 996 mg, 1.6 mmol) were added to toluene (400 mL) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 90 °C for 24 hours. After the reaction mixture cooled to room temperature, water (400 mL) was added, and the mixture was extracted three times with toluene (200 mL), followed by washing with saturated brine. The organic layer was collected, the solvent was removed by distillation, and the reaction mixture was passed through a silica gel short-pass column (eluent / hexane). After removing the solvent by distillation, the mixture was dried at 100°C to obtain 3-bromo-5-chloro-N-(3,5-dimethylphenyl)-N-(m-tolyl)aniline (19.3 g, yield 60%) as a white powder.

[0498] [ka]

[0499] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (δppm in CDCl3,500 MHz); 2.24 (s, 6H),2.28 (s 3H),6.70 (s, 2H),6.76 (s, 1H),6.84 (t, 1H),6.87 (m, 3H),6.69 (t, 1H),6.99 (t, 1H),7.16 (t, 1H) 13 C-NMR (δppm in CDCl3,500 MHz); 21.2 (2C),21.2 (1C),120.0 (1C), 122.3 (1C),122.4 (1C),122.7 (1C),123.3 (1C),123.4 (2C),125.1 (1C),125.9 (1C),126.4 (1C),129.3 (1C),135.2 (1C),139.3 (2C),139.4 (1C),146.3 (1C),146.4 (1C),150.4 (1C)

[0500] [3rd stage] 1,4-Dibromobenzene (7.08 g, 30 mmol), 3,5-Dimethylaniline (9.00 mL, 72 mmol), tert-leaf toxicodium (8.66 g, 90 mmol), bis(dibenzylideneacetone)palladium (0) (549 mg, 0.60 mmol), and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos; 493 mg, 1.2 mmol) were added to toluene (90 mL) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 60 °C for 4 hours. The reaction mixture was cooled to room temperature and washed with hexane and water. Then, it was passed through a silica gel short-pass column (eluent / toluene). After removing the solvent under reduced pressure, washing with hexane yielded a white powder, which was then N 1 ,N 4 -bis(3,5-dimethylphenyl)benzene-1,4-diamine (7.67 g, yield 81%) was obtained.

[0501] [ka]

[0502] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (δppm in CDCl3,500 MHz); 2.25 (s, 12H),5.47 (s, 2H),6.52 (s, 2H),6.61 (s, 4H),7.03 (s, 4H)

[0503] [4th stage] N 1 ,N 4 -bis(3,5-dimethylphenyl)benzene-1,4-diamine (1.58 g, 5.0 mmol), 3-bromo-5-chloro-N-(3,5-dimethylphenyl)-N-(m-tolyl)aniline (4.81 g, 12 mmol), tert-leaf toxicodium (1.45 g, 15 mmol), bis(dibenzylideneacetone)palladium (0) (91.6 mg, 0.10 mmol), and dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos; 81.7 mg, 0.20 mmol) were added to toluene (15 mL) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 100 °C for 12 hours. The reaction mixture was cooled to room temperature and passed through a silica gel short-pass column (eluent / toluene). After removing the solvent under reduced pressure, the crude product was subjected to silica gel column chromatography (eluent / hexane:toluene = 5:1). Subsequently, washing with methanol yielded a white powder containing N2. 1 ,N 1 -(1,4-phenylene)bis(5-chloro-N 1 ,N 3 -Bis(3,5-dimethylphenyl)-N 3 -(m-tolyl)benzene-1,3-diamine) (4.63 g, 97% yield) was obtained.

[0504] [ka]

[0505] 1 H-NMR (δppm in CDCl3,500 MHz); 2.19 (s, 12H),2.21 (s 12H),2.23 (s, 6H),6.49 (d, 4H),6.60 (t, 1H),6.64 (m, 12H),6.80 (m, 6H),6.86 (s, 4H),7.08 (t, 2H)

[0506] [5th ​​stage] N1 ,N 1 -(1,4-phenylene)bis(5-chloro-N 1 ,N 3 -Bis(3,5-dimethylphenyl)-N 3 (m-tolyl)benzene-1,3-diamine) (95.8 mg, 0.10 mmol) and boron triiodide (0.314 g, 0.80 mmol) were added to chlorobenzene (1.0 mL) under a nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 90 °C for 4 hours. After the reaction mixture cooled to room temperature, phosphate buffer solution (pH=6.8, 20 mL) was added, and the mixture was extracted three times with dichloromethane (20 mL). The organic layer was collected, the solvent was removed by distillation, and the reaction mixture was washed with hexane and acetonitrile. The crude product obtained was stirred with hexane at 60°C for 3 hours to obtain 7,17-dichloro-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene (45.7 mg, yield 48%) as a red powder.

[0507] [ka]

[0508] 1 H-NMR (δppm in CDCl3,500 MHz); 2.33 (s, 6H),2.43 (s 12H),2.51 (s, 12H), 6.09 (s, 2H),6.32 (s, 2H),6.32 (s, 2H),6.79 (d, 2H),6.92 (s, 4H),7.14 (s, 4H),7.21 (s, 2H),7.36 (2, 2H),8.05 (d, 2H),8.32 (s, 2H)

[0509] Synthesis example (2) Synthesis of compound (1-313): 5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene-7,17-diamine [ka]

[0510] 7,17-Dichloro-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene (0.292 g, 0.30 mmol), bis(di-tert-butyl(3-methyl2-butenyl)phosphine)dichloropalladium(II) (18.1 mg, 0.030 mmol), and diphenylamine (0.112 mg, 0.66 mmol) were added to a 10 mL Schlenk tube, and then tert-butoxysodium (0.174 g, 1.8 mmol) was added under an argon atmosphere. Subsequently, under a nitrogen atmosphere at room temperature, mesitylene (1.0 mL) was added, and the mixture was heated and stirred at 160°C for 20 hours. After the reaction solution cooled to room temperature, the solvent was removed by distillation, and the resulting crude product was washed with hexane and acetonitrile. The resulting solid was recrystallized using toluene to obtain 5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene-7,17-diamine (0.173 g, yield 47%) as a red powder.

[0511] [ka]

[0512] 1H-NMR (δppm in CDCl3,500 MHz); 2.26 (s, 12H),2.27 (s, 6H),2.36 (s, 12H),5.54 (s, 2H),5.88 (s, 2H), 6.51 (s, 2H),6.67 (d, 2H),6.77 (s, 4H),6.92 (m, 6H),6.98 (m, 12H),7.08 (m, 10H),8.01 (d, 2H),8.25 (s, 2H)

[0513] Synthesis example (3) Synthesis of compound (1-321): 7,17-di(9H-carbazol-9-yl)-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphtho[3,2,1-de:3',2',1'-op]pentacene [ka]

[0514] 7,17-Dichloro-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene (0.292 g, 0.30 mmol), bis(di-tert-butyl(3-methyl2-butenyl)phosphine)dichloropalladium(II) (18.1 mg, 0.030 mmol), and carbazole (0.111 mg, 0.66 mmol) were added to a 10 mL Schlenk tube, and then tert-butoxysodium (0.174 g, 1.8 mmol) was added under an argon atmosphere. Subsequently, under a nitrogen atmosphere at room temperature, mesitylene (1.0 mL) was added, and the mixture was heated and stirred at 160°C for 20 hours. After the reaction solution cooled to room temperature, the solvent was removed by distillation, and the resulting crude product was washed with hexane and acetonitrile. The resulting solid was recrystallized using ortho-dichlorobenzene to obtain 7,17-di(9H-carbazole-9-yl)-5,9,15,19-tetrakis(3,5-dimethylphenyl)-3,13-dimethyl-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphtho[3,2,1-de:3',2',1'-op]pentacene (0.241 g, yield 58%) as a red powder.

[0515] [ka]

[0516] 1 H NMR (δppm in CDCl3,500 MHz); 2.35 (s, 6H),2.38 (s, 12H),2.49 (s, 12H),6.29 (s, 2H), 6.55 (s, 2H),6.68 (s, 2H),6.81 (d, 2H),7.02 (s, 4H),7.07 (s, 2H),7.17 (m, 8H),7.25 (m, 12H),7.42 (m, 8H),8.02 (d, 4H),8.18 (d, 2H),8.51 (s, 2H)

[0517] Synthesis example (4) Compound (1-331): 3,13-di-tert-butyl-7,17-dichloro-5,15-bis(3,5-di-tert-butylphenyl)-9,19-bis(3,5-dimethylphenyl)-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphth[3,2,1-de:3',2',1'-op]pentacene [ka]

[0518] N 1 ,N 1 -(1,4-phenylene)bis(N8-(3-(tert-butyl)phenyl)-5-chloro-(N8-(3,5-di-tert-butylphenyl)-N1(3,5-dimethylphenyl)benzene-1,3-diamine) (0.362 g, 0.30 mmol) was added to a 10 mL Schlenk tube, and then boron triiodide (0.475 g, 1.2 mmol) was added under an argon atmosphere. Subsequently, chlorobenzene (1.0 mL) was added under a nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 80 °C for 20 hours. After the reaction solution cooled to room temperature, phosphate buffer solution (pH=6.8, 20 mL) was added. The following was added, and extraction was carried out three times with toluene (20 mL). The organic layer was collected, and after removing the solvent by distillation, the resulting crude product was washed with hexane and acetonitrile to obtain 3,13-di-tert-butyl-7,17-dichloro-5,15-bis(3,5-di-tert-butylphenyl)-9,19-bis(3,5-dimethylphenyl)-5,9,15,19-tetrahydro-5,9,15,19-tetraaza-10b,20b-diborazinaphtho[3,2,1-de:3',2',1'-op]pentacene (0.199 g, yield 54%) as a vermilion powder.

[0519] [ka]

[0520] 1H-NMR (δppm in CDCl3,500 MHz); 1.20 (s, 18H),1.37 (s, 36H),2.52 (s, 12H),6.22 (s, 2H) 6.35 (s, 2H),6.63 (s, 2H),7.04 (s, 2H),7.17 (s, 8H),7.36 (s, 2H),7.63 (s, 2H),8.13 (s, 2H),8.35 (s, 2H)

[0521] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the synthesis example described above.

[0522] Next, we will describe the evaluation of the basic physical properties of the compound of the present invention and the fabrication and evaluation of an organic EL element using the compound of the present invention.

[0523] <Evaluation of basic physical properties> Sample preparation When evaluating the absorption and emission properties (fluorescence and phosphorescence) of a compound, the evaluation can be performed either by dissolving the compound in a solvent and evaluating it in the solvent, or by evaluating it in a thin film state. Furthermore, when evaluating in a thin film state, depending on how the compound will be used in an organic EL device, the evaluation can be performed by thinning only the compound or by dispersing the compound in an appropriate matrix material and then thinning it for evaluation.

[0524] Commercially available materials such as PMMA (polymethyl methacrylate) can be used as the matrix material. Thin film samples dispersed in PMMA can be prepared, for example, by dissolving PMMA and the compound to be evaluated in toluene, and then forming a thin film on a transparent quartz support substrate (10 mm × 10 mm) using a spin coating method.

[0525] Furthermore, the method for preparing thin film samples when the matrix material is the host material is described below. A transparent quartz support substrate (10 mm × 10 mm × 1.0 mm) is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing the host material and a molybdenum deposition boat containing the dopant material are attached. Next, the vacuum chamber is set to 5 × 10 -4 The pressure is reduced to Pa, and the deposition boats containing the host material and the deposition boat containing the dopant material are heated simultaneously to deposit the materials to the appropriate thickness, forming a mixed thin film of the host material and the dopant material. The deposition rate is controlled according to the set mass ratio of the host material and the dopant material.

[0526] Evaluation of absorption and emission properties The absorption spectrum of the aforementioned sample was measured using a UV-Vis-Near-Infrared spectrophotometer (Shimadzu Corporation, UV-2600). The fluorescence spectrum or phosphorescence spectrum of the aforementioned sample was measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0527] For fluorescence spectrum measurements, the sample was excited at room temperature with an appropriate excitation wavelength, and photoluminescence was measured. For phosphorescence spectrum measurements, the sample was immersed in liquid nitrogen (temperature 77K) using the attached cooling unit, and measurements were taken. To observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time from excitation light irradiation to the start of measurement.

[0528] Evaluation of the basic physical properties of compound (1-307) [Absorption properties] Compound (1-307) 2.0 × 10 -5 A sample was prepared by dissolving M in toluene, and its absorption spectrum was measured (Figure 3). As a result, the maximum absorption wavelength in the visible light region was 522 nm.

[0529] [Luminous properties] Fluorescence spectroscopy was performed on compound (1-307) at a rate of 2.0 × 10⁻⁶. -5A sample was prepared by dissolving it in toluene at a concentration of M, and the photoluminescence was measured after excitation at an excitation wavelength of 470 nm (Figure 3). As a result, the maximum emission wavelength was 533 nm, the full width at half maximum was 18 nm, and the chromaticity was CIE chromaticity (x,y) = (0.314, 0.666). Furthermore, the fluorescence quantum yield was measured by preparing the same solution and exciting it at an excitation wavelength of 470 nm, and it was found to be a high value of 94.5%.

[0530] Evaluation of the basic physical properties of compound (1-313) [Absorption properties] Compound (1-313) 2.0 × 10 -5 A sample was prepared by dissolving M in toluene, and its absorption spectrum was measured (Figure 4). As a result, the maximum absorption wavelength in the visible light region was 528 nm.

[0531] [Luminous properties] Fluorescence spectroscopy was performed on compound (1-313) at a rate of 2.0 × 10⁻⁶. -5 A sample was prepared by dissolving it in toluene at a concentration of M, and the photoluminescence was measured after excitation at an excitation wavelength of 470 nm (Figure 4). As a result, the maximum emission wavelength was 541 nm, the full width at half maximum was 21 nm, and the chromaticity was CIE chromaticity (x,y) = (0.347, 0.642). Furthermore, the fluorescence quantum yield was measured by preparing the same solution and exciting it at an excitation wavelength of 470 nm, and it was found to be a high value of 98.7%.

[0532] Evaluation of the basic physical properties of compound (1-321) [Absorption properties] Compound (1-321) 2.0 × 10 -5 A sample was prepared by dissolving M in toluene, and its absorption spectrum was measured (Figure 5). As a result, the maximum absorption wavelength in the visible light region was 530 nm.

[0533] [Luminous properties] Fluorescence spectroscopy was performed on compound (1-321) at a rate of 2.0 × 10⁻⁶. -5A sample was prepared by dissolving it in toluene at a concentration of M, and the photoluminescence was measured after excitation at an excitation wavelength of 470 nm (Figure 5). As a result, the maximum emission wavelength was 542 nm, the full width at half maximum was 18 nm, and the chromaticity was CIE chromaticity (x,y) = (0.362, 0.628). Furthermore, the fluorescence quantum yield was measured by preparing the same solution and exciting it at an excitation wavelength of 470 nm, and the result was 78.4%.

[0534] Evaluation of the basic physical properties of comparative compound 1 (C545T) The compound (C545T) was purchased from Lumtec (Taiwan) and used without purification. [Absorption properties] Compound (C545T) 2.0 × 10 -5 A sample was prepared by dissolving it in toluene at concentration M, and its absorption spectrum was measured. As a result, the maximum absorption wavelength in the visible light region was 473 nm.

[0535] [Luminous properties] The fluorescence spectrum was measured using a 2.0 × 10⁻⁶ sample of the compound (C545T). -5 A sample was prepared by dissolving it in toluene at concentration M, and the photoluminescence was measured after excitation at an excitation wavelength of 470 nm. As a result, the maximum emission wavelength was 506 nm and the full width at half maximum was 58 nm.

[0536] Evaluation of the basic physical properties of comparative compound 2 (BA-NPB) The compound (BA-NPB) was purchased from Lumtec (Taiwan) and used without purification. [Absorption properties] Compound (BA-NPB) 2.0 × 10 -5 A sample was prepared by dissolving it in toluene at concentration M, and its absorption spectrum was measured. As a result, the maximum absorption wavelength in the visible light region was 441 nm.

[0537] [Luminous properties] The fluorescence spectrum was measured using a 2.0 × 10⁻⁶ sample of the compound (BA-NPB). -5A sample was prepared by dissolving it in toluene at concentration M, and the photoluminescence was measured after excitation at an excitation wavelength of 441 nm. As a result, the maximum emission wavelength was 517 nm and the full width at half maximum was 57 nm.

[0538] Comparative compound 3 (Ir(ppy) 3 Evaluation of the basic physical properties of ) The compound (Ir(ppy)3) was purchased from Lumtec (Taiwan) and used without purification. [Absorption properties] Compound (Ir(ppy)3) 2.0 × 10 -5 A sample was prepared by dissolving M in toluene, and its absorption spectrum was measured. The result showed that the maximum absorption wavelength in the visible light region was 350 nm.

[0539] [Luminous properties] The phosphorescence spectrum was measured using a 2.0 × 10⁻⁶ area of ​​the compound (Ir(ppy)3). -5 A sample was prepared by dissolving it in toluene at concentration M, and the photoluminescence was measured after excitation at an excitation wavelength of 230 nm. As a result, the maximum emission wavelength was 517 nm and the full width at half maximum was 66 nm.

[0540] Fabrication of organic EL elements Organic EL elements according to the examples and comparative examples were fabricated, and current density, brightness, chromaticity, and external quantum efficiency were measured by applying voltage.

[0541] [Table 1]

[0542] In Table 1, "HI1" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, "HT1" is 4,4',4"-tris(N-carbazolyl)triphenylamine, "EB1" is 1,3-bis(N-carbazolyl)benzene, "EMH1" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "ET1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. In Table 1, "AD1" is 2,5-bis-(4-(10H-phenoxazine-10-yl)phenyl)-1,3,4-oxadiazole, and "AD2" is 3,6-bis-(dibenzo[b,d]furan-2-yl)-9-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)-9H-carbazole. The chemical structures of "AD1", "AD2", and "Comparative Compound 1" are shown below.

[0543] [ka]

[0544] <Example 1> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD1, and the emitting dopant is compound (1-307)> A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 50nm by sputtering an ITO film to a thickness of 200nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum deposition boats containing HI1, HT1, EB1, EMH1, AD1, compound (1-307), and ET1, respectively, and aluminum nitride deposition boats containing LiF and aluminum, respectively, were attached.

[0545] The following layers were sequentially deposited onto the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4The pressure was reduced to Pa. First, HI1 was heated and deposited to a thickness of 40 nm, then HT1 was heated and deposited to a thickness of 15 nm to form a two-layer hole injection transport layer. Next, EB1 was heated and deposited to a thickness of 15 nm to form an electron blocking layer. Then, EMH1 as the host, AD1 as the assisting dopant, and compound (1-307) as the emitting dopant were simultaneously heated and co-deposited to a thickness of 20 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of the host, assisting dopant, and emissive dopant was approximately 90:9:1. Next, ET1 was heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for each of the above layers was set to 0.01 to 1 nm / second. After that, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm, and then aluminum was heated and deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the aluminum deposition rate was adjusted to be between 1 nm and 10 nm.

[0546] A DC voltage was applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and luminance, chromaticity, and external quantum efficiency were measured. (100 cd / m²) 2 The emission spectrum during emission had a peak wavelength of 522 nm and a full width at half maximum of 18 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 26.0%, which is a high quantum efficiency.

[0547] <Comparative Example 1> <Configuration A: A device that does not use an emitting dopant, but uses AD1 as the assisting dopant> An EL element was obtained using the same procedure and configuration as in Example 1, except that an emitting dopant was not used and the mass ratio of the host to the assisting dopant was changed to 90:10. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 522 nm and a full width at half maximum of 72 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m².2 The external quantum efficiency during luminescence was 10.2%, which is considered low.

[0548] <Comparative Example 2> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD1, and the emitting dopant is comparative compound 1> An EL element was obtained using the same procedure and configuration as in Example 1, except that the emitting dopant was changed to comparative compound 1. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 520 nm and a full width at half maximum of 55 nm, and green emission was observed.

[0549] <Example 2> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD2, and the emitting dopant is compound (1-307)> An EL element was obtained using the same procedure and configuration as in Example 1, except that the assisting dopant was changed to AD2. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 522 nm and a full width at half maximum of 18 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 24.0%, which is a high quantum efficiency.

[0550] <Comparative Example 3> <Configuration A: A device that does not use an emitting dopant, but uses AD2 as the assisting dopant> An EL element was obtained using the same procedure and configuration as in Example 2, except that an emitting dopant was not used and the mass ratio of the host to the assisting dopant was changed to 90:10. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2The emission spectrum during emission had a peak wavelength of 528 nm and a full width at half maximum of 60 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 9.8%, which is considered low.

[0551] [Table 2]

[0552] In Table 2, "HI2" is N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonnitrile, "HT2" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine, and "HT3" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1 The compounds are ':4',1"-terphenyl]-4-amine, "EMH2" is 1,8,10-tri([1,1'-biphenyl]-4-yl)anthracene, "ET2" is 4,6,8,10-tetraphenyl[1,4]benzoxavorinino[2,3,4-kl]phenoxavorinine, and "ET3" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine). Their chemical structures are shown below along with "Liq", "Comparative Compound 1", and "Comparative Compound 2".

[0553] [ka]

[0554] <Example 3> <Configuration B: A device using compound (1-307) as the dopant and EMH2 as the host> A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 120nm by sputtering an ITO film to a thickness of 200nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum deposition boats containing HI2, HT2, HAT-CN, EB2, EMH2, compound (1-307), Liq, ET2, and ET3, respectively, and aluminum nitride deposition boats containing LiF and aluminum, respectively, were mounted on it.

[0555] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 The pressure was reduced to Pa. First, HI2 was heated and deposited to a thickness of 40 nm, and then HAT-CN was heated and deposited to a thickness of 5 nm to form a hole injection layer. Next, HT2 was heated and deposited to a thickness of 15 nm, and then HT3 was heated and deposited to a thickness of 10 nm to form a hole transport layer. Next, EMH2 as the host and compound (1-307) as the dopant were simultaneously heated and co-deposited to a thickness of 25 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of host to dopant was approximately 98:2. Next, ET2 was heated and deposited to a thickness of 5 nm, and then ET3 and Liq were simultaneously heated and co-deposited to a thickness of 25 nm to form an electron transport layer. The deposition rate was adjusted so that the mass ratio of ET3 and Liq was 50:50. The deposition rate for each of the above layers was 0.01 to 1 nm / second. Subsequently, Liq was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm. Then, magnesium and silver were heated simultaneously and deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate was adjusted so that the mass ratio of magnesium to silver was 90:10, and the deposition rate was adjusted to 0.1 nm to 1 nm.

[0556] A DC voltage was applied to an ITO electrode as the anode and a magnesium-silver electrode as the cathode, and luminance, chromaticity, and external quantum efficiency were measured. (100 cd / m²) 2The emission spectrum during emission had a peak wavelength of 522 nm and a full width at half maximum of 17 nm, and green emission was observed. Furthermore, the emission level was 1000 cd / m². 2 The external quantum efficiency during emission was 7.0%. In particular, the emission spectrum had a small full width at half maximum, achieving a deep green color.

[0557] <Example 4> <Configuration B: A device with compound (1-313) as a dopant> An EL element was obtained using the same procedure and configuration as in Example 3, except that the dopant was changed. As a result, it produced 1000 cd / m² 2 The external quantum efficiency during emission was 7.2%, and the emission spectrum had a maximum emission wavelength of 518 nm and a full width at half maximum (FWHM) of 20 nm. In particular, the small FWHM of the emission spectrum enabled the achievement of a deep green color.

[0558] <Example 5> <Configuration B: A device with compound (1-321) as a dopant> An EL element was obtained using the same procedure and configuration as in Example 3, except that the dopant was changed. As a result, it produced 1000 cd / m² 2 The external quantum efficiency during emission was 6.8%, and the emission spectrum had a maximum emission wavelength of 532 nm and a full width at half maximum (FWHM) of 19 nm. In particular, the small FWHM of the emission spectrum enabled the achievement of a deep green color.

[0559] <Comparative Example 4> <Configuration B: Device with comparative compound 1 as a dopant> An EL element was obtained using the same procedure and configuration as in Example 3, except that the dopant was changed. As a result, it produced 1000 cd / m² 2 The external quantum efficiency during emission was 6.6%, the emission spectrum showed a maximum emission wavelength of 518 nm, and a full width at half maximum (FMAX) of 60 nm. Compared to compound (1-313), the external quantum efficiency was comparable, but the FMAX was wider.

[0560] <Comparative Example 5> <Configuration B: Device with comparative compound 2 as a dopant> An EL element was obtained using the same procedure and configuration as in Example 3, except that the dopant was changed. As a result, it produced 1000 cd / m²2 The external quantum efficiency during emission was 6.8%, and the emission spectrum showed a maximum emission wavelength of 527 nm and a full width at half maximum (FMAX) of 58 nm. Compared to compound (1-321), the external quantum efficiency was comparable, but the FMAX was wider.

[0561] [Table 3]

[0562] Table 3 shows the chemical structures of "AD3", "AD4", "AD5", "AD6", "AD7", "AD8", "EMH3", "EMH4", and "EMH5" below.

[0563] [ka]

[0564] <Example 6> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD3, and the emitting dopant is compound (1-313)> A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 50nm by sputtering an ITO film to a thickness of 200nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum deposition boats containing HI1, HT1, EB1, EMH1, AD3, compound (1-313), and ET1, respectively, and aluminum nitride deposition boats containing LiF and aluminum, respectively, were attached.

[0565] The following layers were sequentially deposited onto the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4The pressure was reduced to Pa. First, HI1 was heated and deposited to a thickness of 40 nm, then HT1 was heated and deposited to a thickness of 15 nm to form a two-layer hole injection transport layer. Next, EB1 was heated and deposited to a thickness of 15 nm to form an electron blocking layer. Then, EMH1 as the host, AD3 as the assisting dopant, and compound (1-313) as the emitting dopant were simultaneously heated and co-deposited to a thickness of 20 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of the host, assisting dopant, and emissive dopant was approximately 90:9:1. Next, ET1 was heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for each of the above layers was set to 0.01 to 1 nm / second. After that, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm, and then aluminum was heated and deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the aluminum deposition rate was adjusted to be between 1 nm and 10 nm.

[0566] A DC voltage was applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and luminance, chromaticity, and external quantum efficiency were measured. (100 cd / m²) 2 The emission spectrum during emission had a peak wavelength of 520 nm and a full width at half maximum of 19 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 27.0%, which is a high quantum efficiency.

[0567] <Example 7> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD4, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the assisting dopant was changed to AD4. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 522 nm and a full width at half maximum of 20 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2The external quantum efficiency during luminescence was 24.4%, which is a high quantum efficiency.

[0568] <Example 8> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD5, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the assisting dopant was changed to AD5. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 518 nm and a full width at half maximum of 17 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during light emission was 22.3%, which is a high quantum efficiency.

[0569] <Example 9> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD6, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the assisting dopant was changed to AD6. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 524 nm and a full width at half maximum of 22 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 23.5%, which is a high quantum efficiency.

[0570] <Example 10> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD7, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the assisting dopant was changed to AD7. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2The emission spectrum during emission had a peak wavelength of 525 nm and a full width at half maximum of 24 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 22.0%, which is a high quantum efficiency.

[0571] <Example 11> <Configuration A: A device in which the host compound is EMH1, the assisting dopant is AD8, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the assisting dopant was changed to AD8. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 520 nm and a full width at half maximum of 20 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 22.6%, which is a high quantum efficiency.

[0572] <Example 12> <Configuration A: A device in which the host compound is EMH3, the assisting dopant is AD3, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the host compound was changed to EMH3. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 523 nm and a full width at half maximum of 25 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 19.0%, which is a high quantum efficiency.

[0573] <Example 13> <Configuration A: A device in which the host compound is EMH4, the assisting dopant is AD3, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the host compound was changed to EMH4. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 523 nm and a full width at half maximum of 22 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 23.2%, which is a high quantum efficiency.

[0574] <Example 14> <Configuration A: A device in which the host compound is EMH5, the assisting dopant is AD3, and the emitting dopant is compound (1-313)> An EL element was obtained using the same procedure and configuration as in Example 6, except that the host compound was changed to EMH5. A DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, and the luminance, chromaticity, and external quantum efficiency were measured. 100 cd / m 2 The emission spectrum during emission had a peak wavelength of 519 nm and a full width at half maximum of 19 nm, and green emission was observed. Furthermore, the emission level was 100 cd / m². 2 The external quantum efficiency during luminescence was 22.0%, which is a high quantum efficiency.

[0575] Thus, the compound of the invention, by using an assisting dopant, enables highly efficient green emission with a very narrow half-width. When applied to displays, this means that highly efficient and high-color-purity green emission can be achieved. Although the example of the present invention describes the use of an assisting dopant, for example, an exciplex host reported by Adachi and Nakanoya et al. of Kyushu University (Adv. Mater. 2020, 1906614) can also be used instead of the assisting dopant.

[0576] <<Fabrication and Evaluation of Coated (Emitting Layer) Organic EL Devices>> <Synthesis Example: Polymer Host Compound: Synthesis of SPH-101> SPH-101 was synthesized according to the method described in International Publication No. 2015 / 008851. A copolymer in which M2 or M3 is bonded to the adjacent position of M1 was obtained, and each unit is 50:26:24 (molar ratio) from the charging ratio.

[0577] [Chemical formula] In the formula, Me is methyl, Bpin is pinacolato boryl, and * indicates the bonding position of each unit. Note that the terminal * is bonded to hydrogen or aryl.

[0578] [Synthesis Example: High Molecular Hole Transport Compound: Synthesis of XLP-101] XLP-101 was synthesized according to the method described in JP-A-2018-61028. A copolymer in which M4, M5 and M6 are bonded was obtained. Each unit is 40:10:50 (molar ratio) from the charging ratio.

[0579] [Chemical formula] In the formula, Bpin is pinacolato boryl, and * indicates the bonding position of each unit. Note that the terminal * is bonded to hydrogen or aryl.

[0580] [Preparation of XLP-101 Solution] XLP-101 was dissolved in xylene to prepare a 0.6 wt% XLP-101 solution.

[0581] [Preparation of Composition for Forming Light-Emitting Layer] The composition for forming a light-emitting layer according to Example F-1 can be prepared. The compounds used in the preparation of the composition are shown below. [Example F-1] The composition for forming a light-emitting layer is prepared by stirring the following components until a uniform solution is obtained. Compound (1-313) 0.02 mass% Compound (AD3) 0.18 mass% SPH-101 1.80 mass% Xylene 69.00 mass% Decalin 29.00 mass% By spin-coating the prepared composition for forming a light-emitting layer on a glass substrate and drying it by heating under reduced pressure, a coating film without film defects and excellent in smoothness can be obtained.

[0582] <Fabrication of Organic EL Device> The method for fabricating an organic EL device using a crosslinkable hole transport material in Example S-1 and Example S-2 and the method for fabricating an organic EL device using an orthogonal solvent system in Example S-3 were shown. The material compositions of each layer in the organic EL device to be fabricated are shown in Table 4.

Table 4

[0583] The structures of "PEDOT:PSS", "OTPD", "PCz", and "ET4" in Table 4 are shown below.

Chemical formula

[0584] <PEDOT:PSS Solution> A commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

[0585] <Preparation of OTPD Solution> OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (a photo cationic polymerization initiator, manufactured by San Apro) are dissolved in toluene to prepare an OTPD solution with an OTPD concentration of 0.7 wt% and an IK-2 concentration of 0.007 wt%.

[0586] <Preparation of PCz Solution> PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7 wt% PCz solution.

[0587] <Example S-1> A glass substrate coated with 150 nm thick ITO is spin-coated with a PEDOT:PSS solution and baked on a 200°C hot plate for 1 hour to form a 40 nm thick PEDOT:PSS film (hole injection layer). Next, an OTPD solution is spin-coated and dried on an 80°C hot plate for 10 minutes. Exposure is performed using an exposure machine at an exposure intensity of 100 mJ / cm². 2 The sample is exposed to light and baked on a hot plate at 100°C for 1 hour to form a solution-insoluble OTPD film with a thickness of 30 nm (hole transport layer). Next, the light-emitting layer formation composition of Example F-1 is spin-coated and baked on a hot plate at 120°C for 1 hour to form a light-emitting layer with a thickness of 20 nm.

[0588] The fabricated multilayer film is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. The vacuum chamber is 5 × 10 -4 After reducing the pressure to Pa, the deposition boat containing ET1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is 1 nm / second. Then, the deposition boat containing LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm. Next, the boat containing aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this way, an organic EL device is obtained.

[0589] <Example S-2> A PEDOT:PSS solution is spin-coated onto a glass substrate coated with 150 nm thick ITO, and baked on a hot plate at 200°C for 1 hour to form a 40 nm thick PEDOT:PSS film (hole injection layer). Next, an XLP-101 solution is spin-coated, dried on a hot plate at 80°C for 10 minutes, and then baked on a hot plate at 180°C for 1 hour to form a 30 nm thick, solution-insoluble XLP-101 film (hole transport layer). Then, the light-emitting layer-forming composition of Example F-1 is spin-coated and baked on a hot plate at 120°C for 1 hour to form a 20 nm thick light-emitting layer.

[0590] Using the fabricated multilayer film, an electron transport layer and a cathode are formed in the same procedure as in Example S-1 to obtain an organic EL device.

[0591] <Example S-3> A PEDOT:PSS solution is spin-coated onto a glass substrate coated with 150 nm thick ITO, and baked on a hot plate at 200°C for 1 hour to form a 40 nm thick PEDOT:PSS film (hole injection layer). Next, a PCz solution is spin-coated, dried on a hot plate at 80°C for 10 minutes, and then baked on a hot plate at 100°C for 1 hour to form a 30 nm thick PCz film insoluble in the light-emitting layer-forming composition (hole transport layer). Next, the light-emitting layer-forming composition of Example F-1 is spin-coated and baked on a hot plate at 120°C for 1 hour to form a 20 nm thick light-emitting layer.

[0592] Using the fabricated multilayer film, an electron transport layer and a cathode are formed in the same procedure as in Example S-1 to obtain an organic EL device. [Industrial applicability]

[0593] This invention provides novel polycyclic aromatic compounds, thereby increasing the range of materials available for organic EL devices. Furthermore, by using these novel polycyclic aromatic compounds as materials for organic electroluminescent devices, it is possible to provide superior organic EL devices, display devices equipped with them, and lighting devices equipped with them. [Explanation of Symbols]

[0594] 100 Organic Electroluminescent Devices 101 circuit board 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode 110 circuit boards 120 electrodes 130 coating film 140 coating film 150 Emitting layer 200 Bank 300 inkjet heads 310 Ink Droplets

Claims

1. Polycyclic aromatic compounds represented by the following formula (1): 【Chemistry 1】 In formula (1), Rings A and C are independently substituted aryl rings or substituted heteroaryl rings. Rings B and D are independently optionally substituted aryl rings or optionally substituted heteroaryl rings. X １ , X ２ , X ３ and X ４ These are, independently, >O, >N-R, >CR ２ , >S or >Se, where R in >N-R is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted cycloalkyl or optionally substituted alkyl, and R in >N-R may be linked to the A ring, B ring, C ring and / or D ring by a linking group or single bond. The above > CR ２ R is hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted cycloalkyl, or an optionally substituted alkyl, and also the >CR ２ R may be linked to the A, B, C, and / or D rings by a linking group or a single bond. R １ and R ２ each independently is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), cyano, or halogen, In the compound represented by formula (1), at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH group in the cycloalkane ２ The - can also be substituted with -O-. At least one hydrogen atom in the compound represented by formula (1) may be substituted with deuterium.

2. Ring A has one substituent Z １ An aryl ring having or one substituent Z １ A heteroaryl ring having, or one substituent Z １ An aryl ring having or one substituent Z １ Z in a heteroaryl ring having １ Z is formed by a single bond or linking group. １ It has a structure to which is bonded to an aryl ring or heteroaryl ring, The C ring has one substituent Z ２ An aryl ring having or one substituent Z ２ A heteroaryl ring having, or one substituent Z ２ An aryl ring having or one substituent Z ２ Z in a heteroaryl ring having ２ Z is formed by a single bond or linking group. ２ It has a structure to which is bonded to an aryl ring or heteroaryl ring, Z １ and Z ２ Each of these is independently one of the following bases: Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryl; aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or diarylamino (the two aryls may be bonded to each other); Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted diheteroarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylhetarylamino; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or alkyl which may be substituted with halogen; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted cycloalkyl; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted aryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroaryloxy; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted arylthio; Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, alkyl-substituted silyl, cyano, or possibly halogen-substituted heteroarylthio; Cyano; or halogen, Rings B and D are independently aryl rings or heteroaryl rings that may be substituted with alkyl, cyano, or halogen atoms. Rings A and B are B, X １ and X ２ Formula (1) consists of a fused two-ring structure on the left and a five-membered or six-membered ring sharing a bond, with the C and D rings being B and X. ３ and X ４ Formula (1) consists of the following: It has a condensed two-ring structure on the right and a five-membered or six-membered ring that shares a bond with it. R １ and R ２ These are, independently, hydrogen, cyano, or halogen. The polycyclic aromatic compound according to claim 1.

3. A polycyclic aromatic compound according to claim 1, represented by the following formula (2); 【Chemistry 2】 In formula (2), R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ Each of these is independently a hydrogen atom or a substituent selected from the substituent group X, and R ５ ~R ７ and R １０ ~R １２ Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the b ring and / or d ring. At least one hydrogen in the formed ring may be substituted with a substituent selected from the substituent group X; Substituent group X: Aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted aryl; Heteroaryls that may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Diarylaminos which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen (the two aryls may be bonded to each other); Diheteroarylaminos which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted arylheteroarylaminos; Alkyl, heteroaryl, cycloalkyl, cyano, or halogen-substituted alkyl; aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen-substituted cycloalkyl; Alkoxy that may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Aryloxys which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Heteroaryloxys which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Arylthio, which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Heteroarylthio, which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Alkyl-substituted silyls which may be substituted with aryl, heteroaryl, cycloalkyl, alkyl, cyano, or halogen; Cyano; and halogen, X １ , X ２ , X ３ and X ４ These are, independently, >O, >N-R, >CR ２ , >S or >Se, The above >N-R and the above >CR ２ Each R is independently one of the following groups: A C6-C12 aryl atom which may be substituted with an alkyl, cyano, or halogen atom of C1-C6; A heteroaryl molecule having 2 to 15 carbon atoms, which may be substituted with an alkyl, cyano, or halogen molecule having 1 to 6 carbon atoms; Cycloalkyl groups having 3 to 12 carbon atoms, which may be substituted with alkyl groups having 1 to 6 carbon atoms, cyano groups, or halogen groups; or A C1-C6 alkyl group which may be substituted with a cyano or halogen, The above >N-R and the above >CR ２ R may be linked to the a, b, c, and / or d rings by a linking group or a single bond. R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cyano group, or a halogen group. Z １ and Z ２ Each of these is independently one of the following bases: Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted aryl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted heteroaryl; Diarylaminos that may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen; Diheteroarylaminos which may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylheteroarylaminos; Aryl, heteroaryl, alkyl-substituted silyl, cyano, or halogen-substituted alkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted cycloalkyl; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted aryloxy; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted heteroaryloxy; Aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted arylthio; aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen-substituted heteroarylthio; Cyano; or halogen, Z １ R ３ and / or R ４ It may also be bonded to form a ring, in which case R ３ and / or R ４ This may represent boron, and may also represent two aryl groups of diarylamino bonded together. Z ２ R ８ and / or R ９ It may also be bonded to form a ring, in which case R ８ and / or R ９ This may represent boron, and may also represent two aryl groups of diarylamino bonded together. At least one hydrogen atom in the compound represented by formula (2) may be substituted with deuterium.

4. X １ , X ２ , X ３ and X ４ The polycyclic aromatic compound according to claim 3, wherein at least one of the elements is >N-R.

5. The polycyclic aromatic compound according to claim 3 or 4, wherein R in N-R is a C6-C10 aryl that may be substituted with a C1-C6 alkyl, a cyano or halogen, or a C1-C4 alkyl that may be substituted with a cyano or halogen.

6. R １ and R ２ A polycyclic aromatic compound according to any one of claims 3 to 5, wherein all of the atoms are hydrogen.

7. R ３ , R ４ , R ８ , and R ９ A polycyclic aromatic compound according to any one of claims 3 to 6, wherein all of the atoms are hydrogen.

8. X １ , X ２ , X ３ and X ４ All of them are >N-R, >The R in N-R is an aryl atom having 6 to 10 carbon atoms, which may be substituted with an alkyl, cyano, or halogen atom having 1 to 6 carbon atoms. Z １ and Z ２ However, all of them are diarylamino compounds which may be substituted with aryl, heteroaryl, alkyl, alkyl-substituted silyl, cyano, or halogen. Z １ and X １ Or X ２ The R in N-R is R ３ or R ４ Boron, which is a linking group, is bonded to the α ring. Z ２ and X ３ or X ４ in which the R of >N-R and R ８ or R ９ The polycyclic aromatic compound according to any one of claims 3 to 6, wherein boron which is R or R is bonded to the c-ring as a linking group.

9. R ５ , R ６ , R ７ , R １０ , R １１ and R １２ is each independently aryl having 6 to 10 carbon atoms which may be substituted with hydrogen, cyano or halogen, cycloalkyl having 3 to 12 carbon atoms which may be substituted with cyano or halogen, or alkyl having 1 to 6 carbon atoms which may be substituted with cyano or halogen. The polycyclic aromatic compound according to any one of claims 3 to 8.

10. A polycyclic aromatic compound according to claim 1, represented by formula (1-307), formula (1-313), formula (1-321), or formula (1-331); 【Transformation 3】 In the formula, Me represents methyl and tBu represents t-butyl.

11. A green light-emitting material containing a polycyclic aromatic compound according to any one of claims 1 to 10.

12. A material for organic devices containing a polycyclic aromatic compound according to any one of claims 1 to 10.

13. The organic device material according to claim 12, wherein the organic device material is a material for an organic electroluminescent device, a material for an organic field-effect transistor, or a material for an organic thin-film solar cell.

14. A light-emitting layer material for forming a light-emitting layer of an organic electroluminescent device, comprising a polycyclic aromatic compound according to any one of claims 1 to 10.

15. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and containing the light-emitting layer material described in claim 14.

16. The light-emitting layer further contains one or more compounds selected from the group consisting of a compound represented by the following formula (3), a compound represented by the following formula (4), and a compound represented by the following formula (5), according to claim 15; 【Chemistry 4】 In formula (3), L １ These are arylenes with 6 to 24 carbon atoms. In formula (4), L ２ and L ３ Each of these is independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. In formula (5), L ４ , L ５ and L ６ Each of these is independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. In each of the compounds represented by the above formulas, at least one hydrogen atom may be substituted with an alkyl, cyano, halogen, or deuterium atom having 1 to 6 carbon atoms.

17. The organic electroluminescent element according to claim 15 or 16, further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

18. The organic electroluminescent element according to claim 17, wherein the electron transport layer and / or electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.

19. A display device comprising an organic electroluminescent element according to any one of claims 15 to 18.

20. A lighting device comprising an organic electroluminescent element according to any one of claims 15 to 18.

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