Polycyclic aromatic compounds

Abstract

This invention provides novel polycyclic aromatic compounds that further enhance organic EL properties such as luminescence characteristics and increase the range of organic EL materials, such as materials for luminescent layers. [Solution] For example, a polycyclic aromatic compound (1-101) is shown in which multiple aromatic rings are linked by a boron atom and a nitrogen atom or an oxygen atom. JPEG2026062718000284.jpg48170

Description

[Technical Field]

[0001] This invention relates to a polycyclic aromatic compound, an organic field-emitting element using the same, and an organic field-effect transistor. Organic devices such as zistas and organic thin-film solar cells, as well as display devices and lighting devices. To relate to. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been able to reduce power consumption and make them thinner. Various studies have been conducted, and furthermore, organic electroluminescent devices made of organic materials are easily made lighter and larger. For this reason, it has been actively studied. In particular, the emission properties of blue light, one of the three primary colors of light Development of organic materials possessing charge transport capabilities such as holes and electrons (potential for semiconductors and superconductors). Regarding the development of organic materials possessing the ability to do so, whether polymer compounds or low molecular weight compounds... This has been actively researched up until now.

[0003] An organic EL element consists of a pair of electrodes, an anode and a cathode, and an electrode placed between the pair of electrodes. The structure consists of one or more layers containing an organic compound. These include light-emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons. However, 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 (International (Publication No. 2004 / 061047). Furthermore, examples of hole transport materials include triphenylamine. Compounds of this type have been developed (Japanese Patent Publication No. 2001-172232). Also, as an electron transport material... For example, anthracene-based compounds have been developed (Japanese Patent Publication No. 2005-170911).

[0005] Furthermore, in recent years, triphenylamine has been used as a material for organic EL elements and organic thin-film solar cells. Materials with improved mine derivatives have also been reported (International Publication No. 2012 / 118164). The material was N,N'-diphenyl-N,N'-bis(3-methylphenyl) Referencing )-1,1'-biphenyl-4,4'-diamine (TPD), triphenyl A material characterized by its enhanced planarity achieved by linking the aromatic rings that make up the amine. This is a material. In this document, for example, the charge transport properties of NO-linked compounds (compound 1 on page 63) are described. Although it has been evaluated, the method for producing materials other than NO-linked compounds is not described. Furthermore, if the linked elements are different, the overall electronic state of the compound will be different, therefore, NO-linked compounds The properties obtained from other materials are still unknown. Other examples of such compounds can be found. (International Publication No. 2011 / 107186). For example, the energy (T1) of a triplet exciton is Compounds with large conjugated structures can emit phosphorescence at shorter wavelengths, thus producing blue light. It is useful as a material for the light-emitting layer. It is also useful as an electron transport material or hole transport material sandwiching the light-emitting layer. There is a need for novel conjugated compounds with a large T1.

[0006] The host material for organic EL elements is generally an existing aromatic ring such as benzene or carbazole. These are molecules in which multiple atoms are linked together by single bonds, phosphorus atoms, or silicon atoms. This is a relatively small conjugated system. By linking numerous small aromatic rings, the large HOMO-LUM required for the host material is achieved. This is because the O gap (band gap Eg in thin films) is ensured. Furthermore, phosphorescence The host material for organic EL elements using materials and thermally activated delayed fluorescence (TADF) materials has high Triplet excitation energy (E T ) is also necessary, but the molecule must have donor or acceptor properties. By linking aromatic rings and substituents, triplet excited state (T1) SOMO1 and SOM By localizing O2 and reducing the exchange interaction between the two orbitals, the triplet excitation energy is increased. (E T This makes it possible to improve the small aromatic rings in the conjugated system. However, redox Due to insufficient stability, molecules formed by linking existing aromatic rings were used as host materials. The element does not have a sufficient lifespan. On the other hand, polycyclic aromatic compounds having an extended π-conjugated system are generally, Redox stability is excellent, but the HOMO-LUMO gap (bandgear in thin films) Cap Eg) and triplet excitation energy (E T Because the ) is low, it is considered unsuitable as a host material. It's getting worse.

[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. This is described in International Publication No. 2015 / 102118. In this document, the dopant material of the light-emitting layer is used. Organic EL elements have been evaluated using compounds formed by condensing multiple aromatic rings, The document in question discloses a very large number of compounds, and among them, the luminescence properties and other characteristics are particularly noteworthy. It is beneficial to investigate compounds with excellent organic EL properties.

[0008] In addition to vacuum deposition, wet deposition is another method for forming the organic layer that constitutes an organic EL element. The method is used. For the development of materials for wet film deposition, in particular, hole injection layer, hole transport layer Active development is underway to create inks for forming the light-emitting layer. Among these, hole injection is being pursued. Regarding the inks for the layers and hole transport layers, these inks were used in a wet deposition method. The properties of each layer have reached a practical level. Furthermore, regarding the ink used to form the luminescent layer... While progress is being made in developing inks for the red and green light-emitting layers to improve their properties, the development of inks for the blue light-emitting layer is progressing. Inks are generally made from polycyclic aromatic compounds with aromatic rings, such as anthracene, or styryl compounds. Although compositions using conductors and the like have been developed, they have not yet achieved practical properties. Currently, we have not been able to develop inks for the blue light-emitting layer with high color purity. [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 [Patent Document 7] International Publication No. 2001 / 072673 [Patent Document 8] International Publication No. 2012 / 102333 [Patent Document 9] Japanese Patent Publication No. 2006-045503 [Patent Document 10] Japanese Patent Publication No. 2013-168411 [Patent Document 11] Japanese Patent Publication No. 2013-247179 [Patent Document 12] U.S. Patent Application Publication No. 2013 / 214259 [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 elements. However, to further enhance organic EL properties such as light emission characteristics, and to select organic EL materials such as light-emitting layer materials, To increase the range of options, the development of compounds that were previously unknown in specific terms is desired. [Means for solving the problem]

[0011] The present inventors have diligently studied to solve the above problem and have found that boron atoms and nitrogen atoms and Among polycyclic aromatic compounds, which have multiple aromatic rings linked by oxygen atoms, etc., this has a specific structure. We have discovered that excellent organic EL elements can be obtained by using a compound, thus completing the present invention. This invention has been achieved. In other words, the present invention relates to the following polycyclic aromatic compounds, and furthermore, to the following poly We provide organic device materials containing cyclic aromatic compounds.

[0012] Section 1. A polycyclic aromatic compound represented by the following general formula (1). [ka] (In the above formula (1), Rings A, B, C, and D are each independently an aryl ring or heteroaryl ring. It is a ring, and at least one hydrogen in these rings may be substituted. Y is B (boron), X 1 , X 2 , X 3 and X 4 These are, independently, >O, >NR, >S, or >S is e, and R in the >N-R is optionally substituted aryl, optionally substituted heteroaryl or optionally substituted alkyl, and R in the >N-R may be bonded to the A ring, B ring, C ring and / or D ring by a linking group or a single bond as well, R 1 and R 2 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, aryl having 6 to 1 2 carbon atoms, heteroaryl having 2 to 15 carbon atoms or diarylamino (however, aryl is aryl having 6 to 12 carbon atoms), Z 1 and Z 2 are each independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, substituted optionally alkyl, optionally substituted cycloalkyl, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylthio or optionally substituted heteroarylthio, and Z 1 is a linking group or is a single bond and may be bonded to the A ring, and Z 2 is a linking group or a single bond and may be bonded to the C ring, and moreover, at least one hydrogen in the compound represented by the formula (1) may be substituted with cyano, halogen or heavy hydrogen. )

[0013] Item 2. The A ring, B ring, C ring and D ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is aryl, heteroaryl, di Arylamino, diheteroarylamino, arylheteroarylamino, alkyl, Cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, They may be substituted with heteroarylthio or alkyl-substituted silyl, and in these cases Even if at least one hydrogen atom is substituted with an aryl, heteroaryl, or alkyl group Often, rings A and B are Y, X 1 and X 2 The above formula on the left consists of a condensed two-ring structure It has a 5-membered or 6-membered ring that shares a structure and bond, and the C ring and D ring are Y, X 3 and X 4 mosquito It has a condensed two-ring structure as shown in the above formula and a five-membered or six-membered ring that shares a bond with it, Y is B (boron), X 1 , X 2 , X 3 and X 4 These are, independently, >O, >NR, >S, or >S e is such that R in >NR is aryl, heteroaryl or alkyl, and R is At least one hydrogen in is aryl, heteroaryl, diarylamino, dihete Loarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy Xy, aryloxy, heteroaryloxy, arylthio, heteroarylthio The R in >NR may be substituted with an alkyl-substituted silyl, and the R in >NR may be -O-, - The A, B, C, and / or D rings are connected by S-, -C(-R)2-, or single bonds. It may be bonded, and the R in -C(-R)2- is hydrogen or alkyl. R 1 and R 2 These are, independently, hydrogen, an alkyl group with 1 to 6 carbon atoms, and an alkyl group with 6 to 1 carbon atoms. 2 aryls, heteroaryls or diarylaminos with 2 to 15 carbon atoms (however aryl) The aryl group is a carbon atom with 6 to 12 carbon atoms. Z 1 and Z 2 These are, independently, aryl, heteroaryl, and diarylamino compounds. Diheteroarylaminos, arylheteroarylaminos, alkyls, cycloalkyls , aryloxy, heteroaryloxy, arylthio or heteroarylthio Furthermore, at least one hydrogen in these is an aryl, heteroaryl, or diaryl. Mino, alkyl, cycloalkyl, alkoxy, aryloxy or alkyl-substituted silica It may be replaced with Z 1 These are -O-, -S-, -C(-R)2- or single bonds. It may be more bonded to the aforementioned ring A, Z 2 -O-, -S-, -C(-R)2- or The C ring may be bonded by a single bond, and the R in -C(-R)2- is hydrogen or a It is Rukiru, and also In the compound represented by formula (1), at least one hydrogen atom is cyano, halogen, or heavy It may be substituted with hydrogen. A polycyclic aromatic compound as described in item 1.

[0014] Section 3. A polycyclic aromatic compound as described in item 1, represented by the following general formula (2). [ka] (In the above formula (2), R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12Each These independently include hydrogen, aryl, heteroaryl, diarylamino, and diheteroaryl. Mino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryl aryloxy, heteroaryloxy, arylthio, heteroarylthio or alkyl oxy These are silyl compounds, and at least one hydrogen atom in them is either aryl or heteroaryl. R may be substituted with alkyl, or R 5 ~R 7 and R 10 ~R 12 of Adjacent groups bond together to form an aryl ring or heteroaryl ring with the b-ring and / or d-ring. A ring may be formed, and at least one hydrogen in the formed ring is aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl Amino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy It may be substituted with silyl, arylthio, heteroarylthio, or alkyl-substituted silyl. Furthermore, at least one hydrogen atom in these is aryl, heteroaryl, or alkyl. It may also be replaced with Y is B (boron), X 1 , X 2 , X 3 and X 4 These are, independently, >O, >NR, >S, or >S e is such that R in >NR is an aryl with 6 to 12 carbon atoms, and a heteroaryl with 2 to 15 carbon atoms. It is a reel or an alkyl group having 1 to 6 carbon atoms, and R in >NR is -O-, -S -, -C(-R)2- or single bonds connect to the a, b, c, and / or d rings. They may be combined, and the R in -C(-R)2- is hydrogen or an alkyl group having 1 to 6 carbon atoms. and R 1 and R 2 are each independently hydrogen, alkyl having 1 to 6 carbon atoms or aryl having 6 to 12 carbon atoms, Z 1 and Z 2 are each independently aryl, heteroaryl, diarylamino , diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl , aryloxy, heteroaryloxy, arylthio or heteroarylthio, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or alkyl-substituted silyl, and Z may be bonded to the a-ring by -O-, -S-, -C(-R) 1 2- or a single bond, and Z may be bonded to the c-ring by -O-, -S-, -C(- 2 R)2- or a single bond, and R of the -C(-R)2- is hydrogen or an alkyl group having 1 to 6 carbon atoms, and at least one hydrogen in the compound represented by formula (2) may be substituted with cyano, halogen or deuterium.) hydrogen or an alkyl group having 1 to 6 carbon atoms, and at least one hydrogen in the compound represented by formula (2) may be substituted with cyano, halogen or deuterium.) hydrogen or an alkyl group having 1 to 6 carbon atoms, and

[0015] Item 4. R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (where the aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms , cycloalkyl having 3 to 30 carbon atoms, arylheteroarylamino (where the aryl is aryl having 6 to 12 carbon atoms), diheteroarylamino (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms), alkyl-substituted silyl, aryloxy (where the aryl is aryl having 6 to 12 carbon atoms), heteroaryloxy (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms), arylthio (where the aryl is aryl having 6 to 12 carbon atoms) or heteroarylthio (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms), and at least one hydrogen in these may be substituted with aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 30 carbon atoms, arylheteroarylamino (where the aryl is aryl having 6 to 12 carbon atoms), diheteroarylamino (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms), alkyl-substituted silyl, aryloxy (where the aryl is aryl having 6 to 12 carbon atoms), heteroaryloxy (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms), arylthio (where the aryl is aryl having 6 to 12 carbon atoms) or heteroarylthio (where the heteroaryl is heteroaryl having 2 to 12 carbon atoms). These are aryloxy or arylthio compounds with 6 to 12 carbon atoms, and At least one hydrogen atom in is an aryl atom with 6 to 12 carbon atoms or an aryl atom with 1 to 6 carbon atoms. It may be replaced by a kill, and also R 5 ~R 7 and R 10 ~R 12 Among the adjacent The groups bond together to form an aryl ring or carbon ring with 9 to 16 carbon atoms, along with the b-ring and / or d-ring. They may form heteroaryl rings number 6 to 15, and at least in the formed ring One hydrogen atom is substituted with an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms. But it's fine, Y is B (boron), X 1 , X 2 , X 3 and X 4 Each of these is independently >O or >NR, and the above >The R in NR is an aryl group with 6 to 10 carbon atoms or an alkyl group with 1 to 4 carbon atoms. R 1 and R 2 These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, or a group with 6 carbon atoms. There are ~12 aryls, Z 1 and Z 2 These are, independently, aryl atoms with 6 to 30 carbon atoms and aryl atoms with 2 to 30 carbon atoms. Heteroaryl, diarylamino (where aryl is an aryl with 6 to 12 carbon atoms), carbon Alkyl groups with 1 to 12 prime numbers, cycloalkyl groups with 3 to 12 carbon atoms, and aryl groups with 6 to 30 carbon atoms. Oxy, heteroaryloxy with 2-30 carbon atoms, arylthio with 6-30 carbon atoms or These are heteroarylthio compounds with 2 to 30 carbon atoms, and at least one hydrogen atom in them is Aryl compounds with 6 to 12 carbon atoms, heteroaryl compounds with 2 to 15 carbon atoms, and alkyl compounds with 1 to 12 carbon atoms. may be substituted with a ring or a trialkyl-substituted silyl (where alkyl is an alkyl having 1 to 6 carbon atoms), and at least one hydrogen in the compound represented by the formula (2) may be substituted with cyano, halogen or a heavy hydrogen, the polycyclic aromatic compound according to item 3.

[0016] Item 5. R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently hydrogen, aryl having 6 to 10 carbon atoms or alkyl having 1 to 6 carbon atoms, Y is B (boron), X 1 , X 2 , X 3 and X 4 are each independently >O or >N-R, and the R in the >N-R is aryl having 6 to 10 carbon atoms or alkyl having 1 to 4 carbon atoms, R 1 and R 2 are each independently hydrogen, alkyl having 1 to 6 carbon atoms or aryl having 6 to 12 carbon atoms, Z 1 and Z 2 are each independently aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (where aryl is aryl having 6 to 10 carbon atoms), carbon alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryloxy having 6 to 12 carbon atoms or arylthio having 6 to 12 carbon atoms, and at least one hydrogen in these may be substituted with aryl having 6 to 10 carbon atoms or alkyl having 1 to 6 carbon atoms, and such that at least one hydrogen in the compound represented by formula (2) may be substituted with cyano, halogen or deuterium and may be substituted with hydrogen the polycyclic aromatic compound described in item 3

[0017] item 6 the polycyclic aromatic compound described in item 1, represented by any of the following formulas [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] [Chemical formula] (at least one hydrogen in the compound represented by each of the above formulas may be substituted with an alkyl having 1 to 6 carbon atoms , an aryl having 6 to 10 carbon atoms, cyano, halogen or deuterium, wherein each R is independently an alkyl having 1 to 6 carbon atoms or an aryl having 6 to 10 carbon atoms and R 100 is independently an aryl having 6 to 10 carbon atoms, carbazolyl, diarylamino (where the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms , a cycloalkyl having 3 to 10 carbon atoms, or an aryloxy having 6 to 10 carbon atoms,[[ID=5L]] where the aryl may be substituted with an alkyl having 1 to 6 carbon atoms, and the carbazolyl may be substituted with an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 6 carbon atoms.)

[0018] ​​​​​Materials for organic devices containing polycyclic aromatic compounds as described in any of items 1 to 6. .

[0019] Section 8. The aforementioned organic device materials include materials for organic electroluminescent devices and materials for organic field-effect transistors. Materials for organic devices as described in item 7, which are materials for organic thin-film solar cells.

[0020] Section 9. The organic device material described in item 8, wherein the aforementioned organic electroluminescent material is a material for the light-emitting layer. Fee.

[0021] Section 10. A composition for forming an emissive layer for coating and forming an emissive layer of an organic electroluminescent device, The first component is at least one polycyclic aromatic compound described in any of sections 1 to 6. , As a second component, at least one host material, As a third component, at least one organic solvent, A composition for forming an emissive layer, comprising the above.

[0022] Section 11. A pair of electrodes consisting of an anode and a cathode, and an electrode placed between the pair of electrodes as described in item 9. An organic electroluminescent element having a light-emitting layer containing a material for the optical layer.

[0023] Section 12. A pair of electrodes consisting of an anode and a cathode, and a device disposed between the pair of electrodes as described in item 10. An organic electroluminescent element having a light-emitting layer formed by applying and drying a light-emitting layer-forming composition.

[0024] Section 13. The light-emitting layer further contains a compound represented by the following general formula (3) and / or the following general formula (4 An organic electroluminescent element according to item 11 or 12, comprising a compound represented by ). [Chemical formula] (In the above formula (3), L 1 is an arylene having 6 to 24 carbon atoms, In the above formula (4), L 2 and L 3 are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, and at least one hydrogen in the compound represented by each of the above formulas may be substituted with an alkyl having 1 to 6 carbon atoms, cyano, halogen or deuterium.)

[0025] Item 14. The organic electroluminescent device according to any one of Items 11 to 13, wherein the light-emitting layer further contains a compound represented by the following general formula (5). [Chemical formula] (In the above formula (5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, diarylamino or alkyl, and adjacent groups among R R 1 ~R 11 may combine with each other to form an aryl ring or a heteroaryl ring together with the a ring, b ring or c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, and at least one in these may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, and at least one At least one hydrogen atom further adds aryl, heteroaryl, diarylamino, or alkyl It may be replaced with 'ru'. In the compound represented by formula (5), at least one hydrogen atom is independently a halo It may be substituted with ion or deuterium.

[0026] Section 15. The cathode has an electron transport layer and / or electron injection layer disposed between it and the light-emitting layer, At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, and Luorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, HO Sphin oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives , benzimidazole derivatives, phenanthroline derivatives and quinolinol-based metal complexes The following is a description of any of items 11 to 14, containing at least one selected from the group. Organic electroluminescent device.

[0027] Section 16. The electron transport layer and / or electron injection layer further comprises alkali metals, alkaline earth metals Groups, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals Oxides of the genus, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals Alkali metal oxidides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes The organic field generator according to item 15, comprising at least one selected from the group consisting of organic complexes. Optical element.

[0028] Section 17. Display device or lighting device equipped with an organic electroluminescent element as described in any of items 11 to 16. . [Effects of the Invention]

[0029] According to a preferred embodiment of the present invention, a conventionally known compound represented by formula (1) By using polycyclic aromatic compounds, organic EL properties such as luminescence characteristics can be further enhanced, and materials for light-emitting layers can be used. This can increase the range of organic EL materials available. [Brief explanation of the drawing]

[0030] [Figure 1] This is a schematic cross-sectional view showing an organic EL element according to this embodiment. [Figure 2] This is the absorption, fluorescence, and phosphorescence spectrum of compound (1-1). [Figure 3] This shows the absorption, fluorescence, and phosphorescence spectra of compound (1-201). [Figure 4] This is the absorption, fluorescence, and phosphorescence spectrum of compound (1-101). [Figure 5] These are the absorption, fluorescence, and phosphorescence spectra of compounds (1-9). [Figure 6] This figure shows the organic EL characteristics (brightness) of compound (1-1). [Figure 7] This figure shows the organic EL properties (external quantum efficiency) of compound (1-1). [Figure 8] This figure shows the organic EL properties (emission spectrum) of compound (1-1). [Figure 9] This diagram illustrates a method for fabricating organic EL elements on a substrate with a bank using an inkjet method. [Modes for carrying out the invention]

[0031] 1. Polycyclic aromatic compounds represented by formula (1) The polycyclic aromatic compound represented by general formula (1) is preferably represented by the following general formula (2). It is a polycyclic aromatic compound. [ka]

[0032] For example, light-emitting materials for organic EL displays include fluorescent materials, phosphorescent materials, and thermally activated materials. Three types of delayed fluorescence (TADF) materials are used, but fluorescent materials have low luminescence efficiency. It is approximately 25-62.5%. On the other hand, phosphorescent materials and TADF materials have a luminous efficiency of 1 While it can sometimes reach 00%, in all cases the color purity is low (wide emission spectrum). There is a problem. Displays mix the light emitted from the three primary colors of light: red, green, and blue. While various colors are expressed using this method, if the purity of each color is low, some colors cannot be reproduced. This causes a significant decrease in display quality. Therefore, commercially available displays, By removing unnecessary colors from the emission spectrum using optical filters, color purity is increased. It is used after (narrowing the spectral width). Therefore, the original spectral width is Because a larger area means a higher percentage of the light is removed, even if the luminescence efficiency is high, the actual efficiency is significantly lower. For example, the full width at half maximum of the blue emission spectrum of a commercially available smartphone is approximately 20. While it is around ~25nm, the full width at half maximum of typical fluorescent materials is around 40~60nm, phosphorescent materials The wavelength is approximately 60-90 nm, and for TADF materials, it is approximately 70-100 nm. Using fluorescent materials In that case, since the half-width is relatively narrow, it is sufficient to remove only some of the unwanted colors, but phosphorescent materials and When using TADF material, more than half needs to be removed. There was a need for the development of luminescent materials that possessed both high emission rates and high color purity.

[0033] Generally, TADF materials consist of electron-donating substituents called donors and acceptors. By using electron-accepting substituents to localize the HOMO and LUMO within the molecule, efficient reverse It is designed so that reverse intersystem crossing occurs, but Donna - Using acceptors increases structural relaxation in the excited state (in some molecules, Because the stable structures differ between the ground state and the excited state, external stimuli cause the ground state to transition to the excited state. When this transformation occurs, the structure then changes to a stable structure in the excited state), and the color purity This will result in a low, broad emission spectrum.

[0034] Therefore, in Patent Document 6 (International Publication No. 2015 / 102118), the color purity of the TADF material is This paper proposes a new molecular design that will dramatically improve performance. For example, compounds disclosed in the document... (1-401) utilizes the multiple resonance effect of boron (electron-donating) and nitrogen (electron-withdrawing). By doing so, the HOMO is attached to three carbon atoms (black circles) on the benzene ring consisting of six carbon atoms, and the remaining We have succeeded in localizing the LUMO to these three carbon atoms (white circles). Due to the crossover, the luminescence efficiency of the compound can reach up to 100%. Furthermore, the compound (1- Boron and nitrogen in 401) not only localize the HOMO and LUMO, but also the three vents By fusing the Zenn ring, a robust planar structure is maintained, and structural relaxation in the excited state is suppressed. It also plays a role in this, and as a result the Stokes shift of the absorption and emission peaks is small. Furthermore, they have succeeded in obtaining an emission spectrum with high color purity. The full width at half maximum is 28 nm, a level of color that surpasses even high-purity fluorescent materials currently in practical use. This indicates purity. Also, in dimeric compounds like formula (1-422), two boron atoms and The two nitrogen atoms bond to the central benzene ring, creating further multiplication within the central benzene ring. The resonance effect is enhanced, resulting in emission with an extremely narrow emission peak width. It is. [ka]

[0035] On the other hand, in dimer compounds like formula (1-422), the molecular planarity is high and the resonance is broad. As a result, the emission wavelength becomes longer, moving away from the practical blue wavelength, and also due to high planarity Perhaps because intermolecular stacking was induced, the efficiency in the light-emitting element was also sufficiently satisfactory. This also presented a challenge: that this was not the case.

[0036] Therefore, as a result of our diligent research, we have found that substituents that regulate the multiple resonance effect can be introduced at appropriate positions. This enables the shortening of the emission wavelength and high device efficiency. Specifically, the general aspects of the present invention The polycyclic aromatic compound represented by formula (1) has two Z(Z 1 and Z 2 ) has. Let Z Due to the electron-withdrawing or electron-donating functional groups, the entire molecule undergoes resonance through the A and C rings. It affects the body's resonance structure and / or multiple resonance effects. For example, introducing electron-withdrawing groups. This reduces the electron density of the LUMO and shortens the emission wavelength. Also, electron-withdrawing or electron Regardless of the donor nature, the introduction of substituents to Z results in them existing on the same plane throughout the entire molecule. Because the proportion of the structure is reduced, intermolecular stacking can be reduced. As a result, The wavelength of light was significantly shortened, and in addition, substituents were introduced to reduce intermolecular stacking. This also makes it possible to increase the efficiency of the element. However, the polycyclic aromatic compound of the present invention The effects are not limited to the above principle.

[0037] In general formula (1), rings A, B, C, and D are each independently aryl rings. Alternatively, a heteroaryl ring, where at least one hydrogen in these rings is substituted. This substituent may be substituted. This substituent may be a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroaryl arylaminos, substituted or unsubstituted aryl heteroarylaminos (aryl and heteroaryl amino groups having a reel, substituted or unsubstituted alkyl groups, substituted or unsubstituted cyclo groups Lukyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or This is an unsubstituted heteroaryloxy, a substituted or unsubstituted arylthio, or a substituted or unsubstituted arylthio. Heteroarylthio or alkyl-substituted silyl groups are preferred. These groups have substituents. Examples of substituents in this case include aryl, heteroaryl, or alkyl groups.

[0038] Furthermore, rings A and B are "Y" and "X" 1 " and "X 2 The above formula (1) consists of " It has a condensed biring structure on the left and a five-membered or six-membered ring that shares a bond, and the C and D rings are "Y" "X 3 " and "X 4 The above formula (1) is composed of the condensed two-ring structure on the right and shares a bond with it. It is preferable that it has a 5-membered ring or a 6-membered ring.

[0039] Here, the "condensed two-ring structure" refers to the "Y" and "X" shown in the left part of general formula (1). 1 "oh Call "X" 2 It refers to a structure in which two saturated hydrocarbon rings, which include '', are condensed. The same applies to the condensed biring structure in the right-hand part of general formula (1). Also, "condensed biring structure and A "six-membered ring sharing a bond" refers to a condensed two-ring structure, as shown in the general formula (2) above. It means an a-ring (benzene ring (6-membered ring)). Also, "(an a-ring) aryl ring or "The heteroaryl ring has this 6-membered ring" means that the A ring is formed by this 6-membered ring alone. Alternatively, other rings may condense around this six-membered ring to form an A ring. This means that it will be done. In other words, the "ant with a 6-membered ring (which is an A-ring)" referred to here. A "heteroaryl ring" refers to a six-membered ring that constitutes all or part of the A ring, which is fused. This means that the ring is condensed into two rings. "B ring (b ring)", "C ring (c ring)", "D ring" The same explanation applies to "(d-ring)" and "5-membered ring".

[0040] In general formula (1), ring A (or ring B, ring C, ring D) corresponds to ring a in general formula (2). and its substituent R 3 and R 4 (or the b-ring and its substituent R) 5 ~R 7 , the c ring and its substituent R 8 and R 9 , the d-ring and its substituent R 10 ~R 12 This corresponds to the general formula (2). This corresponds to the formula in which "a ring A to D having six members" is selected as the A to D rings in general formula (1). Therefore, each ring in general formula (2) is represented by lowercase letters a to d.

[0041] R in general formula (2) 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 oh Call R 12These are, independently, hydrogen, aryl, heteroaryl, and diarylamino. Diheteroarylaminos, arylheteroarylaminos, alkyls, cycloalkyls Alkyl, aryloxy, heteroaryloxy, arylthio, heteroaryl Thio or alkyl-substituted silyl, where at least one hydrogen is ally It may be substituted with a heteroaryl or alkyl group.

[0042] In general formula (2), the substituent R of the b ring 5 ~R 7 and / or substituent R of the d-ring 10 ~R 1 2 Adjacent groups of these groups bond together to form an aryl ring or helium ring with the b-ring and / or d-ring. A teloaryl ring may be formed, and at least one hydrogen in the formed ring is Riehl, heteroaryl, diarylamino, diheteroarylamino, arylhetero Arylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryl Substituted with aryl thio, heteroaryl thio or alkyl-substituted silyl They may be present, and at least one hydrogen in them may be aryl, heteroaryl or a It may be substituted with ruquil. Therefore, the compound represented by general formula (2) has a b-ring Depending on the bonding configuration of substituents in the d-ring, as shown in formula (2-1) below, The ring structure constituting the compound changes. The B' ring and D' ring in equation (2-1) are related to the general formula (1 These correspond to the B ring and D ring in ) respectively. Also, the definitions of each sign in equation (2-1) are The sign is the same as in general formula (2).

[0043] [ka]

[0044] The B' and D' rings in formula (2-1) above can be explained by general formula (2) as substituent R 5 ~R 7 and R 10 ~R 12 Adjacent groups of these groups bond together, forming the b-ring and d-ring respectively. This indicates an aryl ring or heteroaryl ring formed together with the ring (another ring structure attached to the b or d ring). (It can also be said to be a condensed ring formed by the condensation of structures). Also, as can be seen from the above formula (2-1), b Ring R 7 and the R of the d ring 12 These do not fall under the category of "adjacent groups," and they do not bond. i. In other words, "adjacent groups" means groups adjacent to each other on the same ring. Note that Z 1 is connected It may also be bonded to the A ring (a ring) by a group or single bond, and also Z 2 C is a linking group or a single bond. It may also bond with a ring (c ring), and if bonded, it will form a ring structure similar to the B' ring and D' ring described above. This will change.

[0045] The compound represented by formula (2-1) above is, for example, the specific compound listed later. This corresponds to compounds represented by (1-5). That is, for example, a b-ring (or d-ring) For some benzene rings, there are benzene rings; for others, there are indole rings, pyrrole rings, and benzofura rings. It has a B' ring (or D' ring) formed by the condensation of an N ring or a benzothiophene ring, etc. It is a compound in which the resulting fused ring B' (or fused ring D') is a naphthalene ring, and Other rings include the carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring. And so on.

[0046] Y is B (boron).

[0047] X in general formula (1) 1 , X 2 , X 3 and X 4 These are, independently, >O and >N -R, >S or >Se, where R in >NR may be substituted with an aryl, It is an optionally substituted heteroaryl or optionally substituted alkyl, and The R in >NR is a linking group or single bond to the A ring, B ring, C ring and / or D ring. It may be bonded to a ring, and preferred linking groups are -O-, -S-, or -C(-R)2-. It seems so. Furthermore, the R in the aforementioned "-C(-R)2-" is either hydrogen or alkyl. This explanation is X in general formula (2) 1 , X 2 , X 3 and X 4 But it's the same.

[0048] Here, in general formula (1), R in ">NR" is a linking group or a single bond to the A ring, The provision that it is bonded to a B ring, a C ring and / or a D ring is expressed in general formula (2) as ">N- R in R is -O-, -S-, -C(-R)2-, or a single bond to the a, b, or c rings. This corresponds to the provision that it is "bonded to a d-ring and / or a d-ring".

[0049] This provision is represented by the following formula (2-3), X 1 Ya X 3 fused ring B' and fused ring D' It can be represented by a compound having a ring structure incorporated into it. That is, for example, in general formula (2) For a benzene ring which is a b-ring (or d-ring), X 1 (or X 3 ) This compound has a B' ring (or D' ring) that is formed by the condensation of other rings. Compounds are, for example, those represented by formula (1-11), which are listed as specific compounds later. The fused ring B' (or fused ring D') formed in response to the compound is, for example, carbazeo. Other examples include the flu ring, phenoxazine ring, phenothiazine ring, or acridine ring. Note that the definitions of each sign in equation (2-3) are the same as the signs in general equation (2).

[0050] [ka]

[0051] In equation (2-3), X 1 Ya X 3 This shows a ring structure in which the compound is incorporated into fused rings B' and D'. However, X 2 Ya X 4 Similarly, the R in NR can bond to a-rings and c-rings, and When combined, the ring structure will change, similar to the B' and D' rings described above.

[0052] Furthermore, substituent Z in general formula (2) 1 and Z 2 The substitution sites are in ring a and ring c. It is limited to the para position where Y (boron) is bonded. The A ring of general formula (1) and The C ring is not limited to a benzene ring, but can be various aryl rings or heteroaryl rings, and these Substitution Z on the ring 1 and Z 2 The substitution position is not limited, but as with general formula (2), Y is connected It is preferable to replace the position at a location relatively far from the point of alignment, and to replace it at the furthest position. This is more preferable. For example, when ring A is a naphthalene ring or a fluorene ring. This Z 1 (and Z2 The following are examples of preferred substitution positions for ). The symbols in each structure are general The sign has the same definition as in equation (2). Also, A is >CR2, >NR2, >O or > S is hydrogen, and R is hydrogen, alkyl (preferably an alkyl with 1 to 4 carbon atoms), or phenyl. be. [ka]

[0053] R in general formula (1) or general formula (2) 1 and R 2 Each of them independently, hydrogen alkyl groups with 1 to 6 carbon atoms, aryl groups with 6 to 12 carbon atoms, and heteroaryl groups with 2 to 15 carbon atoms. It is either a diarylamino or diarylamino (where aryl has 6 to 12 carbon atoms).

[0054] Z in general formula (1) or general formula (2) 1 and Z 2 Each of them is independent of the others. aryl, heteroaryl, diarylamino, diheteroarylamino, arylhetero Rylamino, alkyl, aryloxy, heteroaryloxy, arylthio or These are heteroarylthios, and at least one hydrogen in them is either aryl or hetero. Aryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy Alternatively, it may be substituted with an alkyl-substituted silyl, Z 1 is a linking group or single bond in A It may also bond with a ring (a ring), Z 2 is linked to the C ring (c ring) by a linking group or single bond. This is also good. Examples of linking groups include -O-, -S-, -C(-R)2-, and the preceding In the notation -C(-R)2-, R is either hydrogen or alkyl.

[0055] Examples of "aryl rings" that are rings A, B, C, and D of general formula (1) include, Examples include aryl rings having 6 to 30 carbon atoms, with aryl rings having 6 to 16 carbon atoms being preferred. An aryl ring having 6 to 12 carbon atoms is more preferred, and an aryl ring having 6 to 10 carbon atoms is particularly preferred. Furthermore, this "aryl ring" is defined in general formula (2) as "R 5 ~R 7 and R 10 ~R 12 Among them, adjacent groups bond together to form an alley ring with the b-ring and / or d-ring. It corresponds to the "L ring," and the B ring (or D ring) is already composed of a benzene ring with 6 carbon atoms. Therefore, the lower limit of carbon numbers is 9, which is the total number of carbon atoms in the fused ring formed by the condensation of a 5-membered ring. Z 1 An aryl ring formed by a linking group or single bond with the A ring (a ring), or Z 2 ga The same applies to aryl rings formed by bonding to a C ring (or c ring) via a binder or single bond.

[0056] Specific examples of "aryl rings" include the monocyclic benzene ring and the bicyclic biphenyl ring. The ring, the condensed bicyclic naphthalene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a condensed tricyclic system, acenaphthylene ring, fluorine Lenne ring, phenalene ring, phenanthrene ring, condensed tetracyclic triphenylene ring, pyrene Examples include rings, naphthacene rings, and condensed pentacyclic systems such as perylene rings and pentacene rings.

[0057] Examples of heteroaryl rings, which are the A, B, C, and D rings of general formula (1), include: Examples include heteroaryl rings with 2 to 30 carbon atoms, and heteroaryl rings with 2 to 25 carbon atoms. A ring is preferred, a heteroaryl ring having 2 to 20 carbon atoms is more preferred, and a heteroaryl ring having 2 to 15 carbon atoms is preferred. A teloaryl ring is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Furthermore, as a "heteroaryl ring," for example, if the ring constituent atoms include oxygen, sulfur, etc., in addition to carbon Examples include heterocycles containing one to five heteroatoms selected from nitrogen. This "heteroaryl ring" is defined by the "R" in general formula (2). 5 ~R 7 and R 10 ~ R 12 Among them, adjacent groups bond together to form a heterozygous ring with the b-ring and / or d-ring. It corresponds to a "roaryl ring," and the b ring (or d ring) is already composed of a benzene ring with 6 carbon atoms. Therefore, the lower limit of carbon numbers is 6, which is the total number of carbon atoms in the fused ring formed by the condensation of a 5-membered ring. Also, Z 1 A heteroaryl compound formed by a linking group or single bond connecting to the A ring (a ring). Rings and Z 2 Heteroaryl rings formed by a linking group or single bond to a C ring (c ring) are also It is the same.

[0058] Specific examples of "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, and iso Oxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole Ring, thiadiazole ring, triazole ring, tetrazol ring, pyrazole ring, pyridine ring, Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindo 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzoth Azole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, synnoline ring , quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine phenoxathiine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenox Thiazine ring, phenazine ring, indoridine ring, furan ring, benzofuran ring, isobenzof Lan ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring Examples include the furazan ring, oxadiazole ring, and thianthlene ring.

[0059] At least one hydrogen in the above "aryl ring" or "heteroaryl ring" is The substituents of 1 are substituted or unsubstituted "aryl" and substituted or unsubstituted "heteroaryl". "diarylamino", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteramino" "arylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted Substitutive "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "al "Coxy," substituted or unsubstituted "aryloxy," substituted or unsubstituted "heteroaryl" "Luoxy", substituted or unsubstituted "arylthio", substituted or unsubstituted "heteroary" The first substituent may be substituted with "lutio" or alkyl-substituted silyl, but as The aryl and diheteroaryl compounds in "arylaminos" and "diarylaminos" "Heteroaryl" in "arylamino," and "aryl" and "heteroarylamino" in "arylheteroarylamino." Roaryl, the aryl in "aryloxy", the heteroaryl in "heteroaryloxy" As for the aryl in "arylthio" and the heteroaryl in "heteroarylthio", the above Examples include the monovalent groups of the aforementioned "aryl rings" or "heteroaryl rings."

[0060] Furthermore, the "alkyl" as the first substituent can be either a straight chain or a branched chain. Examples include linear alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. It is possible. C1-C18 alkyl (C3-C18 branched alkyl) is preferred, Alkyl groups with prime numbers 1 to 12 (branched-chain alkyl groups with 3 to 12 carbon atoms) are more preferred, and C1 ~6 alkyl groups (branched alkyl groups with 3 to 6 carbon atoms) are more preferred, and C1 to C4 alkyl groups are also preferred. Lukyl (branched alkyl group with 3-4 carbon atoms) is particularly preferred.

[0061] Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, and 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-oc Tyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5, 5-Trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl n-Tridecyl, 1-Hexylheptyl, n-Tetradecyl, n-Pentadecyl, n Examples include hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. ru.

[0062] Furthermore, as the first substituent, "cycloalkyl" can be, for example, a cycloalkyl group with 3 to 12 carbon atoms. Examples include cycloalkyls. Preferred cycloalkyls are cycloalkyls having 3 to 10 carbon atoms. It is a cycloalkyl group. More preferable are cycloalkyl groups with 3 to 8 carbon atoms. The preferred cycloalkyl group is a cycloalkyl group having 3 to 6 carbon atoms.

[0063] Specific cycloalkyl groups include cyclopropyl, cyclobutyl, and cyclopentyl. Cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclo Examples include loctyl, dimethylcyclohexyl, or adamantyl.

[0064] Furthermore, as the first substituent, "alkoxy" can be, for example, a linear chain with 1 to 24 carbon atoms. Examples include branched alkoxy compounds with 3 to 24 carbon atoms. Also, alkoxy compounds with 1 to 18 carbon atoms ( Branched alkoxys with 3 to 18 carbon atoms are preferred, and alkoxys with 1 to 12 carbon atoms are preferred. Branched alkoxys with 3 to 12 carbon atoms are more preferred, and alkoxys with 1 to 6 carbon atoms are more preferred. A branched alkoxy with 3 to 6 carbon atoms is more preferable, and an alkoxy with 1 to 4 carbon atoms (3 carbon atoms) is even more preferable. ~4 branched chain alkoxys are particularly preferred.

[0065] Specific alkoxys include methoxy, ethoxy, propoxy, isopropoxy, and b Toxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy Examples include heptyloxy and octyloxy.

[0066] Furthermore, as the first substituent, "alkyl-substituted silyl" is trialkyl-substituted silyl. This is preferable. Regarding the alkyl to be substituted, the "alkyl" as the first substituent as described above is You can refer to the explanation.

[0067] The first substituent is a substituted or unsubstituted "aryl" or a substituted or unsubstituted "hetero" "aryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "dihetero" "Arylamino", substituted or unsubstituted "arylheteroarylamino", substituted or Unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted " "Alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "hetero" "Rieloxy", substituted or unsubstituted "arylthio", substituted or unsubstituted "hetero" "Rilthio" is described as either substituted or unsubstituted, and in those cases, at least One hydrogen atom may be substituted with a second substituent. This second substituent could be, for example, Examples include aryl, heteroaryl, or alkyl groups, and specific examples of these are as described above. A monovalent group of an "aryl ring" or "heteroaryl ring," and also "aryl" as the first substituent. You can refer to the explanation of "kill". Also, aryl or heteroaryl as a second substituent. The reels contain at least one hydrogen atom in them that is an aryl such as phenyl (specific examples are Groups substituted with the aforementioned groups or alkyl groups such as methyl (specific examples are the aforementioned groups) are also secondly substituted. This includes aryl and heteroaryl compounds as substitution groups. For example, the second substituent is In the case of the carbazolyl group, at least one hydrogen at position 9 is a phenyl or other ally Carbazolyl groups substituted with alkyl groups such as methyl or methyl can also be used as a second substituent. It is included in the reel.

[0068] R in general formula (2) 3 ~R 12 In which, aryl, heteroaryl, diarylamino aryl, diheteroarylammonium, heteroaryl, arylheteroarylammonium aryl and heteroaryl, aryloxy of aryl, heteroaryloxy of hetero As for roaryl, arylthio, and heteroaryl, Examples include the monovalent group of the "aryl ring" or "heteroaryl ring" described in general formula (1). It can be. Also, R 3 ~R 12 Alkyl, cycloalkyl, alkoxy or alkyl As for the silyl substitution, the first substituent in the explanation of general formula (1) above is "A Explanation of "Lucyl," "Cycloalkyl," "Alkoxy," or "Alkyl-substituted Silyl" It can be referenced. Furthermore, aryl and heteroaryl groups can be used as substituents on these groups. The same applies to R or alkyl. Also, R 5 ~R 7 and R 10 ~R 12 Among the adjacent The groups bond together to form an aryl ring or heteroaryl ring with the b-ring or d-ring. In this case, substituents on these rings are aryl, heteroaryl, diarylamino, and di Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, a Lucoxy, aryloxy, heteroaryloxy, arylthio, heteroarylthio or alkyl-substituted silyls, and further substituents such as aryl and heteroaryl compounds. The same applies to alkyl groups.

[0069] X in general formula (1) 1 , X 2 , X 3 and X 4 In NR, R stands for aryl, heterozygous. It is aryl or alkyl, and at least one hydrogen in these is aryl, heterozygous. Roaryl, diarylamino, diheteroarylamino, arylheteroarylamino No, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, It may be substituted with an arylthio, heteroarylthio, or alkyl-substituted silyl. Examples of these groups and the substituents that substitute for them are listed above. In particular, groups with 6 to 1 carbon atoms. 0 aryls (e.g., phenyl, naphthyl), heteroaryls with 2-15 carbon atoms (e.g.) For example, carbazolyl is preferred, and alkyl groups with 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) are preferred. This explanation is for X in general formula (2). 1 , X 2 , X 3 and X 4 But it's the same.

[0070] In general formula (1), the linking group "-C(-R)2-" has R as either hydrogen or alkyl. However, the alkyl groups mentioned above are examples of such groups. In particular, groups with 1 to 6 carbon atoms, and even carbon groups. Alkyl atoms with prime numbers 1 to 4 (e.g., methyl, ethyl, etc.) are preferred. This explanation is based on the general formula (2 The same applies to the linking group "-C(-R)2-" in ).

[0071] R in general formula (1) or general formula (2) 1 and R 2 alkyl groups having 1 to 6 carbon atoms aryls with 6 to 12 carbon atoms, heteroaryls or diarylaminos with 2 to 15 carbon atoms (However, aryls are aryls with 6 to 12 carbon atoms) For a more detailed explanation, see above. Explanation of "alkyl," "aryl," "heteroaryl," or "diarylamino" You can refer to this.

[0072] Z in general formula (1) or general formula (2) 1 and Z 2In, aryl, heteroaryl Lu, diarylamino, diheteroarylamino, arylheteroarylamino, aryl Kill, cycloalkyl, aryloxy, heteroaryloxy, arylthio or he Telarylthio, and furthermore, aryl, heteroaryl, and diaryl as substituents to these. Alkylamino, alkyl, cycloalkyl, alkoxy, aryloxy or alkyl Regarding the converted silyls, as mentioned above, there are "aryl," "heteroaryl," and "diarylamino" compounds. "Diheteroarylamino", "Arylheteroarylamino", "Aryloxy "C", "heteroaryloxy", "arylthio", "heteroarylthio", "al See the explanation of "kill," "cycloalkyl," "alkoxy," or "alkyl-substituted silyl." It can be illuminated. Preferred Z 1 and Z 2 Examples include diarylamino and alkyl groups. These include heteroaryl compounds such as cycloalkyl, aryloxy, and carbazole.

[0073] Furthermore, all or part of the hydrogen in the compound represented by general formula (1) or (2) It may be substituted with cyano, halogen or deuterium. For example, in formula (1), Ring A, Ring B, Ring C, Ring D (Rings A-D are aryl rings or heteroaryl rings), back to Rings A-D substituents, X 1 ~X 4 In NR, R (=aryl, heteroaryl, alkyl) is the correct term. ), R 1 , R 2 , Z 1 and Z 2 Hydrogen in this case is replaced by cyano, halogen, or deuterium. However, among these, all or some of the hydrogen in aryl and heteroaryl compounds may be Examples include embodiments substituted with ano, halogen, or deuterium. Halogens include fluorine, chlorine , bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine be.

[0074] A specific example of a polycyclic aromatic compound represented by formula (1) is, for example, the following structural formula: Examples of such compounds include: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] (At least one hydrogen atom in each of the compounds represented by the above formulas is an alkyl group having 1 to 6 carbon atoms) They may be substituted with aryl, cyano, halogen, or deuterium atoms having 6 to 10 carbon atoms. In the formula, R is independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms. (Yes, preferably phenyl, methyl, or t-butyl.)

[0075] Further specific examples of polycyclic aromatic compounds represented by formula (1) include, for example, the following: Examples include compounds represented by their chemical formulas. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0076] In each of the compounds represented by the above formulas, at least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms. They may be substituted with aryl, cyano, halogen, or deuterium atoms having 6 to 10 carbon atoms. R in the formula 100 These are, independently, aryl, carbazolyl, and dia compounds with 6 to 10 carbon atoms. Rylamino (where aryl is an aryl with 6 to 10 carbon atoms), alkyl with 1 to 6 carbon atoms , a cycloalkyl group having 3 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, The aforementioned "aryl", "aryl" in "diarylamino", and "aryloxy" The "aryl" may be substituted with an alkyl group having 1 to 6 carbon atoms, and the carbazolyl is carbon It may be substituted with aryl atoms having 6 to 10 carbon atoms or alkyl atoms having 1 to 6 carbon atoms.

[0077] R 100 The emission wavelength is adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the structure. It can be a group represented by the following formula, preferably methyl, t-br Tyl, 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, more preferably me Chil, 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 and 3,6-di-t-butylcarbazol It is Lil. From the standpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis. Specifically, t-butyl, 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 and 3,6-di -t-butylcarbazol is preferred.

[0078] [ka]

[0079] From the perspective of difficulty of synthesis, the structure has high symmetry and / or p is used for the N binding site. Structures having substituents at the 1-position are preferred, specifically, formula (1-5000-R100), formula (1-5010-R100), Formula (1-5020-R100), Formula (1-5100-R100), Formula (1-5110-R100), Formula (1-5120-R100), Formula (1-7000-R1 00), formula (1-7010-R100), formula (1-7020-R100), formula (1-7100-R100), formula (1-7110-R100), formula (1-71 20-R100), formula (1-7200-R100), formula (1-7210-R100), formula (1-7220-R100), formula (1-7400-R100), formula Formulas (1-7410-R100), (1-7420-R100), and (1-9000-R100) are preferred, and formula (1-5000-R100), Formulas (1-5010-R100), (1-5020-R100), (1-5100-R100), (1-5110-R100), and (1-512 0-R100) is more preferable.

[0080] Furthermore, from the viewpoint of blue light emission and / or high luminescence efficiency, having many N-aryl groups is desirable. Structures having a large amount of the formula and / or carbazolyl structure are preferred, specifically, (1-5000-R100), formula (1-5010-R100), formula (1-5020-R100), formula (1-5100-R100), formula (1-5110-R100) ), formula (1-5120-R100), formula (1-6000-R100), formula (1-6010-R100), formula (1-6020-R100), formula (1-6200 -R100), formula (1-6210-R100), formula (1-6220-R100), formula (1-7400-R100), formula (1-7410-R100) and Formula (1-7420-R100) is preferred.

[0081] Furthermore, from the perspective of enhancing the multiple resonance effect, the one with more nitrogen atoms bonded to the central aromatic ring is preferable. Preferably, formulas (1-5000-R100), formulas (1-5010-R100), formulas (1-5020-R100), and formulas (1- 5100-R100), formula (1-5110-R100), formula (1-5120-R100), formula (1-6100-R100), formula (1-6110-R100), Formula (1-6120-R100), Formula (1-6500-R100), Formula (1-6510-R100), Formula (1-6520-R100), Formula (1-7100-R1 Formulas (00), (1-7110-R100), and (1-7120-R100) are preferred.

[0082] More specific examples of polycyclic aromatic compounds represented by formula (1) include, for example, the following (1 Examples include compounds represented by structural formulas starting with (1) below, as well as compounds starting with formula (1-1) below. This also includes compounds with structural formulas in which the t-butyl group is substituted with a methyl group, and , R of general formula (1) 1 and R 2 In a structural formula where the corresponding site is a phenyl group, R 1 and R 2 A compound with a structural formula in which both phenyl groups are replaced by methyl groups, R 1Phenyl The group is replaced by hydrogen and R 2 A compound whose structural formula consists only of a phenyl group, R 2 The phenyl group of water Substituting into R 1 A compound whose structural formula consists only of a phenyl group, R 1 The phenyl group is a methyl group Replaced with R 2 Compounds with a structural formula in which the phenyl group is replaced by hydrogen, and R 1 Phoenix The R group is substituted with hydrogen. 2 This also includes compounds with structural formulas in which the phenyl group is replaced by a methyl group. For example, taking the structural formulas of equation (1-2) and (1-6) as examples, they are as follows: Yes. Note that "Me" in each formula is a methyl group, t "Bu" is a t-butyl group, and "Ph" is a phosphate group. It is a nyl group.

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[0208] 2. Method for producing polycyclic aromatic compounds Polycyclic aromatic compounds represented by general formulas (1) and (2) are basically each of the ring structures An intermediate is produced by bonding the elements together (first reaction), and then the ring structures of each element are combined. The final product can be produced by bonding with a chlorine atom (second reaction). First reaction For example, common etherification reactions such as nucleophilic substitution reactions and Ullmann reactions, and Buff Common amination reactions such as the Balt-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (a series of electrophilic aromatic substitution reactions) The following schemes can be used. Note that the symbols in the structural formulas in the following schemes are the same as the general formula (1 ) or the same definition as those in general formula (2).

[0209] The second reaction involves the bonding of boron atoms that connect the respective ring structures, as shown in the scheme (1) below. This is a reaction that introduces a child. First, X 1 and X 2 between and X 3 and X 4 The hydrogen atom between them is n- Orthometals such as butyllithium, sec-butyllithium, or t-butyllithium. Next, boron trichloride or boron tribromide is added to perform lithium-boron metal exchange. After this, add a Brønsted base such as N,N-diisopropylethylamine. Then, a tandem Boraf-Friedelcrafts reaction is carried out to obtain the target product. Second reaction In this case, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. [ka]

[0210] In scheme (1), lithium was introduced to the desired location by orthometallation. As shown in the scheme (2) below, halogen atoms (Hal) are pre-placed at the positions where lithium is to be introduced. By introducing this, lithium can also be introduced to the desired position by halogen-metal replacement. This method allows for the formation of the desired product even in cases where orthometallation is not possible due to the influence of substituents. It is useful because it can synthesize objects. [ka]

[0211] By appropriately selecting the above synthesis method and the raw materials used, substituents can be formed at the desired positions. It has Y being boron, X 1 , X 2 , X 3 and X 4 However, independently of each other, >O, >N- Polycyclic aromatic compounds with R, >S, or >Se can be synthesized.

[0212] Furthermore, the tandem bora-Friedelcrafts reaction can be performed by, for example, the rotation of the amino group in the intermediate. Because the location where the reaction occurs may differ, by-products may also be generated. In addition, the desired polycyclic aromaticization is performed from these mixtures by chromatography, recrystallization, etc. The compound can be isolated.

[0213] Examples of orthometalation reagents used in the above scheme include methyllithium, n- Alkyl lithiums such as butyllithium, sec-butyllithium, and t-butyllithium. Lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexam Examples include organic alkali compounds such as tildisilazide and potassium hexamethyldisilazide. ru.

[0214] The metal exchange reagent used in the above scheme for metal-Y (boron) is triphosphate of boron. Boron halides such as trichlorides, tribromides, triiodides, and CIPN (NET) 2) Amination halides of Y, alkoxy compounds of Y, and aryl oxy compounds of Y, such as 2. These are some examples.

[0215] The Brønsted base used in the above scheme is N,N-diisopropylethyl Amine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6 ,6-Pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine N, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate Mu, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B Examples include Ar4Si (where Ar is an aryl group such as phenyl).

[0216] The Lewis acids used in the above scheme are AlCl3, AlBr3, AlF3, and BF3. 3·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(O Tf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrB Examples include r4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0217] In the above scheme, to facilitate the tandem hetero-Friedel-Crafts reaction, Brønste A Lewis base or Lewis acid may be used. However, boron trifluoride, trichloride, and trifluoride may be used. When boron halides such as bromide and triiodide are used, the aromatic electrophilic substitution reaction As the process progresses, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced. The use of Brønsted bases to capture acids is effective. On the other hand, the amination of boron When genides and boron alkoxides are used, the aromatic electrophilic substitution reaction proceeds along Brønsted bases are often used to produce amines and alcohols. Although not necessary, Louis promotes the elimination of amino and alkoxy groups due to their low elimination ability. The use of sulfuric acid is effective.

[0218] Furthermore, polycyclic aromatic compounds represented by general formula (1) or (2) include at least some This also includes compounds in which hydrogen atoms are substituted with cyano, halogen, or deuterium, but For eel compounds and the like, use raw materials in which the desired portion has been cyanated, halogenated, or deuterated. And, as described above, they can be synthesized.

[0219] 3. Organic devices The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of mechanical devices include organic field-emitting diodes, organic field-effect transistors, or organic Examples include thin-film solar cells.

[0220] 3-1. Organic electroluminescent element The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. This is possible. Below, the organic EL element according to this embodiment will be described in detail based on the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

[0221] <Structure of Organic Field-Emitting Light> The organic electroluminescent element 100 shown in Figure 1 comprises a substrate 101 and a substrate 101 provided on the substrate 101. an anode 102, a hole injection layer 103 provided on the anode 102, and on the hole injection layer 103 A hole transport layer 104 is provided therein, and a light-emitting layer 105 is provided on the hole transport layer 104, An electron transport layer 106 provided on the light-emitting layer 105, and an electron transport layer 106 provided on the electron transport layer 106 It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

[0222] Furthermore, the organic electroluminescent element 100 can be manufactured in the reverse order, for example, by using substrate 101 and substrate A cathode 108 provided on 101, and an electron injection layer 107 provided on cathode 108, An electron transport layer 106 provided on top of the electron injection layer 107, and an electron transport layer 106 provided on top of the electron transport layer 106 A light-emitting layer 105, a hole transport layer 104 provided on the light-emitting layer 105, and a hole transport layer 1 A hole injection layer 103 is provided on 04, and an anode 10 is provided on the hole injection layer 103. A configuration having both 2 and 3 may also be used.

[0223] Not all of the above layers are necessarily required; the minimum constituent unit consists of the anode 102 and the light-emitting layer. The structure consists of 105 and cathode 108, with a hole injection layer 103, a hole transport layer 104, and electron The transport layer 106 and the electron injection layer 107 are optional layers. Each layer may consist of a single layer or multiple layers.

[0224] The configuration of the layers constituting the organic electroluminescent element is as described above: "substrate / anode / hole injection layer / In addition to the configuration of "hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", there is also "substrate / anode". / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode", "Substrate / Anode / Hole injection layer / Emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emission" Photolayer / Electron injection layer / Cathode, Substrate / Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport Layer / cathode", Substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", Substrate / anode / Hole transport layer / emissive layer / electron injection layer / cathode, substrate / anode / hole transport layer / emissive layer / electron transport "Transmitting layer / cathode", "Substrate / anode / hole injection layer / emissive layer / electron injection layer / cathode", "Substrate / anode / Hole injection layer / Emitting layer / Electron transport layer / Cathode", "Substrate / Anode / Emitting layer / Electron transport layer / Cathode" The configuration may also consist of "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0225] <Substrate for organic electroluminescent light-emitting devices> The substrate 101 is a support for the organic electroluminescent element 100, and is typically made of quartz, glass, metal, Plastics and the like are used. The substrate 101 can be in the form of a plate, a film, or depending on the purpose. Formed in sheet form, for example, glass plate, metal plate, metal foil, plastic film, plastic Stick sheets are used, among others. Glass plates, and polyester, polymer Transparent synthetic resin sheets such as acrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass are used, and also, The thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more. That's fine. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, it is preferable to use one with fewer ions leached from the glass, so alkali-free glass is recommended. While this is preferable, soda-lime glass with a barrier coating such as SiO2 is also commercially available. Therefore, this can be used. In addition, the substrate 101 has a gas barrier property that enhances the gas barrier properties. Therefore, a gas barrier film such as a dense silicon oxide film may be provided on at least one side, in particular A board, film, or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101. In such cases, it is preferable to provide a gas barrier film.

[0226] <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 layer 105 In this case, holes will be injected into the light-emitting layer 105 via these.

[0227] Materials that can form the anode 102 include inorganic compounds and organic compounds. Examples of compounds include metals (aluminum, gold, silver, nickel, palladium, chromium). (etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (I TO), indium zinc oxide (IZO), metal halides (copper iodide, etc.), Examples include copper sulfide, carbon black, ITO glass, and NESA glass. Organic compounds and For example, polythiophenes such as poly(3-methylthiophene), polypyrrole, Examples include conductive polymers such as polyaniline. Other examples include the anode of an organic electroluminescent device. Substances used for this purpose can be appropriately selected and used.

[0228] The resistance of the transparent electrode is not limited, as long as it can supply enough current for the light-emitting element to emit light. However, from the standpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, 300Ω / □The following ITO substrates will function as element electrodes, but currently, substrates with an impedance of approximately 10Ω / □ are available. Since it is also possible to supply such as, for example, 100~5Ω / □, preferably 50~5Ω / It is especially desirable to use low-resistance components marked with a square. The thickness of the ITO can be arbitrarily selected according to the resistance value. It can be used in a wider range, but it is usually used in the 50-300nm range.

[0229] <Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 efficiently delivers holes moving from the anode 102 into the light-emitting layer 105. Alternatively, it plays the role of injecting into the hole transport layer 104. The hole transport layer 104 is from the anode 102 The injected holes or holes injected from the anode 102 through the hole injection layer 103 are efficiently The hole injection layer 103 and hole transport layer 104 play a role in transporting the holes to the light-emitting layer 105. Each involves laminating or mixing one or more types of hole injection / transport materials, or hole injection / transport materials. It is formed from a mixture of transport material and polymer binder. Additionally, iron chloride is used as the hole injection / transport material. (III) An inorganic salt may be added to form a layer.

[0230] As a hole-injecting and transporting material, it efficiently transports holes from the positive electrode between electrodes under an applied electric field. It is necessary to inject and transport the holes efficiently, and the hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do so. For this to happen, the ionization potential must be small and the hole mobility must be It is large, highly stable, and less likely to generate trapping impurities during manufacturing and use. It is preferable that the substance is fine.

[0231] The material used to form the hole injection layer 103 and the hole transport layer 104 is a photoconductive material. Compounds conventionally used as hole charge transport materials, p-type semiconductors, and organic field generators are examples of such materials. Any compound from among known compounds used in the hole injection layer and hole transport layer of optical devices You can select and use items.

[0232] Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinyl carbazole). (e.g., bazole), bis(N-arylcarbazole), or bis(N-alkylcarbazole) Biscarbazole derivatives such as (aromatic tertiary amino acids), triarylamine derivatives (aromatic tertiary amino acids) A polymer having 1,1-bis(4-di-p-tolylaminophenyl) as its main chain or side chain. Cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4 '-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-di Aminobiphenyl, 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’ -Tetra[1,1'-biphenyl] -4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tri Triphenylamines such as (3-methylphenyl(phenyl)amino)triphenylamine (e.g., amine derivatives, starburst amine derivatives), stilbene derivatives, phthalocyanine derivatives) Conductors (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, ben Zofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (examples) For example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10, Heterocyclic compounds such as 11-hexacarbonnitrile, porphyrin derivatives, and polysilamines. Examples include polycarbonates and styrene derivatives that have the monomer in their side chains. Conductors, polyvinylcarbazole, and polysilane are preferred, but are necessary for the fabrication of the light-emitting element. If a compound can form the necessary thin film, allow holes to be injected from the anode, and further transport holes, then that compound would be suitable. It is not particularly limited.

[0233] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by doping. Such organic semiconductor matrix materials are compounds with good electron-donating properties, or It is composed of compounds with good electron-accepting properties. For doping with electron-donating substances, Tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetra Strong electron acceptors such as cyano-1,4-benzoquinone dimethane (F4TCNQ) are known. (For example, see the reference "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 32 02-3204(1998)" and the document "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., See 73(6), 729-731(1998). These are electron-donating base materials (hole transport materials). The electron transfer process in ) generates so-called holes. The number and mobility of holes This significantly alters the conductivity of the base material. Examples of the compound include benzidine derivatives (such as TPD) or starburst amino acids. Fluorine derivatives (such as TDATA) or certain metal phthalocyanines (especially zinc phthalocyanine) Examples include ZnPc (Japanese Patent Publication No. 2005-167175).

[0234] <Emitting layer in organic electroluminescent element> The light-emitting layer 105 emits holes injected from the anode 102 between electrodes to which an electric field is applied. This is a light-emitting layer that emits light by recombining with electrons injected from cathode 10⁸. The material that forms 105 is a compound that emits light when excited by the recombination of holes and electrons. Any substance (luminescent compound) will suffice, and it must be able to form a stable thin film shape and be in a solid state. It is preferable that the compound exhibits strong luminescence (fluorescence) efficiency in its state. In the present invention, the material for the luminescent layer As a material, a polycyclic aromatic compound represented by the above general formula (1) can be used.

[0235] The light-emitting layer can consist of a single layer or multiple layers, and each layer is made of a material for the light-emitting layer (phosphorus). It is formed from a host material and a dopant material. The host material and the dopant material are, respectively It can be one type or a combination of multiple types. The dopant material is H It may be included in the entire material or in part. As for the coating method, it can be formed by co-deposition with a host material, but The host material is pre-mixed with the host material and then simultaneously deposited, or the host material is pre-mixed with an organic solvent. The film may also be formed by a wet deposition method.

[0236] The amount of host material used varies depending on the type of host material, and should be adjusted according to the characteristics of that host material. You can decide based on that. The guideline for the amount of host material to use is preferably 50% of the total amount of material for the light-emitting layer. It is 99.999% by weight, more preferably 80-99.95% by weight, and even more preferably It is more accurately 90-99.9% by weight.

[0237] The amount of dopant material used varies depending on the type of dopant material. The amount of dopant to use should be determined according to its characteristics. Preferably, the amount of dopant to use is determined by the light-emitting layer material. It is 0.001 to 50% by weight of the total, more preferably 0.05 to 20% by weight, More preferably, the concentration is 0.1 to 10% by weight. Within this range, for example, concentration quenching phenomenon It is preferable in that it can prevent [this].

[0238] On the other hand, in organic field light-emitting devices using thermally activated delayed fluorescence dopant materials, the dopants While it is preferable to use a low concentration of the ant material in order to prevent the concentration quenching phenomenon, 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-assisted dopant materials... In this regard, from the standpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material, It is preferable that the amount of dopant material used is at a lower concentration compared to the amount of dopant material used.

[0239] When assist dopant material is used, the host material and assist dopant The approximate amounts of material and dopant material to be used are 40-99% of the total material for the light-emitting layer. The amounts are 0.999% by weight, 59-1% by weight, and 20-0.001% by weight, preferably so These are 60-99.99% by weight, 39-5% by weight, and 10-0.01% by weight, respectively. More preferably, 70-99.95% by weight, 29-10% by weight, and 5-0.05% by weight. The compounds and polymer compounds according to the present invention can also be used as assist dopant materials. It is also possible.

[0240] As host materials, anthracene and pyrene, which have long been known as luminescent materials, are used. Condensed ring derivatives, bis-styrylanthracene derivatives and distylylbenzene derivatives, etc. Styryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorine Examples include fluorene derivatives and benzofluorene derivatives.

[0241] The T1 energy of the host material does not inhibit but promotes the generation of TADF within the light-emitting layer. From a point of view, the dopant or assisting agent with the highest T1 energy within the luminescent layer is identified. It is preferable that the T1 energy is higher than that of the pant, specifically the T1 energy of the host. Ghee is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and 0.1 eV or lower. The above is even more preferable. Furthermore, a TADF-active compound may be used as the host material.

[0242] Examples of host materials include compounds represented by the following general formula (3) and the following general formula ( Examples of compounds represented in 4) include the following. [ka] In the above formula (3), L 1 These are arylenes with 6 to 24 carbon atoms, and arylenes with 6 to 16 carbon atoms. Len is preferred, arylene with 6 to 12 carbon atoms is more preferred, and arylene with 6 to 10 carbon atoms is preferred. Len is particularly preferred, specifically a benzene ring, a biphenyl ring, a naphthalene ring, or terfen. Nyl ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, triphe Examples of divalent groups include the nilen ring, pyrene ring, naphthacene ring, perylene ring, and pentacene ring. It can be done. In the above formula (4), L 2 and L 3 Each of these is an aryl group with 6 to 30 carbon atoms, independently of the others. These are heteroaryls with 2 to 30 carbon atoms. As for aryls, there are heteroaryls with 6 to 24 carbon atoms. aryls are preferred, aryls with 6 to 16 carbon atoms are more preferred, and aryls with 6 to 12 carbon atoms are preferred. More preferably, aryls having 6 to 10 carbon atoms are particularly preferred, specifically, benzene rings , biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, ph Phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perylene Examples include monovalent groups such as rings and pentacene rings. Heteroaryls include those with 2 carbon atoms. Heteroaryls with ~25 carbon atoms are preferred, and heteroaryls with 2 to 20 carbon atoms are more preferred. Heteroaryls having 2 to 15 carbon atoms are more preferred, and heteroaryls having 2 to 10 carbon atoms are preferred. Particularly preferred are pyrrole rings, oxazole rings, isoxazole rings, and thiazo rings. Isothiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, Triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridadi H-ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazo 1H-ben ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-ben Zotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoki Sarin ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, Acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine Ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran Ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadi Examples include monovalent groups such as azole rings and thianthlene rings. At least one hydrogen atom in the compound represented by formula (3) or formula (4) has a carbon atom. It may be substituted with alkyl, cyano, halogen, or deuterium atoms of ~6.

[0243] Furthermore, examples of host materials include compounds represented by the following general formula (5). . [ka] (In the above formula (5), R 1 ~R 11 These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino or alkyl (the above, (First substituent) and at least one hydrogen in these is further aryl, heteroa It may also be substituted with a reel, diarylamino, or alkyl (the above are secondary substituents). , R 1 ~R 11 Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and It may also be substituted with a reel heteroarylamino or alkyl (the above is the first substituent). Furthermore, at least one hydrogen in these is further aryl, heteroaryl, or diary They may be substituted with a ruamino or alkyl (the above are the second substituents), In the compound represented by formula (5), at least one hydrogen atom is independently a halo It may be substituted with ion or deuterium.

[0244] Preferably, in formula (5) above, R 1 ~R 11 These are, independently, hydrogen, aryl atoms with 6 to 30 carbon atoms, and aryl atoms with 2 to 3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) Or an alkyl group having 1 to 12 carbon atoms, where at least one hydrogen atom is further Aryls with 6-30 carbon atoms, heteroaryls with 2-30 carbon atoms, diarylaminos (but The aryl is substituted with an aryl (with 6 to 12 carbon atoms) or an alkyl (with 1 to 12 carbon atoms). It's okay to be there, R 1 ~R 11 Among them, adjacent groups bond together to form an a-ring, b-ring, or c-ring, resulting in a total of 9 carbon atoms. They may form an aryl ring with ~16 carbon atoms or a heteroaryl ring with 6 to 15 carbon atoms, At least one hydrogen in the formed ring is an aryl group with 6 to 30 carbon atoms, and a group with 2 to 3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) Alternatively, it may be substituted with an alkyl group having 1 to 12 carbon atoms, and in these, at least 1 Each hydrogen atom can be further divided into aryl atoms (6-30 carbon atoms), heteroaryl atoms (2-30 carbon atoms), and diaryl atoms. arylamino (where aryl has 6 to 12 carbon atoms) or arylamino (where aryl has 1 to 12 carbon atoms) It may be replaced with a kill.

[0245] More preferably, in formula (5) above, R 1 ~R 11 These are, independently, hydrogen, aryl atoms with 6 to 16 carbon atoms, and aryl atoms with 2 to 1 carbon atoms. 5 heteroaryl and diarylamino (where aryl is an aryl with 6 to 10 carbon atoms) Alternatively, an alkyl group having 1 to 6 carbon atoms, where at least one hydrogen atom is further carbon Aryls with 6 to 16 prime numbers, heteroaryls with 2 to 15 carbon atoms, diarylaminos (however The aryl group is substituted with an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 6 carbon atoms. Often, R 1 ~R 11 Among them, adjacent groups bond together to form an a-ring, b-ring, or c-ring, resulting in a total of 9 carbon atoms. They may form an aryl ring with ~12 carbon atoms or a heteroaryl ring with 6 to 12 carbon atoms, At least one hydrogen in the formed ring is an aryl group with 6 to 16 carbon atoms, and a group with 2 to 1 carbon atoms. 5 heteroaryl and diarylamino (where aryl is an aryl with 6 to 10 carbon atoms) Alternatively, it may be substituted with an alkyl group having 1 to 6 carbon atoms, and at least one of these is The hydrogen is further divided into aryl atoms with 6 to 16 carbon atoms, heteroaryl atoms with 2 to 15 carbon atoms, and diaryl atoms. aryl (where aryl has 6 to 10 carbon atoms) or alkyl (with 1 to 6 carbon atoms) It may be replaced with .

[0246] In the first and second substituents described above, aryl, heteroaryl, diarylar The "aryl" in mino, diheteroarylamino, and arylheteroarylamino Examples of "heteroaryls" include the following:

[0247] Specific examples of "aryl" include aryls with 6 to 30 carbon atoms. aryls with 6 to 24 carbon atoms are preferred, and aryls with 6 to 20 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. ~16 aryls are more preferred, and aryls with 6 to 12 carbon atoms are particularly preferred. 6 to 10 aryl groups are most preferred. For example, monocyclic aryl groups such as phenyl and bicyclic aryl groups. The reel is (2-,3-,4-)biphenylyl, and the condensed bicyclic aryl is (1-,2 -) Naphthyl, a tricyclic aryl terpheniryl (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-terf phenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p -Terphenyl-2-yl, p-Terphenyl-3-yl, p-Terphenyl-4-yl ), a condensed tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, Luoren-(1-,2-,3-,4-,9-)yl, Phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, a tetracyclic aryl quaterphenyl Nilyl(5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl) Nyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl (Lu) Triphenylene-(1-,2-)yl, pyrene-(1- ,2-,4-)yl, naphthasen-(1-,2-,5-)yl, condensed pentacyclic aryl Perylene-(1-,2-,3-)yl and pentasene-(1-,2-,5-,6-)yl These are some examples.

[0248] Specific examples of "heteroaryls" include heteroaryls with 2 to 30 carbon atoms. A heteroaryl with 2 to 25 carbon atoms is preferred, and a heteroaryl with 2 to 20 carbon atoms is preferred. More preferably, heteroaryls having 2 to 15 carbon atoms are even more preferred, and those having 2 to 10 carbon atoms are more preferably Heteroaryls are particularly preferred. For example, furyl, thienyl, pyrrolyl, oxazolyl, Isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadi Azolyl, Flazanil, Thiadiazolyl, Triazolyl, Tetrazolyl, Pyridyl, Pyridyl Midinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl Nyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, ben Zoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinoryl, Isoquinolyl, Synnoryl, Quinazolyl, Quinoxalinyl, Phthalazinyl, Na Futilidinil, prinil, pteridinil, carbazolyl, acridinil, phenoxadini Indri, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indri Examples include Zinil.

[0249] In the first and second substituents described above, "alkyl" refers to a linear chain and a branched chain. Either of these is acceptable, for example, a linear alkyl group with 1 to 24 carbon atoms or a branched alkyl group with 3 to 24 carbon atoms. Examples include alkyl chains, which have 1 to 18 carbon atoms (branched-chain alkyls have 3 to 18 carbon atoms). C1-C12 alkyl groups are preferred, and C3-C12 branched alkyl groups are more preferred. Furthermore, alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms) are more preferred. Alkyl groups with 1 to 4 prime numbers (branched alkyl groups with 3 to 4 carbon atoms) are particularly preferred, and methyl is the most preferred. Preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isopropyl butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl Tyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimeth 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t- Octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl Lu, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimeth Tylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-to Lidecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexade Examples include syl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0250] When the first substituent is aryl, the substitution position is R 1 , R 3 , R 4 , R 5 , R 10 and R 11 Preferably, R 1 and R 3 Substitution to R 5 and R 10 Substitution to R 4 oh Call R 11 Substitution to is more preferable, and the aryl group is preferably a phenyl group.

[0251] When the first substituent is a heteroaryl compound, the substitution site is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 and R 11 Preferably, R 1 Substitution to R 2 Substitution to R 3 Substitution to R 1 and R 3 Substitution to R 4 and R 11 Substitution to R 5 and R 10 to Replacement, R 6 and R 9 Substitution to is more preferable, and the heteroaryl group is preferably a carbazolyl group. This heteroaryl (e.g., carbazolyl) is placed at the above position via a phenylene group. It's okay to exchange it.

[0252] A specific example of a compound represented by formula (5) is, for example, the compound represented by the following structural formula. The following are examples. Note that "Me" in the formula represents a methyl group.

[0253] [ka]

[0254] The compound represented by formula (5) is formed by first bonding the a-c rings with a bonding group (-O-). The interpolymer is produced (first reaction), and then the a-c rings are bonded with B (boron) to form the final ring. The product can be produced (second reaction). In the first reaction, for example, nucleophilic substitution reactions and Uru Common etherification reactions such as the Mann reaction can be used. In addition, in the second reaction, tandem etherification can be performed. The Telo-Friedel-Crafts reaction (a series of electrophilic aromatic substitution reactions) can be used. For details of the second reaction, please refer to the explanation in International Publication No. 2015 / 102118. It can be done.

[0255] Furthermore, regarding host materials, another example is, for instance, Advanced Materials, 2017, 29, 1 605444, Journal of Material Chemistry C,2016,4,11355-11381, Chemical Science, 20 Use the host material described in 16, 7, 3355-3363, Thin Solid Films, 2016, 619, 120-124, etc. It is possible to do so. In addition, TADF organic EL elements have a high T1 energy in the host material of the light-emitting layer. To obtain ghee, see the link described in Chemistry Society Reviews, 2011, 40, 2943-2970. Host materials for photovoltaic organic EL devices can also be used as host materials for TADF organic EL devices. It is possible.

[0256] More specifically, the host compound is selected from the group of substructures (HA) represented by the following formula. A compound having at least one structure, wherein each structure in the substructure (HA) group At least one hydrogen atom in the substructure is from the substructure (HA) group or the substructure (HB) group. The water may be replaced by any of the structures in the middle, and at least one water in these structures The elements are deuterium, halogens, cyano, and alkyl groups with 1 to 4 carbon atoms (e.g., methyl and t-butyl). ), may be substituted with trimethylsilyl or phenyl.

[0257] [ka]

[0258] [ka]

[0259] The host compound is preferably a compound represented by one of the following structural formulas. And among these, more preferably a structure selected from the above substructure (HA) group. A compound having 1 to 3 of the above substructures (HB) and one structure selected from the above substructure (HB) group. And more preferably, the above substructure (HA) group has a carbazole group It is a substance, and is particularly preferably of the following formulas (3-201), (3-202), and (3-203) , formula (3-204), formula (3-212), formula (3-221), formula (3-222), formula (3 It is a compound represented by formula (3-262) or formula (261). Note that the structure is listed below. In the formula, at least one hydrogen is a halogen, cyano, or alkyl group having 1 to 4 carbon atoms. For example, it may be substituted with methyl or t-butyl, phenyl, or naphthyl.

[0260] [ka]

[0261] [ka]

[0262] [ka]

[0263] [ka]

[0264] [ka]

[0265] Additionally, the following polymer host materials can also be used. [ka] In equation (B-6), MU is independent of each other, as in general equations (B-1) to (B-5). At least one selected from the group consisting of divalent groups of the compound represented by , in MU Two hydrogens are substituted with EC or MU, and EC is independently substituted with hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl It is an amino or aryloxy, and at least one hydrogen in these is further aryl. It may be substituted with a heteroaryl or diarylamino, and k is 2 to 500. It is an integer of 00. k is preferably an integer between 100 and 40000, and between 500 and 25. It is more preferable that the value be an integer of 000.

[0266] Here, the compounds represented by general formulas (B-1) to (B-5) are the following compounds. [ka]

[0267] In equations (B-1) to (B-4), Ar is independently of hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl It is an amino or aryloxy, and at least one hydrogen in these is further aryl. It may be substituted with a heteroaryl or diarylamino, and among the neighboring Ars The contacting groups bond together, forming an anthracene ring, pyrene ring, fluorene ring, or cal, respectively. The baseol ring may form an aryl ring or a heteroaryl ring together with the baseol ring's parent skeleton. At least one hydrogen atom in the formed ring is an aryl, heteroaryl, or diaryl. amino, diheteroarylamino, arylheteroarylamino, or aryloxy It may be substituted with . For a detailed explanation of each group, see general formula (1) and general formula (2) above. The explanation for polycyclic aromatic compounds can be cited. In each formula, n is an integer from 1 to 6. Preferably, the integer is between 1 and 4, more preferably between 1 and 2, and most preferably 1.

[0268] In equations (B-1) to (B-4), a specific example of "Ar" is, Examples of monovalent groups in the structural formulas listed below, or groups in combinations of the structures shown below, are given below.

[0269] [ka]

[0270] In equation (B-5), R 1 ~R 11 These are, independently, hydrogen, aryl, and hetero aryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, where at least one hydrogen is further aryl, They may be substituted with heteroaryl or diarylamino compounds. R 1 ~R 11 Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and They may be substituted with a reel heteroarylamino or aryloxy, and these may be substituted with At least one hydrogen atom is further aryl, heteroaryl, or diarylamino It may be replaced. For a detailed explanation of each group, please refer to the polycyclic aromatic compounds of general formula (1) and general formula (2) mentioned above. You can quote the explanation provided.

[0271] At least one hydrogen atom in the compounds represented by formulas (B-1) to (B-5) is described below. The group represented by formula (FG-1), the group represented by formula (FG-2) described later, or the number of carbon atoms They may be substituted with 1 to 24 alkyl groups, halogens, or deuterium, and furthermore, the a Even if any -CH2- in Kill is substituted with -O- or -Si(CH3)2- Often, the compounds represented by the above formulas (B-1) to (B-5) in the alkyl group are directly related. Any -CH2- group other than the -CH2- group is substituted with arylene having 6 to 24 carbon atoms. It is also possible that any hydrogen atom in the alkyl group may be substituted with fluorine.

[0272] At least one hydrogen in the EC in formula (B-6) is represented by the following general formula (FG-1). The group to be used, the group represented by the following general formula (FG-2), alkyl groups having 1 to 24 carbon atoms, halogens Alternatively, it may be substituted with deuterium, and furthermore, any -CH2- in the alkyl The alkyl group may be substituted with -O- or -Si(CH3)2-, and the formula in the alkyl group (B-6) Any -CH2- group other than the -CH2- group directly connected to EC has 6 to 24 carbon atoms. The alkyl group may be substituted with arylene, and any hydrogen atom in the alkyl group may be substituted with fluorine. It's fine if it is done. [ka] (In the above formula (FG-1), R is independently fluorine, trimethylsilyl, trifluoromethyl, and carbon-1. ~24 alkyl or cycloalkyl having 3 to 24 carbon atoms, and in the alkyl Any -CH2- may be substituted with -O-, and the alkyl group may also be phenyl or Any -CH2- except for the -CH2- directly attached to phenylene has 6 to 24 carbon atoms. It may be substituted with -ene, and at least one hydrogen in the cycloalkyl is carbon It may be substituted with alkyl groups with prime numbers 1 to 24 or aryl groups with 6 to 12 carbon atoms. When two adjacent Rs are alkyl or cycloalkyl, they bond to form a ring. It is fine if it is formed, m are independent integers from 0 to 4, n are integers from 0 to 5, and p are integers from 1 to 5. It is a number. [ka] (In the above formula (FG-2), R is independently fluorine, trimethylsilyl, trifluoromethyl, and carbon-1. ~24 alkyl groups, cycloalkyl groups with 3 to 24 carbon atoms, or aryl groups with 6 to 12 carbon atoms. Yes, any -CH2- in the alkyl may be substituted with -O-, and the a Any -CH2- except for the -CH2- directly attached to phenyl or phenylene in Lukil 2- may be substituted with arylene having 6 to 24 carbon atoms, in the cycloalkyl group At least one hydrogen atom is an alkyl group with 1 to 24 carbon atoms or an aryl group with 6 to 12 carbon atoms. Substitutions may be made, and at least one hydrogen in the aryl group has 1 to 24 carbon atoms. It may also be substituted with alkyl groups. When two adjacent Rs are alkyl or cycloalkyl, they bond to form a ring. It is fine if it is formed, m is an integer between 0 and 4, and n is an independent integer between 0 and 5.

[0273] For example, MU is represented by the following general formulas (MU-1-1) to (MU-1-12), and the following one General formula (MU-2-1) ~ formula (MU-2-202), general formula (MU-3-1) ~ formula (M U-3-201), the following general formulas (MU-4-1) to (MU-4-122) and the following one Examples include divalent groups represented by general formulas (MU-5-1) to (MU-5-12). Furthermore, as EC, for example, the base represented by the following general formulas (EC-1) to (EC-29) is These are listed. In these, MU is combined with MU or EC in *, and EC is in * It then combines with MU.

[0274] Furthermore, the compound represented by formula (B-6) has, from the viewpoint of charge transport, a molecule containing formula (B-6) Preferably, it has at least one divalent group represented by formula (B-6-X 1) The divalent group represented by formula (B-6) is present in an amount of 10% or more relative to the molecular weight of the compound represented by formula (B-6). It is more preferable to do so. Here, the divalent group represented by formula (B-6-X1) is at * It combines with MU or EC.

[0275] [ka]

[0276] [ka]

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] The compound represented by formula (B-6) has MU in its molecule, from the viewpoint of solubility and coating film-forming properties. Preferably, 10 to 100% of the total number (n) of MUs have alkyl groups with 1 to 24 carbon atoms. , 30-100% of the total number of MUs (n) in the molecule are alkyl groups with 1-18 carbon atoms (carbon number It is more preferable to have 3 to 18 branched alkyl groups, and the total number of MUs (n) in the molecule is 5 0-100% MU is alkyl with 1-12 carbon atoms (branched alkyl with 3-12 carbon atoms) It is even more preferable to have it. On the other hand, from the viewpoint of in-plane orientation and charge transport, in the molecule It is preferable that 10-100% of the total number of MUs (n) have alkyl groups with 7-24 carbon atoms. Furthermore, 30-100% of the total number of MUs (n) in the molecule are alkyl (carbon) with 7-24 carbon atoms. It is more preferable that the branched alkyl group has prime numbers 7 to 24.

[0283] Furthermore, the dopant material is not particularly limited, and known compounds can be used. A variety of materials can be selected depending on the desired emission color. Specifically, for example, Phenanthlene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopedics Len, dibenzopyrene, rubrene, and chrysene, condensed ring derivatives, benzoxazole Benzothiazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives Conductors, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazoles Derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives Conductors, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives , bisstyryl derivatives such as bisstyrylanthracene derivatives and distylylbenzene derivatives Body (Japanese Patent Publication No. 1-245087), bis-styryl arylene derivative (Japanese Patent Publication No. 2-24 (Publication No. 7278), diazinadene derivatives, furan derivatives, benzofuran derivatives, phen Nylisobenzofuran, Dimethylisobenzofuran, Di(2-methylphenyl)isobe Isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobe Isobenzofuran derivatives such as dibenzofuran, dibenzofuran derivatives, 7-dialkylamine Nocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7 - Methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcuma Phosphorus derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin Coumarin derivatives such as dicyanomethylenepyran derivatives, dicyanomethylenelenthiops Lan derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, Santen derivatives, rhodamine derivatives, fluorescein derivatives, pyryllium derivatives, carbo Styryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, Quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, phlopyridine derivatives, 1,2,5-Thiasiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrene Roll derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, acrylic acid Lidone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives These are some examples.

[0284] Examples of dopant materials for each colored light include naphthalene and anthracite. Sen, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, ku Aromatic hydrocarbon compounds such as lysene and their derivatives, furan, pyrrole, thiophene, siloxane 9-Silafluorene, 9,9'-Spirobicilafluorene, Benzothiophene, Indole, dibenzothiophene, dibenzofuran, imidazopyridine, f Xenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxan Aromatic heterocyclic compounds such as tene and their derivatives, distylylbenzene derivatives, tetraphen Rubutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazo thiazole, thiadiazole, carbazole, oxazole, oxadiazole, Azole derivatives such as triazoles and their metal complexes and N,N'-diphenyl-N Representative example: N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine Examples include aromatic amine derivatives.

[0285] Additionally, green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, and naphth. Thalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives , acridone derivatives, quinacridone derivatives and naphthacene derivatives such as rubrene, etc. Furthermore, the compounds exemplified above as blue to blue-green dopant materials include aryl and helium. Introducing substituents that enable longer wavelengths, such as teloaryl, arylvinyl, amino, and cyano. The compound described above is also a suitable example.

[0286] Furthermore, as an orange-to-red dopant material, bis(diisopropylphenyl)perylene Naphthalimide derivatives such as tetracarboxylate imide, perinone derivatives, acetylacetate Rare earth complexes such as Eu complexes with ligands like benzoylacetone and phenanthroline. Body, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4 H-pyran and its analogues, magnesium phthalocyanine, aluminum chlorophthalocyanine Metal phthalocyanine derivatives such as nin, rhodamine compounds, deazaflavin derivatives, bear Phosphorus derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazori Derivatives of phenylalanide, pyrrolopyridine derivatives, squarylium derivatives, biolantron derivatives, phenylalanide derivatives Examples include nazine derivatives, phenoxazone derivatives, and thiadiazolopylene derivatives, Furthermore, the compounds exemplified above as blue to blue-green and green to yellow dopant materials include aryl, We introduce substituents that enable long-wavelength propagation, such as heteroaryl, arylvinyl, amino, and cyano compounds. The compound that was added is also a suitable example.

[0287] Other dopants are listed in the June 2004 issue of Chemical Industry, page 13, and the list therein. Compounds can be appropriately selected and used from those listed in the references provided.

[0288] Among the dopant materials mentioned above, amines and perylene derivatives having a stilbene structure are particularly noteworthy. The derivative, borane derivative, aromatic amine derivative, coumarin derivative, pyrane derivative, or pyrene derivative A conductor is preferred.

[0289] 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 Oh biAr 3 These are each independently aryl atoms with 6 to 30 carbon atoms, but Ar 1 ~Ar 3 few At least one has a stilbene structure, Ar 1 ~Ar 3 are aryl, heteroaryl, Alkyl, trisubstituted silyl (silyl trisubstituted with aryl and / or alkyl) Alternatively, it may be substituted with a cyano, and m is an integer between 1 and 4.

[0290] Among amines having a stilbene structure, diaminostilbene, represented by the following formula, is more preferred. stomach. [ka] In the said formula, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms. Ar 2 and Ar3 These are aryl, heteroaryl, alkyl, and trisubstituted silyl (aryl) Even if substituted with tri-substituted silyl (and / or alkyl) or cyano good.

[0291] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, and flu. Olenyl, phenalenyl, phenantrenyl, anthril, fluoranthenyl, triphe Nirenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, stilbenyl, distyly Examples include fluorenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0292] A specific example of an amine having a stilbene structure is N,N,N',N'-tetra(4-biphene). Niryl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl) )-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4 ,4'-diaminostilbene,N,N'-di(2-naphthyl)-N,N'-diphenyl- 4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diph phenyl-4,4'-diaminostilbene, 4,4'-bis[4”-bis(diphenylamylbene) [(no)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl] ]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-di Methylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl Examples include 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. ru. Furthermore, stills described in Japanese Patent Publication No. 2003-347056 and Japanese Patent Publication No. 2001-307884, etc. Amines having a ben structure may also be used.

[0293] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)peri Len, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-dife Nylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butyl Lylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,1 1-Di(t-butyl)perylene, 3-(9'-anthryl)-8,11-Di(t-butyl) Examples include perylene and 3,3'-bis(8,11-di(t-butyl)perylenel). ru. Also, Japanese Patent Publication No. 11-97178, Japanese Patent Publication No. 2000-133457, Japanese Patent Publication No. 2000-26324, Japanese Patent Publication No. 2 Japanese Patent Publication No. 001-267079, Japanese Patent Publication No. 2001-267078, Japanese Patent Publication No. 2001-267076, Japanese Patent Publication No. 2000-34234 Perylene described in the Public Gazette, Japanese Patent Publication No. 2001-267075, and Japanese Patent Publication No. 2001-217077, etc. Derivatives may also be used.

[0294] Examples of borane derivatives include 1,8-diphenyl-10-(dimethylboryl) Anthracene, 9-phenyl-10-(dimethylboryl)anthracene, 4-(9'- Anthril) Dimethylborylnaphthalene, 4-(10'-phenyl-9'-anthryl) Dimethylborylnaphthalene, 9-(dimethylboryl)anthracene, 9-(4'-bi Phenylyl)-10-(dimethylboryl)anthracene, 9-(4'-(N-carbazol Examples include lyl(phenyl)-10-(dimethylboryl)anthracene. Furthermore, even if you use borane derivatives described in International Publication No. 2000 / 40586, etc. good.

[0295] 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 Oh biAr 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is, aryl, heteroaryl, alkyl, trisubstituted silyl (aryl and / or alkyl) It may be substituted with a tri-substituted silyl or cyano, and n is an integer from 1 to 4. It is a number.

[0296] In particular, Ar 4 anthracene, chrysene, fluorene, benzofluorene or pyrene It is a divalent group derived from Ar 5 and Ar 6 Each of them independently has 6 to 30 carbon atoms. It is a reel, Ar 4 ~Ar 6 These are aryl, heteroaryl, alkyl, and trisubstituted silica substituted with aryl and / or alkyl tri-substituted silyl or cyano It is also acceptable, and an aromatic amine derivative where n is 2 is more preferred.

[0297] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, and flu. Olenyl, phenalenyl, phenantrenyl, anthril, fluoranthenyl, triphe Examples include nirenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, and pentacenyl. It is possible.

[0298] As for aromatic amine derivatives, as for chrysene derivatives, for example, N,N,N',N'-the Traphenylchrysene-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) Chrysen-6,12-diamine, N,N,N',N'-tetra(naphthalene-2-yl) Chrysene-6,12-diamine, N,N'-diphenyl-N,N'-di(p-tolyl) Lysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl Nyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-) Sopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N' -Bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4 -Isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine These are some examples.

[0299] Furthermore, as a pyrene derivative, for example, N,N,N',N'-tetraphenylpyrene-1, 6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N', N'-Tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N ',N'-Tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N '-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-di Phenyl-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-dimethylphenicol (Lu)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenyl Pyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diamine Phenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 -Bis-(4- Examples include trimethylsilanylphenyl)-1H,8H-pyrene-1,6-diamine. It can be done.

[0300] Furthermore, an anthracene-based compound is, for example, N,N,N,N-tetraphenylanthracene. N-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)anthrace N-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthrate Sen-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)ant Spiral-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl Nyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4 -Isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl- N,N'-Bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N '-Bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9 ,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl Anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl -N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2 ,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di( p-Tolyl)anthracene-9,10-diamine,2,6-dicyclohexyl-N,N' -Bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9, 10-Diamine, 2,6-Dicyclohexyl-N,N'-Bis(4-Isopropylphenicol) (Lu)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-Bis(4-diphenylaminophenyl)anthracene, 9,10-Bis(4 -di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-na Phthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di- p-Tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4- Diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6- Examples include diphenylamino-2-naphthyl)anthracene.

[0301] In addition, there is [4-(4-diphenylaminophenyl)naphthalene-1-yl]- Diphenylamine, [6-(4-diphenylaminophenyl)naphthalene-2-yl] -Diphenylamine, 4,4'-bis[4-diphenylaminonaphthalene-1-yl]bi Phenyl, 4,4'-bis[6-diphenylaminonaphthalene-2-yl]biphenyl, 4,4"-Bis[4-diphenylaminonaphthalene-1-yl]-p-terphenyl, 4 ,4"-bis[6-diphenylaminonaphthalene-2-yl]-p-terphenyl etc. It can be listed. Alternatively, aromatic amine derivatives described in Japanese Patent Publication No. 2006-156888, etc., may be used.

[0302] Examples of coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, Japanese Patent Publication No. 2004-43646, Japanese Patent Publication No. 2001-76876, and Japanese Patent Publication No. Hei 6-298758 Any of the coumarin derivatives described above may be used.

[0303] Examples of pyran derivatives include DCM and DCJTB, listed below. [ka] Also, 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, etc. The listed pyran derivatives may also be used.

[0304] A polycyclic aromatic compound represented by general formula (1) is used in combination with an organic solvent to form a light-emitting layer composition. It can also be used as a first component. The composition contains at least one polycyclic aromatic compound A substance, a second component consisting of at least one host material, and a third component consisting of at least one It contains an organic solvent. The first component is a dopant component of the luminescent layer obtained from the composition. The second component functions as the host component of the light-emitting layer. The third component is the first component in the composition. It functions as a solvent that dissolves the component and the second component, and during application, it controls the evaporation of the third component itself. The speed provides a smooth and uniform surface shape.

[0305] <organic solvents> The above-mentioned light-emitting layer forming composition contains at least one organic solvent as a third component. By controlling the evaporation rate of organic solvents, it is possible to control film formation, the presence or absence of defects in the coating film, and surface roughness. Smoothness can be controlled and improved. Also, when forming a film using the inkjet method, Controlling meniscus stability at pinholes in inkjet heads to control and improve ejection performance. This can be achieved by controlling the drying rate of the film and the orientation of the derivative molecules. Electrical characteristics, luminescence characteristics, and effects of an organic EL element having a light-emitting layer obtained from a light-emitting layer forming composition. Rate and lifespan can be improved.

[0306] (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. A boiling point of 13°C is more preferable, and 150°C to 250°C is even more preferable. Temperatures above 0°C are preferable from the viewpoint of inkjet ejection performance. Also, a boiling point of 300°C is desirable. Lower values ​​are preferable in terms of coating defects, surface roughness, residual solvent, and smoothness. The components offer good inkjet ejection, film formation, smoothness, and low residual solvent properties. A configuration containing two or more organic solvents is more preferable. On the other hand, depending on the circumstances, transportability, etc. Considering this, the composition was made into a solid state by removing the solvent from the composition for forming the light-emitting layer. That's fine.

[0307] Furthermore, the third component is a good solvent (GS) and a poor solvent (PS) for the host material of the second component. It contains the boiling point (BP) of a good solvent (GS). GS ) is the boiling point (BP) of a poor solvent (PS) PS ) Low, the composition is particularly preferable. By adding a high-boiling point poor solvent, the low-boiling point good solvent volatilizes first during film formation, and the content of the composition The concentration of the substance and the concentration of the poor solvent increase, promoting rapid film formation. As a result, there are fewer defects. A coating film with low surface roughness and high smoothness can be obtained.

[0308] Difference in solubility (S GS -S PS ) is preferably 1% or more, and preferably 3% or more. More preferably, and even more preferably, the difference in boiling points (BP) PS -BP G S ) is preferably 10℃ or higher, more preferably 30℃ or higher, and 50 It is even more preferable that the temperature be above ℃.

[0309] The organic solvent is removed from the coating film after film formation by drying processes such as vacuum, reduced pressure, and heating. When heating is performed, from the viewpoint of improving coating film formation properties, the glass transition temperature (Tg) of the first component is increased. It is preferable to carry out the process at 30°C or below. Furthermore, from the viewpoint of reducing residual solvent, the first component is glass. It is preferable to heat to a transition temperature (Tg) of -30°C or higher. Even at low temperatures, the thin film ensures that the organic solvent is sufficiently removed. Furthermore, multiple tests can be performed at different temperatures. Drying may be performed, or multiple drying methods may be used in combination.

[0310] (2) Specific examples of organic solvents Organic solvents used in compositions for forming the light-emitting layer include alkylbenzene solvents and phenyl Lu ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, Examples include monocyclic ketone solvents, solvents with a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, and nonanol. Lu, Decanol, Undecanol, Dodecanol, Tetradecanol, Hexane-2-O Heptane-2-ol, octan-2-ol, decane-2-ol, dodecane- 2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol Pineol, δ-terpineol, terpineol (mixture), ethylene glycol mono Methyl ether acetate, propylene glycol monomethyl ether acetate, die Diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol Ethylene 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 Tel, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether Ethylene glycol monobutyl ether, diethylene glycol monophenyl ether Ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether Polyethylene glycol butyl methyl ether, polyethylene glycol dimethyl methyl ether Lu ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o- Xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluoro Toluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobe Nzen, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethyl Nisol, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2- Chillanisole, phenetol, benzodioxole, 4-methylanisole, s-buty Benzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1 ,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile Lu, 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-torni Tolyl, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene Ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene 1-Methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxyl E, 2,2'-vitryl, dodecylbenzene, dipentylbenzene, tetramethylbenzyl Zene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-Methyl-4-(propoxymethyl)benzene, 1-Methyl-4-(butyloxymethyl)benzene Benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl) Xymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzenebenzylbutyl Lu ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl Examples include ether and benzyl octyl ether, but it is not limited to these. Furthermore, the solvent may be used alone or in mixtures.

[0311] <Optional ingredients> The composition for forming the light-emitting layer may contain optional components as long as they do not impair its properties. Optional components include binders and surfactants.

[0312] (1) Binder The light-emitting layer forming composition may contain a binder. The binder is used during film formation. A film is formed, and the resulting film is bonded to the substrate. Furthermore, in the light-emitting layer forming composition... It plays a role in dissolving, dispersing, and binding other components.

[0313] Examples of binders used in compositions for forming light-emitting layers include acrylic resin and polyethylene. Teylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol Polymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers , chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene Polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate Nyl, Teflon, Acrylonitrile-butadiene-styrene copolymer (ABS) resin, A Crylonitrile-styrene copolymer (AS) resin, phenolic resin, epoxy resin, melamine Min resin, urea resin, alkyd resin, polyurethane, and the above resins and polymers Copolymers are one example, but the term is not limited to them.

[0314] The binder used in the composition for forming the light-emitting layer may be of one type only, or multiple types may be mixed. It may be used in this way.

[0315] (2) Surfactants The composition for forming the light-emitting layer has, for example, uniformity of the film surface and solvent-friendly properties of the film surface. And it may contain a surfactant to control the liquid repellency. The surfactant is a hydrophilic group structure They are classified into ionic and nonionic based on their structure, and further, alkyl groups are classified based on the structure of their hydrophobic groups. They are classified into silicon-based and fluorine-based types. Also, due to their molecular structure, they have relatively small molecular weights. This includes monomolecular systems with simple structures and polymeric systems with large molecular weights and side chains or branching. It is classified into the following categories based on its composition: single system, mixture of two or more surfactants and a base material. It is classified as a compound. The surfactants that can be used in the light-emitting layer forming composition are all Various types of surfactants can be used.

[0316] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Poly Flow No. 75, Polyflow No. 90, Polyflow No. 95 (product names, Kyoeisha Chemical) Industrial Co., Ltd., Disperbyk 161, Disperbyk 1 62, Disper Bake 163, Disper Bake 164, Disper Bake 166, De Disper Bake 170, Disper Bake 180, Disper Bake 181, Disper Bake 182, BYK300, BYK306, BYK310, BYK320, BYK33 0, BYK342, BYK344, BYK346 (product name, BYK Chemie Japan Co., Ltd.) ), KP-341, KP-358, KP-368, KF-96-50CS, KF-5 0-100CS (product name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflo KH-40 (product name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futergent Ent 251, FTX-218 (product name, manufactured by Neos Co., Ltd.), EFTOP EF-351 , EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (product name, manufactured by Mitsubishi Materials Corporation), MegaFac F-47 0, Megafuck F-471, Megafuck F-475, Megafuck R-08, Megaf F-477, Megafuck F-479, Megafuck F-553, Megafuck F -554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluor Alalkylcarboxylates, fluoroalkyl polyoxyethylene ethers, fluoroalkyl Killammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate , diglycerin tetrakis(fluoroalkyl polyoxyethylene ether), fluoro Alkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxy Ethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, poly Oxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene Oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, so Sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan o Laurate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, poly Oxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, Polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, aldehyde Examples include carboxymethylbenzenesulfonate and alkyldiphenyl ether disulfonate. It is possible.

[0317] Furthermore, a single surfactant may be used, or two or more may be used in combination.

[0318] <Composition and physical properties of compositions for forming light-emitting layers> The content of each component in the light-emitting layer forming composition is important for the quality of each component in the light-emitting layer forming composition. The solubility, storage stability, and film-forming properties, as well as the coating film obtained from the light-emitting layer-forming composition. The composition provides excellent film quality, good ejection properties when using an inkjet method, and Observations of good electrical characteristics, luminescence characteristics, efficiency, and lifespan of organic EL elements having a fabricated light-emitting layer. From this point, the first component is 0.0001% to 2.0% by weight of the total weight of the composition for forming the light-emitting layer. Weight %, the second component is 0.0999% to 8.0% by weight of the total weight of the composition for forming the light-emitting layer. By weight, the third component is 90.0% to 99.9% by weight of the total weight of the composition for forming the light-emitting layer. Amount in percent is preferred.

[0319] More preferably, the first component is 0.005% by weight of the total weight of the composition for forming the light-emitting layer. ~1.0% by weight, with the second component making up 0.095% by weight of the total weight of the composition for forming the light-emitting layer~ 4.0% by weight, the third component is 95.0% to 99% by weight of the total weight of the composition for forming the light-emitting layer. It is 0.9% by weight. More preferably, the first component is equal to the total weight of the composition for forming the light-emitting layer. , 0.05% by weight to 0.5% by weight, the second component is 0 0.25% by weight to 2.5% by weight, the third component is 97% of the total weight of the composition for forming the light-emitting layer. The weight range is from 0% to 99.7%.

[0320] The composition for forming the light-emitting layer is prepared by stirring, mixing, heating, cooling, and dissolving the above-mentioned components in a known manner. It can be manufactured by appropriately selecting and performing dispersion, etc. Furthermore, after preparation, filtration, degassing ( Degassing (also known as degassing), ion exchange treatment, and inert gas replacement / sealing treatment are performed as appropriate. That's fine.

[0321] Regarding the viscosity of the composition for forming the light-emitting layer, a higher viscosity is preferable for better film formation and inkjet properties. Good discharge performance can be obtained using the T method. On the other hand, a lower viscosity makes it easier to form a thin film. Therefore, the viscosity of the light-emitting layer forming composition is 0.3 mPa at 25°C. It is preferable that the pressure is between 1 mPa·s and 3 mPa·s, and preferably between 1 mPa·s and 3 mPa·s. It is preferable. In the present invention, viscosity is measured using a cone-plate type rotational viscometer. These are the values ​​measured using this method.

[0322] A lower surface tension in the composition for forming the light-emitting layer results in better film formation and a defect-free coating. This can be obtained. On the other hand, a higher value can be obtained to obtain better inkjet ejection performance. The viscosity of the light-emitting layer forming composition is such that the surface tension at 25°C is 20 mN / m to 40 mN / m. It is preferable that there be a certain amount, and more preferably 20 mN / m to 30 mN / m. In this case, the surface tension was measured using the suspension drop method.

[0323] <Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 efficiently directs electrons moving from the cathode 108 into the light-emitting layer 105. Alternatively, it plays the role of injecting into the electron transport layer 106. The electron transport layer 106 is from the cathode 108 The injected electrons or electrons injected from the cathode 108 through the electron injection layer 107 are efficiently The electron transport layer 106 and electron injection layer 107 play a role in transporting electrons to the light-emitting layer 105. Each involves laminating or mixing one or more types of electron transport / injection materials, or electron transport / injection materials. It is formed from a mixture of injection material and polymer binder.

[0324] The electron injection and transport layer is the layer responsible for the injection of electrons from the cathode and the subsequent transport of electrons. Therefore, it is desirable to have high electron injection efficiency and to efficiently transport the injected electrons. For this to work, it needs to have high electron affinity, high electron mobility, and excellent stability. It is preferable that the substance is one that is less likely to generate impurities during manufacturing and use. However, when considering the balance of hole and electron transport, holes from the anode do not recombine with the cathode. If the primary role is to efficiently prevent flow to the side, then the electron transport capacity is not that high. Even without this, the effect of improving luminescence efficiency is equivalent to that of materials with high electron transport capability. Therefore, the electron injection / transport layer in this embodiment is a layer that can efficiently block the movement of holes. Functions may also be included.

[0325] The material used to form the electron transport layer 106 or the electron injection layer 107 (electron transport material) is: Compounds that have been conventionally used as electron transfer compounds in photoconductive materials, organic EL elements From among known compounds used in the electron injection layer and electron transport layer, any one compound may be selected and used. It is possible to be there.

[0326] Materials used in electron transport layers or electron injection layers include carbon, hydrogen, oxygen, sulfur, and kerosene. Aromatic rings or heterofragrances composed of one or more atoms selected from inium and phosphorus Compounds consisting of group rings, pyrrole derivatives and their fused ring derivatives, and electron-accepting nitrogen compounds It is preferable to contain at least one selected from among the metal complexes. Specifically, Naphthalene, anthracene and other condensed ring aromatic ring derivatives, 4,4'-bis(diphenyl Styryl aromatic ring derivatives, such as ethenyl biphenyl, perinone derivatives, and coumari. Quinone derivatives, naphthalimide derivatives, and quinone derivatives such as anthraquinone and diphenoquinone. Examples include phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyphenyloxazole. Complexes such as hydroxyazole complexes, azomethine complexes, tropolone metal complexes, and flavonoids Examples include metal complexes and benzoquinoline metal complexes. These materials can be used individually or individually. It can be used as is, but it is also acceptable to mix it with other materials.

[0327] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, and ammonium compounds. Tracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalene Imide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives , perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl (e.g., 1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazoles Derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadi Azole derivatives, oxine derivative metal complexes, quinolinol-based metal complexes, quinoxaline derivatives Conductors, quinoxaline derivative polymers, benzazole compounds, gallium complexes, pyrazole phenylene derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzyl derivatives Zoquinoline derivative (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-s Pyrobifluorene, imidazopyridine derivatives, borane derivatives, benzimidazole Derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzo Oxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine, etc. Ligopyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-( 2,2':6'2"-terpyridinyl))benzene etc), naphthyridine derivatives (bis( 1-Naphthyl)-4-(1,8-Naphthyridine-2-yl)phenylphosphine oxa (e.g., aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide) Examples include derivatives and bis-styryl derivatives.

[0328] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, for example, quinolinol-based Metal complexes and hydroxyazole complexes such as hydroxyphenyloxazole complexes, azometh Tin complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes Some examples include:

[0329] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0330] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO System derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives Pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives The isomer, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0331] <Bolan derivatives> Borane derivatives are compounds represented by the following general formula (ETM-1), for example, and in detail... This is disclosed in Japanese Patent Publication No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 These are, independently, hydrogen and alkyl. , optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing A heterogeneous ring, or at least one cyano, R 13 ~R 16 Each is independent of the others. , an optionally substituted alkyl, or an optionally substituted aryl, where X is It is an arylene which may be substituted, and Y may be substituted, having 16 or fewer carbon atoms. The aryl, substituted boryl, or optionally substituted carbazolyl, And each n is an independent integer between 0 and 3.

[0332] Among the compounds represented by the above general formula (ETM-1), the following general formula (ETM-1-1) Compounds represented by the formula shown below or compounds represented by the general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12 These are, independently, hydrogen and alkyl. , optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing A heterogeneous ring, or at least one cyano, R 13 ~R 16 Each is independent of the others. , an optionally substituted alkyl, or an optionally substituted aryl, R 21 and R 22 Each of these independently consists of hydrogen, alkyl, and optionally substituted aryl. Substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano at least Another is X 1 is an arylene having 20 or fewer carbon atoms, which may be substituted, and n is Each is an independent integer between 0 and 3, and each of m is an independent integer between 0 and 4. ru. [ka] In formula (ETM-1-2), R 11 and R 12 These are, independently, hydrogen and alkyl. , optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing A heterogeneous ring, or at least one cyano, R 13 ~R 16 Each is independent of the others. , an optionally substituted alkyl, or an optionally substituted aryl, X 1 teeth , an arylene having 20 or fewer carbon atoms, which may be substituted, and n is independent in each case. And it is an integer between 0 and 3.

[0333] X 1 A concrete example of this is the divalent base represented by the following equations (X-1) to (X-9). It can be done. [ka] (In each formula, R aEach is independently an alkyl group or an optionally substituted phenyl group. (That is the case.)

[0334] Specific examples of these borane derivatives include the following compounds. [ka]

[0335] This borane derivative can be produced using known raw materials and known synthesis methods.

[0336] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably It is a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0337] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an énylene ring, and n is an integer from 1 to 4.

[0338] In the above formula (ETM-2-1), R 11 ~R 18 These are, independently, hydrogen and A Lukyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably with 3 carbon atoms) (~12 cycloalkyls) or aryls (preferably aryls with 6 to 30 carbon atoms) ru.

[0339] In the above formula (ETM-2-2), R 11 and R 12 Each of them independently, hydrogen , alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably carbon Cycloalkyls (3 to 12 carbon atoms) or aryls (preferably aryls with 6 to 30 carbon atoms) And R 11 and R 12 They may be joined together to form a ring.

[0340] In each formula, the "pyridine substituent" is one of the following: (Py-1) to (Py-15) In either case, the pyridine substituents are independently substituted with alkyl groups having 1 to 4 carbon atoms. It may also be possible to use pyridine substituents in each formula via phenylene or naphthylene groups. The φ may be bonded to an anthracene ring or a fluorene ring.

[0341] [ka]

[0342] The pyridine substituent is one of the above formulas (Py-1) to (Py-15), however Among these, it is preferable that it be one of the following equations (Py-21) to (Py-44). stomach. [ka]

[0343] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium, Furthermore, the two "pyridine-based" compounds in the above formulas (ETM-2-1) and (ETM-2-2) One of the substituents may be replaced with an aryl group.

[0344] R 11 ~R 18 In this context, "alkyl" can be either a linear or branched chain. Examples include linear alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. The preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (branched chain alkyl group with 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (3 to 12 carbon atoms). It is a branched alkyl group with 12 carbon atoms. A more preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms. It is a branched alkyl group (with 3 to 6 carbon atoms). Particularly preferred alkyl groups are those with 1 to 6 carbon atoms. It is an alkyl group with 4 carbon atoms (a branched alkyl group with 3 to 4 carbon atoms).

[0345] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopen Tyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-Dimethylbutyl, 2-Ethylbutyl, n-Heptyl, 1-Methylhexyl, n- Octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl Tyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3, 5,5-Trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n- Decyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl Examples include n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. It is possible.

[0346] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, see the above explanation of alkyl groups. It can be quoted.

[0347] R 11 ~R 18Examples of "cycloalkyl" in this context include cycloalkyl groups with 3 to 12 carbon atoms. Examples include cycloalkyl groups. Preferred "cycloalkyl groups" are cycloalkyl groups with 3 to 10 carbon atoms. It is a kill. A more preferred "cycloalkyl" is a cycloalkyl with 3 to 8 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl , cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, Examples include cyclooctyl or dimethylcyclohexyl.

[0348] R 11 ~R 18 In this context, preferred aryls are those with 6 to 30 carbon atoms. It is an aryl, and more preferably an aryl with 6 to 18 carbon atoms, and even more preferably More preferably, an aryl compound having 6 to 14 carbon atoms, and particularly preferably an aryl compound having 6 to 12 carbon atoms. ru.

[0349] Specific examples of "aryls with 6 to 30 carbon atoms" include monocyclic aryls such as phenyl and fuzzy aryls. (1-,2-)naphthyl is a bicyclic aryl compound, and asenaphthyl is a tricyclic aryl compound. Chilen-(1-,3-,4-,5-)yl, Fluorene-(1-,2-,3-,4-,9 -) yl, phenalene-(1-,2-) yl, (1-,2-,3-,4-,9-) phenalene Triphenylene-(1-,2-)yl, pyrene-( 1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl Perylene-(1-,2-,3-)yl, pentasene-(1-,2-,5-,6-) Examples include Il.

[0350] Preferred "aryls with 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, and cyanoacrylate. Examples include lysenyl or triphenylenyl, and more preferably phenyl, 1-naphthol. Examples include phenyl, 2-naphthyl, or phenanthryl, with phenyl, 1-naphthyl being particularly preferred. Phthyl or 2-naphthyl are examples.

[0351] In the above formula (ETM-2-2), R 11 and R 12 Even if they are bonded together to form a ring Often, as a result, the five-membered ring of the fluorene skeleton contains cyclobutane, cyclopentane, and cyclo Pentene, cyclopentadiene, cyclohexane, fluorene, or indene are among the stimulants. It is acceptable for them to be joined together.

[0352] Specific examples of pyridine derivatives include the following compounds. [ka]

[0353] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0354] <Fluorantene derivative> Fluoranthene derivatives are compounds represented by the following general formula (ETM-3), Further details are disclosed in International Publication No. 2010 / 134352. [ka]

[0355] In the above formula (ETM-3), X 12 ~X 21 These are hydrogen, halogen, linear, branched, or cyclic elements. alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0356] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0357] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0358] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, hetero aryl or alkyl.

[0359] Also, adjacent groups among R 1 ~R 11 may combine with each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring 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 at least one hydrogen in these 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. It may be substituted with an alkyl group.

[0360] Furthermore, at least one hydrogen in the compound or structure represented by formula (ETM-4) It may be substituted with a halogen or deuterium.

[0361] The substituents and ring formation morphology in formula (ETM-4), and the structure of formula (ETM-4) are multiple. The explanation of the polymers formed by the combination can be found in the formulas represented by the general formulas (1) and (1') above. You can cite explanations of compounds and their polymers.

[0362] Specific examples of these BO derivatives include the following compounds. [ka]

[0363] This BO derivative can be produced using known raw materials and known synthesis methods.

[0364] <Anthracene derivatives> One anthracene derivative is, for example, the compound represented by the following formula (ETM-5-1). ru. [ka]

[0365] Ar is independently either divalent benzene or naphthalene, and R 1 ~R 4 teeth, Each of these independently consists of hydrogen, alkyl groups with 1 to 6 carbon atoms, and cycloalkyl groups with 3 to 6 carbon atoms. These are aryl atoms with 6 to 20 carbon atoms.

[0366] Ar can be independently selected from divalent benzene or naphthalene as appropriate. The two Ar atoms may be different or the same, but the synthesis of anthracene derivatives From the standpoint of ease, it is preferable that they be the same. Ar combines with pyridine to form "Ar and It forms a "part consisting of bipyridine," and this part is, for example, the following formula (Py-1) ~ formula ( It is attached to anthracene as a group represented by one of the following (Py-12):

[0367] [ka]

[0368] Among these groups, the group represented by any of the above formulas (Py-1) to (Py-9) is Preferably, a group represented by any of the above formulas (Py-1) to (Py-6) is preferred. The two "Ar and pyridine moieties" that bind to anthracene have the same structure. They may be the same or different, but from the viewpoint of the ease of synthesis of anthracene derivatives, they are the same. It is preferable that the structure be the same. However, from the viewpoint of device characteristics, two "Ar and pyramidal" The structure of the "part consisting of din" is preferable whether it is the same or different.

[0369] R 1 ~R 4 For alkyl groups with 1 to 6 carbon atoms, both linear and branched chains are available. Good. That is, a linear alkyl group with 1 to 6 carbon atoms or a branched alkyl group with 3 to 6 carbon atoms. More preferably, an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isopropyl. butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl Tyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimeth Examples include methyl, ethyl, n-propyl, and ethylbutyl, as well as methyl, ethyl, n-propyl, and ethylbutyl. Sopropyl, n-butyl, isobutyl, s-butyl, or t-butyl are preferred, and methyl ethyl, t-butyl, or t-butyl are more preferred.

[0370] R 1 ~R 4 A specific example of a cycloalkyl group with 3 to 6 carbon atoms is cyclopropyl Cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cyclohexyl Examples include chlorohexyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl. It is possible.

[0371] R 1 ~R 4 Regarding aryls with 6 to 20 carbon atoms, the aryls with 6 to 16 carbon atoms are... A C6-C12 aryl is preferred, a C6-C10 aryl is particularly preferred. It is preferable.

[0372] Specific examples of "aryls with 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, ( o-,m-,p-) trill, (2,3-,2,4-,2,5-,2,6-,3,4-,3 ,5-)xylyl, mesityl(2,4,6-trimethylphenyl), (o-,m-,p- )Cumenyl, a bicyclic aryl (2-,3-,4-)biphenylyl, a condensed bicyclic aryl (1-,2-)naphthyl is a aryl compound, and terpheniryl (m-terphthyl) is a tricyclic aryl compound. Enyl-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 Lu-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terf Phenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl Anthracene-(1-,2-,9) is a condensed tricyclic aryl compound. -)yl, asenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2 -,3-,4-,9-)il, phenalene-(1-,2-)il, (1-,2-,3-, 4-,9-)phenanthryl, a condensed tetracyclic aryl triphenylene-(1-,2- )yl, pyren-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl, Examples include perylene-(1-,2-,3-)yl, a condensed pentacyclic aryl.

[0373] Preferred "aryl compounds with 6 to 20 carbon atoms" include phenyl, biphenylyl, and terphenylyl. or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2- Naphthyl or m-terphenyl-5'-yl, more preferably phenyl, bian The material is phenylyl, 1-naphthyl, or 2-naphthyl, most preferably phenyl.

[0374] One anthracene derivative is, for example, the compound represented by the following formula (ETM-5-2). ru. [ka]

[0375] Ar 1 These are, independently, single bonds, divalent benzene, naphthalene, anthracene, It is either fluorene or phenalene.

[0376] Ar 2Each of these is an aryl group with 6 to 20 carbon atoms, and the above formula (ETM-5 The same explanation as in -1) for "aryls with 6 to 20 carbon atoms" can be cited. aryls with 6 to 16 carbon atoms are preferred, aryls with 6 to 12 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. Aryl compounds of ~10 are particularly preferred. Specific examples include phenyl, biphenylyl, and naphthyl. terpheniryl, anthracenyl, acenaphtyrenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perirenyl. It can be done.

[0377] R 1 ~R 4 These are, independently, hydrogen, alkyl with 1 to 6 carbon atoms, and alkyl with 3 to 6 carbon atoms. It is a cycloalkyl or aryl with 6 to 20 carbon atoms, and the above formula (ETM-5-1) You can quote the explanation provided.

[0378] Specific examples of these anthracene derivatives include the following compounds, for example. [ka]

[0379] These anthracene derivatives can be produced using known raw materials and known synthesis methods. Cut.

[0380] <Benzofluorene derivatives> Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0381] Ar 1 Each of these is an aryl group with 6 to 20 carbon atoms, and the above formula (ETM-5 The same explanation as in -1) for "aryls with 6 to 20 carbon atoms" can be cited. aryls with 6 to 16 carbon atoms are preferred, aryls with 6 to 12 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. Aryl compounds of ~10 are particularly preferred. Specific examples include phenyl, biphenylyl, and naphthyl. terpheniryl, anthracenyl, acenaphtyrenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perirenyl. It can be done.

[0382] Ar 2 These are, independently, hydrogen and alkyl (preferably alkyl having 1 to 24 carbon atoms). ), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms) or aryl (preferably The most common aryl group has 6 to 30 carbon atoms, and consists of two Ar 2 They are joined together to form a ring. That's good too.

[0383] Ar 2 The "alkyl" in this context can be either a linear or branched chain, for example, Examples include linear alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. The term "alkyl" refers to alkyl groups with 1 to 18 carbon atoms (branched-chain alkyl groups with 3 to 18 carbon atoms). Therefore, a more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (a fraction of which has 3 to 12 carbon atoms). It is a branched alkyl group. A more preferred alkyl group is an alkyl group with 1 to 6 carbon atoms (carbon It is a branched alkyl group with 3 to 6 carbon atoms. Particularly preferred alkyl groups are those with 1 to 4 carbon atoms. It is a methyl alkyl group (a branched alkyl group with 3-4 carbon atoms). A specific example of "alkyl" is methyl. ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl Tyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1- Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl Examples include 1-methylhexyl, n-heptyl, and 1-methylhexyl.

[0384] Ar 2 In this context, "cycloalkyl" refers to, for example, cycloalkyl groups with 3 to 12 carbon atoms. Examples include: A preferred "cycloalkyl" is a cycloalkyl with 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl with 3 to 8 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl with 3 to 6 carbon atoms. Examples of "roalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl Methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl Examples include dimethylcyclohexyl.

[0385] Ar 2 In this context, preferred aryls are those with 6 to 30 carbon atoms. A more preferred aryl is an aryl with 6 to 18 carbon atoms, and even more preferably a carbon aryl. The aryl group has 6 to 14 prime numbers, and is particularly preferably an aryl group with 6 to 12 carbon atoms.

[0386] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, and acenaphthyl Nyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, na Examples include phthalenyl, perilenyl, and pentacenyl.

[0387] Two Ar 2 These may be bonded together to form a ring, resulting in a five-membered ring of the fluorene skeleton. It contains cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, and cyclohexane. Xane, fluorene, or indene may be spiro-bonded to it.

[0388] Specific examples of these benzofluorene derivatives include the following compounds. [ka]

[0389] This benzofluorene derivative can be produced using known raw materials and known synthesis methods. Cut.

[0390] <Phosphine oxide derivatives> Phosphine oxide derivatives are compounds represented by the following formula (ETM-7-1), for example. Yes, it exists. Further details are also described in International Publication No. 2013 / 079217. [ka] R 5 These are substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms and aryl groups with 6 to 20 carbon atoms. Alternatively, it is a heteroaryl with 5 to 20 carbon atoms. R 6 This includes CN, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, and helium groups with 1 to 20 carbon atoms. Telolalkyl, aryl with 6-20 carbon atoms, heteroaryl with 5-20 carbon atoms, 1 carbon atom It is an alkoxy with ~20 carbon atoms or an aryloxy with 6 to 20 carbon atoms. R 7 and R 8 Each of these is independently a substituted or unsubstituted Ally with 6 to 20 carbon atoms. It is a heteroaryl 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 from 0 to 4, and q is an integer from 1 to 3 It is an integer.

[0391] Phosphine oxide derivatives are compounds represented by the following formula (ETM-7-2), for example. That's good too. [ka]

[0392] R 1 ~R 3 They may be the same or different, and include hydrogen, alkyl groups, cycloalkyl groups, Aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkyl group Circulthio group, aryl ether group, arylthioether group, aryl group, heterocyclic group, ha Logen, cyano group, aldehyde group, carbonyl group, carboxyl group, amino group, nitro group It is selected from among the silyl group and the fused ring formed between it and the adjacent substituent.

[0393] Ar 1 These may be the same or different, and are either an arylene group or a heteroarylene group. ri, Ar 2 These may be the same or different, and are either an aryl group or a heteroaryl group. However, Ar 1 and Ar 2 At least one of them has a substituent, or adjacent A fused ring is formed between the substituent and the compound. n is an integer from 0 to 3, and when n is 0, it is unsaturated. There are no structural parts, and when n is 3, R 1 It does not exist.

[0394] Among these substituents, alkyl groups include, for example, methyl, ethyl, propyl, and b This group exhibits saturated aliphatic hydrocarbon groups such as til groups, and these can be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted; for example, alkyl groups, aryl groups. Examples include heterocyclic groups, and this point is also common to the following description. The number of carbon atoms in the group is not particularly limited, but due to availability and cost considerations, it is usually 1 to 20. It is within the range.

[0395] Furthermore, cycloalkyl groups include, for example, cyclopropyl, cyclohexyl, norbornyl. It exhibits saturated alicyclic hydrocarbon groups such as ru and adamantyl, which are either unsubstituted or substituted. That's fine. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20. be.

[0396] Furthermore, aralkyl groups are aliphatic carbonized groups such as benzyl groups and phenylethyl groups. It shows an aromatic hydrocarbon group via an element, and both aliphatic hydrocarbons and aromatic hydrocarbons are unsubstituted. However, substitution is acceptable. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually 1. The range is ~20.

[0397] Furthermore, alkenyl groups are double bonds such as vinyl groups, allyl groups, and butadienyl groups. This represents an unsaturated aliphatic hydrocarbon group containing a compound, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0398] Furthermore, cycloalkenyl groups include, for example, cyclopentenyl and cyclopentadienyl groups. It shows an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclohexene group, and this is ostagmoid. It doesn't matter whether it's a substitution or a replacement.

[0399] Furthermore, an alkynyl group is an unsaturated aliphatic group containing a triple bond, such as an acetylenyl group. This represents a hydrocarbon group, which may be unsubstituted or substituted. The carbon of the alkynyl group. The number is not particularly limited, but it is usually in the range of 2 to 20.

[0400] Furthermore, alkoxy groups are, for example, aliphatic carbon groups that undergo ether bonding. It represents a hydrogen group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the group is not particularly limited, but it is usually in the range of 1 to 20.

[0401] Furthermore, an alkylthio group is defined as a group in which the oxygen atom in the ether bond of an alkoxy group is replaced by a sulfur atom. It is the basis.

[0402] Furthermore, aryl ether groups are aromatic compounds that are linked to ether bonds, such as phenoxy groups. It represents a fragrant hydrocarbon group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the reel ether group is not particularly limited, but is usually in the range of 6 to 40.

[0403] Furthermore, an arylthioether group is defined as the oxygen atom of the ether bond of an aryl ether group. It is a group substituted with a sulfur atom.

[0404] Furthermore, aryl groups include, for example, phenyl, naphthyl, biphenylyl, and phenane groups. This represents aromatic hydrocarbon groups such as tolyl groups, terphenyl groups, and pyrenyl groups. Aryl groups are, It can be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but generally It is usually in the range of 6 to 40.

[0405] Furthermore, heterocyclic groups include, for example, furanyl groups, thiophenyl groups, oxazolyl groups, and pyridyl groups. It shows cyclic structural groups having atoms other than carbon, such as a quinolinyl group and a carbazolyl group. This can be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited. The range is usually between 20 and 30.

[0406] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0407] Aldehyde groups, carbonyl groups, and amino groups include aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic compounds. Groups substituted with cyclic hydrocarbons, heterocyclic rings, etc., can also be included.

[0408] Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons can be substituted even if they are unsubstituted. It's okay if it's included.

[0409] A silyl group refers to a silicon compound group such as a trimethylsilyl group, and this is an unassigned group. It can be either a substitution or a substitution. The number of carbon atoms in the silyl group is not particularly limited, but usually it is 3. The range is ~20. Also, the silicon number is usually between 1 and 6.

[0410] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 Ar 1 and R 3 , A r 2 and R 2 Ar 2 and R 3 , R 2 and R 3 Ar 1 and Ar 2 Conjugation formed between the above and is a non-conjugated fused ring. Here, when n is 1, two R 1 Conjugated or non-conjugated A condensed ring may be formed. These condensed rings contain nitrogen, oxygen, and sulfur atoms in their intraring structure. Alternatively, it may be fused with another ring.

[0411] Specific examples of these phosphine oxide derivatives include the following compounds. . [ka]

[0412] This phosphine oxide derivative is manufactured using known raw materials and known synthesis methods. It is possible.

[0413] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably This compound is represented by the following formula (ETM-8-1). For details, see International Publication No. 2011 / 02. It is also mentioned in Official Gazette No. 1689. [ka]

[0414] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3. More preferably, 2 or 3.

[0415] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0416] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-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 (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentasenium-(1-,2-,5-,6-)il. It is possible.

[0417] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0418] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, and oxazoli. Lu, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxy Sadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl Lu, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl Naphthilidinyl, Purinyl, Pteridinyl, Carbazolyl, Acridinyl, Phenoxa Zinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, yn Examples include dridinyl.

[0419] Furthermore, the above aryl and heteroaryl may be substituted, for example, the above It may be substituted with an aryl or heteroaryl.

[0420] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

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

[0422] <Carbazole derivatives> Carbazole derivatives include, for example, compounds represented by the following formula (ETM-9), or compounds that are... It is a polymer formed by multiple single bonds or other linkages. For details, see U.S. Public Notice 2014 / 0197386. It is listed in the official gazette. [ka]

[0423] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. n is an independent integer between 0 and 4, preferably between 0 and 3. It is, and more preferably, 0 or 1.

[0424] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0425] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-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 (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentasenium-(1-,2-,5-,6-)il. It is possible.

[0426] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0427] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, and oxazoli. Lu, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxy Sadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl Lu, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl Naphthilidinyl, Purinyl, Pteridinyl, Carbazolyl, Acridinyl, Phenoxa Zinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, yn Examples include dridinyl.

[0428] Furthermore, the above aryl and heteroaryl may be substituted, for example, the above It may be substituted with an aryl or heteroaryl.

[0429] Carbazole derivatives are compounds represented by the above formula (ETM-9) with multiple bonds such as single bonds. It may also be a combined polymer. In this case, in addition to single bonds, there may be an aryl ring (preferably a polyvalent one). Benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phen They may be linked by a narene ring, a phenanthrene ring, or a triphenylene ring.

[0430] Specific examples of these carbazole derivatives include the following compounds. [ka]

[0431] This carbazole derivative can be produced using known raw materials and known synthesis methods. .

[0432] <Triadine derivatives> Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), and are preferred. The compound is represented by the following formula (ETM-10-1). For details, see U.S. Public Notice 2011. It is listed in Gazette No. / 0156013. [ka]

[0433] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3. More preferably, 2 or 3.

[0434] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0435] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-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 (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentasenium-(1-,2-,5-,6-)il. It is possible.

[0436] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0437] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, and oxazoli. Lu, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxy Sadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl Lu, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl Naphthilidinyl, Purinyl, Pteridinyl, Carbazolyl, Acridinyl, Phenoxa Zinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, yn Examples include dridinyl.

[0438] Furthermore, the above aryl and heteroaryl may be substituted, for example, the above It may be substituted with an aryl or heteroaryl.

[0439] Specific examples of these triazine derivatives include the following compounds. [ka]

[0440] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0441] <Benzimidazole derivatives> Benzimidazole derivatives are compounds represented by the following formula (ETM-11), for example. . [ka]

[0442] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an phenylene ring, where n is an integer from 1 to 4, and the "benzoimidazole substituent" is above The "peri" in notation (ETM-2), formula (ETM-2-1), and formula (ETM-2-2) A substituent in which the pyridyl group in the "zin-based substituent" is replaced by a benzimidazole group. In benzimidazole derivatives, at least one hydrogen atom may be substituted with deuterium. stomach. [ka]

[0443] R in the above benzimidazole group 11 It consists of hydrogen, alkyl groups with 1 to 24 carbon atoms, and carbon atoms. The above formula (ETM- 2-1) and R in equation (ETM-2-2) 11 You can quote the explanation.

[0444] φ is further preferably an anthracene ring or a fluorene ring, in this case The structure can be described by referring to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2). And in each equation, R 11 ~R 18 This is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation can be cited. Also, the above formula (ETM-2-1) or formula (ETM- In 2-2), it is described as a form in which two pyridine substituents are bonded, but these are bent When replacing with zoimidazole substituents, replace both pyridine substituents with benzimidazole substituents. It may be replaced with a zole substituent (i.e., n=2), or any one of the pyridine substituents Replace one substitution group with a benzimidazole substituent and the other pyridine substituent with R 11 ~R 1 8 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) Okeru R 11 ~R 18 Replace at least one of the benzimidazole substituents to form "P "Lysine substituent"11 ~R 18 You can replace it with this.

[0445] A specific example of this benzimidazole derivative is, 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]imi Dazole, 5-(10-(naphthalene-2-yl)anthracene-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2- Il)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imida Zol, 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, 5-(9,10-di(naphthalene-2-yl)anthrace Examples include 1,2-diphenyl-1H-benzo[d]imidazole. ru. [ka]

[0446] This benzimidazole derivative can be produced using known raw materials and known synthesis methods. can.

[0447] <Phenanthroline derivatives> Phenanthroline derivatives include, for example, those of the following formula (ETM-12) or formula (ETM-12- It is the compound represented by 1). Details are described in International Publication No. 2006 / 021982. It is. [ka]

[0448] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an énylene ring, and n is an integer from 1 to 4.

[0449] R in each formula 11 ~R 18 These are, independently, hydrogen, alkyl (preferably with 1 carbon atom) 24 alkyl groups, cycloalkyl groups (preferably cycloalkyl groups with 3 to 12 carbon atoms), and is an aryl (preferably an aryl with 6 to 30 carbon atoms). Also, the above formula (ETM-1 In 2-1), R 11 ~R 18 One of these bonds with φ, which is an aryl ring.

[0450] Even if at least one hydrogen atom in each phenanthroline derivative is substituted with deuterium good.

[0451] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula ( R in ETM-2) 11 ~R 18 The explanation can be quoted. Also, φ is as described above. In addition to the above example, the following structural formulas can be cited. Note that R in the following structural formulas represents each These are independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-na These are phthyl, 2-naphthyl, biphenylyl, or terpheniryl. [ka]

[0452] A specific example of this phenanthroline derivative is, for example, 4,7-diphenyl-1,10 -Phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrone Phosphorus, 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'-difluorobis(1,10-phenphenyl Nanthrolin-5-yl), basocuproine and 1,3-bis(2-phenyl-1,10- Examples include phenanthroline-9-ylbenzene. [ka]

[0453] This phenanthroline derivative can be produced using known raw materials and known synthesis methods. Cut.

[0454] <Quinolinol-based metal complexes> Quinolinol-based metal complexes are compounds represented by the following general formula (ETM-13), for example. ru. [ka] In the formula, R 1 ~R 6 is hydrogen or a substituent, and M is Li, Al, Ga, Be, or Zn The expression is such that n is an integer between 1 and 3.

[0455] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium and tris(8- Aluminum (4-methyl-8-quinolinolate), Tris(4-methyl-8-quinolinolate)aluminium Tris(5-methyl-8-quinolinolate)aluminum, Tris(3,4-dimethicone) (Lu-8-Quinolinolate) Aluminum, Tris(4,5-Dimethyl-8-Quinolinolate) Aluminum, Tris(4,6-dimethyl-8-quinolinolate)aluminum, S(2-methyl-8-quinolinolate)(phenolate)aluminum, bis(2-methyl) (Lu-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-Me (3,4-dimethylphenolate)aluminum, bis(2 -Methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis (2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminium Um, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate) Luminium, bis(2-methyl-8-quinolinolate)(2,4,6-triphenylphenyl (Nolat) Aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-tri Methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4 ,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolino (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-quinol) (4-phenylphenolate)aluminum, bis(2,4-dimethyl-8- (3,5-Dimethylphenolate) Aluminum, Bis(2,4-Dimethyl (3,5-di-t-butylphenolate)aluminum, butylphenolate S(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl- 8-Quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)a Luminium-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum , bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bi S(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-quino Linolate) Aluminum, bis(2-methyl-5-trifluoromethyl-8-quinoline (RAH) Aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8- (Quinoline) Aluminum, Bis(10-hydroxybenzo[h]quinoline) Beryl Examples include Um.

[0456] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods. Cut.

[0457] <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). ru. [ka]

[0458] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or ant). Helical ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or It is a triphenylene ring, and n is an integer from 1 to 4, and it is a "thiazole substituent" or "ben The "zothiazole substituents" are the above formulas (ETM-2), (ETM-2-1), and (E In TM-2-2), the pyridyl group among the "pyridine substituents" is a thiazole group or a benzo A substituent that replaces the thiazole group, and is used in thiazole derivatives and benzothiazole derivatives. At least one hydrogen atom in the conductor may be replaced by deuterium. [ka]

[0459] φ is further preferably an anthracene ring or a fluorene ring, in this case The structure can be described by referring to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2). And in each equation, R 11 ~R 18 This is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation can be cited. Also, the above formula (ETM-2-1) or formula (ETM- In 2-2), it is described as a form in which two pyridine substituents are bonded, but these are When replacing with a zole substituent (or benzothiazole substituent), both pyri Even if you replace the din substituent with a thiazole substituent (or benzothiazole substituent) Okay (i.e., n=2), and replace any one of the pyridine substituents with a thiazole substituent ( (or a benzothiazole substituent) is replaced with the other pyridine substituent R 11 ~R 18 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) Keru R 11 ~R 18 At least one of them is a thiazole substituent (or benzothiazole substituent) Replace with a substituent to make a "pyridine substituent" R 11 ~R 18 You can replace it with this.

[0460] These thiazole derivatives or benzothiazole derivatives are synthesized using known raw materials and known synthesis methods. It can be manufactured using the law.

[0461] The electron transport layer or electron injection layer further comprises the material forming the electron transport layer or electron injection layer. It may contain a substance that can reduce the material. This reducing substance is a substance that has a certain degree of reducing properties. Therefore, various substances are used, for example, alkali metals, alkaline earth metals, rare earth metals Groups, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, Alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, A Organic complexes of lucid metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals At least one selected from the group can be suitably used.

[0462] Preferred reducing substances include Na (work function 2.36 eV) and K (work function 2.28 eV). , alkali metals such as Rb (2.16 eV) or Cs (1.95 eV), and Ca ( (2.9eV), Sr (2.0-2.5eV), or Ba (2.52eV), etc. Examples include earth metals with a work function of 2.9 eV or less. Of these, the more preferred reducing substances are alkali metals such as K, Rb, or Cs, and even more preferred These alkali metals are either Rb or Cs, with Cs being the most preferred. In particular, it has high reducing ability and is used as an additive in relatively small amounts to materials that form electron transport layers or electron injection layers. This will improve the luminescence brightness and extend the lifespan of organic EL elements. As reducing substances with a voltage of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred. In particular, combinations containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, Alternatively, a combination of Cs, Na, and K is preferred. Including Cs enhances the reducing ability. It can be efficiently exerted by adding it to the material forming the electron transport layer or electron injection layer. This will improve the luminescence brightness and extend the lifespan of organic EL elements.

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

[0464] Any material that can efficiently inject electrons into the organic layer can be used as the material for forming cathode 108. While not particularly limited, materials similar to those used to form the anode 102 can be used. However, tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold Platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, etc. The metal or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, f Lithium oxide (such as aluminum-lithium alloys like aluminum) is preferred. To increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium Alloys containing cesium, calcium, magnesium, or these low work function metals are effective. Yes, they exist. However, these low work function metals are generally unstable in the atmosphere. To improve this point, for example, trace amounts of lithium, cesium, and magnesium can be added to the organic layer. A method is known to use doping to create highly stable electrodes. Other dopants Examples include lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. Inorganic salts can also be used, however, they are not limited to these.

[0465] Furthermore, platinum, gold, silver, copper, iron, tin, aluminum, and indigo are used for electrode protection. Metals such as um, or alloys using these metals, as well as silica, titania, and silicon nitride. Inorganic materials such as ions, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. Layering is a preferred example. Methods for fabricating these electrodes include resistance heating and electronic heating. Beam deposition, sputtering, ion plating, and coating, etc., to remove electrical conductivity. If you can do that, there are no particular restrictions.

[0466] <Binding agents that may be used in each layer> Materials used in the above hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer The material can form each layer on its own, but polyvinyl chloride and polycarbonate are used as polymer binders. Polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate Polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide Polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl Solvent-soluble resins such as cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, Phenolic resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester Dispersed in curable resins such as epoxy resins, alkyd resins, epoxy resins, and silicone resins. It can also be used in combination.

[0467] <Method for fabricating organic electroluminescent devices> Each layer constituting the organic electroluminescent element is prepared by depositing the material to be made up of each layer using a deposition method, resistance heating deposition, Electron beam deposition, sputtering, molecular stacking, printing, spin coating, or casting It can be formed by creating a thin film using methods such as coating. There are no particular limitations on the thickness of each layer formed in this way; it can be set appropriately according to the properties of the material. It is possible, but usually in the range of 2nm to 5000nm. Film thickness is usually measured using a quartz oscillator. It can be measured with a film thickness measuring device. When thinning is done using the vapor deposition method, the vapor deposition conditions are related to the material. The type of film, the desired crystal structure, and the associated structure all vary. Heating temperature of the crucible for deposition: +50 to +400°C, vacuum level: 10 -6 ~10 -3 Pa, deposition rate Temperature range: 0.01 to 50 nm / second, substrate temperature: -150 to +300°C, film thickness range: 2 nm to 5 μm. It is preferable to set it appropriately.

[0468] Next, as an example of a method for fabricating an organic electroluminescent device, we have the anode / hole injection layer / hole transport layer. / Emitting layer consisting of host material and dopant material / electron transport layer / electron injection layer / cathode This section describes the method for fabricating organic electroluminescent devices.

[0469] <Vapor deposition method> After fabricating an anode by forming a thin film of anode material on a suitable substrate using a vapor deposition method, A thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dove are placed on top of this. A thin film is formed by co-depositing a pantothenic material to create a light-emitting layer, and an electron transport layer is placed on top of this light-emitting layer. An injection layer is formed, and then a thin film made of cathode material is formed by vapor deposition or the like to create the cathode. By doing so, the desired organic electroluminescent element can be obtained. In the fabrication process, the fabrication order is reversed: cathode, electron injection layer, electron transport layer, light emission layer, hole transport layer. It is also possible to fabricate the layers in the order of feeding layer, hole injection layer, and anode.

[0470] <Wet film formation method> In the case of compositions for forming luminescent layers, the film is formed by using a wet film deposition method.

[0471] Wet film deposition generally involves a coating step of applying a light-emitting layer-forming composition to a substrate and a coating step of applying a light-emitting layer to the substrate. A coating film is formed by a drying process that removes the solvent from the light-emitting layer-forming composition. Depending on the fabric processing steps, the method using a spin coater is called the spin coating method, and the slit coater... Slit coating method using plates, gravure, offset, reverse offset, and f Lexographic printing, the inkjet method, is a method that uses an inkjet printer, spraying in a mist. The method used is called the spray method. Drying processes include methods such as air drying, heating, and vacuum drying. The drying process may be performed only once, or it may be performed multiple times using different methods and conditions. Alternatively, different methods may be used in combination, such as firing under reduced pressure.

[0472] Wet film deposition is a film deposition method that uses a solution, and is used, for example, in some printing methods (inkjet method). These include methods such as spin coating or casting, and coating. Wet film deposition methods include vacuum vapor Unlike conventional methods, this method does not require expensive vacuum deposition equipment and allows for film formation under atmospheric pressure. In addition, the wet film deposition method allows for large-area deposition and continuous production, leading to a reduction in manufacturing costs. .

[0473] On the other hand, compared to vacuum deposition, wet deposition is difficult to achieve in terms of layering. When using to fabricate a multilayer film, it is necessary to prevent the lower layer from dissolving due to the composition of the upper layer, and solubility A controlled composition, a lower crosslinking and an orthogonal solvent, which dissolves in each other. (Solvents that are not present) and other techniques are employed. However, even with these techniques, the coating of all films is not possible. In some cases, it is difficult to use wet film deposition methods.

[0474] Therefore, generally, only a few layers are deposited using the wet deposition method, and the rest are deposited using the vacuum deposition method with organic E The method of fabricating an L element is adopted.

[0475] 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) Formation of a light-emitting layer composition containing a host material and a dopant material by wet deposition method film (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 This procedure involves the anode / hole injection layer / hole transport layer / host material and dopant material. An organic EL element can be obtained consisting of a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode.

[0476] <Other film formation methods> Laser heating lithography (LITI) can be used to form the film of the light-emitting layer composition. LITI is a method of depositing a compound attached to a substrate using a laser heating and vapor deposition. A composition for forming an luminescent layer can be used in the material being fabricated.

[0477] <Optional steps> Appropriate processing steps, cleaning steps, and drying steps may be added before and after each film formation step. The processing steps include, for example, exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, Examples include washing and heating treatments using appropriate solvents. Furthermore, a bank is prepared. The series of steps involved can also be cited.

[0478] Photolithography technology can be used to create the image bank. Positive-type resist materials and negative-type resist materials are used as available bank materials. It is possible to use inkjet printing, gravure offset printing, and reverse offset printing. Printing methods that allow for patterns, such as printing and screen printing, can also be used. It is also possible to use a durable resist material.

[0479] Materials used in banks include polysaccharides and their derivatives, and hydroxyl compounds. Homopolymers and copolymers of ethylene monomers, biopolymers, polyacryloylated polymers Polyethylene, polyester, polystyrene, polyimide, polyamideimide, polyetherimide Polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyure Tan, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin , cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (AB S) Silicone resin, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, Polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetraphth Fluorinated polymers such as polyethylene, polyhexafluoropropylene, and fluoroolefins Examples include copolymer polymers of n-hydrocarbon olefins and fluorocarbon polymers. However, it is not limited to that.

[0480] Referring to Figure 9, an organic EL element is fabricated on a substrate with a bank using the inkjet method. The manufacturing method will be explained. First, the bank (200) is the electrode (120) on the substrate (110) It is located above. In this case, the inkjet head (300) is above the bank (200) A coating film (130) is created by dropping ink droplets (310) between the two layers and allowing them to dry. This can be done. By repeating this process, the next coating (140) and then the light-emitting layer (150) can be produced. By using vacuum deposition to form electron transport layers, electron injection layers, and electrodes, the light-emitting part can be formed using a bank material. It is possible to fabricate organic EL elements with separated positions.

[0481] When applying a DC voltage to the organic electroluminescent element obtained in this way, the anode is set to +, Simply apply the voltage with the cathode as the negative polarity, and when a voltage of about 2 to 40V is applied, it will appear transparent or semi-transparent. Light emission can be observed from the transparent electrode side (anode or cathode, or both). The field-emitting element will also emit light when a pulsed current or alternating current is applied. The waveform can be anything.

[0482] <Application examples of organic electroluminescent devices> Furthermore, the present invention relates to a display device equipped with an organic electroluminescent element or an organic electroluminescent element It can also be applied to lighting devices and other applications. A display device or lighting device equipped with an organic electric field light-emitting element is an organic electric field light-emitting element according to this embodiment. It can be manufactured by known methods, such as connecting an optical element with a known driving device, and is DC. It can be driven using known driving methods such as drive, pulse drive, and AC drive as appropriate.

[0483] As a display device, for example, a panel display such as a color flat panel display Ray, flexible display such as flexible color organic electroluminescent (EL) displays Examples include playing (for example, Japanese Patent Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, etc.) (See Publication No. 2004-281086, etc.). Also, as a display method for the display, for example, Examples include the trix and / or segmentation method. Mention displays can coexist within the same panel.

[0484] In a matrix, pixels for display are arranged in two dimensions, such as a grid or mosaic. A collection of pixels displays characters and images. The shape and size of the pixels are determined by their purpose. Example For example, images and text displayed on personal computers, monitors, and televisions typically have sides of 300 μm or less. The pixels in the square shape below are used, and in the case of large displays such as display panels, This will involve using pixels with sides on the order of millimeters. In the case of monochrome display, pixels of the same color will be arranged. You can simply arrange them, but in the case of color display, the red, green, and blue pixels are displayed side by side. In total, there are typically delta type and stripe type. And the driving of this matrix Either a linear sequential drive method or an active matrix method can be used. While it has the advantage of a simpler structure, when considering the operating characteristics, the active matrix In some cases, Rix may be superior, so it's necessary to choose the appropriate one depending on the application. .

[0485] In the segmentation method (type), patterns are formed to display predetermined information. This causes a designated area to emit light. For example, in digital clocks and thermometers. Time and temperature displays, operating status displays for audio equipment and induction cookers, and automotive panel displays. Examples include the following.

[0486] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays. Examples include (for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, Japanese Patent Publication No. 2004-1 (See Publication No. 19211, etc.) Backlights are primarily used to improve the visibility of non-self-illuminating display devices. Used for purposes such as liquid crystal displays, clocks, audio equipment, automotive panels, display boards, and It is used for signs and other applications. In particular, liquid crystal display devices, especially PCs where miniaturization is a challenge. For backlight applications, conventional methods consist of fluorescent lamps and light guide plates, making them thinner. Given the difficulties involved, the backlight using the light-emitting element according to this embodiment is thin and lightweight. Quantity is the defining characteristic.

[0487] 3-2. Other Organic Devices The polycyclic aromatic compound according to the present invention, in addition to the above-mentioned organic field light-emitting device, is also an organic field effect device. It can be used to fabricate transistors or organic thin-film solar cells.

[0488] Organic field-effect transistors control current using an electric field generated by a voltage input. A transistor is a device that has a source electrode, a drain electrode, and a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, and electricity flows between the source electrode and the drain electrode. A transistor that can control the current by arbitrarily blocking the flow of particles (or holes). It is a field-effect transistor. A field-effect transistor is a simple transistor (bipolar transistor) In comparison, it is easier to miniaturize and is often used as a component in integrated circuits and other devices.

[0489] The structure of an organic field-effect transistor is typically formed using the polycyclic aromatic compound according to the present invention. Source electrodes and drain electrodes are provided in contact with the organic semiconductor active layer that is formed, Furthermore, a gate electrode is provided with an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. That would be fine. Examples of such element 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 The organic field-effect transistor configured in this way is an active matrix driven system. Pixel driving switches for liquid crystal displays and organic electroluminescent displays It can be applied as a component, etc.

[0490] Organic thin-film solar cells consist of an anode made of ITO, a hole transport layer, and a light source on a transparent substrate such as glass. It has a structure in which an electron conversion layer, an electron transport layer, and a cathode are stacked. The photoelectric conversion layer has a p-type semiconductor on the anode side. It has a body layer and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention is Depending on the physical properties, the materials used for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer are selected. It can be used. The polycyclic aromatic compound according to the present invention can be used in organic thin-film solar cells. It can function as a hole transport material or electron transport material. Organic thin-film solar cells can function as hole transport materials in addition to the above. A holoblocking layer, electron blocking layer, electron injection layer, hole injection layer, smoothing layer, etc. are appropriately provided. It is acceptable. For organic thin-film solar cells, known materials used in organic thin-film solar cells are appropriately selected. They can be selected and used in combination. [Examples]

[0491] The present invention will be described in detail below with reference to examples, but the present invention is described by these examples No limitations apply. The following are compounds synthesized in the examples.

[0492] Synthesis example (1) Compound (1-1):N 7 ,N 7 ,N 13 ,N 13 ,5,9,11,15-octapheni Lu-5,9,11,15-tetrahydro-5,9,11,15-tetraaza-19b,2 0b-diborazinaphth [3,2,1-de:1',2',3'-jk]pentacene-7, Synthesis of 13-diamines [ka]

[0493] [1st stage] Under a nitrogen atmosphere, 1,3-dibromobenzene (25.0 g, 106 mmol), aniline (20.3 ml, 223 mmol), Tris(dibenzylideneacetone) dipalladium ( 0)(Pd2(dba)3)(971mg, 1.06 mmol), 2,2'-bis(diphthol) (Phenylphosphino)-1,1'-Binaphthyl (BINAP: 1.98g, 3.18mmo) l) Contains NaOtBu (25.5g, 265mmol) and toluene (400ml) The flask was heated to 110°C and stirred for 18 hours. The reaction mixture was cooled to room temperature, and silica was added. The mixture was filtered using a gel (eluent: toluene), and the solvent was removed under reduced pressure to obtain the crude product. The crude product was dissolved in toluene, then an appropriate amount was removed by distillation under reduced pressure, and hexane was added to reprecipitation. By doing so, N 1 ,N 3 -Diphenylbenzene-1,3-diamine (16.5g, yield 60 %) was obtained as a white solid. [ka]

[0494] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=5.63(s,2H), 6.60(d d,2H), 6.74(t,1H), 6.90(t,2H), 7.06(d,4H), 7 0.12 (t, 1H), 7.24 (dt, 4H).

[0495] [Second stage] Under a nitrogen atmosphere, 1,3-dibromo-5-chlorobenzene (8.11 g, 30 mmol) , diphenylamine (10.1g, 60mmol), Pd2(dba)3 (550mg, (0.6 mmol), 2-dicyclohexylphenylphosphino-2',6'-dimethoxy Diphenyl (SPhos: 0.493g, 1.2 mmol), NaOtBu (8.60g) Heat a flask containing 90 mmol of toluene (90 mmol) and toluene (300 ml) to 80°C, 1 The mixture was stirred for 5 hours. The reaction mixture was cooled to room temperature and filtered using silica gel (eluent: True). (n) The solvent was removed by vacuum distillation to obtain the crude product. After dissolving the obtained crude product in toluene, A saturated solution is prepared by removing the solution under reduced pressure, and hexane is added to reprecipitation, thereby obtaining 5-chlorohydrate. Ro-N 1 ,N 1 ,N 3 ,N 3 -Tetraphenylbenzene-1,3-diamine (5.66g) A white solid was obtained with a yield of 43%. [ka]

[0496] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=6.56(d,2H), 6.64(t ,1H), 7.00(t,4H), 7.05(d,8H), 7.21(dd,8H).

[0497] [3rd stage] Under a nitrogen atmosphere, N synthesized in the first stage 1 ,N 3 -Diphenylbenzene-1,3-diamine (1.34g, 5.1 mmol), 5-chloro-N synthesized in the second step 1 ,N 1 ,N 3 ,N 3 -Tetraphenylbenzene-1,3-diamine (4.80g, 11mmol), Pd2 (dba)3 (0.140g, 0.15 mmol), tri-tert-butylphosphine (60.7 mg, 0.30 mmol), NaOtBu (1.47 g, 15 mmol) A flask containing toluene (200 ml) was heated to 110°C and stirred for 8 hours. The liquid was cooled to room temperature, filtered using silica gel (eluent: toluene), and the solvent was removed by vacuum distillation. The crude product was then obtained by washing the crude product with hexane and methanol in that order. N 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 - Pentaph Phenylbenzene-1,3,5-triamine (4.80 g, yield 87%) as a white solid. I got it. [ka]

[0498] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=6.38(d,4H), 6.41(t ,2H), 6.58(dd,2H), 6.70(t,1H), 6.88-6.90(m, 14H), 6.85(t,1H), 6.99(d,16H), 7.08-7.15(m, 20H).

[0499] [4th stage] N 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 - Penta Phenylbenzene-1,3,5-triamine (3.24g, 3.0mmol) and ol In a flask containing todichlorobenzene (400 ml), under a nitrogen atmosphere at room temperature, tribromation was performed. Boron (1.13 ml, 12 mmol) was added. After the dropwise addition was complete, the temperature was raised to 180°C and 2 Stirred for 0 hours. Then, cooled again to room temperature, N-diisopropylethylamine (7 Add 0.70 ml (45 mmol) and stir until the heat dissipates. Then, reduce the pressure to 60°C. The reaction solution was then removed by distillation to obtain the crude product. The obtained crude product was then mixed with acetonitrile and methanol. Wash with toluene in that order, then perform silica gel column chromatography (eluent: toluene). After purification, the crude product was recrystallized twice with o-dichlorobenzene, and then 1 × 10⁻⁶ -4 mmHg By sublimation purification under reduced pressure at 440°C, 1.17 g of compound (1-1) was obtained. [ka]

[0500] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=5.72(s,2H), 5.74(s ,2H), 5.86(s,1H), 6.83(d,2H), 6.88-6.93(m,1 2H), 7.05(t,8H), 7.12-7.19(m,6H), 7.24-7.26 (m,4H), 7.05(d,4H), 7.12(dd,8H), 7.12-7.19( m,6H), 7.32(d,4H), 7.38(dd,2H), 7.42(t,2H), 7.46(dd,2H), 7.47(dd,4H), 9.30(d,2H), 10.5( s,1H).

[0501] 13 C-NMR (101MHz, CDCl3):99.5(2C+2C), 103.4(1 C), 116.8(2C), 120.0(2C), 123.1(4C), 125.3(8C) ), 127.1(2C), 127.6(2C), 128.5(8C), 129.6(4C), 129.8(4C), 130.2(4C+2C), 130.3(4C), 135.0(2C) , 142.1(2C), 142.5(2C), 143.3(1C), 146.8(4C) , 147.9(2C+2C), 148.0(2C), 150.1(2C), 151.1(2 C).

[0502] Synthesis example (2) Compound (1-201):N 7 ,N 7 ,N 13 ,N 13 ,5,15-Hexaphenyl-5 ,15-dihydro-5,15-diaza-9,11-dioxy-19b,20b-diborazina ft[3,2,1-de:1',2',3'-jk]pentacene-7,13-diamine synthesis [ka]

[0503] [1st stage] Under a nitrogen atmosphere, 1,3-dibromo-5-fluorobenzene (15.5 g, 61 mmol) ), resorcinol (3.10g, 29mmol), potassium carbonate (10.0g, 73mg) A flask containing (mol) and N-methyl-2-pyrrolidone (NMP: 300 ml) The mixture was heated to 140°C and stirred for 13 hours. The reaction mixture was cooled to room temperature, and NMP was removed by distillation under reduced pressure. Afterward, water and toluene were added and the mixture was separated. Then, it was filtered using silica gel (eluent: The solvent (toluene) was removed by vacuum distillation to obtain the crude product. The obtained crude product was washed with hexane. By doing so, 1,3-bis(3,5-dibromophenoxy)benzene (14.9g, yield 8 9% was obtained. [ka]

[0504] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.41(t,2H), 7.37(t ,1H), 7.10(d,4H), 6.82(dd,2H), 6.70(t,1H).

[0505] [Second stage] Under a nitrogen atmosphere, 1,3-bis(3,5-dibromophenoxy)benzene (8.00 g, 14 mmol), diphenylamine (10.0 g, 59 mmol), Pd2(dba)3 (0.256g, 0.28mmol), tri-tert-butylphosphine (0.113 (g, 0.56 mmol), NaOtBu (6.70 g, 70 mmol) and toluene ( A flask containing 300 ml of the reaction mixture was heated to 110°C and stirred for 6 hours. Allow the reaction mixture to cool to room temperature. Cooling, filtering through silica gel (eluent: toluene), and removing the solvent under reduced pressure to obtain the crude product. The crude product obtained was washed with hexane to obtain 5,5'-(1,3-phenylene Nbis(oxy)bis(N 1 ,N 1 ,N 3 ,N 3 -tetraphenylbenzene-1,3- Diamine (11.2 g, 86% yield) was obtained as a white solid. [ka]

[0506] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.24-7.28(m,1H), 7 .18(dd,16H), 7.05(d,16H), 6.94(t,8H), 6.57( t,2H), 6.54(d,1H), 6.51(d,2H), 6.29(d,4H).

[0507] [3rd stage] 5,5'-(1,3-phenylenebis(oxy))bis(N 1 ,N 1 ,N 3 ,N 3 -Te Traphenylbenzene-1,3-diamine (2.03g, 2.2mmol) and ortho In a flask containing xylene (500 ml), under a nitrogen atmosphere at room temperature, boron tribromide (0 0.832 ml (8.8 mmol) was added. After the dropwise addition was complete, the temperature was raised to 150°C for 24 hours. Stirring was performed. Then, it was cooled again to room temperature and N,N-diisopropylethylamine (5.6 Add 0 ml (33 mmol) and stir until the exothermic reaction subsides. Then, remove the reaction solution by distillation. Next, the mixture was filtered using silica gel (eluent: toluene), and the solvent was removed by distillation under reduced pressure to obtain the crude product. The product was obtained. The crude product obtained was subjected to silica gel column chromatography (eluent: True). The product was filtered using a solvent (1 / 2 hexane / 2 by volume) and the solvent was removed under reduced pressure to obtain the crude product. By washing with toluene, compound (1-201) was obtained (50.0 mg, yield 2.4%). %). [ka]

[0508] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=5.79(d,2H), 6.70(d ,2H), 6.80(d,2H), 7.07(t,4H), 7.12(t,8H), 7. 21-7.28(m,12H), 7.31(s,1H), 7.35(dd,2H), 7. 40(t,2H), 7.44-7.51(m,6H), 9.12(d,2H), 10.2 (s,1H).

[0509] 13 C-NMR (101MHz, CDCl3): 98.6 (2C), 100.8 (2C), 104.9(1C), 117.4(2C), 120.1(2C), 124.1(4C), 12 6.0(8C), 128.4(2C), 129.2(8C), 130.0(4C), 130. 7(4C), 131.3(2C), 134.9(2C), 141.6(2C), 142.3( 1C), 146.6(4C), 147.1(2C), 148.1(2C), 152.6( 2C), 159.1(2C), 163.0(2C).

[0510] Synthesis example (3) Compound (1-9): 2,18-dimethyl-N 7 ,N7 ,N 13 ,N 13 ,9,11-he Xaparatril-5,9,11,15-tetrahydro-5,9,11,15-tetraaza -19b,20b-Diborazinaft[3,2,1-de:1',2',3'-jk]Penta Synthesis of sen-7,13-diamine [ka]

[0511] [1st stage] Under a nitrogen atmosphere, 1,3-dibromobenzene (10.8 g, 1.9 mmol), parathol Idin (20.3g, 190 mmol), Pd2(dba)3 (1.60g, 1.8mg) (ol), tri-tert-butylphosphine (0.728g, 3.6 mmol), NaO Flask containing tBu (25.9g, 270 mmol) and toluene (500ml) The mixture was stirred at room temperature for 10 hours. The reaction solution was filtered using silica gel (eluent: toluene). The solvent was removed by vacuum distillation to obtain the crude product. The obtained crude product was washed with methanol. N 1 ,N 3 -Diparathrylbenzene-1,3-diamine (19.3g, yield 74%) It was obtained as a colored solid. [ka]

[0512] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.06-7.11(m,5H), 6 .99(d,4H), 6.64(t,1H), 6.52(dd,2H), 5.54(s, 2H), 2.29(s,6H).

[0513] [Second stage] Under a nitrogen atmosphere, 1,3-dibromo-5-chlorobenzene (13.5 g, 50 mmol) Paraditolylamine (19.7g, 0.10mol), Pd2(dba)3(1.15 (g, 2.0 mmol), 2-dicyclohexylphenylphosphino-2',6'-dimeth Xydiphenyl (0.986g, 2.4mmol), NaOtBu (14.5g, 0.1 A flask containing 5 mol of toluene and 200 ml of toluene was heated to 80°C and left for 15 hours. The mixture was stirred. The reaction mixture was filtered using silica gel (eluent: toluene), and the solvent was removed by distillation under reduced pressure. A crude product was obtained. The obtained crude product was washed with methanol and then hexane in that order, and 5 -Chloro-N 1 ,N 1 ,N 3 ,N 3 -Tetraparathorylbenzene-1,3-diamine(2 1.7 g was obtained as a white solid (86% yield). [ka]

[0514] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.01(d,8H), 6.92(d ,8H), 7.00(t,4H), 6.51(t,1H), 6.45(sd,2H), 2 .28 (s, 12H).

[0515] [3rd stage] Under a nitrogen atmosphere, N synthesized in the first stage 1 ,N 3 -Diparathrylbenzene-1,3-Diami (3.1g, 11 mmol), 5-chloro-N synthesized in the second step 1,N 1 ,N 3 ,N 3 -Tetraparathorylbenzene-1,3-diamine (11.2g, 22 mmol), Pd2 (dba)3 (0.503g, 0.55 mmol), tri-tert-butylphosphine (0.223g, 1.1mmol), NaOtBu (3.20g, 33mmol) and A flask containing toluene (300 ml) was heated to 110°C and stirred for 18 hours. The liquid was filtered using silica gel (eluent: toluene), and the solvent was removed under reduced pressure to obtain the crude product. The crude product obtained was washed with methanol and then toluene, and N 1 ,N 1 '-( 1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N 5 ,N 5 -Pentaparatrilbenzene -1,3,5-triamine (11.4 g, 85% yield) was obtained as a white solid. [ka]

[0516] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=6.86-6.93(m,37H), 6.80(d,4H), 6.74(t,1H), 6.44(dd,2H), 6.30(d ,4H), 6.29(t,2H), 2.23(s,6H), 2.20(s,24H).

[0517] [4th stage] N 1 ,N 1 '-(1,3-phenylene)bis(N 1 ,N 3 ,N 3 ,N5 ,N 5 - Penta Paratolylbenzene-1,3,5-triamine (0.661 g, 0.5 mmol) and In a flask containing orthodichlorobenzene (10 ml), under a nitrogen atmosphere at room temperature, three odors were detected. Boron oxide (0.819 ml, 2.0 mmol) was added. After the dropwise addition was complete, the temperature was raised to 180°C. The mixture was stirred for 24 hours. After that, it was cooled again to room temperature and N,N-diisopropylethyl alcohol was added. Add 1.28 ml of mine (7.5 mmol) and stir until the exothermic reaction subsides. Then, 6 The reaction solution was removed by distillation under reduced pressure at 0°C. Then, it was filtered using silica gel (eluent: Tol The solvent was removed under reduced pressure to obtain the crude product. The obtained crude product was washed with toluene. Compounds (1-9) were obtained (0.365 g, yield 59%). [ka]

[0518] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=δ=2.32(s,12H), 2. 39(s,6H), 2.47(s,6H), 2.59(s,6H), 5.47-5.51 (m,4H), 5.97(s,1H), 6.80(d,2H), 6.87-6.94(m ,20H), 7.05(d,4H), 7.18(d,4H), 7.27(d,2H), 7 .31(d,4H), 9.00(s,2H), 10.5(s,1H).

[0519] 13 C-NMR(126MHz,(CDCl2)2):=20.4(4C), 20.6(2 C), 20.7(2C), 21.0(2C), 97.8(2C), 97.9(2C), 103 .5(1C), 116.7(2C), 125.7(8C), 128.1(2C), 129.0 (8C), 129.5(4C), 130.0(4C), 130.1(4C), 130.7(4 C), 131.2(2C), 132.6(4C), 134.7(2C), 136.5(2 C), 137.3(2C), 139.6(2C), 140.1(2C), 143.0(1 C), 144.1(4C), 146.1(2C), 147.9(2C+2C), 150. 1(2C), 151.1(2C).

[0520] Synthesis example (4) Compound (1-101): 7,13-diphenoxy-5,9,11,15-tetraphenoxy Lu-5,9,11,15-tetrahydro-5,9,11,15-tetraaza-19b,2 Synthesis of 0b-diborazinaphte[3,2,1-de:1',2',3'-jk]pentacene [ka]

[0521] [1st stage] Under a nitrogen atmosphere, 1-bromo-3-chloro-5-fluorobenzene (5.50 ml, 45 mmol), phenol (4.40 g, 47 mmol), potassium carbonate (9.30 g, 6 Heat a flask containing 8 mmol) and NMP (300 ml) to 150°C, and at 5 PM The mixture was stirred. The reaction mixture was cooled to room temperature, and NMP was removed by distillation under reduced pressure, followed by water and toluene. The mixture was separated. Then, it was filtered using silica gel (eluent: toluene), and the solvent was distilled under reduced pressure. After removal, 1-bromo-3-chloro-5-phenoxybenzene (12.2g, yield 98%) I got it. [ka]

[0522] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.37(m,2H), 7.16-7 .21(m,2H), 7.00-7.03(m,3H), 6.90(t,1H).

[0523] [Second stage] Under a nitrogen atmosphere, 1-bromo-3-chloro-5-phenoxybenzene (5.30 ml, 2 7 mmol), diphenylamine (4.80 g, 28 mmol), Pd2(dba)3( 0.247g, 0.27 mmol), tri-tert-butylphosphine (109mg, (0.54 mmol), NaOtBu (3.90 g, 41 mmol) and Toluene (30 A flask containing 0 ml of the solution was heated to 80°C and stirred for 14 hours. The reaction solution was then placed in silica gel. The solution is filtered using (eluent: toluene), and the solvent is removed by vacuum distillation to obtain 3-chloro-5-phenyl. Noxy-N,N-diphenylaniline (8.30 g, yield 83%) was obtained as a white solid. . [ka]

[0524] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=7.24-7.28(m,1H), 7 .18(dd,16H), 7.05(d,16H), 6.94(t,8H), 6.57( t,2H), 6.54(d,1H), 6.51(d,2H), 6.29(d,4H).

[0525] [3rd stage] Under a nitrogen atmosphere, N 1 ,N 3 -Diphenylbenzene-1,3-diamine (1.56g, 6 0 mmol), 3-chloro-5-phenoxy-N,N-diphenylaniline (4.69 g, 13 mmol), Pd2(dba)3 (0.110 g, 0.12 mmol), Tri- tert-butylphosphine (49.0 mg, 0.24 mmol), NaOtBu (1. Add 44g (15 mmol) and toluene (200 ml) to a flask and heat to 110°C. The mixture was heated and stirred for 18 hours. The reaction solution was filtered using silica gel (eluent: toluene), and dissolved The medium was removed by vacuum distillation to obtain the crude product. The obtained crude product was washed with methanol to obtain N 1 ,N 1 '-(1,3-phenylene)bis(5-phenoxy-N 1 ,N 3 ,N 3 -Truffle Phenylbenzene-1,3-diamine (4.9 g, yield 87%) was obtained as a white solid. [ka]

[0526] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=6.88-7.27(m,41H), 6.79(t,1H), 6.65(dd,2H), 6.51(t,1H), 6.30-6 0.32 (m, 4H).

[0527] [4th stage] N 1 ,N 1 '-(1,3-phenylene)bis(5-phenoxy-N 1 ,N 3 ,N 3 -to Riphenylbenzene-1,3-diamine (0.559g, 0.60 mmol) and ol In a flask containing 10 ml of todichlorobenzene, under a nitrogen atmosphere at room temperature, add tribromide. U-cell (0.227 ml, 2.4 mmol) was added. After the dropwise addition was complete, the temperature was raised to 180°C. The mixture was stirred for 24 hours. After that, it was cooled again to room temperature and N,N-diisopropylethylamine was added. (1.5 ml, 9 mmol) was added and stirred until the exothermic reaction subsided. Then, the mixture was cooled to 60°C under reduced pressure. Next, the reaction solution was removed by distillation. Then, it was filtered using silica gel (eluent: toluene), and dissolved The medium was removed by reduced pressure distillation to obtain the crude product. The obtained crude product was then subjected to silica gel column chromatography. Filter using a solvent (eluent: toluene / hexane = 1 / 2 (volume ratio)) and distill the solvent under reduced pressure. By removing the compound (1-101), compound (57.3 mg, yield 10%) was obtained. [ka]

[0528] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=5.71-5.74(m,5H), 6 .79(d,2H), 6.82(d,4H), 6.96(t,2H), 7.09(d,4 H), 7.15(dd,4H), 7.28-7.38(m,12H), 7.45-7.5 2(m,4H), 7.61(t,4H), 9.24(d,2H), 10.5(s,1H) .

[0529] 13 C-NMR (101MHz, CDCl3): δ=96.1(2C), 96.2(2C) , 103.4(1C), 117.1(2C), 119.1(4C), 120.3(2C), 1 23.2(2C), 128.0(2C), 128.5(8C), 129.3(4C), 129 .8(4C), 130.3(4C), 130.6(4C), 130.8(2C), 131.0 (4C), 135.2(2C), 141.6(2C), 142.0(2C), 143.8 (1C), 147.7(2C), 148.4(2C), 148.6(2C), 150.0 (2C), 156.0(2C), 160.6(2C).

[0530] Synthesis example (5): Compound (1-2001):N 7 ,N 7 ,N 13 ,N 13 ,5,9,15-tetrahydro -5,9,15-Triaza-11-oxa-19b,20b-diborazinaphthate[3,2, Synthesis of 1-de:1',2',3'-jk]pentacene-7,13-diamine [ka]

[0531] Under a nitrogen atmosphere, 1,3-dibromo-5-fluorobenzene (25.4g, 0.10mo) l), m-chlorophenol (16.7g, 0.13mol), cesium carbonate (40.1 A fructose containing g, 0.12 mol) and N-methylpiperidone (NMP, 300 ml) The SCO was heated to 120°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and the NMP was reduced under reduced pressure. After evaporation, the solvent was filtered using a silica gel short-pass column (eluent: hexane). The crude product was obtained by removing the under reduced pressure. The obtained crude product was divided into 1 × 10⁻⁶ units. -4 Under reduced pressure of mmHg, 8 By sublimation purification at 0°C, 1,3-dibromo-5-(3-chlorophenoxy)benzase is obtained. We obtained (27.7g, yield 77%). [ka]

[0532] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (400MHz, CDCl3): δ=6.90(d,1H), 7.02(s ,1H), 7.07(s,2H), 7.15(d,1H), 7.29(t,1H), 7. 41(s,1H).

[0533] Under a nitrogen atmosphere, 1,3-dibromo-5-(3-chlorophenoxy)benzene (10.2 (g, 28 mmol), diphenylamine (10.6 g, 62 mmol), Pd2 (dba )3 (131 mg, 0.14 mmol), tri-tert-butylphosphine (56.7 mg, 0.28 mmol), NaO t Bu (6.37g, 70 mmol) and toluene The flask containing (300 ml) was heated to 80°C and stirred for 30 minutes. The reaction solution was then allowed to cool to room temperature. Cooled, filtered using a Florisil short-pass column (eluent: toluene), and the solvent was removed. The crude product was obtained by distillation under reduced pressure. The obtained crude product was washed with methanol to obtain 5-( 3-Chlorophenoxy)N 1 ,N 1 ,N 3 ,N 3 -tetraphenylbenzene-1,3-di The amine (12.6 g, 83% yield) was obtained as a white solid. [ka]

[0534] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (400MHz, CDCl3): δ=6.28(d,2H), 6.56(t ,1H), 6.82(dd,1H), 6.91(t,1H), 6.95-6.99(m, 5H)7.07(d,8H), 7.15(t,1H), 7.21(t,8H).

[0535] Under a nitrogen atmosphere, 5-(3-chlorophenoxy)N 1 ,N 1 ,N 3 ,N 3 -Tetraphen Benzene-1,3-diamine (10.2g, 18mmol), aniline (3.35g, 36mmol), Pd2(dba)3(0.330g, 0.36mmol), 2-disic Rohexylphosphino-2',6'-dimethoxybiphenyl (0.296g, 0.72mg) mol), NaO t Bu (5.19g, 54mmol) and toluene (200ml) The flask containing the mixture was heated to 110°C and stirred for 2 hours. The reaction solution was cooled to room temperature and then flushed. Filter using a lysyl short-pass column (eluent: toluene), remove solvent under reduced pressure, and obtain crude The product was obtained. The crude product obtained was washed with hexane and methanol in that order, and N 1 , N 1 ,N 3 ,N 3 -Tetraphenyl 5-(3-(phenylamino)phenoxy)benzene -1,3-diamine (9.49 g, 89% yield) was obtained as a white solid. [ka]

[0536] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (400MHz, CDCl3): δ=5.65(s,1H), 6.34(t ,2H), 6.47(d,1H), 6.55(dd,1H), 6.65(dd,2H), 6.94-6.98(m,5H), 7.03-7.08(m,10H), 7.10(t, 1H), 7.19(t,8H), 7.27(t,2H).

[0537] Under a nitrogen atmosphere, N 1 ,N 1 ,N 3 ,N 3 -Tetraphenyl 5-(3-(phenylamino )Phenoxy)benzene-1,3-diamine (4.29g, 7.2mmol), 5-chloro Ro-N 1 ,N 1 ,N 3 ,N 3 -Tetraphenylbenzene-1,3-diamine (2.67g) (6.0 mmol), Pd2(dba)3 (0.165 g, 0.18 mmol), Tri- tert-butylphosphine (72.8 mg, 0.36 mmol), NaO t Bu(1. Add 15g (12 mmol) and toluene (200 ml) to a flask and heat to 110°C. The mixture was heated and stirred for 20 hours. The reaction solution was cooled to room temperature and tested using a Florisil short-pass column. The crude product was obtained by filtering with eluent (toluene) and removing the solvent under reduced pressure. By washing the product with acetonitrile, N 1 -(3-(3,5-bis)diphenylamine (N)phenoxy)phenol-(N 1 ,N 3 ,N 3 ,N 5 ,N 5 - Pentaphenylbenz n-1,3,5-triamine (4.93 g, 82% yield) was obtained as a white solid. [ka]

[0538] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(500MHz,(CDCl2)2):δ=6.28(d,2H), 6.3 8(d,2H), 6.40-6.42(m,2H), 6.52(s,1H), 6.58- 6.60(m,2H), 6.86(t,4H), 6.92-7.07(m,24H), 7 .11-7.20 (m, 18H).

[0539] N 1 -(3-(3,5-bis)diphenylamino)phenoxy)phenol-(N 1 , N 3 ,N 3 ,N 5 ,N 5 -Pentaphenylbenzene-1,3,5-triamine(1.05 A flask containing g, 1.0 mmol) and chlorobenzene (50 ml) is subjected to a nitrogen atmosphere. Under gas pressure and at room temperature, boron tribromide (0.569 ml, 6.0 mmol) was added. The mixture was heated to 140°C and stirred for 24 hours. After that, it was cooled back to room temperature and N-diiso was added. Add propylethylamine (3.13 ml, 18 mmol) and stir until the exothermic reaction subsides. Then, the reaction solution was removed by distillation under reduced pressure at 60°C to obtain the crude product. By washing with heptane, compound (1-2001) was obtained (0.251 g, yield 24%). ). [ka]

[0540] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(500MHz,(CDCl2)2):δ=5.67(s,1H), 5.6 8(s,1H), 5.75(d,1H), 6.51(d,1H), 6.58(s,1H) ,6.77(m,2H),6.92-7.12(m,18H),7.18-7.51(m ,21H), 9.17(m,2H), 10.3(s,1H). 13 C-NMR(126MHz,(CDCl2)2):98.5(1C), 98.9(1 C), 99.0(1C), 100.6(1C), 103.3(1C), 117.0(1C ), 117.3(1C), 120.0(1C), 120.1(1C), 123.5(2C ), 124.0(2C), 124.4(1C), 125.6(4C), 126.0(4C ), 128.1(1C), 128.3(2C), 128.8(4C), 129.0(1C ), 129.1(4C), 130.0(2C), 130.2(2C), 130.5(1C ), 130.6(2C), 130.7(2C), 130.8(2C), 131.2(1C ), 135.0(1C), 135.1(1C), 141.7(1C), 141.8(1C ), 142.1(1C), 143.0(1C), 146.5(2C), 146.7(2C ), 147.1(1C), 146.8(1C), 147.8(1C), 147.9(1C ), 148.0(1C), 151.1(1C), 151.2(1C), 152.3(1C ), 159.2 (1C), 161.9 (1C).

[0541] Synthesis example (6): Compound (1-31):2,18-ジメチル-N 7 N 7 N 13 N 13 ,9,11- ヘキサパトリル-5,9,11,15-テトラヒドロ-5,9,11,15-テトラア The-19b,20b-Diborazinaft[3,2,1-de:1',2',3'-jk]pen Synthesis of tacen-7,13-diamine [ka]

[0542] [1st stage] Under a nitrogen atmosphere, 1,3-dibromo-5-chlorobenzene (13.7 g, 51 mmol) Metaditolylamine (19.8g, 0.10mol), Pd2(dba)3(0.93 g, 1.0 mmol), 2-dicyclohexylphenylphosphino-2',6'-dimeth Xydiphenyl (SPhos: 0.838g, 2.0mmol), NaOtBu (14. Heat a flask containing 6g (0.15mol) and toluene (640ml) to 80°C. The mixture was stirred for 1.5 hours. After adding water to stop the reaction, extraction was performed using toluene. Solvent The crude material obtained by distilling off the excess was subjected to a silica gel column (eluent: heptane:toluene = 6:4 (volume) By purifying using the (quantitative ratio), 5-chloro-N 1 ,N 1 ,N 3 ,N 3 - Tetrametat Lylbenzene-1,3-diamine (27.0 g, 84% yield) was obtained as a white paste. . [ka]

[0543] [Second stage] Under a nitrogen atmosphere, N 1 ,N 3 -Diphenylbenzene-1,3-diamine (4.22g, 1 6 mmol), 5-chloro-N 1 ,N 1 ,N 3 ,N 3-Tetramethatrolbenzene-1, 3-diamine (21.5g, 43mmol), Pd-132 (0.12g, 0.17mmol) Contains (100ml), NaOtBu (3.89g, 40mmol), and Toluene (80ml) The flask was heated to 110°C and stirred for 2 hours. After adding water to stop the reaction, toluene was added. Extraction was carried out. The crude material obtained by removing the solvent by distillation was collected on a silica gel column (eluent: toluene). The crude product was purified using ) and reprecipitation of the obtained crude product with heptane, and N 1 ,N 1 '-( 1,3-phenylene)bis(N 1 -phenyl-N 3 ,N 3 ,N 5 ,N 5 - Tetrametr Lubenzene-1,3,5-triamine (19.9 g, 80% yield) was obtained as a white solid. . [ka]

[0544] [3rd stage] N 1 ,N 1 '-(1,3-phenylene)bis(N 1 -phenyl-N 3 ,N 3 ,N 5 ,N 5 -Tetramethatrolbenzene-1,3,5-triamine (0.661g, 0.5mmo l) and orthodichlorobenzene (10 ml) are placed in a flask under a nitrogen atmosphere in the chamber. Boron tribromide (0.819 ml, 2.0 mmol) was added at warm temperature. After the dropwise addition was complete, the mixture was heated to 180°C. The temperature was raised to [temperature] and stirred for 24 hours. After that, it was cooled again to room temperature and N,N-diisopropyl Ethylamine (1.28 ml, 7.5 mmol) was added and the mixture was stirred until the exothermic reaction subsided. Afterward, the reaction solution was removed by distillation under reduced pressure at 60°C. Then, it was filtered using silica gel (elution). The solvent (toluene) was removed under reduced pressure to obtain the crude product. The obtained crude product was washed with toluene. By purification, compound (1-31) was obtained (0.365 g, yield 59%). [ka]

[0545] The compound structure obtained by NMR spectroscopy was confirmed. 1 H-NMR (400MHz, CDCl3): δ=2.32(s,12H), 2.39 (s,6H), 2.47(s,6H), 2.59(s,6H), 5.47-5.51(m ,4H), 5.97(s,1H), 6.80(d,2H), 6.87-6.94(m,2 0H), 7.05(d,4H), 7.18(d,4H), 7.27(d,2H), 7.3 1(d,4H), 9.00(s,2H), 10.5(s,1H). 13 C-NMR (101MHz, CDCl3): 20.4 (4C), 20.6 (2C), 20.7(1C), 21.0(2C), 97.8(2C), 97.9(2C), 103.5( 1C), 116.7(2C), 125.7(8C), 128.1(2C), 129.0(8C ), 129.5(4C), 130.0(4C), 130.1(4C), 130.7(4C), 131.2(2C), 132.6(4C), 134.7(2C), 136.5(2C), 137.3(2C), 139.6(2C), 140.1(2C), 143.0(1C), 144.1(4C), 146.1(2C), 147.9(2C+2C), 150.1(2 C), 151.1(2C).

[0546] By appropriately changing the raw material compounds, the present invention can be reproduced in a manner similar to the synthesis example described above. The compounds can be synthesized.

[0547] Next, we evaluate the basic physical properties of the compound of the present invention and fabricate an organic EL element using the compound of the present invention. The evaluation will be described below.

[0548] <Evaluation of basic physical properties> Sample preparation When evaluating the absorption and emission properties (fluorescence and phosphorescence) of a compound to be evaluated, the chemical composition of the compound to be evaluated is used. The compound can be evaluated either by dissolving it 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, the evaluation method depends on how the compound being evaluated is used in an organic EL device. Therefore, there are two approaches: one where only the compound to be evaluated is thinned and evaluated, and another where the compound to be evaluated is subjected to an appropriate matrix. In some cases, the material is dispersed in a synthetic material to form a thin film for evaluation.

[0549] Commercially available PMMA (polymethyl methacrylate) is used as the matrix material. This can be done. For example, a thin film sample dispersed in PMMA can be evaluated by comparing the PMMA with the target of evaluation. After dissolving the mixture in toluene, a transparent support substrate made of quartz is coated by a spin coating method. It can be fabricated by forming a thin film on a 10mm x 10mm surface.

[0550] Furthermore, the method for preparing thin film samples when the matrix material is the host material is described below. A transparent support substrate made of quartz (10mm x 10mm x 1.0mm) is used with a commercially available vapor deposition apparatus (Showa Era). A molybdenum deposition boat containing host material is fixed to a substrate holder (manufactured by Vacuum Co., Ltd.). Next, a molybdenum deposition boat containing the dopant material is attached. Then, a vacuum chamber is set to 5 x 1 0 -4The pressure is reduced to Pa, and a deposition boat containing the host material and a deposition boat containing the dopant material are placed inside. The boat is heated simultaneously to deposit the host material and dopant material to achieve the appropriate film thickness. A mixed thin film is formed. The deposition rate is controlled according to the set weight ratio of the host material and the dopant material. To control.

[0551] Evaluation of absorption and emission properties The absorption spectrum of the aforementioned sample was measured using a UV-Vis-Near-Infrared Spectrophotometer (Shimadzu Corporation). The procedure was performed using UV-2600. Furthermore, the fluorescence spectrum or phosphorescence spectrum of the sample was also analyzed. The spectrum was measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000). went.

[0552] For fluorescence spectrum measurement, the photoluminescent element is excited at an appropriate excitation wavelength at room temperature. The phosphorescence spectrum was measured. For the measurement of the phosphorescence spectrum, the attached cooling unit was used as described above. The sample was measured while immersed in liquid nitrogen (temperature 77K). The phosphorescence spectrum was observed. Therefore, an optical chopper was used to adjust the delay time from excitation light irradiation to the start of measurement. The pull was excited at an appropriate excitation wavelength, and its photoluminescence was measured.

[0553] In addition, we used an absolute PL quantum yield analyzer (Hamamatsu Photonics K.K., C9920-02G). The fluorescence quantum yield is measured using this method.

[0554] Evaluation of fluorescence lifetime (delayed fluorescence) Using a fluorescence lifetime analyzer (Hamamatsu Photonics K.K., C11367-01) at 300K The fluorescence lifetime is measured at the maximum emission wavelength, which is measured at an appropriate excitation wavelength. Observe the fast and slow components. Fluorescence of typical organic EL materials at room temperature. In lifetime measurement, the deactivation of the triplet component due to heat leads to the involvement of the triplet component derived from phosphorescence. Slow components are rarely observed. Slow components are observed in the compound being evaluated. If this occurs, the triplet energy with a long excitation lifetime is transferred to the singlet energy by thermal activation. This indicates that it was observed as delayed fluorescence.

[0555] Calculation of the energy gap (Eg) From the long-wavelength end A (nm) of the absorption spectrum obtained by the method described above, Eg = 1240 / A It is calculated as follows.

[0556] E S 、E T and calculation of ΔEST Singlet excitation energy (E S ) is from the maximum emission wavelength B (nm) of the fluorescence spectrum to E S It is calculated as =1240 / B. Also, the triplet excitation energy (E T ) is the phosphorescence spectrum From the maximum emission wavelength C (nm) to E T It is calculated as =1240 / C.

[0557] ΔEST is E S and E T The energy difference is ΔEST = E S -E T It is defined as follows. ΔEST is, for example, "Purely organic electroluminescent material realizing 100% "conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shi zu, K. Katsuaki, S. Kubo, T. Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, It can also be calculated using the method described in C. Adachi, Nat. Commun. 2015, 6, 8476.

[0558] Evaluation of the basic physical properties of compound (1-1) [Absorption properties] A thin film substrate (made of silica) in which compound (1-1) is dispersed in PMMA at a concentration of 1% by weight is prepared. The absorption spectrum was measured (Figure 2). As a result, the maximum absorption wavelength in the visible light region was 4 The wavelength was 57 nm. Furthermore, a thin film substrate consisting only of compound (1-1) was prepared, and the absorption spectrum was measured. The measurement of the clef revealed that the long-wavelength absorption edge of the absorption spectrum was 477 nm, and Eg = 2. The calculated value was 60 eV, indicating that it has an appropriate energy gap.

[0559] [Luminous properties] The fluorescence spectrum was measured by dispersing compound (1-1) in PMMA at a concentration of 1% by weight. A film-forming substrate (made of silica) is prepared and excited at an excitation wavelength of 340 nm to produce photoluminescence. The measurement was performed (Figure 2). As a result, the maximum emission wavelength was 467 nm. From this, E S is 2 The calculated value is 0.66 eV. Furthermore, the same substrate was prepared and excited at an excitation wavelength of 340 nm to obtain fluorescence. The quantum yield was measured and found to be a high value of 92%.

[0560] The phosphorescence spectrum was measured by dispersing compound (1-1) in PMMA at a concentration of 1% by weight. A film-forming substrate (made of silica) is prepared and excited at an excitation wavelength of 340 nm to produce photoluminescence. The measurement was performed (Figure 2). As a result, the maximum emission wavelength was 470 nm. From this, E T is 2 The reading was 0.64 eV, indicating a high value.

[0561] The calculated ΔEST was 0.02 eV.

[0562] Based on the above, it can be confirmed that compound (1-1) is a material capable of achieving a high efficiency and deep blue color. This was confirmed. In particular, because it has a small ΔEST, it is expected to be a thermally activated delayed fluorescence material. ru.

[0563] Comparative compound 1 The compound of formula (1-2676) disclosed in International Publication No. 2015 / 102118 is a comparative compound. It was set to 1. Except for changing compound (1-1) of the present invention to comparative compound 1, compound (1-1) ΔEST was calculated using the same method as in the previous example. The maximum emission wavelength of the fluorescence spectrum was 469n The maximum emission wavelength of the phosphorescence spectrum is 502 nm, and the ΔEST is calculated to be 0.17 eV. This ΔEST value is small enough to obtain thermally activated delayed fluorescence, but the present invention Compared to compound (1-1), it is larger and is suitable for an organic EL device configuration that exhibits thermally activated delayed fluorescence. Therefore, the external quantum efficiency is expected to be lower than that of compound (1-1). [ka]

[0564] Comparative compound 2 Compound (1-422) disclosed in International Publication No. 2015 / 102118 is compared to Compound 2. This was done. Except for changing compound (1-1) of the present invention to comparative compound 2, the same as compound (1-1). The evaluation was performed using the same method as in the examples. As a result, the maximum emission wavelength of the fluorescence spectrum was 477° The emission wavelength is in nm, which is 10 nm larger than that of compound (1-1), resulting in a deep blue color. The result was not achieved. [ka]

[0565] From the above, compound (1-1) has an appropriate energy gap and high triplet excitation energy. Because it has -, it is ideal as a material for the light-emitting layer. In particular, because it has a small ΔEST, It also shows promise as a thermally activated delayed fluorescence material for photolayers.

[0566] Evaluation of the basic physical properties of compound (1-201) Thin film forming group obtained by dispersing compound (1-201) in PMMA under the same conditions as compound (1-1). A plate was fabricated, and its absorption and emission spectra were measured (Figure 3). The excitation wavelength during spectral measurement is 375 nm. As a result, the maximum emission of the fluorescence spectrum is observed. The wavelength was 438 nm. Additionally, the same substrate was prepared and excited at an excitation wavelength of 375 nm, resulting in fluorescence. The quantum yield was measured and found to be a high value of 87%. Furthermore, the maximum emission wave of the phosphorescence spectrum... The length was 466 nm. From this, E T The value was 2.66 eV, indicating a high value. The ΔEST was calculated to be 0.17 eV.

[0567] Based on the above, compound (1-201) is a material capable of achieving a deep blue color with high efficiency. This was confirmed. In particular, its small ΔEST makes it promising as a thermally activated delayed fluorescence material. can.

[0568] Evaluation of the basic physical properties of compound (1-101) Thin film forming group obtained by dispersing compound (1-101) in PMMA under the same conditions as compound (1-1). A plate was fabricated, and its absorption and emission spectra were measured (Figure 4). The excitation wavelength during spectral measurement is 407 nm. As a result, the maximum emission of the fluorescence spectrum is observed. The wavelength was 457 nm. Additionally, the same substrate was prepared and excited at an excitation wavelength of 407 nm, resulting in fluorescence. The quantum yield was measured and found to be a high value of 91%. Furthermore, the maximum emission wave of the phosphorescence spectrum... The length was 461 nm. From this, E T The value was 2.69 eV, indicating a high value. The ΔEST was calculated to be 0.02 eV.

[0569] Based on the above, compound (1-101) is a material capable of achieving a high efficiency and deep blue color. This was confirmed. In particular, its small ΔEST makes it promising as a thermally activated delayed fluorescence material. can.

[0570] Evaluation of the basic physical properties of compounds (1-9) A thin film substrate was prepared by dispersing compound (1-9) in PMMA under the same conditions as compound (1-1). The sample was prepared, and its absorption and emission spectra were measured (Figure 5). The excitation wavelength during the clef measurement is 374 nm. As a result, the maximum emission wavelength of the fluorescence spectrum is The wavelength was 473 nm. Additionally, the same substrate was prepared and excited at an excitation wavelength of 374 nm to obtain fluorescence quantum The yield was measured and found to be a high value of 89%. Furthermore, the maximum emission wavelength of the phosphorescence spectrum was It was 477 nm. From this, E T The value was 2.60 eV, indicating a high value. The ΔEST was calculated to be 0.02 eV.

[0571] Based on the above, it can be confirmed that compounds (1-9) are materials capable of achieving a high efficiency and deep blue color. This was confirmed. In particular, because it has a small ΔEST, it is expected to be a thermally activated delayed fluorescence material. ru.

[0572] <Evaluation of Organic EL Devices> As described above, the compounds of the present invention have an appropriate energy gap (Eg) and high triple excitation. Electromotive force (E T) and small ΔEST are characteristic, for example, the light-emitting layer Furthermore, it is expected to be applicable to charge transport layers, and in particular to light-emitting layers.

[0573] Evaluation items and evaluation methods The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), and external These include quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. These evaluation items can use values ​​at appropriate luminous intensity.

[0574] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, but internal quantum efficiency is... External energy injected as electrons (or holes) into the light-emitting layer of a light-emitting element is purely converted into photons. This indicates the conversion rate. On the other hand, the external quantum efficiency indicates how far these photons go beyond the light-emitting element. Based on the amount emitted, the photons generated in the light-emitting layer are calculated, and some of them become light-emitting elements. It is absorbed or continuously reflected inside the light-emitting element and is not emitted outside the light-emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency.

[0575] The measurement methods for spectral radiance (emission spectrum) and external quantum efficiency are as follows: Using the R6144 voltage / current generator manufactured by N-Test Corporation, the element generates power by applying voltage. The light was emitted. A TOPCON SR-3AR spectroradiometer was used perpendicular to the light-emitting surface. The spectral radiance in the visible light region was measured from the direction. Assuming the light-emitting surface is a perfectly diffusive surface, The measured spectral radiance value for each wavelength component is obtained by dividing it by the wavelength energy and multiplying by π. This is the number of photons in the wavelength range. Next, the number of photons is integrated across the entire wavelength range observed, and the element This was defined as the total number of photons emitted from the device. The applied current value was divided by the elementary charge and injected into the device. As the carrier number, divide the total number of photons emitted from the element by the number of carriers injected into the element. The resulting value is the external quantum efficiency. Furthermore, the full width at half maximum of the emission spectrum is centered around the maximum emission wavelength. This is then determined as the width between the upper and lower wavelengths at which the intensity is 50%.

[0576] Fabrication of organic EL elements Organic EL elements according to the examples and comparative examples were fabricated, and voltage was applied to measure current density, brightness, and color. The degree and external quantum efficiency were measured. The fabricated organic EL element has the following configuration. There are four configurations: A (Tables 1 and 3), B (Table 2), C (Table 4), and D (Table 5). Selection and evaluation were performed. Configurations A, C, and D are suitable for thermally activated delayed fluorescence materials. Yes, and configuration B is a more common configuration. Configuration A is described in the literature (Adv. Mater. 2016, 28, 2777-2 This device configuration is expected to have high efficiency as shown in 781). Configuration C is described in the literature (Scientific Repo The element shown in rts, 6, 2016, 22463) is expected to provide relatively high efficiency and long-term driving stability. It is a substructure. Structure D is shown in the reference (Thin Solid Films, 619, 2016, 120-124), structure This device configuration uses a different host material than A and C. However, the compound of the present invention The application is not limited to these configurations, and the film thickness and constituent materials of each layer are the fundamental physical properties of the compound of the present invention. It can be modified as needed.

[0577] [Table 1]

[0578] In Table 1, "HI" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'- It is a diaminobiphenyl, and "HT" is 4,4',4"-tris(N-carbazolyl) It is riphenylamine, and "EB" is 1,3-bis(N-carbazolyl)benzene. "EMH1" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "ET" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures of both compounds are shown below, along with comparative compound 1.

[0579] [ka]

[0580] [Table 2]

[0581] In Table 2, "HI-1" is N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9- Phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-di It is an amine, and "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenyl It is an hexacarbonnitrile, and "HT-1" is N-([1,1'-biphenyl]-4- Il)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl )phenyl)-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4 -(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1”-therm] It is phenyl]-4-amine, and "EMH2" is 9-phenyl-10-(4-phenylna It is phthalen-1-yl)anthracene, and "ET-1" is 4,6,8,10-tetraph It is phenyl[1,4]benzoxavorinino[2,3,4-kl]phenoxavorinin, "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4 It is 1-phenylene bis(4-methylpyridine), and together with "Liq", the following chemical Show the structure.

[0582] [ka]

[0583] <Example 1> <Configuration A: A device using compound (1-1) as a dopant> ITO, deposited to a thickness of 200 nm by sputtering, was polished to 150 nm. A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.) is transparently supported. This was used as the substrate. This transparent support substrate was placed in the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.). Immobilized, HI, HT, EB, EMH1, compound (1-1), ET and LiF respectively The molybdenum deposition boat and the tungsten deposition boat containing aluminum I attached it.

[0584] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 Pa The pressure is reduced to a certain level, and first, HI is heated and deposited to a thickness of 40 nm to form a hole injection layer. Next, the HT was heated and deposited to a thickness of 15 nm to form a hole transport layer. Next, the electron barrier layer was formed by heating the electron beam (EB) and depositing it to a thickness of 15 nm. EMH1 and compound (1-1) are heated simultaneously and deposited to a film thickness of 20 nm to form the light-emitting layer. A compound was formed. The deposition rate was set so that the weight ratio of EMH1 to compound (1-1) was approximately 99:1. The temperature was adjusted. Next, the ET was heated and deposited to a thickness of 40 nm to form the electron transport layer. The process was completed. The deposition rate of each layer was 0.01 to 1 nm / second.

[0585] Subsequently, the LiF is heated and deposited at a rate of 0.01-0.1 nm / second until the film thickness reaches 1 nm. Deposition is performed at a certain temperature, and then aluminum is heated and deposited to a film thickness of 100 nm on the cathode. This formed an organic EL element. At this time, the aluminum deposition rate was 1 nm to 10 nm. I adjusted it to be / second.

[0586] A DC voltage is applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and the brightness, chromaticity, and External quantum efficiency was also measured. The results are shown in Figures 6 and 7. The brightness when 7V was applied was 59 1 cd / m 2 And it achieves high brightness of 250 cd / m². 2 The emission spectrum during emission is the full width at half maximum (F). The peak wavelength is 473 nm at WHM 19 nm, and the chromaticity is CIE chromaticity (x,y) = (0. A deep blue emission of 118,0.104 was obtained, with a density of 50 cd / m². 2 , 100 cd / m² 2 Oh 250 cd / m² 2 The external quantum efficiencies during emission are 16.8%, 15.7%, and The result showed a high value of 14.3% and a small roll-off.

[0587] <Comparative Example 1> <Configuration A: Device using comparative compound 1 as a dopant> An EL element was obtained using the same procedure and configuration as in Example 1, except that the dopant was changed. The results are shown in Figures 6 and 7. The brightness at 7V application was 322 cd / m². 2 And so, 250c d / m 2 The chromaticity during emission is CIE chromaticity (x,y)=(0.126,0.108), and 5 0 cd / m 2 , 100 cd / m² 2 and 250 cd / m² 2 The external quantum efficiency during light emission is The results were 14.0%, 12.0%, and 9.0%, respectively. Compared to Example 1, the achieved brightness was The results were low, with low external quantum efficiency and a large roll-off.

[0588] <Example 2> <Configuration B: Element using compound (1-1) as a dopant> An EL element of configuration B was obtained using the same procedure as for configuration A. However, EMH2 and compound (1-1) The deposition rate was adjusted so that the weight ratio was approximately 98:2. As a result, 100 0 cd / m 2 The applied voltage during emission was 4.1V, the external quantum efficiency was 6.7%, and the emission spectrum was ( Figure 8) shows that the maximum emission wavelength is 471 nm and the full width at half maximum is 18 nm, and the CIE chromaticity (x,y) = The values ​​were (0.118, 0.106). In particular, the half-width of the emission spectrum was small, and the deep blue color was... This has been achieved. This narrow half-width allows for deep blue chromaticity and cutoff in the low-wavelength region. This makes it possible to achieve both simultaneously, and also enables device designs that are gentle on the eyes and circadian rhythms. Yes.

[0589] <Comparative Example 2> <Configuration B: Device using comparative compound 1 as a dopant> An EL element was obtained using the same procedure and configuration as in Example 2, except that the dopant was changed. As a result, 1000 cd / m² 2 The applied voltage during light emission was 4.1V, and the external quantum efficiency was 6.6%. The light spectrum (Figure 8) shows a maximum emission wavelength of 468 nm and a full width at half maximum of 26 nm, and is CIE color. The values ​​(x,y) were (0.124,0.111). Compared to compound (1-1), the applied voltage... While pressure and external quantum efficiency were comparable, the result showed a wider full width at half maximum.

[0590] The above compounds (1-201), (1-101), and (1-9) are compounds Organic EL elements can be fabricated and evaluated using configurations A and B, similar to (1-1).

[0591] [Table 3]

[0592] <Comparative Example 3> <Configuration A: Device using comparative compound 2 as a dopant> ITO, deposited to a thickness of 200 nm by sputtering, was polished to 150 nm. A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.) is transparently supported. This was used as the substrate. This transparent support substrate was placed in the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.). After fixation, HI, HT, EB, EMH1, comparison compound 2, ET, and LiF were added respectively. Equipped with a molybdenum-based deposition boat and a tungsten-based deposition boat containing aluminum. did.

[0593] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 Pa The pressure is reduced to a certain level, and first, HI is heated and deposited to a thickness of 40 nm to form a hole injection layer. Next, the HT was heated and deposited to a thickness of 15 nm to form hole transport layer 1. Next, the EB was heated and deposited to a thickness of 15 nm to form hole transport layer 2. Then, EMH1 and comparative compound 2 are heated simultaneously and deposited to a film thickness of 20 nm to form the light-emitting layer. The deposition rate was adjusted so that the weight ratio of EMH1 to comparative compound 2 was approximately 99:1. The adjustment was made. Next, the ET was heated and deposited to a thickness of 40 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / second. After that, the LiF was heated to reduce the film thickness to 1 Deposition was carried out at a deposition rate of 0.01 to 0.1 nm / second to achieve a certain nm, and then aluminum The material was heated and deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL element. At that time, the aluminum deposition rate was adjusted to be between 1 nm and 10 nm / second.

[0594] A DC voltage is applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and the brightness, chromaticity, and External quantum efficiency was measured. 10 cd / m³ 2 , 100 cd / m² 2 and 250 cd / m² 2 The emission spectra during emission all have a half-width (FWHM) of 18 nm and a peak wavelength of 480 nm. Although a very narrow emission was observed, the peak wavelength was long, so the chromaticity was CIE chromaticity (x, The result was y) = (0.092, 0.224), which was a pale blue color. Also, 100 cd / m 2 Departure The external quantum efficiency during light was 4.9%.

[0595] <Example 3> <Configuration A: A device using compounds (1-9) as dopants> An EL element was obtained using the same procedure and configuration as in Comparative Example 3, except that the dopant was changed. 00 cd / m 2 The emission spectrum during emission has a half-width (FWHM) of 21 nm and a peak wavelength of 47 It is 3nm and a very narrow emission is observed, and the chromaticity is CIE chromaticity (x,y) = (0.105,0 The result was 0.210, which was a slightly deeper blue compared to Comparative Example 3. Also, 100 cd / m² 2 Luminous The external quantum efficiency was 19.0%, which was higher than that of Comparative Example 3.

[0596] <Example 4> <Configuration A: Element using compound (1-31) as a dopant> An EL element can be obtained using the same procedure and configuration as in Comparative Example 3, except that the dopant is changed. .

[0597] <Example 5> <Configuration A: A device using compound (1-2001) as a dopant> An EL element was obtained using the same procedure and configuration as in Comparative Example 3, except that the dopant was changed. 00 cd / m 2 The emission spectrum during emission has a half-width (FWHM) of 22 nm and a peak wavelength of 46 nm. It is 4nm and a very narrow emission is observed, and the chromaticity is CIE chromaticity (x,y) = (0.132,0 The color density was 0.079), which was a much deeper blue than that of Comparative Example 3. Also, 100 cd / m² 2 Luminous The external quantum efficiency was 14.0%, which was higher than that of Comparative Example 3.

[0598] [Table 4]

[0599] In Table 4, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphen It is lenhexacarbonnitrile, and "Tris-PCz" is 9,9',9"-triphenyl It is called "T2T " is 2,4,6-tri[[1,1'-biphenyl]-3-yl]-1,3,5-triazi "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl) It is lyphenylene. Its chemical structure is shown below.

[0600] [ka]

[0601] <Example 6> <Configuration C: Device using compound (1-1) as a dopant> ITO film deposited by sputtering, polished to 50nm, 26mm x 28mm x A 0.7mm glass substrate (OptoScience Co., Ltd.) is used as the transparent support substrate. The substrate is fixed to the substrate holder of a commercially available deposition apparatus (Choshu Sangyo Co., Ltd.), HAT-CN, T ris-PCz, EMH1, compound (1-1), T2T, BPy-TP2 and LiF Tantalum crucibles for vapor deposition, and aluminum nitride crucibles containing aluminum, respectively. Attach the crucible for vapor deposition.

[0602] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is 2.0 × 10 -4 Reduce the pressure to Pa, first heat the HAT-CN and deposit it to a film thickness of 10 nm, then... Then, Tris-PCz is heated and deposited to a film thickness of 30 nm, resulting in a two-layer structure. A hole layer is formed. Next, EMH1 and compound (1-1) are heated simultaneously to a film thickness of 30 nm. The light-emitting layer is formed by vapor deposition in such a manner. The weight ratio of EMH1 to compound (1-1) is approximately 9 The deposition rate is adjusted to a 0:10 ratio. Next, T2T is heated to a film thickness of 10 nm. The electron transport layer is formed by depositing BPy-TP2 to a thickness of 30 nm and then depositing it to form a two-layer electron transport layer. A layer is formed. The deposition rate of each layer is 0.01 to 1 nm / second. After that, the LiF is heated. Deposition is carried out at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm, and then aluminum The nium is heated and deposited at a deposition rate of 0.1 nm to 2 nm / second to achieve a film thickness of 100 nm. By forming a cathode in this way, an organic EL element can be obtained.

[0603] [Table 5]

[0604] <Example 7> <Configuration D: Device using compound (1-1) as a dopant> ITO film deposited by sputtering, polished to 50nm, 26mm x 28mm x A 0.7mm glass substrate (OptoScience Co., Ltd.) is used as the transparent support substrate. The substrate is fixed to the substrate holder of a commercially available deposition apparatus (Choshu Sangyo Co., Ltd.), HAT-CN, T ris-PCz, EB, compound (3-262), compound (1-1), BPy-TP2 and Tantalum deposition crucibles containing LiF and aluminum, and nitrided aluminum crucibles containing LiF A luminium crucible for vapor deposition is attached.

[0605] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is 2.0 × 10 -4 Reduce the pressure to Pa, first heat the HAT-CN and deposit it to a film thickness of 10 nm, then... Then, Tris-PCz is heated and deposited to a film thickness of 25 nm, and then EB is heated. Then, by depositing it so that it reaches 10 nm, a hole layer consisting of three layers is formed. Next, the compound (3-262) and compound (1-1) are heated simultaneously and deposited to a film thickness of 30 nm. A light-emitting layer is formed. The weight ratio of the combined portion (3-262) to the compound (1-1) is approximately 90 to 1. Adjust the deposition rate so that it becomes 0. Next, heat the compounding section (3-262) to a film thickness of 10n Deposited to a certain degree of m, and BPy-TP2 was deposited to a degree of 40 nm to form a two-layer structure. A transport layer is formed. The deposition rate of each layer is 0.01 to 1 nm / second. After that, LiF is used. The film is heated and deposited at a deposition rate of 0.01 to 0.1 nm / second until the film thickness reaches 1 nm, and then... The aluminum is heated and deposited at a rate of 0.1 nm to 2 nm / second to achieve a film thickness of 100 nm. An organic EL element can be obtained by depositing a cathode at a certain temperature.

[0606] [Table 6]

[0607] In Table 6, compound (5-102) is 3,11-di-o-tolyl-5,9-dioxa -13b-boranaphtho[3,2,1-de]anthracene, compound (5-201) is 9- (5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene-7-yl) It is )-9H-carbazole. The chemical structure is shown below. [ka]

[0608] <Example 8> <Configuration A: A device using compound (1-1) as the dopant and compound (5-201) as the host> ITO, deposited to a thickness of 200 nm by sputtering, was polished to 150 nm. A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.) is transparently supported. This was used as the substrate. This transparent support substrate was placed in the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.). Immobilize HI, HT, EB, compound (5-201), compound (1-1), and ET. Tantalum deposition boats containing LiF and aluminum nitrided aluminum A luminium deposition boat was installed.

[0609] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 Pa Reduce the pressure to a certain level, first heat the HI to deposit a film thickness of 40 nm, then heat the HT to deposit the film. The layer is deposited to a thickness of 15 nm, and then EB is heated to deposit another layer to a film thickness of 15 nm, resulting in three layers. A hole layer consisting of the following was formed. Next, compound (5-201) and compound (1-1) were added simultaneously. A light-emitting layer was formed by heating and depositing the material to a thickness of 20 nm. Compound (5-201) was used. The deposition rate was adjusted so that the weight ratio of the compound (1-1) was approximately 99:1. Next, ET The electron transport layer was formed by heating and depositing the material to a thickness of 40 nm. The deposition rate for each layer was The rate was 0.01-1 nm / second. Afterward, the LiF was heated to a film thickness of 1 nm. The aluminum is deposited at a deposition rate of 0.1 to 0.1 nm / second, and then heated to a film thickness of 100 nm. An organic EL element was obtained by depositing aluminum to a size of nm to form a cathode. The deposition rate was adjusted to be between 1 nm and 10 nm / second.

[0610] A DC voltage is applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and the brightness, chromaticity, and External quantum efficiency was measured. 100 cd / m² 2 The emission spectrum during emission is the full width at half maximum (FWH). At M)21nm, the peak wavelength is 473nm, and very high color purity emission is observed, and the chromaticity is The CIE chromaticity (x,y) was (0.116,0.199), resulting in a slightly deep blue color. , 100 cd / m² 2 The external quantum efficiency during emission is 33.6%, indicating a very high quantum efficiency. It was done.

[0611] <Example 9> <Configuration A: A device using compound (1-1) as the dopant and compound (5-102) as the host> The procedure and configuration were the same as in Example 8, except that the host was changed to compound (5-102). An EL element was obtained. 100 cd / m² 2 The emission spectrum during emission has a half-width (FWHM) of 21n. At m, the peak wavelength is 471 nm, and very high color purity emission is observed, and the chromaticity is CIE chromaticity ( The values ​​for x,y were (0.118, 0.137), resulting in a deep blue color. Also, the color density was 100 cd / m². 2 The external quantum efficiency during luminescence was 28.0%, demonstrating a very high quantum efficiency.

[0612] <Comparative Example 4> <Configuration A: A device using comparative compound 1 as the dopant and compound (5-102) as the host> Example 8 is the same except that the dopant is changed to comparative compound 1 and the host is changed to compound (5-102). An EL element was obtained using the same procedure and configuration. 100 cd / m 2 Emission spectrum during emission It has a full width at half maximum (FWHM) of 28 nm and a peak wavelength of 465 nm, and is more colorful than Examples 8 and 9. The emission was of lower purity, and the chromaticity was CIE chromaticity (x,y)=(0.128,0.124). Yes, there was. On the other hand, 100 cd / m 2 The external quantum efficiency during light emission was 15.4%, as in Example 8. It had lower quantum efficiency compared to Y-9. [Table 7]

[0613] <Example 10> <Configuration A: A device using compound (1-1) as the dopant and compound (5-102) as the host> ITO, deposited to a thickness of 200 nm by sputtering, was polished to 150 nm. A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.) is transparently supported. This was used as the substrate. This transparent support substrate was placed in the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.). Immobilize HI, HT, EB, compound (5-102), compound (1-1), and ET. Tantalum deposition boats containing LiF and aluminum nitrided aluminum A luminium deposition boat was installed.

[0614] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 Pa Reduce the pressure to a certain level, first heat the HI to deposit a film thickness of 40 nm, then heat the HT to deposit the film. The layer is deposited to a thickness of 15 nm, and then EB is heated to deposit another layer to a film thickness of 15 nm, resulting in three layers. A hole layer consisting of the following was formed. Next, compound (5-102) and compound (1-1) were added simultaneously. A light-emitting layer was formed by heating and depositing the material to a thickness of 20 nm. Compound (5-102) was then used. The deposition rate was adjusted so that the weight ratio of the compound (1-1) was approximately 99:1. Next, ET The electron transport layer was formed by heating and depositing the material to a thickness of 30 nm. The deposition rate for each layer was The rate was 0.01-1 nm / second. Afterward, the LiF was heated to a film thickness of 1 nm. The aluminum is deposited at a deposition rate of 0.1 to 0.1 nm / second, and then heated to a film thickness of 100 nm. An organic EL element was obtained by depositing aluminum to a size of nm to form a cathode. The deposition rate was adjusted to be between 1 nm and 10 nm / second.

[0615] A DC voltage is applied to an ITO electrode as the anode and an aluminum electrode as the cathode, and the brightness, chromaticity, and External quantum efficiency was measured. 100 cd / m² 2 The emission spectrum during emission is the full width at half maximum (FWH). M) At 17nm, the peak wavelength is 470nm, and very high color purity emission is observed, with a chromaticity of C The IE chromaticity (x,y) was (0.119,0.122), resulting in a deep blue color. Also, 10 0 cd / m 2 The external quantum efficiency during luminescence was 30.1%, indicating a very high quantum efficiency. . [Industrial applicability]

[0616] This invention provides a novel polycyclic aromatic compound, thereby offering an option for materials used in organic EL devices. This can increase the amount of [unclear value]. In addition, novel polycyclic aromatic compounds can be used as materials for organic electroluminescent devices. By using it, a superior organic EL element, a display device equipped therewith, and a lighting device equipped therewith can be developed. We can provide things like that. [Explanation of symbols]

[0617] 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

Claims

1. A polycyclic aromatic compound represented by the following general formula (1). 【Chemistry 1】 (In the above formula (1), Rings A, B, C, and D are each independently an aryl ring or heteroaryl ring. It is a ring, and at least one hydrogen in these rings may be substituted. Y is B (boron), X １ , X ２ , X ３ and X ４ These are, independently, >O, >N-R, >S, or >S e is the case, and R in >N-R is an aryl that may be substituted, or may be substituted. It is a heteroaryl or optionally substituted alkyl, and the R in >N-R is The rings A, B, C, and / or D may be bonded by linking groups or single bonds. Ku, R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, and a group having 6 to 1 carbon atoms. 2 aryls, heteroaryls or diarylaminos with 2 to 15 carbon atoms (however, aryl The aryl group is a carbon atom with 6 to 12 carbon atoms. Z １ and Z ２ These are, independently, aryls that may be substituted and aryls that may be substituted. A heteroaryl, a diarylamino which may be substituted, or which may be substituted. diheteroarylamino, optionally substituted arylheteroarylamino, substituted Alkyl that may be substituted, cycloalkyl that may be substituted, aryloxy, which may be substituted heteroaryloxy, which may be substituted is arylthio or optionally substituted heteroarylthio, and Z １ is a linking group or Z may be bonded to the A ring by a single bond, ２ is bonded to the C ring by a linking group or single bond. Also, In the compound represented by formula (1), at least one hydrogen atom is cyano, halogen, or heavy (It may be substituted with hydrogen.)

2. Rings A, B, C, and D are each independently an aryl ring or heteroaryl ring. It is a ring, and at least one hydrogen in these rings is aryl, heteroaryl, or di Arylamino, diheteroarylamino, arylheteroarylamino, alkyl, Cycloalkyl, alkoxy, aryloxy, heteroaryloxy, arylthio, They may be substituted with heteroarylthio or alkyl-substituted silyl, and in these cases Even if at least one hydrogen atom is substituted with an aryl, heteroaryl, or alkyl group Often, ring A and ring B are Y, X １ and X ２ The above formula on the left consists of a condensed two-ring structure It has a five-membered or six-membered ring that shares a structure and bond, and the C ring and D ring are Y, X ３ and X ４ mosquito It has a condensed two-ring structure as shown in the above formula, and a five-membered or six-membered ring that shares a bond with it. Y is B (boron), X １ , X ２ , X ３ and X ４ These are, independently, >O, >N-R, >S, or >S e is, and the R in >N-R is aryl, heteroaryl or alkyl, and R is At least one hydrogen in is aryl, heteroaryl, diarylamino, dihete Loarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy Xy, aryloxy, heteroaryloxy, arylthio, heteroarylthio It may be substituted with an alkyl-substituted silyl, and R in >N-R may be -O-, - S-, -C (-R) ２ -or by single bonds with the A, B, C and / or D rings They may be bonded, and the -C(-R) ２ The R in - is hydrogen or alkyl, R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, and a group having 6 to 1 carbon atoms. 2 aryls, heteroaryls or diarylaminos with 2 to 15 carbon atoms (however, aryl The aryl group is a carbon atom with 6 to 12 carbon atoms. Z １ and Z ２ These are, independently, aryl, heteroaryl, and diarylamino compounds. Diheteroarylaminos, arylheteroarylaminos, alkyls, cycloalkyls , aryloxy, heteroaryloxy, arylthio or heteroarylthio Furthermore, at least one hydrogen in these is an aryl, heteroaryl, or diarylar Mino, alkyl, cycloalkyl, alkoxy, aryloxy or alkyl-substituted silica It may also be replaced with Z １ is -O-, -S-, -C(-R) ２ - or single bond It may be more bonded to the A ring, Z ２ is -O-, -S-, -C(-R) ２ -or The C ring may also be bonded by a single bond, and the -C(-R) ２ - R is hydrogen or a It is Rukiru, and also In the compound represented by formula (1), at least one hydrogen atom is cyano, halogen, or heavy It may be substituted with hydrogen. The polycyclic aromatic compound as described in claim 1.

3. A polycyclic aromatic compound as described in claim 1, represented by the following general formula (2). 【Chemistry 2】 (In the above formula (2), R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ Each These independently include hydrogen, aryl, heteroaryl, diarylamino, and diheteroaryl. Mino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryl aryloxy, heteroaryloxy, arylthio, heteroarylthio or alkyl oxy These are silyl compounds, and at least one hydrogen atom in them is aryl, heteroaryl, or R may be substituted with alkyl, or R ５ ~R ７ and R １０ ~R １２ of Adjacent groups bond together to form an aryl ring or heteroaryl ring with the b-ring and / or d-ring. A ring may be formed, and at least one hydrogen in the formed ring is aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl Amino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy It may be substituted with silyl, arylthio, heteroarylthio, or alkyl-substituted silyl. Furthermore, at least one hydrogen atom in these is aryl, heteroaryl, or alkyl. It may also be replaced with Y is B (boron), X １ , X ２ , X ３ and X ４ These are, independently, >O, >N-R, >S, or >S e is such that R in >N-R is an aryl group with 6 to 12 carbon atoms, and a heteroaryl group with 2 to 15 carbon atoms. It is a reel or an alkyl group having 1 to 6 carbon atoms, and R in >N-R is -O- or -S -, -C (-R) ２ - Or by single bonds to the a, b, c and / or d rings. They may be combined, and the above-mentioned -C(-R) ２ The R in - is hydrogen or an alkyl group having 1 to 6 carbon atoms. the law of nature, R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, or a group having 6 carbon atoms. These are aryl numbers up to 12. Z １ and Z ２ These are, independently, aryl, heteroaryl, and diarylamino compounds. Diheteroarylaminos, arylheteroarylaminos, alkyls, cycloalkyls , aryloxy, heteroaryloxy, arylthio or heteroarylthio Furthermore, at least one hydrogen in these is aryl, heteroaryl, alkyl or Z may be substituted with an alkyl-substituted silyl, １ is -O-, -S-, -C(-R) ２ - Alternatively, it may be bonded to the a ring by a single bond, Z ２ is -O-, -S-, -C(- R) ２ - Alternatively, the c ring may be bonded by a single bond, and the -C(-R) ２ - The R is water It is an element or an alkyl group having 1 to 6 carbon atoms, and, In the compound represented by formula (2), at least one hydrogen atom is cyano, halogen, or heavy (It may be substituted with hydrogen.)

4. R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ , R １０ , R １１ and R １２ Each These independently include hydrogen, aryl atoms with 6 to 30 carbon atoms, heteroaryl atoms with 2 to 30 carbon atoms, and diaryl atoms. Rylamino (where aryl has 6 to 12 carbon atoms), alkyl has 1 to 6 carbon atoms These are aryloxy or arylthio compounds having 6 to 12 carbon atoms, and At least one hydrogen atom in is an aryl atom having 6 to 12 carbon atoms or an aryl atom having 1 to 6 carbon atoms. It may be replaced by Kill, and also R ５ ~R ７ and R １０ ~R １２ Among the adjacent The groups are bonded together with the b-ring and / or d-ring to form an aryl ring or carbon ring with 9 to 16 carbon atoms. They may form heteroaryl rings number 6 to 15, and at least in the formed ring One hydrogen atom is substituted with an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms. But it's fine, Y is B (boron), X １ , X ２ , X ３ and X ４ Each of these is independently >O or >N-R, and the above > In N-R, R is an aryl group with 6 to 10 carbon atoms or an alkyl group with 1 to 4 carbon atoms. R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, or a group having 6 carbon atoms. These are aryl numbers up to 12. Z １ and Z ２ These are, independently, aryl atoms with 6 to 30 carbon atoms and aryl atoms with 2 to 30 carbon atoms. Heteroaryl, diarylamino (where aryl has 6 to 12 carbon atoms), carbon Alkyl groups with 1 to 12 prime numbers, cycloalkyl groups with 3 to 12 carbon atoms, and aryl groups with 6 to 30 carbon atoms. Oxy, heteroaryloxy with 2 to 30 carbon atoms, arylthio with 6 to 30 carbon atoms or These are heteroarylthio compounds having 2 to 30 carbon atoms, and at least one hydrogen atom in them is Aryl compounds with 6 to 12 carbon atoms, heteroaryl compounds with 2 to 15 carbon atoms, and alkyl compounds with 1 to 12 carbon atoms. Substituted with a silyl or trialkyl-substituted silyl (where alkyl is an alkyl with 1 to 6 carbon atoms) It's fine if it's included, and In the compound represented by formula (2), at least one hydrogen atom is cyano, halogen, or heavy It may be substituted with hydrogen. The polycyclic aromatic compound as described in claim 3.

5. R ３ 、 R ４ 、 R ５ 、 R ６ 、 R ７ 、 R ８ 、 R ９ 、 R １０ 、 R １１ and R １２ are respectively These are independently hydrogen, an aryl group having 6 to 10 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. Y is B (boron), X １ , X ２ , X ３ and X ４ Each of these is independently >O or >N-R, and the above > In N-R, R is an aryl group with 6 to 10 carbon atoms or an alkyl group with 1 to 4 carbon atoms. R １ and R ２ These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, or a group having 6 carbon atoms. These are aryl numbers up to 12. Z １ and Z ２ are each independently aryl having 6 to 16 carbon atoms, having 2 to 15 carbon atoms Heteroaryl, diarylamino (where aryl has 6 to 10 carbon atoms), carbon Alkyl atoms with 1 to 6 prime numbers, cycloalkyl atoms with 3 to 10 carbon atoms, and aryl alkyl atoms with 6 to 12 carbon atoms. xy or arylthio having 6 to 12 carbon atoms, and at least one hydrogen in these It may be substituted with an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 6 carbon atoms, do, In the compound represented by formula (2), at least one hydrogen atom is cyano, halogen, or heavy It may be substituted with hydrogen. The polycyclic aromatic compound as described in claim 3.

6. A polycyclic aromatic compound according to claim 1, represented by one of the following formulas. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 【Transformation 6】 【Transformation 7】 (At least one hydrogen atom in each of the compounds represented by the above formulas is an alkyl group having 1 to 6 carbon atoms) They may be substituted with aryl, cyano, halogen, or deuterium atoms having 6 to 10 carbon atoms. In the formula, R is independently an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 10 carbon atoms. Yes, R １００ These are, independently, aryl, carbazolyl, and dia compounds with 6 to 10 carbon atoms. Rylamino (where aryl has 6 to 10 carbon atoms), alkyl with 1 to 6 carbon atoms , a cycloalkyl group having 3 to 10 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, The aryl may be substituted with an alkyl having 1 to 6 carbon atoms, and the carbazolyl is carbon (It may be substituted with aryl atoms with 6 to 10 prime numbers or alkyl atoms with 1 to 6 carbon atoms.)

7. A material for organic devices containing a polycyclic aromatic compound as described in any one of claims 1 to 6. 。

8. The aforementioned organic device materials include materials for organic electroluminescent devices and materials for organic field-effect transistors. The organic device material according to claim 7, which is a material or an organic thin-film solar cell material.

9. The organic device according to claim 8, wherein the aforementioned organic electroluminescent material is a material for the light-emitting layer. Materials for use.

10. A composition for forming an emissive layer for coating and forming an emissive layer of an organic electroluminescent device, The first component is at least one polycyclic aromatic compound as described in any one of claims 1 to 6. Things and, As a second component, at least one host material, As a third component, at least one organic solvent, A composition for forming an emissive layer, comprising the above.

11. A pair of electrodes consisting of an anode and a cathode, and disposed between the pair of electrodes, as described in claim 9. An organic electroluminescent element having a light-emitting layer containing a material for light-emitting layers.

12. A pair of electrodes consisting of an anode and a cathode, and disposed between the pair of electrodes, as described in claim 10. An organic electroluminescent element having a light-emitting layer formed by applying and drying a light-emitting layer-forming composition. 。

13. The light-emitting layer further contains a compound represented by the following general formula (3) and / or the following general formula (4) The organic electroluminescent element according to claim 11 or 12, comprising a compound represented by ). 【Transformation 8】 (In the above formula (3), L １ These are arylenes with 6 to 24 carbon atoms. In the above formula (4), L ２ and L ３ Each of these is independently an aryl group with 6 to 30 carbon atoms. or are heteroaryls having 2 to 30 carbon atoms, In each of the compounds represented by the above formulas, at least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms. (It may be substituted with cyano, halogen, or deuterium.)

14. Claims 11 to 13 further contain a compound represented by the following general formula (5) in the light-emitting layer. Organic electroluminescent element as described in any of the following. 【Chemistry 9】 (In the above formula (5), R １ ~R １１ These are, independently, hydrogen, aryl, heteroaryl, and diarylia. It is a mino, diheteroarylamino, arylheteroarylamino, or alkyl, At least one hydrogen in these is further aryl, heteroaryl, diaryl They may be substituted with mino or alkyl groups. R １ ~R １１ Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and They may be substituted with a heteroarylamino or alkyl group, and in small amounts At least one hydrogen atom further constitutes an aryl, heteroaryl, diarylamino, or alkyl group. It may be replaced with 'ru'. At least one hydrogen atom in the compound represented by formula (5) is independently a halo It may be substituted with ion or deuterium.

15. The cathode has an electron transport layer and / or electron injection layer disposed between it and the light-emitting layer, At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, and Luorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, ho Sphin oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives , benzimidazole derivatives, phenanthroline derivatives and quinolinol-based metal complexes The claim according to any one of claims 11 to 14, which contains at least one selected from the group. Organic electroluminescent element.

16. The electron transport layer and / or electron injection layer further comprises alkali metals, alkaline earth metals Groups, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals Oxides of the genus, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals Alkali metal oxidides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes The organic electrochemical compound according to claim 15, comprising at least one selected from the group consisting of organic complexes. World-emitting diode.

17. Display device or lighting device equipped with an organic electroluminescent element as described in any one of claims 11 to 16. Device.

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