Organic electroluminescent device

Abstract

To provide an organic EL element, having an excellent light emission efficiency, and indicating a good balance performance.SOLUTION: The present invention provides an organic EL element with, for example, a light emission efficiency, by manufacturing an organic EL element by using a light emission layer material in which a pyrene compound expressed by the following formula (2) is a host material, and a polycyclic aromatic compound obtained by coupling a plurality of aromatic rings with a boron atom and a nitrogen atom or an oxygen atom is a dopant material. (Compound 161) In the above formula (2), at least one hydrogen of a pyrene part may be replaced by an aryl or the like of 6 to 10 of carbons, and Ar is an aryl of 14 to 40 of carbons or a hetero aryl of 12 to 40 of carbons, and they may be replaced with the aryl or the like of 6 to 10 of carbons. s and p are an integration number of 1 or 2 independently, and the s and p do not become 2 at the same time. At least one hydrogen in a compound expressed by the formula (2) may be replaced with halogen, cyano, or heavy hydrogen, independently.

Description

[Technical Field]

[0001] The present invention relates to a polycyclic aromatic compound as a dopant material and a specific pyrene as a host material. Organic electroluminescent device having a light-emitting layer containing a fluorine compound, and display and lighting devices using the same Regarding placement. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been developed to be energy-efficient and thin. Various researches have been conducted on organic electroluminescent devices (hereinafter referred to as organic EL devices) made of organic materials. It has been actively studied because it is easy to make it lighter and larger. We are developing organic materials with luminescent properties such as blue, which is suitable for light emission, and we are also developing multiple materials with optimal luminescent properties. Combinations of these compounds have been actively studied, regardless of whether they are high molecular weight compounds or low molecular weight compounds. came.

[0003] The organic EL element comprises a pair of electrodes consisting of an anode and a cathode, and a light-emitting element disposed between the pair of electrodes. The layer containing the organic compound has a structure consisting of one or more layers. The layers include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons. However, a variety of organic materials suitable for these layers have been developed.

[0004] As a material for the light-emitting layer, for example, benzofluorene-based compounds have been developed (International (Publication No. 2004 / 061047) Examples of hole transport materials include triphenylamine. Compounds based on ZnO have been developed (Japanese Patent Application Laid-Open No. 2001-172232). For example, anthracene-based compounds have been developed (Japanese Patent Laid-Open Publication No. 2005-170911).

[0005] In recent years, compounds in which multiple aromatic rings are condensed with a central atom such as boron have also been reported. In this document, a dopant material for the light-emitting layer is Therefore, a compound in which multiple aromatic rings are fused can be selected, and an extremely large number of materials can be used as the host material. Among the listed compounds, especially anthracene compounds (BH1 on page 442) are selected. Organic EL element evaluation has been carried out, but other combinations have not been specifically verified. Furthermore, since different combinations of materials constituting the light-emitting layer have different light-emitting characteristics, other combinations The properties that can be obtained from this are still unknown. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] Japanese Patent Application Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0007] As mentioned above, various materials have been developed for use in organic EL devices, but the light-emitting properties In order to further enhance the performance and increase the options for materials for the light-emitting layer, we are developing unconventional material combinations. In particular, the specific host and dopa compounds reported in the examples of Patent Document 4 have been developed. The organic EL characteristics (especially the optimal luminescence characteristics) that can be obtained from other combinations of materials are unknown. not present. [Means for solving the problem]

[0008] As a result of extensive research to solve the above problems, the present inventors have found that a boron atom and a nitrogen atom or Contains polycyclic aromatic compounds in which multiple aromatic rings are linked by oxygen atoms and specific pyrene compounds. By configuring an organic EL element by placing a light-emitting layer between a pair of electrodes, it is possible to achieve excellent organic EL We have found that an L element can be obtained, and have completed the present invention.

[0009] According to a preferred embodiment of the present invention, a compound represented by formula (1) and, in combination therewith, and a compound represented by formula (2) which can provide suitable luminescence properties. By using a combination of these materials for the light-emitting layer to fabricate an organic EL device, it is possible to improve the chromaticity, driving voltage, and It is possible to provide an organic EL device that is excellent in one or more of the following:

[0010] Section 1. The light-emitting device has a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. An organic electroluminescent device, The light-emitting layer comprises a compound represented by the following general formula (1) and a compound represented by the following general formula (1): At least one polymer having a plurality of structures and a pyrene-based compound represented by the following general formula (2): and at least one of the following: [ka] In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted, X 1 and X 2 are each independently >O or >NR, and R in >NR is a substituent. optionally substituted aryl, optionally substituted heteroaryl, optionally substituted and the above-mentioned >NR is an optionally substituted alkyl or an optionally substituted cycloalkyl. R may be bonded to the ring A, ring B and / or ring C via a linking group or a single bond. ,and, At least one hydrogen atom in the compound or structure represented by formula (1) is independently and optionally substituted with halogen, cyano or deuterium, In the above formula (2), s pyrene moieties and p Ar moieties are arranged such that the positions of * in the pyrene moieties and * in the Ar moieties are Binds at either position, At least one hydrogen atom in the pyrene moiety is independently selected from aryl groups having 6 to 10 carbon atoms. , heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms alkyl, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or alkoxy having 6 carbon atoms may be substituted with up to 30 aryloxy groups, and at least one hydrogen atom in these groups each independently represents an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, Alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkoxy having 2 to 30 carbon atoms substituted with aryl, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms. It's okay to be there, Ar each independently represents an aryl having 14 to 40 carbon atoms or a hexaaryl having 12 to 40 carbon atoms. and at least one hydrogen atom in each of the groups is independently selected from the group consisting of aryl, ... aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, Cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 1 to 30 carbon atoms may be substituted by koxy or aryloxy having 6 to 30 carbon atoms, s and p are each independently an integer of 1 or 2, and s and p are both 2; When s is 2, the two pyrene moieties are structurally identical, including the substituents. When p is 2, the two Ar moieties, including the substituents, may be structurally may be the same or different, and At least one hydrogen atom in the compound represented by formula (2) is independently selected from the group consisting of halo, It may be substituted with gen, cyano or deuterium.

[0011] Section 2. The Ars are each independently represented by the following general formula (Ar-1) or (Ar-2): Item 2. The organic electroluminescent device according to item 1, wherein the group is represented by the formula: [ka] In each of the above formulas, Z is >CR2, >NR, >O or >S; In CR2, each R is independently alkyl having 1 to 6 carbon atoms, alkyl having 3 to 14 carbon atoms, cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms. At least one hydrogen atom in the aryl and heteroaryl is a C1-C4 and R may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms. may be linked to form a ring, >R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom in the heteroaryl is replaced by an alkyl or carbon atom having 1 to 4 carbon atoms. It may be substituted with a cycloalkyl having 5 to 10 prime numbers, R 1 From R 8 and R 10 From R 19 are each independently hydrogen, a group having 6 to 10 carbon atoms, Aryl, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and alkyl having 3 to 2 carbon atoms. 4 cycloalkyl, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or Aryloxy having 6 to 30 carbon atoms, and at least one hydrogen atom in these is may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and R 1 From R 8 adjacent groups or R 10 From R 19 Adjacent groups are bonded to each other may be bonded to form a condensed ring, and each of the formed rings independently has 6 to 1 carbon atoms. aryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and alkyl having 3 carbon atoms cycloalkyl having 2 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or or aryloxy having 6 to 30 carbon atoms, Another hydrogen is substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and At least one hydrogen atom in the group represented by the formula (Ar-1) or (Ar-2) are each independently optionally substituted with halogen, cyano, or deuterium; In formula (2), the pyrene moiety is a group represented by formula (Ar-1) or formula (Ar-2). It binds at one of the positions.

[0012] Section 3. The compound represented by the general formula (1) is a compound represented by the following general formula (1'): 3. The organic electroluminescent device according to 1 or 2. [ka] (In the above formula (1'), R 1 From R 11 are each independently hydrogen, aryl, heteroaryl, or diaryl Amino, diheteroarylamino, arylheteroarylamino, alkyl, cycloa alkyl, alkoxy or aryloxy, and at least one hydrogen atom in these are each independently aryl, heteroaryl, alkyl, or cycloalkyl. may be replaced with R 1 From R 11 Adjacent groups of the rings are bonded to form ring a and ring b. The ring or ring c may together form an aryl ring or a heteroaryl ring, and At least one hydrogen atom in the ring is independently selected from aryl, heteroaryl, Diarylamino, diheteroarylamino, arylheteroarylamino, alkyl , cycloalkyl, alkoxy or aryloxy, At least one hydrogen atom in each of the groups is independently selected from aryl, heteroaryl, alkyl, and substituted with aryl or cycloalkyl; X 1 and X 2 are each independently >O or >NR, and R in the >NR is carbon. Aryl with 6 to 12 carbon atoms, heteroaryl with 2 to 15 carbon atoms, alkyl with 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and At least one hydrogen atom is an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. R in the above >NR may be substituted with -O-, -S-, -C(-R)2 or may be bonded to the ring a, ring b and / or ring c via a single bond, R in C(-R)2- is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. There is, and At least one hydrogen atom in the compound represented by formula (1') is independently It may be substituted with halogen, cyano or deuterium.

[0013] Section 4. The Ars each independently represent the following general formulae (Ar-1-1) to (Ar-1-12): and a group represented by any one of general formulas (Ar-2-1) to (Ar-2-4), 1. The organic electroluminescent device according to any one of claims 1 to 3. [ka] In each of the above formulas, Z is >CR2, >NR, >O or >S; In CR2, each R is independently alkyl having 1 to 6 carbon atoms, alkyl having 3 to 14 carbon atoms, or an aryl having 6 to 12 carbon atoms, and R are bonded to each other to form a ring. It's okay to have >R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or or 6-12 aryl, At least one hydrogen atom in the group represented by each of the above formulae is independently selected from the group having 6 carbon atoms. aryl having 2 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, or It may be substituted with a cycloalkyl having 3 to 24 carbon atoms, and At least one hydrogen atom in the group represented by each of the above formulae is independently a halogen atom. , optionally substituted with cyano or deuterium; In formula (2), the pyrene moiety is represented by the above formulae (Ar-1-1) to (Ar-1-12) and formula A bond may be formed at any position in the group represented by any one of formulas (Ar-2-1) to (Ar-2-4). Combine.

[0014] Section 5. The pyrene compound represented by the general formula (2) is a compound represented by any one of the following structural formulas: Item 5. The organic electroluminescent device according to any one of items 1 to 4, wherein the organic electroluminescent device is an organic electroluminescent device. [ka]

[0015] Section 6. an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer; At least one of the electron transport layer and the electron injection layer is formed using a compound selected from the group consisting of borane derivatives, pyridine derivatives, fluorine derivatives, and the like. Fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, Sphingoxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives , benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes 6. The compound according to any one of items 1 to 5, containing at least one selected from the group consisting of: Electroluminescent device.

[0016] Section 7. The electron transport layer and / or the electron injection layer may further comprise an alkali metal, an alkaline earth metal, or metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metals oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals genides, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals Item 7. The organic electroluminescence according to item 6, containing at least one selected from the group consisting of organic complexes. element.

[0017] Section 8. Item 8. A display device comprising the organic electroluminescent device according to any one of items 1 to 7.

[0018] Section 9. Item 8. A lighting device comprising the organic electroluminescent device according to any one of Items 1 to 7.

[0019] Section 10. A pyrene-based compound represented by the following general formula (2): [ka] In the above formula, s pyrene moieties and p Ar moieties are arranged such that the positions of * in the pyrene moieties and * in the Ar moieties are Binds at either position, At least one hydrogen atom in the pyrene moiety is independently selected from aryl groups having 6 to 10 carbon atoms. , heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms alkyl, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or alkoxy having 1 to 30 carbon atoms may be substituted with up to 30 aryloxy groups, and at least one hydrogen atom in these groups may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. Ku, Ar is a group represented by the following general formula (Ar-1) or general formula (Ar-3): [ka] In each of the above formulas, Z is >CR2, In CR2, each R is independently alkyl having 1 to 6 carbon atoms, alkyl having 3 to 14 carbon atoms, cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms. At least one hydrogen atom in the aryl and heteroaryl is a C1-C4 and R may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms. may be linked to form a ring, R 1 From R 8 and R 20 From R 35 are each independently hydrogen, a group having 6 to 10 carbon atoms, Aryl, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and alkyl having 3 to 2 carbon atoms. 4 cycloalkyl, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms, and at least one hydrogen atom in these is may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and R 1 From R 8 Adjacent groups among R are bonded to each other to form a condensed ring, 20 From R 3 5 Adjacent groups among these may be bonded to each other to form a condensed ring, and the ring formed is , each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, a carbon Alkyl with 1 to 30 prime numbers, cycloalkyl with 3 to 24 carbon atoms, alkenyl with 1 to 30 carbon atoms substituted with aryl, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms. At least one hydrogen atom in these groups may be replaced by an alkyl group having 1 to 6 carbon atoms or a group having 1 to 6 carbon atoms. optionally substituted with 3 to 14 cycloalkyl; and s and p are each independently an integer of 1 or 2, and s and p are both 2; When s is 2, the two pyrene moieties are structurally identical, including the substituents. When p is 2, the two Ar moieties, including the substituents, may be structurally may be the same or different, At least one hydrogen atom in the compound represented by formula (2) is independently selected from the group consisting of halo, It may be substituted with gen, cyano or deuterium.

[0020] Section 11. Item 11. A pyrene-based compound according to item 10, which is represented by any one of the following structural formulas: [ka] [Effects of the Invention]

[0021] According to a preferred embodiment of the present invention, a polycyclic aromatic compound represented by formula (1) and a compound thereof and a pyrene-based compound represented by formula (2) that can provide optimal light-emitting properties. By using a combination of these materials for the light-emitting layer to produce an organic EL element, In particular, an organic EL element exhibiting excellent luminous efficiency and well-balanced performance can be provided. do.

[0022] In addition, the compound of the above general formula (1) and its polymers can be obtained by introducing a cycloalkyl group. This means that the melting point and sublimation temperature can be expected to decrease. In sublimation purification, which is almost essential as a method for purifying materials for organic devices such as silicon, This means that the material can be purified by the same process, and thermal decomposition of the material can be avoided. The vacuum deposition process is a powerful method for producing organic devices such as organic EL elements. The process is also similar, and can be carried out at relatively low temperatures, avoiding thermal decomposition of the material. As a result, high performance organic devices can be obtained. Many of them have high sublimation temperatures due to factors such as molecular weight and high flatness, so they are difficult to introduce cycloalkyl groups into. The sublimation temperature is more effectively reduced by introducing a cycloalkyl group. As the solubility in organic solvents is improved, it can also be used for device fabrication using coating processes. Furthermore, by introducing a large substituent such as a cycloalkyl, However, the present invention is not limited to these principles. isn't it. [Brief explanation of the drawings]

[0023] [Figure 1] 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0024] 1. Organic electroluminescent device of the present invention The present invention provides a light-emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. and the light-emitting layer is a polycyclic compound represented by the following general formula (1): An aromatic compound and at least one polymer thereof having a plurality of structures represented by the following general formula (1): and an organic electrolytic solution containing at least one pyrene-based compound represented by the following general formula (2): It is a field light emitting element. [ka] The symbols in formulas (1) and (2) are defined as above. In other formulas, the definitions of symbols are the same as those in the corresponding formulas described above unless otherwise specified. It is the same as righteousness.

[0025] 2. Polycyclic aromatic compounds and their polymers The polycyclic aromatic compound and its multimer used in the present invention are represented by the following general formula (1): or a multimer thereof having a plurality of structures represented by the following general formula (1), Alternatively, a compound represented by the following general formula (1') or a structure represented by the following general formula (1'): These compounds basically function as dopants. [ka]

[0026] In the general formula (1), the rings A, B and C are each independently an aryl ring or Heteroaryl rings, in which at least one hydrogen atom is replaced with a substituent. The substituent may be a substituted or unsubstituted aryl, a substituted or unsubstituted heterocyclic group, or the like. Aryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroaryl Amino, substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl an amino group having the formula (I), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl , substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy is preferred. When these groups have a substituent, the substituent may be an aryl, heteroaryl, alkyl, or alkyl group. The aryl ring or heteroaryl ring may be cycloalkyl or cycloalkyl. , central element B (boron), X 1 and X 2 General formula (1) consisting of a central fused two-ring structure It is preferred to have a five- or six-membered ring that shares a bond with the structure.

[0027] Here, the "fused two-ring structure" refers to a ring structure in which the central element B (boron) shown in the center of general formula (1) is , X 1 and X 2 It means a structure in which two saturated hydrocarbon rings containing the following are fused together. The "six-membered ring sharing a bond with the fused bicyclic structure" is, for example, a ring represented by the above general formula (1'). In addition, "a" means a ring (a benzene ring (6-membered ring)) fused to the fused two-ring structure. The phrase "the aryl ring or heteroaryl ring (which is ring A) has this 6-membered ring" means that this 6 The A ring is formed by only the six-membered ring, or the six-membered ring is further joined to the A ring to include the six-membered ring. In other words, the "6-membered" ring is formed by condensing the rings of The term "aryl or heteroaryl ring having a ring (which is ring A)" refers to the entire ring A or It means that the 6-membered ring constituting a part is fused to the fused 2-ring structure. The same explanation applies to "5-membered ring", "C ring (c ring)", and "5-membered ring".

[0028] The ring A (or ring B or ring C) in the general formula (1) is the same as the ring a in the general formula (1'). The substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , ring c and its substituent R 4 ~R 7 That is, general formula (1') corresponds to a "6-membered ring" as rings A to C of general formula (1). In this sense, each ring of general formula (1') corresponds to the selected structure. They are represented by lowercase letters a to c.

[0029] In the general formula (1'), the substituents R 1 ~R 11 adjacent groups among They bond together to form an aryl or heteroaryl ring together with ring a, ring b, or ring c. At least one hydrogen atom in the formed ring may be substituted by an aryl, heteroaryl, or , diarylamino, diheteroarylamino, arylheteroarylamino, alkyl These may be substituted with alkyl, cycloalkyl, alkoxy or aryloxy. At least one hydrogen atom in Therefore, the polycyclic aromatic compound represented by the general formula (1') is represented by the following formula (1'-1 ) and formula (1'-2), the ring structure that constitutes the compound changes. A in each formula Ring ', ring B' and ring C' correspond to ring A, ring B and ring C in general formula (1), respectively. Respond.

[0030] [ka]

[0031] The rings A', B' and C' in the formula (1'-1) and (1'-2) are represented by the general formula As explained in (1'), the substituent R 1 ~R 11 Adjacent groups in indicates an aryl or heteroaryl ring formed together with rings a, b, and c (ring a) (It can also be said that the ring b or ring c is a fused ring formed by fusing another ring structure to the ring b or ring c.) However, there are compounds in which the a, b and c rings have all been changed to A', B' and C' rings. As can be seen from the above formulas (1'-1) and (1'-2), for example, , b-ring R 8 and R in c-ring 7 , b-ring R 11 and a-ring R 1 , R of ring c 4 and a-ring R 3 etc. They do not fall under the category of "adjacent groups" and are not bonded to each other. The term "groups" refers to adjacent groups on the same ring.

[0032] The compounds represented by the above formula (1'-1) and formula (1'-2) can be prepared by, for example, forming an a ring (or a b ring or Benzene ring, indole ring, pyrrole ring, benzophenone ring, A' ring (or B' ring or C' ring) formed by condensation of an orchid ring or a benzothiophene ring ring), and the resulting fused ring A' (or fused ring B' or fused ring Ring C') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or or a dibenzothiophene ring.

[0033] X in general formula (1) 1 and X 2 are each independently >O or >NR. and R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, alkyl, optionally substituted alkyl, or optionally substituted cycloalkyl. R of the >NR is bonded to the ring B and / or ring C via a linking group or a single bond. The linking group is preferably -O-, -S- or -C(-R)2-. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. The explanation is as follows: X in general formula (1') 1 and X 2 But it's the same.

[0034] Here, in the general formula (1), "R of NR" is a linking group or a single bond that connects the A ring and B ring together. The definition of "bonded to the ring and / or C ring" means that in general formula (1'), "R of NR is The a ring, the b ring and / or the c ring are connected by -O-, -S-, -C(-R)2- or a single bond. This corresponds to the provision that "bonded to a ring."

[0035] This provision is based on the following formula (1'-3-1): 1 or X 2 is fused ring B' and fused That is, for example, a compound having a ring structure incorporated into ring C' can be represented by the general formula (1 ') to the benzene ring which is the b ring (or the c ring) 1 (or X 2 ) It is a compound having ring B' (or ring C') formed by condensing other rings in such a way that The fused ring B' (or fused ring C') formed is, for example, a phenoxazine ring, a phenoxazine ring, or a phenoxazine ring. It is a thiazine ring or an acridine ring.

[0036] In addition, the above definition is based on X represented by the following formula (1'-3-2) or (1'-3-3). 1 oh and / or X 2 It can also be expressed as a compound having a ring structure in which A is incorporated into the fused ring A'. That is, for example, X for the benzene ring which is the a ring in the general formula (1') 1 (and / or or X 2 ) and other rings are fused to form ring A'. The fused ring A' formed is, for example, a phenoxazine ring, a phenothiazine ring, or an azine ring. It is a cridine ring.

[0037] [ka]

[0038] The "aryl ring" which is the ring A, ring B and ring C in the general formula (1) includes, for example, Examples thereof include aryl rings having 6 to 30 carbon atoms, and aryl rings having 6 to 16 carbon atoms are preferred. An aryl ring having 12 carbon atoms is more preferred, and an aryl ring having 6 to 10 carbon atoms is particularly preferred. This "aryl ring" is defined as "R 1 ~R 11 adjacent groups among and a, b, or c, and Since the ring (or b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, The minimum carbon number is 9 in total in the fused ring formed by condensing the membered rings.

[0039] Specific examples of the "aryl ring" include a monocyclic benzene ring and a bicyclic biphenyl ring. ring, a fused bicyclic ring, a naphthalene ring, a tricyclic ring, a terphenyl ring (m-terphenyl, o-Terphenyl, p-Terphenyl), fused tricyclic ring system, acenaphthylene ring, fluoro phenylene ring, phenalene ring, phenanthrene ring, triphenylene ring which is a fused tetracyclic ring system, pyrene ring, naphthacene ring, and fused five-ring system perylene ring and pentacene ring.

[0040] Examples of the "heteroaryl ring" which is ring A, ring B and ring C in general formula (1) include: Examples include heteroaryl rings having 2 to 30 carbon atoms, and heteroaryl rings having 2 to 25 carbon atoms are preferred. Heteroaryl rings having 2 to 20 carbon atoms are preferred, and heteroaryl rings having 2 to 15 carbon atoms are even more preferred. An aryl ring is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Examples of "heteroaryl rings" include ring-constituting atoms such as oxygen, sulfur, and nitrogen in addition to carbon. Examples of heterocyclic rings include those containing 1 to 5 heteroatoms selected from the group consisting of aryl, aryl, aryls ... The "heteroaryl ring" is defined as "R 1~R 11 Adjacent of "a heteroaryl ring formed together with ring a, ring b, or ring c by bonding groups together" In addition, since the a ring (or b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, The lower limit of the carbon number is 6, which is the total carbon number of the fused ring formed by fusing this with a 5-membered ring.

[0041] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoaryl ring, and an aryl ring. Oxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole 1H-indazole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, Azole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring , quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridin ring ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenon Thiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring Ran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring , furazan ring, thianthrene ring, etc.

[0042] At least one hydrogen atom in the above "aryl ring" or "heteroaryl ring" is 1, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroaryl" substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy"; The first substituents are "aryl", "heteroaryl", and "diarylamino". Aryl, heteroaryl of "diheteroarylamino", "arylheteroaryl The aryl and heteroaryl in "amino" and the aryl in "aryloxy" are as described above. Examples thereof include monovalent "aryl ring" or "heteroaryl ring" groups.

[0043] The "alkyl" as the first substituent may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, Alkyl having 1 to 12 prime numbers (branched alkyl having 3 to 12 carbon atoms) is more preferred, Alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is more preferred, and alkyl having 1 to 4 carbon atoms is more preferred. Alkyl (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0044] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, and n-butyl. butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl , n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5, 5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n -hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc. do.

[0045] The "cycloalkyl" as the first substituent is a cycloalkyl having 3 to 24 carbon atoms. cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 cycloalkyl, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.

[0046] Specific examples of cycloalkyl include cyclopropyl, methylcyclopropyl, cyclobutyl, and cyclopropyl. cyclobutyl, methylcyclopentyl, methylcyclopentyl, cyclohexyl, Methylcyclohexyl, cycloheptyl, methylcycloheptyl, cyclooctyl, methyl Cycloctyl, cyclononyl, methylcyclononyl, cyclodecyl, methylcyclodecyl Sil, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2 .0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl , diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0047] Furthermore, the "alkoxy" as the first substituent includes, for example, straight chain or alkyl groups having 1 to 24 carbon atoms. or branched alkoxy having 3 to 24 carbon atoms. Branched alkoxy having 3 to 18 carbon atoms) is preferred, and alkoxy having 1 to 12 carbon atoms (carbon Alkoxy having 3 to 12 carbon atoms) is more preferred, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred. Alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred. Particularly preferred are alkoxy groups having up to 4 branched chains.

[0048] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, and butyl. butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy , heptyloxy, octyloxy, and the like.

[0049] The first substituent is a substituted or unsubstituted "aryl", a substituted or unsubstituted "hetero aryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "dihetero arylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "arylheteroarylamino", Unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted " "Alkoxy" or "substituted or unsubstituted aryloxy" means substituted or unsubstituted As described, at least one hydrogen therein is replaced with a second substituent. The second substituent may be, for example, an aryl, a heteroaryl, an alkyl, or a methyl group. cycloalkyl, and specific examples thereof include the above-mentioned "aryl ring" or Monovalent radicals of "heteroaryl rings" and "alkyl" or "cyclo" as first substituents The explanation of "aryl alkyl" can be found in the following. Heteroaryls include those in which at least one hydrogen is replaced by an aryl (e.g., phenyl). Examples of the alkyl groups are those mentioned above, alkyl groups such as methyl, and cyclohexyl. Any cycloalkyl-substituted group (examples of which are given above) may also be used with an aryl group as the second substituent. An example of such a group is a carbazolyl group in which the second substituent is a In this case, at least one hydrogen atom at the 9-position is an aryl such as phenyl or an alkyl such as methyl. Carbazolyl groups substituted with alkyl or cycloalkyl, such as cyclohexyl, are also suitable as second substituents. The substituent heteroaryl is included in the group.

[0050] R in general formula (1') 1 ~R 11 Aryl, heteroaryl, diarylamino in aryl, diheteroarylamino, heteroaryl, arylheteroarylamino The aryl and heteroaryl in the above, or the aryl in the aryloxy, are those represented by the general formula (1) Examples of the aryl ring include a monovalent group of an "aryl ring" or a "heteroaryl ring" described above. R 1 ~R 11 The alkyl, cycloalkyl or alkoxy in the formula (I) is any one of the above. The first substituent in the description of the general formula (1) is "alkyl", "cycloalkyl" or " Further, the description of "alkoxy" as a substituent on these groups can be referred to. The same applies to aryl, heteroaryl, alkyl, or cycloalkyl. 1 ~R 11 Adjacent groups among these are bonded to form an aryl ring or a hexacyclic ring together with the a, b or c ring. When a heteroaryl ring is formed, the heteroaryl and diaryl groups that are substituents on the ring arylamino, diheteroarylamino, arylheteroarylamino, alkyl, cyclo alkyl, alkoxy or aryloxy, and a further substituent aryl The same applies to heteroaryl, alkyl, or cycloalkyl.

[0051] X in general formula (1) 1 and X 2 In the formula, R in >NR is substituted with the second substituent described above. aryl, heteroaryl, alkyl or cycloalkyl, optionally containing aryl; At least one hydrogen atom in the alkyl, heteroaryl, alkyl, or cycloalkyl group is, for example, The aryl, heteroaryl, and cycloaryl may be substituted, for example, by alkyl or cycloalkyl. Examples of alkyl, cycloalkyl include the groups described above. Aryl (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), alkyl having 3 carbon atoms Cycloalkyl having 1 to 16 carbon atoms (e.g., bicyclooctyl, adamantyl, etc.) is preferred. The explanation is as follows: X in general formula (1') 1 and X 2 But it's the same.

[0052] In the general formula (1), R in the linking group "-C(-R)2-" is hydrogen, alkyl, or is cycloalkyl, and the alkyl or cycloalkyl includes the groups described above. In particular, alkyl having 1 to 4 carbon atoms (such as methyl and ethyl) is preferred. The same explanation applies to the linking group "-C(-R)2-" in general formula (1').

[0053] The present invention also provides a method for producing a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1). A polymer, preferably a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1') The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and more preferably a dimer. The polymer is particularly preferably in the form of a compound having a plurality of the above unit structures. For example, the unit structure is preferably a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthalene group, or the like. In addition to the form in which multiple rings are bonded together via a linking group such as a butylene group, any ring contained in the above unit structure (A ring, B ring or C ring, a ring, b ring or c ring) are shared by multiple unit structures. In addition, any ring (A ring, B ring or or C ring, a ring, b ring or c ring) may be bonded together in a condensed form. stomach.

[0054] Examples of such multimers include those represented by the following formula (1'-4), formula (1'-4-1), and formula ( 1'-4-2), Formula (1'-5-1) to Formula (1'-5-4) or Formula (1'-6) The multimeric compound represented by the following formula (1'-4) is a multimeric compound represented by the general formula: As explained in (1'), multiple compounds of the general formula (1 It is a polymeric compound having a unit structure represented by the following formula ( The polymer compound represented by general formula (1') is a venetrone compound having an a-ring. Two unit structures represented by general formula (1') are combined into one compound so as to share a benzene ring. The polymer compound is a polymer compound having the following formula (1'-4-2): The substance is, as explained in general formula (1'), three benzene rings, each of which is a ring, are shared by the other ring. It is a polymeric compound having a unit structure represented by the general formula (1') in one compound. The multimeric compounds represented by the following formulae (1'-5-1) to (1'-5-4) are also represented by the general formula ( 1') As explained above, multiple benzene rings are shared by the b-ring (or c-ring). It is a polymeric compound having a unit structure represented by the general formula (1') in one compound. In addition, the multimeric compound represented by the following formula (1'-6) can be explained by the general formula (1'), for example, For example, a benzene ring, which is the b-ring (or a-ring, c-ring) of a certain unit structure, and a b-ring (or and a ring (a, c) are fused to form a compound represented by a plurality of general formulas (1'): It is a polymeric compound having the unit structure shown in FIG.

[0055] [ka]

[0056] The polymeric compound is represented by formula (1'-4), formula (1'-4-1) or formula (1'-4-2). The polymerized form expressed by the formula (1'-5-1) to the formula (1'-5-4) or the formula ( 1'-6) and a polymerized form represented by the formula (1' -5-1) to (1'-5-4), and a polymerized form represented by any one of formulas (1'-6) and a polymer in which the polymerized form represented by the formula (1'-4) and the formula (1'-4-1) or the polymerized form represented by formula (1'-4-2) and the polymerized form represented by formula (1'-5-1 ) to (1'-5-4) and a polymerized form represented by formula (1'-6). The polymer may be a combination of a polymerized form of the hydroxylase and a polymerized form of the hydroxylase.

[0057] Also, the polycyclic aromatic compounds represented by the general formula (1) or (1') and their polymers are All or some of the hydrogen atoms in the chemical structure are replaced by halogens, cyano, or deuterium. For example, in formula (1), ring A, ring B and ring C (rings A to C are aryl rings or is a heteroaryl ring), substituents on rings A to C, and X 1 and X 2 is >NR When R (=aryl, heteroaryl, alkyl, cycloalkyl) is They may be substituted with halogen, cyano or deuterium, among which aryl and heteroaryl are preferred. In the above formula, all or part of the hydrogen atoms are replaced by halogen, cyano, or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, It is preferably chlorine or bromine, more preferably fluorine or chlorine.

[0058] Specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas: In the structural formula below, "Me" stands for methyl group, and "tBu" stands for tertiary butyl. "iPr" indicates an isopropyl group, "Ph" indicates a phenyl group, and "D" indicates deuterium.

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[0086] 3. Method for producing polycyclic aromatic compounds represented by formula (1) and their multimers The polycyclic aromatic compounds represented by the general formula (1) or (1') and their multimers are disclosed in International Publication No. According to the methods described in many publicly known documents, including Publication No. 2015 / 102118, For reference, in the synthesis examples described below, the polycyclic aromatic compound A specific manufacturing method is described.

[0087] Basically, first, the A ring (a ring), the B ring (b ring) and the C ring (c ring) are connected by bonding groups (X 1 or X 2 (a group containing) to produce an intermediate (first reaction), and then ), B ring (b ring) and C ring (c ring) are bonded by a bonding group (a group containing the central element B (boron)) The final product can be produced by the second reaction. For esterification reactions, general reactions such as nucleophilic substitution and Ullmann reaction can be used. For oxidation reactions, common reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (successive aromatic electrophiles) Substitution reactions (and the same below) can be used. Also, halogenation, Cyanide or deuterated raw materials are used, and halogenated, cyanide or deuterated By adding additional steps, the desired position can be halogenated, cyanated, or deuterated. The compound can be prepared.

[0088] The second reaction is as shown in the following schemes (1) and (2), which converts the A ring (a ring) and the B ring (b ring) and C ring (c ring) and the central element B (boron) is introduced. For example, X 1 and X 2 The case where is > O is shown below. First, X 1 and X 2 The hydrogen atom between n-butyl Orthometalation is performed with lithium, sec-butyllithium, t-butyllithium, or the like. Next, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange. By adding a Bronsted base such as N,N-diisopropylethylamine, The target product can be obtained by the Mbola-Friedel-Crafts reaction. To accelerate the reaction, a Lewis acid such as aluminum trichloride may be added. The symbols in the structural formulae in groups (1) and (2) are defined as above.

[0089] [ka] [ka]

[0090] The above schemes (1) and (2) are based on polycyclic aromatic compounds represented by general formulas (1) and (1'). The method for producing the compound is mainly shown, but for the multimer, multiple A rings (a rings), B It can be produced by using an intermediate having a ring (b ring) and a C ring (c ring). This will be explained in detail in the following schemes (3) to (5). The desired product can be obtained by doubling or tripling the amount of reagent.

[0091] [ka] [ka] [ka]

[0092] In addition, X 1 and X 2 Even if either is > NR or either is > NR, By using an amine compound as the intermediate, the production can be carried out in the same manner as above.

[0093] Specific examples of the solvent used in each of the above schemes include t-butylbenzene and xylene. do.

[0094] Orthometalation reagents include methyllithium, n-butyllithium, and sec- Alkyl lithium such as butyl lithium and t-butyl lithium, lithium diisopropyl lithium Lithium tetramethylpiperidide, Lithium hexamethyldisilazide, Potassium hexamethyldisilazide Examples of suitable organic alkali compounds include hexamethyldisilazide.

[0095] In addition, examples of Bronsted bases include N,N-diisopropylethylamine, triethylamine, Aminomethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethyl N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-dichloroisothiazolinone, Zin, sodium tetraphenylborate, potassium tetraphenylborate, triphenyl Borane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, Ar4Si (etc. and Ar is an aryl such as phenyl.

[0096] Lewis acids include AlCl3, AlBr3, AlF3, BF3·OEt2, B Cl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf) 3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2 , ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiO Tf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YC l3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3 , FeBr3, CoCl3, CoBr3, etc.

[0097] 4. Pyrene-based compounds represented by general formula (2) The pyrene compound represented by the general formula (2) basically functions as a host. [ka]

[0098] In the above formula (2), s pyrene moieties and p Ar moieties are arranged such that the positions of * in the pyrene moieties and * in the Ar moieties are Binds at either position, At least one hydrogen atom in the pyrene moiety is independently selected from aryl groups having 6 to 10 carbon atoms. , heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms alkyl, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or alkoxy having 6 carbon atoms may be substituted with up to 30 aryloxy groups, and at least one hydrogen atom in these groups each independently represents an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, Alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkoxy having 2 to 30 carbon atoms substituted with aryl, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms. It's okay to be there, Ar each independently represents an aryl having 14 to 40 carbon atoms or a hexaaryl having 12 to 40 carbon atoms. and at least one hydrogen atom in each of the groups is independently selected from the group consisting of aryl, ... aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, Cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 1 to 30 carbon atoms may be substituted by koxy or aryloxy having 6 to 30 carbon atoms, s and p are each independently an integer of 1 or 2, and s and p are both 2; When s is 2, the two pyrene moieties are structurally identical, including the substituents. When p is 2, the two Ar moieties, including the substituents, may be structurally may be the same or different, and At least one hydrogen atom in the compound represented by formula (2) is independently selected from the group consisting of halo, It may be substituted with gen, cyano or deuterium.

[0099] Ar is an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms. Various substituents can be bonded to these groups, and specific examples of Ar include those represented by the following general formula (Ar-1): Alternatively, a group represented by general formula (Ar-2) may be mentioned. 1 From R 8 and R 10 From R 19 is a substituent. [ka]

[0100] In addition, in the group represented by formula (Ar-2), adjacent R18 and R 19 are bonded to each other An example of a condensed ring formed by R is a group represented by the following general formula (Ar-3): 20 From R 35 is a substituent. [ka]

[0101] More specific examples of the group represented by formula (Ar-1) or formula (Ar-2) include the following: Among these, groups represented by the formula (Ar-1-1), Formula (Ar-1-2), Formula (Ar-1-3), Formula (Ar-1-4), Formula (Ar-2-2) or a group represented by formula (Ar-2-4), and a group represented by formula (Ar-1-2), formula (Ar-1- 3), groups represented by formula (Ar-1-4) or formula (Ar-2-4) are more preferred. Although the substituents are not specified in each structural formula, at least one hydrogen atom in each structure is substituted. The group represented by the following formula (Ar-2-4) may be substituted with the group represented by the above formula (Ar-3). This corresponds to the group represented by the formula: [ka]

[0102] Ar is an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms; The first substituent on the pyrene moiety (aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms) alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms, preferably or aryl having 6 to 10 carbon atoms) and a second substituent (having 6 to 1 carbon atoms) on the first substituent aryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and alkyl having 3 carbon atoms cycloalkyl having 2 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or or aryloxy having 6 to 30 carbon atoms, preferably aryl having 6 to 10 carbon atoms), and , a substituent to Ar (R in formula (Ar-1) 1 From R 8 , R in formula (Ar-2) 10 From R 19 , R in formula (Ar-3) 20 From R 35 and Formula (Ar-1-1) to Formula (Ar-2-4) ) is a substituent not explicitly stated, such as an aryl having 6 to 10 carbon atoms, a heterocyclic group having 2 to 11 carbon atoms, or Aryl, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 2 to 3 carbon atoms alkenyl having 0 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms, The alkyl groups (preferably alkyl having 1 to 30 carbon atoms) will be explained below.

[0103] Ar is an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms. Preferably, it is an aryl having 14 to 35 carbon atoms or a heteroaryl having 12 to 35 carbon atoms. More preferably, it is an aryl having 14 to 30 carbon atoms or a heteroaryl having 12 to 30 carbon atoms. More preferably, it is an aryl having 14 to 25 carbon atoms or a heteroaryl having 12 to 25 carbon atoms. aryl having 14 to 20 carbon atoms or aryl having 12 to 20 carbon atoms is particularly preferred. and most preferably an aryl having 14 to 18 carbon atoms or an aryl having 12 carbon atoms. 18-19 heteroaryl.

[0104] Specific examples of the aryl include phenyl, which is a monocyclic ring, biphenylyl, which is a bicyclic ring, and fused aryl. The bicyclic ring system is naphthyl, the tricyclic ring system is terphenylyl (m-terphenylyl, o-terphenylyl), p-Terphenylyl), fused tricyclic ring systems, anthracenyl, acenaphthylene fluorenyl, phenalenyl, phenanthrenyl, and triphenylenyl, a fused tetracyclic ring system. Examples include naphthacenyl, naphthacenyl, and the fused five-ring systems perylenyl and pentacenyl.

[0105] Specific examples of heteroaryl include pyrrolyl, oxazolyl, and isoxazolyl. thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, Triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyridyl Razinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoyl Midazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinoline quinazolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyl Lysinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl , phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzo Zofuranil, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl , dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenzof benzothienyl and naphthobenzothienyl.

[0106] Also, a first substituent on the pyrene moiety and a second substituent on the first substituent, and A Regarding the substituent on r, specific examples of the aryl having 6 to 10 carbon atoms include phenyl and naphthalene. phenyl, and specific examples of heteroaryl having 2 to 11 carbon atoms include the above-mentioned heteroaryls. The alkyl groups can be cited from the alkyl groups.

[0107] Aryloxy with 6 to 30 carbon atoms is an aryloxy group in which the hydrogen of the hydroxyl group is The aryl is preferably an aryl having 6 to 25 carbon atoms. More preferably, it is an aryl having 6 to 20 carbon atoms, and even more preferably, it is an aryl having 6 to 15 carbon atoms. Aryl is particularly preferably an aryl having 6 to 10 carbon atoms. Examples can be cited from among the aryl groups mentioned above.

[0108] The alkyl having 1 to 30 carbon atoms may be either a straight chain or a branched chain. For example, A linear alkyl having 3 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms is preferred, and a branched alkyl having 1 to 1 Alkyl having 3 to 18 carbon atoms is more preferred, and alkyl having 1 to 12 carbon atoms is more preferred. alkyl (branched alkyl having 3 to 12 carbon atoms) is more preferred, and alkyl having 1 to 6 carbon atoms is (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred. methyl, ethyl, isopropyl or t- Butyl is more preferred among them, and methyl or t-butyl is most preferred.

[0109] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, and n-butyl. butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl , n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5, 5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. can be.

[0110] The cycloalkyl having 3 to 24 carbon atoms includes, for example, cycloalkyl having 3 to 20 carbon atoms, Cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms and cycloalkyl of the following formula.

[0111] Specific examples of cycloalkyl include cyclopropyl, methylcyclopropyl, cyclobutyl, and cyclopropyl. cyclobutyl, methylcyclopentyl, methylcyclopentyl, cyclohexyl, Methylcyclohexyl, cycloheptyl, methylcycloheptyl, cyclooctyl, methyl Cycloctyl, cyclononyl, methylcyclononyl, cyclodecyl, methylcyclodecyl Sil, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2 .0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl , diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0112] The alkenyl having 2 to 30 carbon atoms is, for example, preferably an alkenyl having 2 to 20 carbon atoms. More preferably, it is an alkenyl having 2 to 10 carbon atoms, and even more preferably, it is an alkenyl having 2 to 6 carbon atoms. Alkenyl having 2 to 4 carbon atoms is particularly preferred.

[0113] Specific examples of alkenyl include vinyl, 1-propenyl, 2-propenyl, and 1-butenyl. 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and and 5-hexenyl.

[0114] The alkoxy having 1 to 30 carbon atoms is, for example, preferably an alkoxy having 1 to 24 carbon atoms (carbon A branched alkoxy having 3 to 24 carbon atoms is preferable, and an alkoxy having 1 to 18 carbon atoms is more preferable. (branched alkoxy having 3 to 18 carbon atoms), and more preferably alkoxy having 1 to 12 carbon atoms. Alkoxy (branched alkoxy having 3 to 12 carbon atoms), particularly preferably alkoxy having 1 to 12 carbon atoms. alkoxy having 3 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms), and most preferably alkoxy having 1 carbon atom It is an alkoxy having 3 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms).

[0115] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, and butyl. butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy , heptyloxy and octyloxy, and the like.

[0116] In formula (Ar-1) and formula (Ar-2), R 1 From R 8 Adjacent groups among or R 10 From R 19 Adjacent groups may be bonded to each other to form a condensed ring. The adjacent group is R 4 and R 5 or R 13 and R 14 Combinations other than R 1 and R 2 The structures in which the fused rings are formed in this way are represented by the above formulae (Ar-1-2) to ( Ar-1-12) and the above formulas (Ar-2-2) to (Ar-2-4) (formula (Ar-3)) On the other hand, the above formula (Ar-1-1) and formula (Ar-2-1) are structures that do not contain a fused ring. The formed fused ring may be, for example, a benzene ring, a naphthalene ring, or a phenanthrene ring. , thiophene ring, pyrrole ring, or furan ring, but preferably an aryl ring. a benzene ring, a naphthalene ring or a phenanthrene ring, more preferably a benzene ring It is a ring.

[0117] The fused ring formed by bonding adjacent groups to each other is an aryl having 6 to 10 carbon atoms, Heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or alkoxy having 6 to 30 carbon atoms These may be substituted with alkyl or aryloxy having 1 to 6 carbon atoms. It may be substituted with a cycloalkyl having 3 to 14 carbon atoms, and detailed descriptions of these groups are given above. The above description can be cited.

[0118] Z is >CR2, >NR, >O or >S, and among these, is >CR2 or >O, more preferably >CR2, and R (carbon alkyl having 1 to 6 prime numbers, cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or is an aryl having 6 to 12 carbon atoms which may be substituted by a cycloalkyl having 5 to 10 carbon atoms, Or substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Heteroaryl having 2 to 12 carbon atoms, and R in >NR (heteroaryl having 1 to 4 carbon atoms) alkyl having 5 to 10 carbon atoms, cycloalkyl having 1 to 4 carbon atoms or alkyl having 5 carbon atoms an aryl having 6 to 12 carbon atoms, optionally substituted with cycloalkyl having 6 to 10 carbon atoms; A carbon atom optionally substituted with alkyl having 1 to 4 prime numbers or cycloalkyl having 5 to 10 carbon atoms. Regarding heteroaryl having 2 to 12 carbon atoms, the details of these groups are the same as those of alkyl, cyclohexyl, and cyclohexyl groups described above. The descriptions of chloroalkyl, aryl and heteroaryl can be cited.

[0119] For Z >CR2, the Rs may be bonded to each other to form a ring, In this case, a spiro structure is formed.

[0120] The above formula (2) shows that s pyrene moieties and p Ar moieties are bonded at the positions * (1st position) of the pyrene moieties. and / or 2-position), and s and p are each independently 1 or 2, and s and p cannot be 2 at the same time. The pyrene moiety has a symmetric structure. Therefore, when s=1, p=1 or when s=2, p=1, the first and second positions of the pyrene moiety are can be indicated by two *s, but when s=1 and p=2, the two Ar moieties are pyrene moieties. The six * symbols indicate that the compound can be bonded to six positions. When s is 2, two pyrenes can be bonded to the compound. The moieties may be structurally identical or different, including the substituents, and when p is 2, The two Ar moieties may be structurally identical or different, including the substituents. As described above, the pyrene moiety may have various substituents bonded to the pyrene structure. When a group is bonded, the bonded substituent also constitutes the pyrene moiety. The Ar moiety includes both the Ar moiety and the substituents attached thereto. When pyrene or Ar moieties are contained in pyrene-based compounds, the pyrene moieties including the substituents are The Ar moieties, including the moieties and substituents, may be structurally identical or different, Preferably they are the same.

[0121] Regarding the bond between the pyrene moiety and the Ar moiety, the position of * in the pyrene moiety (1 Ar is bonded at the 2-position and / or 3-position of the pyrene moiety, but conversely, the pyrene moiety is bonded at the 3-position of the Ar moiety. For example, in the formula (Ar-1) or (Ar-2), which is an example of Ar, In this case, R 1 From R 8 and R 10 From R 19 The pyrene moiety is attached at any position of Furthermore, when adjacent groups are bonded to each other to form a condensed ring, the condensed ring may It may be bonded to the ring. 1 From R 8 and R 10 From R 19 Aryl etc. Any position on the aryl when a substituent is selected, or >CR2 as Z and When a substituent such as an aryl is selected as R in NR, the aryl Among these bonding positions, the bonding position of the group represented by formula (Ar-1) or R in Formula (Ar-2) 1 From R 8 or R 10 From R 19 Either position is preferred. These explanations also apply to the sub-formulae of formula (Ar-1) and formula (Ar-2).

[0122] In addition, all or part of the hydrogen atoms in the pyrene-based compound represented by formula (2) may be halo. For example, in formula (2), pyrene may be substituted with cyano or deuterium. Hydrogen in the N and Ar moieties can be replaced with halogen, cyano, or deuterium. The fluorine is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably More preferably, it is fluorine.

[0123] Specific examples of the pyrene-based compound of the present invention include compounds represented by the following structural formulas: In the following structural formula, "Me" is a methyl group, "Et" is an ethyl group, and "tBu" is tertiary butyl group, "iPr" is an isopropyl group, and "D" indicates deuterium.

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] [ka]

[0128] [ka]

[0129]

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[0130]

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[0131]

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[0132]

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[0133]

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[0134]

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[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140] [ka]

[0141] [ka]

[0142] [ka]

[0143] [ka]

[0144] [ka]

[0145] [ka]

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] Among the above compounds, the compounds represented by formula (2-1), formula (2-2) to formula (2-20), and formula (2-41) ) ~ formula (2-43) formula (2-46), formula (2-47) ~ formula (2-173), formula (2-17) 4), Formula (2-175) ~ Formula (2-215), Formula (2-351) ~ Formula (2-354), Formula (2-356), formula (2-357), formula (2-358), formula (2-359), formula (2-3) 60) ~ Formula (2-430), Formula (2-1001), Formula (2-1002) ~ Formula (2-101) 2), (2-1080), (2-1081) to (2-1091) Compounds that can be used are preferred.

[0150] Also, equation (2-1), equation (2-46), equation (2-174), equation (2-350), equation (2 -356), equation (2-359), equation (2-1001), or equation (2-1080) More preferred are compounds represented by the formula:

[0151] 5. Method for producing pyrene-based compound represented by formula (2) The pyrene compound represented by formula (2) has a pyrene skeleton or a skeleton of a compound represented by Ar. and can be produced by known methods. Intermediates used in halogenation, boronation or boronate esterification reactions The intermediates are used in Suzuki coupling reactions and other metalation reactions. Cross-coupling reactions via metal species (Negishi coupling reaction, Kumada-Tamao coupling reaction) By carrying out the reaction (such as Kosugi-Migita-Stille coupling reaction), the reaction can be carried out as follows: In addition, it is possible to produce pyrene compounds represented by the formula (I). Prepare an intermediate having a substituent such as a silyl group and demethylate it using pyridine hydrochloride, etc. After converting to the -OH form in the reaction, it is sucrose using a reagent such as trifluoromethanesulfonic anhydride. By converting it into a sulfonic acid ester and carrying out a cross-coupling reaction such as Suzuki coupling reaction, The pyrene-based compound represented by formula (2) can also be produced. Intermediates containing boronic acids, boronic acid esters, or sulfonic acid esters are commercially available. For reference, in the synthesis examples described below, the pyrene-based compound A specific manufacturing method is described.

[0152] 6. Organic electroluminescent devices The organic EL element according to this embodiment will be described in detail below with reference to the drawings. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention.

[0153] <Structure of organic electroluminescent device> The organic EL device 100 shown in FIG. 1 comprises a substrate 101 and an anode provided on the substrate 101. 102, a hole injection layer 103 provided on the anode 102, and a a hole transport layer 104 formed on the hole transport layer 104; a light emitting layer 105 formed on the hole transport layer 104; An electron transport layer 106 is provided on the layer 105, and an electron transport layer 108 is provided on the electron transport layer 106. The device has an injection layer 107 and a cathode 108 provided on the electron injection layer 107 .

[0154] The organic EL element 100 can be fabricated in the reverse order, for example, by fabricating the substrate 101 and the substrate 102. a cathode 108 provided on the cathode 108; an electron injection layer 107 provided on the cathode 108; An electron transport layer 106 provided on the injection layer 107, and a a light-emitting layer 105, a hole transport layer 104 provided on the light-emitting layer 105, and a hole transport layer 104 a hole injection layer 103 provided thereon, and an anode 102 provided on the hole injection layer 103; The configuration may also include the following.

[0155] Not all of the above layers are necessary, but the minimum structural unit is the anode 102 and the light-emitting layer. The cathode 108 is made up of a hole injection layer 103, a hole transport layer 104, an electron The transport layer 106 and the electron injection layer 107 are layers that are optionally provided. Each of them may consist of a single layer or multiple layers.

[0156] The organic EL element may be configured as a layer structure of the above-mentioned "substrate / anode / hole injection layer / hole In addition to the "transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, there is also the "substrate / anode / cathode" configuration. Hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode," "Substrate / anode / hole injection layer / light-emitting layer" layer / electron transport layer / electron injection layer / cathode," "substrate / anode / hole injection layer / hole transport layer / light-emitting layer" / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / positive electrode hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", The structure may be "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0157] <Substrate in organic electroluminescent device> The substrate 101 is a support for the organic EL element 100 and is usually made of quartz, glass, metal, or plastic. The substrate 101 may be in the form of a plate, a film, or a sheet depending on the purpose. For example, glass plates, metal plates, metal foils, plastic films, plastics, etc. Among them, glass plates, polyester, polymethacrylate, etc. are used. Plates made of transparent synthetic resins such as glass, polycarbonate, and polysulfone are preferred. For glass substrates, soda lime glass or alkali-free glass is used, and the thickness is It is sufficient that the thickness is sufficient to maintain mechanical strength, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material, it is better to have fewer ions dissolved from the glass, so alkali-free glass is better. Although it is preferable, soda lime glass coated with a barrier coating such as SiO2 is also commercially available. In addition, the substrate 101 is provided with a material for enhancing the gas barrier property. A gas barrier film such as a dense silicon oxide film may be provided on at least one surface of the substrate. When a synthetic resin plate, film, or sheet with low barrier properties is used as the substrate 101, It is preferable to provide a gas barrier film.

[0158] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the layer 105 In this case, holes are injected into the light-emitting layer 105 via these.

[0159] Materials for forming 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), etc.), metal halides (copper iodide, etc.), Examples include copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of such polythiophenes include poly(3-methylthiophene), polypyrrole, Examples include conductive polymers such as polyaniline. The material can be appropriately selected from those currently used.

[0160] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emitting element to emit light. However, from the viewpoint of power consumption of the light emitting element, low resistance is desirable. For example, 300Ω / ITO substrates with a resistance of 10Ω / □ or less can function as device electrodes, but currently, substrates with a resistance of about 10Ω / □ are required. Therefore, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □ It is especially desirable to use a low resistance product. The thickness of the ITO can be selected arbitrarily according to the resistance value. Although it is possible to increase the thickness, it is usually used in the range of 50 to 300 nm.

[0161] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 efficiently injects holes moving from the anode 102 into the light emitting layer 105. The hole transport layer 104 serves to inject electrons from the anode 102 into the hole transport layer 104. The injected holes or holes injected from the anode 102 through the hole injection layer 103 are efficiently The hole injection layer 103 and the hole transport layer 104 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of hole injection and transport materials are laminated or mixed, or hole injection and It is formed by a mixture of a transport material and a polymer binder. Also, iron chloride is used as the hole injection / transport material. An inorganic salt such as (III) may be added to form a layer.

[0162] As a hole injection / transport material, it efficiently transports holes from the positive electrode between electrodes with an applied electric field. It is necessary to have good hole injection and transport efficiency, and to have high hole injection efficiency and efficient transport of injected holes. To achieve this, it is necessary to have a small ionization potential and a high hole mobility. It is large and has excellent stability, making it difficult for impurities to be trapped during manufacturing and use. It is preferable that the material is a non-ionic surfactant.

[0163] The hole injection layer 103 and the hole transport layer 104 are made of a photoconductive material. Compounds that have been conventionally used as charge transport materials for holes, p-type semiconductors, organic EL devices, Any compound can be selected from known compounds used in the hole injection layer and hole transport layer of the polymer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, carbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or Biscarbazole derivatives such as bis(N-alkylcarbazole), triarylamine Derivatives (polymers with aromatic tertiary amino groups in the main chain or side chain, 1,1-bis(4-di- p-Tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3 -methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N' -dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di( 3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphtho N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 ’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl) -[1,1'-biphenyl]-4,4'-diamine, N 4 ,N4 ,N 4’ ,N 4’ -Tet La[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-dia amine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenyl amines, triphenylamine derivatives, starburst amine derivatives, etc.), stilbe Phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives , hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene benzophenone-2,3,6,7,10,11-hexacarbonitrile, porphyrin derivatives, etc. In the polymer system, the polymer having the above-mentioned monomer in the side chain is Preferred are polycarbonates, styrene derivatives, polyvinylcarbazole and polysilane. However, it is necessary to form a thin film necessary for manufacturing a light-emitting element, and it is also necessary to inject holes from the anode. There is no particular limitation as long as the compound can transport the

[0164] It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials are compounds with good electron donating properties, or , and is composed of compounds with good electron-accepting properties. For doping with electron-donating substances, Tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetrafluoroethane 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., 73(6), 729-731(1998)). These are electron-donating base materials (hole-transporting materials) ) generates so-called holes by an electron transfer process. The conductivity of the base material changes considerably depending on the Examples of the oxidizing agent include benzidine derivatives (such as TPD) or starburst amine. derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanines) ZnPc and the like) are known (Japanese Patent Laid-Open Publication No. 2005-167175).

[0165] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 reacts with holes injected from the anode 102 between the electrodes to which an electric field is applied. The layer emits light by recombining with the electrons injected from the cathode 108. The material for forming 105 is a compound that emits light when excited by the recombination of holes and electrons. Any substance (luminescent compound) can be used, and it can be formed into a stable thin film shape and can be used in a solid state. In the present invention, the material for the light-emitting layer is preferably a compound that exhibits strong luminescence (fluorescence) efficiency in the light-emitting state. As the material, for example, a pyrene-based compound represented by the above general formula (2) as a host material and, for example, For example, the polycyclic aromatic compound represented by the above general formula (1) and its polycyclic aromatic compounds as dopant materials. A monomer can be used.

[0166] The light-emitting layer may be a single layer or a multi-layer. The host material and the dopant material are The dopant material may be one kind or a combination of two or more kinds. It may be contained entirely or partially in the stock material. The doping method can be a co-evaporation method with the host material. Alternatively, the material may be mixed with the catalyst material in advance and then vapor-deposited simultaneously.

[0167] The amount of the host material used varies depending on the type of host material, and should be adjusted to suit the properties of the host material. The amount of the host material to be used is preferably 50 to 100% of the total amount of the materials for the light-emitting layer. 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably The content is preferably 90 to 99.9% by weight.

[0168] The amount of dopant material used varies depending on the type of dopant material. The amount of dopant used should preferably be determined according to the characteristics of the light-emitting layer material. It is 0.001 to 50% by weight of the total, more preferably 0.05 to 20% by weight, and even more preferably It is more preferably 0.1 to 10% by weight. Within the above range, for example, concentration quenching phenomenon can be prevented. This is preferable in that it can prevent the above.

[0169] As a host material that can be used in combination with the pyrene compound represented by formula (2), Condensed ring derivatives such as anthracene, which have been known as light emitters since bisstyryl derivatives such as benzene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene Diene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives Examples include:

[0170] Dopa that can be used in combination with the polycyclic aromatic compound represented by formula (1) and its multimer The material for the light emitting element is not particularly limited, and known compounds can be used to obtain the desired luminescent color. Depending on the requirements, various materials can be selected. Specifically, for example, phenanthrene , anthracene, tetracene, pentacene, perylene, rubrene, and chrysene Ring-conjugated derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, Azole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, Lazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives compounds, cyclopentadiene derivatives, bisstyryl anthracene derivatives and distyrylbenzene Bisstyryl derivatives such as derivatives (JP-A-1-245087), bisstyryl aryl Benzene derivatives (JP 2-247278 A), diazaindacene derivatives, furan derivatives benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di (2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)iso Benzofuran, isobenzofuran derivatives such as phenylisobenzofuran, dibenzofuran coumarin derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7- Hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives 3-benzothiazolyl coumarin derivatives, 3-benzimidazolyl coumarin derivatives, 3 - Coumarin derivatives such as benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives Conductors, dicyanomethylene thiopyran derivatives, polymethine derivatives, cyanine derivatives, oxo Benzanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives compounds, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, Phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine Derivatives, furopyridine derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives compounds, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives Examples include fluorene derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives. can be done.

[0171] <Electron injection layer and electron transport layer in organic electroluminescent device> The electron injection layer 107 efficiently injects electrons moving from the cathode 108 into the light-emitting layer 105. The electron transport layer 106 serves to inject electrons from the cathode 108 into the electron transport layer 106. The injected electrons or the electrons injected from the cathode 108 through the electron injection layer 107 are efficiently The electron transport layer 106 and the electron injection layer 107 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of electron transporting and injecting materials are laminated or mixed, or electron transporting and It is formed by a mixture of an injectable material and a polymeric binder.

[0172] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them further. It is desirable that the layer has high electron injection efficiency and efficiently transports the injected electrons. To achieve this, the electron affinity must be large, the electron mobility must be large, and the stability must be excellent. It is preferable that the material be one that is unlikely to generate impurities that act as traps during production and use. However, when considering the balance of hole and electron transport, the holes from the anode do not recombine and When the electron transport ability is the main function of the cathode, the electron transport ability is the main function of the cathode. Even if the electron transport capacity is not so high, the effect of improving the luminous efficiency is equivalent to that of a material with a high electron transport capacity. Therefore, the electron injection / transport layer in this embodiment can efficiently block the movement of holes. The functions of the layer may also be included.

[0173] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 is: Compounds that have been conventionally used as electron transport compounds in photoconductive materials, organic EL devices The compound is arbitrarily selected from known compounds used in the electron injection layer and electron transport layer. You can be there.

[0174] The materials used for the electron transport layer or the electron injection layer include carbon, hydrogen, oxygen, sulfur, ketone, and the like. Aromatic or heteroaromatic rings composed of one or more atoms selected from among silicon and phosphorus Compounds consisting of a ring, pyrrole derivatives and their fused ring derivatives, and compounds having an electron-accepting nitrogen It is preferable that the compound contains at least one metal complex selected from the group consisting of naphthalene, ... Condensed ring aromatic derivatives such as phthalene and anthracene, 4,4'-bis(diphenylene) Styryl aromatic ring derivatives, represented by (thenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, Examples include phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having an electron-accepting nitrogen include hydroxyphenyloxazole complexes. Hydroxyazole complexes, azomethine complexes, tropolone metal complexes, flavonols, etc. These materials can be used alone. However, it is acceptable to use a mixture of different materials.

[0175] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, and ammonium salts. Thracene 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 )1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazoles Derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiazides Azole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives Conductors, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazoles perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzophenone derivatives, benzoquinoline derivative (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-s pyrobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole Derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzo Oxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridines, etc. Polypyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-( 2,2':6'2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis( 1-Naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, etc.

[0176] Metal complexes having an electron-accepting nitrogen atom can also be used, for example, quinolinol-based Metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomes tin complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Examples include:

[0177] The above-mentioned materials may be used alone or in combination with other materials.

[0178] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives , pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives The compounds, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0179] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and in detail This is disclosed in Japanese Patent Application Laid-Open No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is optionally substituted arylene or optionally substituted aryl; and Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl or optionally substituted carbazolyl, and n is independently 0 to The integer is 3. Also, the substitution in the case of "optionally substituted" or "substituted" The group may be an aryl, heteroaryl, alkyl, or cycloalkyl. do.

[0180] Among the compounds represented by the above general formula (ETM-1), the compound represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, R is an alkyl or optionally substituted aryl; 21 and R 22 are independent of each other. and hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted at least one of silyl, an optionally substituted nitrogen-containing heterocycle, or cyano; X 1 represents an optionally substituted arylene having 20 or less carbon atoms, and each n is independently Each m is an integer of 0 to 3, and each m is independently an integer of 0 to 4. In the case of "optionally substituted" or "substituted", the substituents include aryl, heteroaryl, Examples of the alkyl include aryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is an alkyl group or an optionally substituted aryl group; 1 is an optionally substituted carbon atom number of 2 0 or less, and n is independently an integer of 0 to 3. Substituents in the "optionally substituted" or "substituted" cases include aryl, Examples include heteroaryl, alkyl, and cycloalkyl.

[0181] X 1 Specific examples of the divalent groups include those represented by the following formulae (X-1) to (X-9). It can be obtained. [ka] (In each formula, R a are each independently an alkyl group, a cycloalkyl group, or a substituted It is a phenyl group that may be

[0182] Specific examples of the borane derivative include the following compounds: [ka]

[0183] This borane derivative can be produced using known raw materials and known synthesis methods.

[0184] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably The compound is represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0185] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0186] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably alkyl having 3 to 4 carbon atoms), cycloalkyl having 6 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). do.

[0187] In the above formula (ETM-2-2), R 11 and R 12 are each independently hydrogen , alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms) and R 11 and R 12 may be bonded to form a ring.

[0188] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15): The pyridine-based substituents are each independently an alkyl group having 1 to 4 carbon atoms or a carbon atom. The pyridine-based substituent may be substituted with a cycloalkyl having 5 to 10 carbon atoms. In each formula, the φ is bonded to an anthracene ring or a fluorene ring via an ethylene group or a naphthylene group. They may be combined.

[0189] [ka]

[0190] The pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15). Among these, any one of the following formulas (Py-21) to (Py-44) is preferred. stomach. [ka]

[0191] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium. In addition, the two "pyridine-based compounds" in the above formula (ETM-2-1) and formula (ETM-2-2) One of the "substituents" may be replaced by an aryl.

[0192] R 11 ~R 18 The "alkyl" in the formula (I) may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms. Particularly preferred "alkyl" is a branched alkyl having 1 to 6 carbon atoms. 4 alkyl (branched alkyl having 3 to 4 carbon atoms).

[0193] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n- Octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl ethyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3, 5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-do Decyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl , n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc. can be done.

[0194] The alkyl having 1 to 4 carbon atoms that is substituted on the pyridine-based substituent is the same as the alkyl described above. It can be cited.

[0195] R 11 ~R 18 In the above, the "cycloalkyl" includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl. cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, Examples include cyclooctyl and dimethylcyclohexyl.

[0196] The cycloalkyl having 5 to 10 carbon atoms that is substituted on the pyridine-based substituent includes the above-mentioned cycloalkyl. We can quote Lukil's explanation:

[0197] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. Aryl is more preferably an aryl having 6 to 18 carbon atoms, and even more preferably Preferably, it is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms. do.

[0198] Specific examples of "aryl having 6 to 30 carbon atoms" include monocyclic aryl such as phenyl, condensed aryl, and the like. (1-,2-)naphthyl is a fused bicyclic aryl; acenaphthyl is a fused tricyclic aryl; ethylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9 -)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenalen triphenylene-(1-,2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl Perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-) Examples include Iru.

[0199] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, and chlorine. phenyl, 1-naphthyl, and the like are preferred. Particularly preferred are phenyl, 1-naphthyl and phenanthryl. Examples thereof include 2-naphthyl and 2-naphthyl.

[0200] R in the above formula (ETM-2-2) 11 and R 12 Even if they bond to form a ring, As a result, the five-membered ring of the fluorene skeleton is often cyclobutane, cyclopentane, cyclopentane, Pentene, cyclopentadiene, cyclohexane, fluorene, or indene are spin It may be bonded to the

[0201] Specific examples of the pyridine derivative include the following compounds: [ka]

[0202] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0203] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3): Details are disclosed in International Publication No. 2010 / 134352. [ka]

[0204] In the above formula (ETM-3), X 12 ~X 21 is hydrogen, halogen, straight chain, branched or cyclic alkyl, straight-chain, branched or cyclic alkoxy, substituted or unsubstituted aryl, or represents a substituted or unsubstituted heteroaryl. Here, when it is substituted, the substituents include aryl, heteroaryl, alkyl, cycloalkyl, etc. .

[0205] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0206] <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

[0207] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Further, adjacent groups among R

[0208] 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 aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy.​​​​ At least one hydrogen atom in these groups may be substituted with an aryl, hydroxyl, or methyl. It may be substituted with cycloaryl, alkyl or cycloalkyl.

[0209] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) It may be substituted with halogen or deuterium.

[0210] The substituents and ring formation form in formula (ETM-4) are explained in the same manner as in the above general formula (1). The description of the polycyclic aromatic compound represented by the formula (I) can be cited.

[0211] Specific examples of the BO derivative include the following compounds: [ka]

[0212] This BO derivative can be produced using known raw materials and known synthesis methods.

[0213] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1): do. [ka]

[0214] Ar are each independently a divalent benzene or naphthalene; R 1 ~R 4 teeth, Each independently represents hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or or an aryl having 6 to 20 carbon atoms.

[0215] Ar may be independently selected from divalent benzene or naphthalene. The two Ar groups may be different or the same, but the synthesis of anthracene derivatives From the viewpoint of easiness, it is preferable that they are the same. Ar is bonded to pyridine, and and a pyridine moiety" is formed, and this moiety is, for example, represented by the following formula (Py-1) to formula ( Py-12) is bonded to anthracene.

[0216] [ka]

[0217] Among these groups, the group represented by any one of the above formulas (Py-1) to (Py-9) A group represented by any one of the above formulae (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" that bind to anthracene have the same structure. However, from the viewpoint of ease of synthesis of the anthracene derivative, it is preferable to use the same However, from the viewpoint of device characteristics, it is preferable that the two "Ar and pyrimidine" structures are the same. The structures of the "sin-containing moieties" may be the same or different.

[0218] R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms can be either a straight chain or a branched chain. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl. butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl ethyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethyl methyl, ethyl, n-propyl, ethyl, or 2-ethylbutyl. isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl More preferred are butyl, ethyl, or t-butyl.

[0219] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl Examples include cyclohexyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl. can be done.

[0220] R 1 ~R 4 For aryls having 6 to 20 carbon atoms, aryls having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Preferred.

[0221] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryl such as phenyl, ( o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6-,3,4-,3 ,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p- ) cumenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, fused bicyclic aryl (1-,2-)naphthyl, a tricyclic aryl; terphenylyl (m-terphenyl); m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-Terphenyl-3'-yl, o-Terphenyl-4'-yl, p-Terphenyl-2 '-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terpheny o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terfenyl p-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, ... phenyl-4-yl), fused tricyclic aryl anthracene-(1-, 2-, 9-phenyl-4-yl), -)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2 -,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2- )yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, Examples include perylene-(1-, 2-, 3-)yl, which is a fused pentacyclic aryl.

[0222] Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, and terphenylyl. or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2- naphthyl or m-terphenyl-5'-yl, more preferably phenyl, biphenyl It is preferably phenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0223] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2): do. [ka]

[0224] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, an anthracene, fluorene or phenalene.

[0225] Ar 2are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0226] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, is a cycloalkyl or an aryl having 6 to 20 carbon atoms, and in the above formula (ETM-5-1), The explanations given can be cited.

[0227] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0228] These anthracene derivatives can be produced using known raw materials and known synthesis methods. Cut.

[0229] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0230] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0231] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), ), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably Preferably, it is an aryl having 6 to 30 carbon atoms, and two Ar 2 are bonded to form a ring Good too.

[0232] Ar 2 The "alkyl" in the above may be either a straight chain or a branched chain, for example, Examples include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. The preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (e.g., alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (a branched alkyl). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms. alkyl (branched alkyl with 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl ethyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1- Methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl Examples include butyl, n-heptyl, and 1-methylhexyl.

[0233] Ar 2 The "cycloalkyl" in the above formula includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or or dimethylcyclohexyl.

[0234] Ar 2 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. The aryl is more preferably an aryl having 6 to 18 carbon atoms, and further preferably an aryl having 6 to 18 carbon atoms. It is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms.

[0235] Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, and acenaphthyl. nyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, na Examples include phthalocenyl, perylenyl, and pentacenyl.

[0236] Two Ar 2 may be bonded to form a ring, resulting in a five-membered ring of the fluorene skeleton. These include cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, and cyclohexene. The oxane, fluorene, or indene may be spiro-linked.

[0237] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0238] This benzofluorene derivative can be produced using known raw materials and known synthesis methods. Cut.

[0239] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in International Publication No. 2013 / 079217. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, alkyl, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms; R 6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, silyl having 3 to 20 carbon atoms chloroalkyl, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, aryl having 5 carbon atoms Heteroaryl with up to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, or aryl with 6 to 20 carbon atoms It is oxy, R 7 and R 8 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. aryl or heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. is an integer. In the case where the group is substituted, the substituent may be an aryl, a heteroaryl, an alkyl, or the like. Or cycloalkyl, etc.

[0240] The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-2): Good too. [ka]

[0241] R 1 ~R 3 may be the same or different and are hydrogen, an alkyl group, a cycloalkyl group, Aralkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, alkoxy groups, alkoxy groups, alkylthio group, cycloalkylthio group, aryl ether group, aryl thioether group, aryl Aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl Among the fused rings formed between the substituted groups, amino groups, nitro groups, silyl groups, and adjacent substituents, are selected.

[0242] Ar 1 may be the same or different and are arylene or heteroarylene groups. Ar 2 may be the same or different and are aryl or heteroaryl groups However, Ar 1 and Ar 2 At least one of the groups has a substituent, or the adjacent groups A condensed ring is formed between the substituted and unsaturated groups. n is an integer of 0 to 3. When n is 0, the unsaturated group is When n is 3, R 1 does not exist.

[0243] Among these substituents, the alkyl group includes, for example, a methyl group, an ethyl group, a propyl group, a bromine group, and the like. refers to a saturated aliphatic hydrocarbon group, such as a methyl group, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and examples thereof include alkyl groups and aryl groups. , heterocyclic groups, etc., which are also included in the following description. The number of carbon atoms in the group is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost. It is an enclosure.

[0244] The cycloalkyl group includes, for example, cyclopropyl, cyclohexyl, norbornyl, It refers to saturated alicyclic hydrocarbon groups such as benzoyl, benzoyl, and adamantyl, which can be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20. be.

[0245] The aralkyl group is an aliphatic hydrocarbon group such as a benzyl group or a phenylethyl group. It indicates an aromatic hydrocarbon group mediated by a substituent, and both aliphatic and aromatic hydrocarbons are unsubstituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but it is usually 1. The range is ~20.

[0246] The alkenyl group is a double bonded group such as a vinyl group, an allyl group, or a butadienyl group. represents an unsaturated aliphatic hydrocarbon group containing a bond, 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.

[0247] The cycloalkenyl group includes, for example, a cyclopentenyl group, a cyclopentadienyl group, and the like. It refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclohexene group or a cyclohexene group. It doesn't matter if it's a substitution or a replacement.

[0248] The alkynyl group is an unsaturated aliphatic group containing a triple bond, such as an acetylenyl group. represents a hydrocarbon group, which may be unsubstituted or substituted. The number is not particularly limited, but is usually in the range of 2 to 20.

[0249] The alkoxy group is an aliphatic carbonized group via an ether bond, such as a methoxy group. 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 is usually in the range of 1-20.

[0250] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced with a sulfur atom. It is a group that has been

[0251] A cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is sulfur. It is a group substituted with a yellow atom.

[0252] The aryl ether group is an aromatic group formed via an ether bond, such as a phenoxy group. The aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0253] In addition, an aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is It is a group substituted with a sulfur atom.

[0254] The aryl group includes, for example, a phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, and the like. The aryl group refers to an aromatic hydrocarbon group such as an alkyl group, a terphenyl group, or a pyrenyl group. The number of carbon atoms in the aryl group is not particularly limited, but is usually , ranging from 6 to 40.

[0255] The heterocyclic group includes, for example, a furanyl group, a thiophenyl group, an oxazolyl group, a pyridinyl group, and the like. a cyclic structural group having atoms other than carbon, such as a quinolinyl group, a carbazolyl group, The heterocyclic group may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited. , usually in the range of 2 to 30.

[0256] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0257] Aldehyde groups, carbonyl groups, and amino groups are used in aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons. It may also include groups substituted with aromatic hydrocarbons, heterocycles, etc.

[0258] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be unsubstituted or substituted. It doesn't matter if it's broken.

[0259] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which is an unsubstituted silyl group. The number of carbon atoms in the silyl group is not particularly limited, but is usually 3. The silicon number is usually in the range of 1 to 20.

[0260] 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 Ar2 Conjugates formed between etc. or It is a non-conjugated fused ring. Here, when n is 1, two R 1 Conjugate or non-conjugate condensation These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure. Alternatively, it may be condensed with another ring.

[0261] Specific examples of the phosphine oxide derivative include the following compounds: . [ka]

[0262] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods. can be done.

[0263] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably is a compound represented by the following formula (ETM-8-1). This is also described in Publication No. 1689. [ka]

[0264] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 4, preferably an integer of 1 to 3, More preferably, it is 2 or 3.

[0265] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0266] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be

[0267] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0268] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0269] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0270] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0271] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0272] <Carbazole derivatives> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or It is a polymer formed by multiple bonds such as single bonds. For details, see U.S. Patent Publication 2014 / 0197386 This is described in publication no. [ka]

[0273] Ar each independently represents an optionally substituted aryl or an optionally substituted Each n is independently an integer of 0 to 4, preferably 0 to 4. 3, and more preferably 0 or 1.

[0274] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0275] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be

[0276] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0277] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0278] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0279] The carbazole derivative is a compound represented by the above formula (ETM-9) that is bonded by multiple bonds such as single bonds. In this case, in addition to the single bond, an aryl ring (preferably a polyvalent Benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phen The rings may be bonded together via a naphthylene ring, a naphthylene ring, a phenanthrene ring, or a triphenylene ring).

[0280] Specific examples of the carbazole derivative include the following compounds: [ka]

[0281] This carbazole derivative can be produced using known raw materials and known synthesis methods. .

[0282] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and is preferably The compound is represented by the following formula (ETM-10-1). This is described in Publication No. / 0156013. [ka]

[0283] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 3, preferably 2 or 3.

[0284] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0285] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be

[0286] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0287] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0288] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0289] Specific examples of the triazine derivative include the following compounds: [ka]

[0290] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0291] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11): . [ka]

[0292] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring a phenylene ring), n is an integer of 1 to 4, and the "benzimidazole-based substituent" is The "pyriferous" in formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) It is a substituent in which the pyridyl group in the "pyridyl-based substituent" is replaced with a benzimidazole group, At least one hydrogen atom in the benzimidazole derivative may be replaced by deuterium. stomach. [ka]

[0293] R in the benzimidazole group 11 is hydrogen, alkyl with 1 to 24 carbon atoms, carbon cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, 2-1) and R in Equation (ETM-2-2) 11 The explanation can be cited.

[0294] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing both pyridine-based substituents with benzimidazole-based substituents, It may be replaced by an azole-based substituent (i.e., n=2), or any one of the pyridine-based substituents. The substituent is replaced with a benzimidazole-based substituent and the other pyridine-based substituent is replaced with R 11 ~R 1 8 (i.e., n=1). Furthermore, for example, in the above formula (ETM-2-1), R in 11 ~R 18 At least one of the groups is replaced with a benzimidazole-based substituent to form a "pi Lysine-based substituents" R 11 ~R 18 may be replaced with .

[0295] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-( 10-Phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole , 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)- 1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2 -yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imide dazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2- (yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imida 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)azole phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10- Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H -benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracene) (2-phenyl-1H-benzo[d]imidazole) do. [ka]

[0296] This benzimidazole derivative can be produced using known raw materials and known synthesis methods. can.

[0297] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or the formula (ETM-12- 1). Details are described in International Publication No. 2006 / 021982. are. [ka]

[0298] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0299] R in each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably having 1 to 10 carbon atoms), 24 alkyl), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or is an aryl (preferably an aryl having 6 to 30 carbon atoms). 2-1) R 11 ~R 18 Either of these bonds to φ, an aryl ring.

[0300] At least one hydrogen atom in each phenanthroline derivative is replaced with a deuterium atom. good.

[0301] R 11 ~R18 The alkyl, cycloalkyl and aryl in the formula ( R in ETM-2 11 ~R 18 The explanation of the above can be cited. In addition to the above examples, the following structural formulas are also available. In the structural formulas below, R represents Independently, hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, It is phenylyl, 2-naphthyl, biphenylyl or terphenylyl. [ka]

[0302] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10 -phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Phosphorus, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6- Di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10- phenanthrolin-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl)benzene anthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10- phenanthrolin-9-yl)benzene and the compound represented by the following structural formula: . [ka]

[0303] This phenanthroline derivative can be produced using known raw materials and known synthesis methods. Cut.

[0304] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13): do. [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, It is Ga, Be or Zn, and n is an integer of 1 to 3.

[0305] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium and tris(8- Tris(4-methyl-8-quinolinolato)aluminum, Tris(4-methyl-8-quinolinolato)aluminum aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl Tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum tris(4,6-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, Bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl Bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum -8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl- 8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(4-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl -8-quinolinolato)(2,6-dimethylphenolato)aluminum, bis(2-methyl- bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum -methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis (2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminium ammonium, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)a Aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenyl) Aluminum bis(2-methyl-8-quinolinolate)(2,4,6-trimethyl-8-quinolinolate) Methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4 ,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinol) bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate) (2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)( 2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinol) bis(2,4-dimethyl-8-quinolinyl)aluminum(triphenylphenolate) bis(2,4-dimethyl-8-)(4-phenylphenolate)aluminum Quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2,4-dimethylphenolato)aluminum (3,5-di-t-butylphenolate)aluminum, bis(methyl-8-quinolinolato) Bis(2-methyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl- 8-quinolinolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)aluminum Aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum , bis(2-methyl-4-ethyl-8-quinolinolato)aluminum-μ-oxo-bi Bis(2-methyl-4-ethyl-8-quinolinolato)aluminum, Bis(2-methyl- 4-Methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4 -Methoxy-8-quinolinolato)aluminum, bis(2-methyl-5-cyano-8- Quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quino Aluminum linoleate, bis(2-methyl-5-trifluoromethyl-8-quinolinol) bis(2-methyl-5-trifluoromethyl-8-methyl-2-oxo-2-methyl-5-trifluoromethyl-4-methyl-2-methyl-2-oxo ... Quinolinolate)aluminum, Bis(10-hydroxybenzo[h]quinoline)beryl Examples include Umu.

[0306] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods. Cut.

[0307] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2): do. [ka]

[0308] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, a helical ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4. The "zothiazole-based substituent" is a group represented by the above formula (ETM-2), formula (ETM-2-1) and formula (E The pyridyl group in the "pyridine-based substituent" in TM-2-2) is the following thiazole group or It is a substituent substituted for the benzothiazole group, and is used in thiazole derivatives and benzothiazo At least one hydrogen atom in the alkyl derivative may be substituted with deuterium. [ka]

[0309] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing with an azole-based substituent (or a benzothiazole-based substituent), both pyridines Even if the thiazole-based substituent is replaced with a thiazole-based substituent (or a benzothiazole-based substituent), (i.e., n=2), any one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or or benzothiazole-based substituent) and the other pyridine-based substituent is replaced by R 11 ~R 18 (i.e., n=1). Furthermore, for example, in the above formula (ETM-2-1), KerR 11 ~R18 At least one of the following is a thiazole-based substituent (or a benzothiazole-based substituent) Substituent) and replace "pyridine-based substituent" with R 11 ~R 18 may be replaced with .

[0310] These thiazole derivatives or benzothiazole derivatives are synthesized using known raw materials and known synthesis methods. It can be produced using the method.

[0311] The electron transport layer or the electron injection layer may further include a material for forming the electron transport layer or the electron injection layer. The reducing agent may contain a substance capable of reducing the feedstock. If so, various substances can be used, such as alkali metals, alkaline earth metals, and rare earth metals. alkali metal oxides, alkali metal halides, alkaline earth metal oxides, Alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, Organic complexes of alkaline metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. At least one selected from the following group can be suitably used.

[0312] 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 ( 2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV) Alkali earth metals are preferred, and substances with a work function of 2.9 eV or less are particularly preferred. Among them, the more preferred reducing substance is an alkali metal such as K, Rb or Cs, and even more preferred Preferably, Rb or Cs, and most preferably Cs. These alkali metals are In particular, it has a high reducing ability and is useful when added in a relatively small amount to a material forming an electron transport layer or an electron injection layer. By adding the above, the luminance of the organic EL element can be improved and the life span can be extended. As a reducing substance having a valence of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred. Preferably, combinations containing Cs, such as Cs and Na, Cs and K, Cs and Rb, Alternatively, a combination of Cs, Na and K is preferred. By including Cs, the reduction ability is effectively improved. By adding it to the material that forms the electron transport layer or the electron injection layer, This will improve the luminance and extend the life of organic EL elements.

[0313] <Cathode in organic electroluminescent device> The cathode 108 supplies electricity to the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 . It plays a role in injecting the offspring.

[0314] The material for forming the cathode 108 can be any material that can efficiently inject electrons into the organic layer. Although not particularly limited, the same material as that 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. metals or their alloys (magnesium-silver alloy, magnesium-indium alloy, Aluminum-lithium alloys such as lithium fluoride / aluminum are preferred. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, and potassium Cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, trace amounts of lithium, cesium, or magnesium are added to the organic layer. A method is known in which highly stable electrodes are obtained by doping with other dopants. Examples include lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, other inorganic salts can also be used, including, but not limited to, the following:

[0315] In addition, platinum, gold, silver, copper, iron, tin, aluminum and indium are used to protect the electrodes. Metals such as titanium, or alloys using these metals, as well as silica, titania and silicon nitride Inorganic materials such as silicon dioxide, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is also based on resistance heating, electron Conductive materials such as ion beam evaporation, sputtering, ion plating and coating There are no particular restrictions as long as it can be obtained.

[0316] <Binders that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer are Each layer can be formed using a single material, but polyvinyl chloride, polycarbonate, etc. can be used as a polymer binder. Carbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate Polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide Polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl Solvent-soluble resins such as cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, Phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester Dispersed in curable resins such as terephthalate resin, alkyd resin, epoxy resin, and silicone resin. It is also possible to use them together.

[0317] <Method for producing organic electroluminescent device> Each layer that makes up an organic EL element is made by depositing the material that makes up each layer using evaporation, resistance heating evaporation, electron deposition, etc. beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, It can be formed by forming a thin film using a coating method or the like. There are no particular limitations on the thickness of each layer formed, and it is set appropriately depending on the properties of the material. The film thickness is usually in the range of 2 nm to 5000 nm. When thinning is performed using a vapor deposition method, the vapor deposition conditions depend on the type of material. The deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Heating temperature +50 to +400℃, vacuum degree 10 -6 ~10 -3 Pa, deposition rate 0.01~ 50 nm / sec, substrate temperature -150 to +300°C, film thickness 2 nm to 5 μm. It is preferable that

[0318] Next, as an example of a method for fabricating an organic EL element, anode / hole injection layer / hole transport layer / hole The organic layer consists of an emitting layer made of a resist material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. The method for fabricating an EL element is explained. A thin film of anode material is deposited on a suitable substrate by evaporation or other methods. After forming an anode by this method, a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the layer to form a thin film, which serves as an emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film made of a cathode material is then formed on the light-emitting layer. The cathode is formed by vapor deposition or the like, and the desired organic EL element is obtained. In the above-mentioned production of the organic EL element, the production order is reversed, and the cathode, electron injection layer, and electrode are formed. It is also possible to fabricate the electron transport layer, light emitting layer, hole transport layer, hole injection layer and anode in this order.

[0319] When applying a DC voltage to the organic EL element obtained in this way, the anode is connected to + and the cathode is connected to When a voltage of 2 to 40 V is applied, the material becomes transparent or translucent. Light emission can be observed from the electrode side (anode or cathode, or both). The element also emits light when a pulse current or an AC current is applied. It can be optional.

[0320] <Application examples of organic electroluminescent devices> The present invention also relates to a display device including an organic EL element or a lighting device including an organic EL element. It can also be applied to the following: A display device or a lighting device including an organic EL element is provided with the organic EL element according to this embodiment. It can be manufactured by a known method, for example by connecting it to a known driving device, and can be driven by DC, power The driving method can be appropriately selected from known driving methods such as pulse driving and AC driving.

[0321] The display device may be, for example, a panel display such as a color flat panel display. flexible displays such as flexible color organic electroluminescent (EL) displays Examples of such games include the game of the same name (for example, Japanese Patent Application Laid-Open No. 10-335066, Japanese Patent Application Laid-Open No. 2003-321546, (See, for example, Japanese Patent Application Laid-Open Publication No. 2004-281086.) In addition, the display method may be, for example, The matrix and segment display methods are also available. The display may coexist in the same panel.

[0322] In a matrix, the pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern. A set of pixels is used to display characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions usually have a side length of 300 μm or more. The square pixels below are used, and in the case of large displays such as display panels, In the case of monochrome display, pixels of the same color are arranged. In the case of a color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta type and stripe type. The method may be either a line sequential driving method or an active matrix method. has the advantage of being simpler in structure, but when considering the operating characteristics, the active matrix There are cases where Ricks is superior, so it is necessary to use it depending on the purpose. .

[0323] In the segment type, patterns are formed to display predetermined information. For example, the time on a digital clock or thermometer is Time and temperature displays, operating status displays for audio equipment and induction cookers, and automobile panel displays Examples include:

[0324] Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (For example, Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patent Application Laid-Open No. 2004-1 (See, for example, Patent Publication No. 19211.) Backlights are primarily used to improve the visibility of non-self-luminous display devices. It is used for the purpose of displaying images, and is used in LCD displays, clocks, audio equipment, automobile panels, display boards, and They are used in LCD displays, especially in personal computers, where thinning is an issue. Backlights for LCD screens have traditionally been made using fluorescent lamps and light guide plates, making them thinner. Considering the difficulty of this, the backlight using the light-emitting element according to this embodiment is thin and lightweight. Quantity is a feature. [Example]

[0325] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples. First, synthesis examples of polycyclic aromatic compounds and pyrene-based compounds will be described below. do.

[0326] Synthesis Example (1): Synthesis of Compound (1-290) [ka]

[0327] Under a nitrogen atmosphere, methyl 4-methoxysalicylate (50.0 g), pyridine (anhydrous) (3 The flask containing 50 ml of trifluoromethanesulfone was cooled in an ice bath. Acid anhydride (154.9 g) was added dropwise to this solution. After the addition was completed, the ice bath was removed and the mixture was allowed to stand at room temperature for 2 After stirring for 1 hour, water was added to stop the reaction. Toluene was added to separate the organic layer, and then silica By purifying with a gel short-path column (eluent: toluene), methyl 4-methoxy 4-(((trifluoromethyl)sulfonyl)oxy)benzoate (86.0 g). [ka]

[0328] Under a nitrogen atmosphere, methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl) (oxy)benzoate (23.0 g), (4-(diphenylamino)phenyl)boronic acid (25.4g), tripotassium phosphate (31.1g), toluene (184ml), ethanol A suspension of Pd(PPh3)4 (2. 5g) was added and stirred at reflux temperature for 3 hours. The reaction mixture was cooled to room temperature and diluted with water and toluene. The organic layer was separated by adding ethanol, and the solvent in the organic layer was evaporated under reduced pressure. The mixture was purified with hexane / toluene mixed solvent (eluent) to give methyl 4'-(diphenylamine). (amino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (29 .7g). At this time, "Guide to Organic Chemistry Experiments (1) - Methods of Handling Materials and Separation and Purification -" Co., Ltd. By referring to the method described on page 94 of the Kagaku Dojin Publishing Co., Ltd., gradually increase the ratio of toluene in the eluent. The concentration was increased to elute the target substance. [ka]

[0329] Under a nitrogen atmosphere, methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl phenyl]-2-carboxylate (11.4 g) dissolved in THF (111.4 ml) The solution was cooled in a water bath and methylmagnesium bromide in THF (1.0 M, After the addition was completed, the water bath was removed and the temperature was raised to reflux, followed by stirring for 4 hours. After that, the mixture was cooled in an ice bath, and an aqueous solution of ammonium chloride was added to stop the reaction. The organic layer was separated by adding 100 ml of ethyl acetate, and the solvent was evaporated under reduced pressure. Purify with toluene (eluent) to obtain 2-(4'-(diphenylamino)-5-methoxy-[1 ,1'-biphenyl]-2-yl)propan-2-ol (8.3 g). [ka]

[0330] Under a nitrogen atmosphere, 2-(4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl] (phenyl)-2-yl)propan-2-ol (27.0 g), TAYCACURE-15 A flask containing (13.5 g) and toluene (162 ml) was stirred at reflux temperature for 2 hours. The reaction mixture was cooled to room temperature and then loaded onto a silica gel short-path column (eluent: toluene). After removing TAYCACURE-15 by passing it through the reactor, the solvent was removed by distillation under reduced pressure. , 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluorene-2-a Min was obtained (25.8g). [ka]

[0331] Under a nitrogen atmosphere, 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoro Oleno-2-amine (25.0 g), pyridine hydrochloride (36.9 g) and N-methyl- A flask containing 2-pyrrolidone (NMP) (22.5 ml) was stirred at reflux temperature for 6 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added to separate the organic layer. After distillation under reduced pressure, the product was purified with a silica gel column (eluent: toluene) to obtain 7-(diphenyl (nylamino)-9,9'-dimethyl-9H-fluoren-3-ol (22.0 g ). [ka]

[0332] Under a nitrogen atmosphere, 7-(diphenylamino)-9,9'-dimethyl-9H-fluorene- 3-ol (14.1 g), 2-bromo-1,3-difluorobenzene (3.6 g), charcoal A flask containing potassium carbonate (12.9 g) and NMP (30 ml) was heated at reflux for 5 min. After the reaction was stopped, the reaction mixture was cooled to room temperature, and water was added to remove the precipitate. The precipitate was collected by suction filtration. The obtained precipitate was washed with water and then with methanol, and then The product was purified using a column (eluent: heptane / toluene mixed solvent) to give 6,6'-((2-bromo (9,9-dimethyl-N,N-diphenyl)bis(oxy)bis(9,9-dimethyl-N,N-diphenyl)bis(1,3-phenylene)bis(oxy)bis(9,9-dimethyl-N,N-diphenyl ... The toluene in the eluent was used to obtain 12.6 g of toluene-9H-fluoren-2-amine. The ratio of ethanol was gradually increased to elute the target compound. [ka]

[0333] Under a nitrogen atmosphere, 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis s(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (11. The flask containing 2.0 g of HCl and xylene (60.5 ml) was cooled to -40°C and A solution of n-butyllithium in hexane (5.1 ml) was added dropwise. After stirring at 40°C for 0.5 hours, the temperature was raised to 60°C and stirring was continued for 3 hours. After distilling off the low boiling point components, the mixture was cooled to -40°C and boron tribromide (4.3 g) was added. The mixture was warmed to room temperature and stirred for 0.5 hours, then cooled to 0°C and diluted with N-ethyl-N-isopropyl Pyrpropan-2-amine (3.8 g) was added, and the mixture was heated and stirred at 125° C. for 8 hours. The solution was cooled to room temperature, and an aqueous solution of sodium acetate was added to stop the reaction. The organic layer was separated by a silica gel short-path column, then a silica gel column. The column (eluent: heptane / toluene = 4 (volume ratio)) was used, and then an activated carbon column (eluent: toluene) was used. The resulting mixture was purified by HPLC to give compound (1-290) (1.2 g). [ka]

[0334] The structure of the obtained compound (1-290) was confirmed by NMR measurement. 1 H-NMR (400MHz, CDCl3): δ=8.64(s,2H), 7.75(m ,3H), 7.69(d,2H), 7.30(t,8H), 7.25(s,2H), 7. 20(m,10H), 7.08(m,6H), 1.58(s,12H).

[0335] Synthesis Example (2): Synthesis of Compound (1-139) [ka]

[0336] Compound (1-139) was synthesized using the same method as in the above synthesis example. [ka]

[0337] The structure of the obtained compound (1-139) was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl3): δ=1.47(s,36H), 2.17( s,3H), 5.97(s,2H), 6.68(d,2H), 7.28(d,4H), 7 .49(dd,2H), 7.67(d,4H), 8.97(d,2H).

[0338] Synthesis Example (3): Synthesis of Compound (1-151) [ka]

[0339] Compound (1-151) was synthesized using the same method as in the above synthesis example. [ka]

[0340] The structure of the obtained compound (1-151) was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl3): δ=1.46(s,18H), 1.47( s,18H), 6.14(d,2H), 6.75(d,2H), 7.24(t,1H), 7.29(d,4H), 7.52(dd,2H), 7.67(d,4H), 8.99(d ,2H).

[0341] Synthesis Example (4): Compound (2-1) "11,11-diphenyl-6-(pyren-1-yl) Synthesis of 11H-benzo[a]fluorene [ka]

[0342] Under a nitrogen atmosphere, a flask was charged with 1-bromo-2-methoxynaphthalene (9.5 g), bis( (Pinacolate)diboron (12.2g), potassium acetate (11.8g), palladium catalyst (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride Chloride dichloromethane complex (0.98 g) and cyclopentyl methyl ether (CP ME (143 mL) was placed in the flask and stirred at reflux temperature under a nitrogen atmosphere for 4 hours. The liquid was cooled to room temperature, water was added, and then ethyl acetate was added for liquid separation and extraction. After that, it was dried, concentrated, and purified with an activated carbon short-path column (eluent: toluene) to obtain intermediate A. (11.3g) was obtained. [ka]

[0343] Under a nitrogen atmosphere, intermediate A (11.3 g), methyl 2-bromobenzoate (8.6 g), potassium phosphate (16.9 g), tetrakis(triphenylphosphine) as a palladium catalyst (Iron)palladium (1.4 g), toluene (85 mL), ethanol (17 mL) and water (9 mL) was placed in a flask and stirred at reflux temperature for 7 hours under a nitrogen atmosphere. The mixture was cooled to rt, water was added, and toluene was then added for liquid separation and extraction. The crude product was purified on a silica gel column (eluent: toluene) to obtain intermediate B (9.1 g). [ka]

[0344] Under a nitrogen atmosphere, intermediate B (9.1 g) and tetrahydrofuran (THF, 21 mL) was placed in a flask, cooled in an ice bath, and then added to a 1M solution of phenylmagnesium bromide under a nitrogen atmosphere. A solution of ethanol / THF (94 mL) was added dropwise and stirred at reflux temperature for 3 hours. The reaction was stopped by adding an aqueous ammonium solution, and then ethyl acetate was added for solvent extraction. After separating the organic layer, it was dried and concentrated, and the crude material was purified using a silica gel column (eluent: toluene). Intermediate C was obtained (12.3 g). [ka]

[0345] Under a nitrogen atmosphere, intermediate C (12.3 g) and acetic acid (117 mL) were placed in a flask. After adding one drop of concentrated sulfuric acid, the mixture was stirred at 90°C for 3 hours under a nitrogen atmosphere. After cooling, water was added and the precipitate was filtered. The precipitate was washed with water and dried to obtain intermediate D. (10.6g). [ka]

[0346] Under a nitrogen atmosphere, intermediate D (10.6 g), pyridine hydrochloride (15.4 g) and N-methyl NMP (10 mL) was placed in a flask and heated at 185°C for 4 hours under a nitrogen atmosphere. After cooling, water was added, and the precipitate was filtered, washed with water, and dried. Intermediate E was obtained (10.1 g). [ka]

[0347] Under a nitrogen atmosphere, intermediate E (10 g) and pyridine (100 mL) were placed in a flask. After cooling in an ice bath, trifluoromethanesulfonic anhydride (18.3 g) was added under a nitrogen atmosphere. After stirring for 3 hours, water was added to stop the reaction. The precipitate was filtered. The resulting mixture was purified using a silica gel short-path column (eluent: toluene) to obtain intermediate F. (13.4g). [ka]

[0348] Under a nitrogen atmosphere, intermediate F (3 g), 1-pyreneboronic acid (2.1 g), and potassium phosphate (2.5g), tetrakis(triphenylphosphine)palladium as palladium catalyst (0.2 g), 1,2,4-trimethylbenzene (24 mL), t-butyl alcohol ( The flask was charged with 3 mL of ethanol and 1.5 mL of water, and the mixture was stirred at reflux temperature for 4 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water was added, followed by the addition of toluene for liquid separation and extraction. After separating the organic layer, it was dried and concentrated, and the crude product was purified by silica gel column (eluent: toluene / heptane = After purifying with a 3 / 1 (volume ratio) mixture, the compound (2-1) was obtained by sublimation purification. .2g). [ka]

[0349] The structure of the obtained compound (2-1) was confirmed by NMR measurement. 1 H-NMR(CDCl3):6.0(d,1H), 6.6(dt,1H), 7.0(d t,1H), 7.2~7.5(m,13H), 7.9~8.0(m,5H), 8.0(t ,1H), 8.2~8.3(m,5H), 8.4(d,1H).

[0350] Synthesis Example (5): Compound (2-46) "6-(6-(naphthalen-2-yl)pyrene-1 Synthesis of (11,11-yl)-11,11-diphenyl-11H-benzo[a]fluorene [ka]

[0351] Under a nitrogen atmosphere, 1,6-dibromopyrene (3.5 g), 2-naphthylboronic acid (1.7 g), potassium carbonate (2.7 g), tetrakis(triphenylphosphine) as a palladium catalyst (fin)palladium (0.3 g), toluene (35 mL), and water (9 mL) were placed in a flask. The reaction mixture was cooled to room temperature and water was added. Toluene was further added for liquid separation and extraction. The organic layer was separated, dried, and concentrated, and the crude product was extracted with silica. Purify the mixture on a gel column (eluent: toluene / heptane = 6 / 1 (volume ratio)) to obtain intermediate G. (2.1g). [ka]

[0352] Under a nitrogen atmosphere, intermediate F (7 g), bis(pinacolato)diboron (4.1 g), and acetic acid were Potassium (4.0 g), palladium (1,1'-bis(diphenylphosphino) )Ferrocene)palladium(II) dichloride·dichloromethane complex (0.3 g) and Cyclopentyl methyl ether (CPME, 67 mL) was placed in a flask and heated under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and water was added, followed by further addition of ethyl acetate. The organic layer was separated, dried, concentrated, and then passed through an activated carbon short-path column (eluent Purification with hexane (toluene) gave intermediate H (4.6 g). [ka]

[0353] Under a nitrogen atmosphere, intermediate G (0.8 g), intermediate H (0.9 g), potassium phosphate (0. 9g), and tetrakis(triphenylphosphine)palladium (0. 1g), 1,2,4-trimethylbenzene (12mL), t-butyl alcohol (2mL ) and water (1 mL) were placed in a flask, and the mixture was stirred at reflux temperature under a nitrogen atmosphere for 14 hours. The reaction mixture was cooled to room temperature, and water was added, followed by the addition of toluene for liquid separation and extraction. After separation, the crude product was dried and concentrated, and then purified by silica gel column (eluent: toluene / heptane = 1 / 3 (volume ratio)), and then purified by sublimation to obtain compound (2-46) (1.0 g). [ka]

[0354] The structure of the obtained compound (2-46) was confirmed by NMR measurement. 1 H-NMR(CDCl3):6.0(d,1H), 6.6(dt,1H), 7.0(d t,1H), 7.2~7.6(m,15H), 7.8~8.2(m,14H), 8.2~ 8.3(m,2H).

[0355] Synthesis Example (6): Compound (2-1001) "3,9-di(pyren-1-yl)spiro[benzyl] Synthesis of benzo[a]fluorene-11,9'-fluorene [ka]

[0356] Under a nitrogen atmosphere, pyrene-1-boronic acid (5 g), ethylene glycol (3.8 g) and The flask containing the reaction mixture and toluene (30 mL) was stirred at reflux temperature for 3 hours. Water was then added and the mixture was stirred, the organic layer was separated, and the organic layer was concentrated under reduced pressure to obtain a crude product. After passing through a silica gel short-path column (eluent: toluene), the eluate was concentrated. This gave 2-(pyren-1-yl)-1,3,2-dioxaborolane (4.2 g). [ka]

[0357] Intermediate I synthesized under a nitrogen atmosphere by the method described in Japanese Patent Publication No. 2009-184993 (3.8g), 2-(pyren-1-yl)-1,3,2-dioxaborolane (3.3g) , chlorophenylallyl [1,3-bis(2,6-diisopropyl [phenyl)imidazol-2-ylidene]palladium(II) (19 mg), potassium carbonate ammonium bromide (3.2 g), tetrabutylammonium bromide (TBAB, 0.6 g), cyclopentasiloxane CPME (20 mL) and water (2 mL) were placed in a flask and heated to reflux. After the reaction, the mixture was cooled, water was added to the reaction mixture, and the mixture was stirred. After drying the precipitate, it was dissolved in chlorobenzene by heating and then filtered with a silica gel short circuit filter. The solid obtained by filtering through a column (eluent: toluene) and concentrating the eluate was After filtration and drying, the product was purified by sublimation to obtain compound (2-1001) (2.2 g). [ka]

[0358] The structure of the obtained compound (2-1001) was confirmed by NMR measurement. 1 H-NMR(CDCl3):6.9~7.0(m,4H), 7.2(t,2H), 7. 4(dd,1H), 7.4(dt,2H), 7.7(dd,1H), 7.8~7.9(m ,2H), 7.9~8.1(m,9H), 8.1~8.2(m,13H).

[0359] Synthesis Example (7): Compound (2-350) "2-(pyren-1-yl)triphenylene" synthesis [ka]

[0360] Under a nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(triphenylene-2 -yl)-1,3,2-dioxaborolane (3.0 g), 1-bromopyrene (2.2 g) , chlorophenylallyl [1,3-bis(2,6-diisopropyl [phenyl)imidazol-2-ylidene]palladium(II) (25 mg), potassium carbonate ammonium bromide (2.2 g), tetrabutylammonium bromide (TBAB, 0.8 g), cyclopentasiloxane CPME (20 mL) and water (2 mL) were placed in a flask and heated to reflux. After the reaction, the mixture was cooled, water was added to the reaction mixture, and the mixture was stirred. After drying the precipitate, it was dissolved in chlorobenzene by heating and then filtered with a silica gel short circuit filter. The solid obtained by filtration through a column (eluent: toluene) and concentrating the eluate was filtered. The mixture was filtered, dried, and purified by sublimation to obtain compound (2-350) (3.3 g). [ka]

[0361] The structure of the obtained compound (2-350) was confirmed by NMR measurement. 1 H-NMR(CDCl3):7.6~7.7(m,4H), 7.9(dd,1H), 8 .0(m,2H), 8.1~8.2(m,4H), 8.2(m,1H), 8.3(m,2 H), 8.7~8.8(m,4H), 8.8(d,1H), 8.9(d,1H).

[0362] Synthesis Example (8): Compound (2-1080) "3,9-bis(7-(t-butyl)pyrene- Synthesis of 2-yl)spiro[benzo[a]fluorene-11,9'-fluorene] [ka]

[0363] Under a nitrogen atmosphere, an intermediate synthesized by the method described in WO 2015 / 141608 Compound J (1.7 g), 2-bromo-7-(t-butyl)pyrene (2 g), a palladium catalyst, Chlorophenylallyl [1,3-bis(2,6-diisopropylphenyl)imidazoline] [2-phenyl-2-ylidene]palladium(II) (9 mg), potassium carbonate (1.6 g), bromide Tetrabutylammonium (TBAB, 0.3 g), cyclopentyl methyl ether (C PME (20 mL) and water (2 mL) were placed in a flask and heated and stirred at reflux temperature for 4 hours. After the reaction, the reaction mixture was cooled, water was added to the reaction mixture, and the mixture was stirred. The precipitate was then filtered. After drying, it was dissolved in chlorobenzene by heating and then passed through a silica gel short-path column (eluent: The solid obtained by filtration through toluene and concentrating the eluate is filtered, dried, and then sublimed. After purification, compound (2-1080) was obtained (1.6 g). [ka]

[0364] The structure of the obtained compound (2-1080) was confirmed by NMR measurement. 1 H-NMR(CDCl3):1.6(s,9H), 1.6(s,9H), 6.9(d, 2H), 6.9(d,1H), 7.1(dt,2H), 7.2(d,1H), 7.5(d t,2H), 7.6(dd,1H), 7.9(dd,1H), 8.0~8.2(m,19 H), 8.3(s,3H).

[0365] Synthesis Example (9): Compound (2-174) "2-(pyren-1-yl)naphtho[2,3-b Synthesis of benzofuran [ka]

[0366] Under a nitrogen atmosphere, 1-pyreneboronic acid (1.0 g) was added to the solution. 2-Bromobenzo[b]naphtho[2,3-d]furan ( 1.1g), tetrakis(triphenylphosphine)palladium ( 0.09g), potassium phosphate (1.7g), xylene (15mL), t-butyl alcohol A flask was charged with alcohol (5 mL) and water (3 mL), and the mixture was heated and stirred at reflux temperature for 2 hours. After the reaction, the reaction mixture was cooled, and water and ethyl acetate were added to the reaction mixture, and the mixture was stirred. The precipitate was then filtered and The crude product was washed with ethanol. After drying the precipitate, it was dissolved in chlorobenzene by heating and then added to silica gel. By filtering through a gel short-path column (eluent: toluene) and concentrating the eluate, The resulting solid was further purified by chlorobenzene / reprecipitation. The resulting extract was purified to give compound (2-174) (1.0 g). [ka]

[0367] The structure of the obtained compound (2-174) was confirmed by NMR measurement. 1 H-NMR(CDCl3):7.5(m,1H), 7.5~7.6(m,1H), 7. 7~7.8(m,2H), 8.0~8.3(m,13H), 8.5(s,1H).

[0368] Synthesis Example (10): Compound (2-356) "2-(pyren-1-yl)dibenzo[g,p Synthesis of chrysene [ka]

[0369] 3-Bromo-3-isopropyl ether (3-bromo-3-isopropyl ether) synthesized under a nitrogen atmosphere by the method described in Japanese Patent Publication No. 2011-006397 Bromodibenzo[g,p]chrysene (14g) and tetrahydrofuran (THF, 200 mL) was placed in a flask, and after making a homogeneous solution, it was cooled to -78°C in a dry ice-acetone bath. Then, 1.6 M n-butyllithium / hexane solution (28 mL) was added dropwise. After stirring for 0.5 hours, 2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-Dioxaborolane (12.8 g) was added. After stirring at the same temperature for 3 hours, the temperature was raised. The reaction was stopped by adding dilute hydrochloric acid. Toluene was added, and after extraction, the organic layer was concentrated. The crude product was purified with a silica gel column (eluent: toluene / heptane = 7 / 3 (volume ratio)). By this purification, intermediate K was obtained (11.5 g). [ka]

[0370] Under a nitrogen atmosphere, intermediate K (1.0 g), 1-bromopyrene (0.59 g), and palladium Bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropa as a catalyst Radium (16 mg), potassium phosphate (0.9 g), xylene (10 mL), t-butyl Add alcohol (3 mL) and water (2 mL) to the flask and stir at reflux for 2 hours. After the reaction, the reaction mixture was cooled, water and ethyl acetate were added, and the mixture was stirred. The crude product was purified using a silica gel short-path column (eluent: toluene). After that, it was purified by reprecipitation with toluene / heptane. The obtained solid was dried and then purified by sublimation. Compound (2-356) was obtained (0.7 g). [ka]

[0371] The structure of the obtained compound (2-356) was confirmed by NMR measurement. 1 H-NMR(CDCl3):7.7(m,6H), 7.9(dd,1H)8.0~8. 1(m,2H), 8.1~8.3(m,5H), 8.3(d,1H), 8.4(d,1H ), 8.7~8.8(m,5H), 8.9(m,1H), 8.9(d,1H), 9.0( d,1H).

[0372] Synthesis Example (11): Compound (2-359) "1,6-bis(naphtho[2,3-b]benzo Furan-2-yl)-3a 1 ,5a 1 Synthesis of α-dihydropyrene [ka]

[0373] 2 synthesized under a nitrogen atmosphere by the method described in WO 2014 / 141725 -Bromobenzo[b]naphtho[2,3-d]furan (10.8 g) and tetrahydrofuran (THF, 200 mL) was placed in a flask and cooled to -78°C in a dry ice-acetone bath. To this was added dropwise 1.6 M n-butyllithium / heptane solution (25 mL). After stirring at room temperature for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-Dioxaborolane (10 g) was added. After stirring at the same temperature for 2 hours, the temperature was raised and The reaction was stopped by adding dilute hydrochloric acid. Toluene was added, and after extraction, the organic layer was concentrated. The crude product was purified using a silica gel column (eluent: toluene / heptane = 7 / 3 (volume ratio)). Intermediate L was obtained by this procedure (9.2 g). [ka]

[0374] Under a nitrogen atmosphere, 1,6-dibromopyrene (1.0 g), intermediate L (2.0 g), and paradiphenyl ether were Bis(di-t-butyl(4-dimethylaminophenyl)phosphine) dichloromethane as a sulphur catalyst Palladium (20 mg), potassium phosphate (2.4 g), xylene (15 mL), t- Butyl alcohol (3 mL) and water (2 mL) were placed in a flask and stirred at reflux temperature for 2 hours. After the reaction, the reaction mixture was cooled, and water and ethyl acetate were added and stirred. The crude product was purified using a silica gel short-path column (eluent: toluene). After that, it was washed with hot chlorobenzene and purified. The obtained solid was dried and then purified by sublimation. Compound (2-359) was obtained (1.6 g). [ka]

[0375] The obtained compound (2-359) was confirmed by LC-MS measurement. MS(ACPI) m / z=635(M+H)

[0376] By appropriately changing the raw material compounds, the compounds used in the present invention can be prepared in a manner similar to the synthesis examples described above. Other compounds for use can be synthesized.

[0377] In order to explain the present invention in more detail, the following describes the organic EL device using the compound of the present invention. Examples are given below, but the present invention is not limited to these.

[0378] Organic EL devices according to Examples 1 to 12 and Comparative Example 1 were fabricated, and each had a luminance of 1000 cd / m 2 Measure the voltage (V), emission wavelength (nm), and external quantum efficiency (%), which are the characteristics of light emission. did.

[0379] The quantum efficiency of a light-emitting element is divided into internal quantum efficiency and external quantum efficiency. The internal quantum efficiency is External energy injected into the light-emitting layer of a light-emitting device as electrons (or holes) is converted purely into photons. On the other hand, the external quantum efficiency indicates the rate at which these photons are converted outside the light-emitting element. The amount of photons emitted from the light-emitting layer is calculated based on the amount of photons emitted from the light-emitting element. Because the light is absorbed or reflected inside the , the external quantum efficiency is lower than the internal quantum efficiency.

[0380] The external quantum efficiency was measured using the Advantest R6 voltage / current generator. 144, the brightness of the element is 1000 cd / m 2 The device emits light by applying a voltage that Using a TOPCON SR-3AR spectroradiometer, the The spectral radiance in the visible light region was measured from the light source. The spectral radiance value of each wavelength component is divided by the wavelength energy and multiplied by π. Next, the number of photons is integrated over the entire wavelength range observed, and the number of photons emitted from the element is calculated. The applied current value divided by the elementary charge is the total number of photons injected into the element. The photon number is calculated by dividing the total number of photons emitted from the element by the number of carriers injected into the element. is the external quantum efficiency.

[0381] The material configuration of each layer in the organic EL devices according to Examples 1 to 12 and Comparative Example 1 that were fabricated; The EL characteristic data are shown in Table 1 below.

[0382] [Table 1]

[0383] In Table 1, "HI" stands for N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-phen (9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamino "HAT-CN" is a compound of 1,4,5,8,9,12-hexaazatriphenylene. and "HT-1" is N-([1,1'-biphenyl]-4-yl -9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]phenyl (nyl)-9H-fluoren-2-amine[1,1'-biphenyl]-4-amine, "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl) -[1,1':4',1"-terphenyl]-4-amine, and "HT-3" is N-( [1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluorene- 2-yl)-9,9'-spirobi[fluorene]-4-amine, and "ET-1" is 4 ,6,8,10-tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]f enoxaborinin, and "ET-2" is 3,3'-((2-phenylanthracene-9 ,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine) ET-3 is 9-(7-(dimesitylboryl)-9,9-dimethyl-9H-fluorene- 2-yl)-3,6-dimethyl-9H-carbazole, "ET-4" is 4-(3-( 4-(10-phenylanthracen-9-yl)naphthalen-1-yl)phenyl)pyridine Comparative compound A is 9-([1,2'-binaphthalen]-7-yl)-10-furan. The chemical structure is shown below along with "Liq."

[0384] [ka]

[0385] Example 1 <Device in which the host is compound (2-1) and the dopant is compound (1-139)> ITO film formed by sputtering to a thickness of 180 nm was polished to 150 nm. Transparent support for a 26mm x 28mm x 0.7mm glass substrate (manufactured by Optoscience Co., Ltd.) This transparent support substrate was placed on a substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.). Fixed, HI, HAT-CN, HT-1, HT-2, Compound (2-1), Compound (1-1 39), ET-1 and ET-2 were placed in molybdenum evaporation boats, Liq, An aluminum nitride evaporation boat containing magnesium and silver was installed.

[0386] The following layers were formed in order on the ITO film of the transparent support substrate. -4 Pa The pressure was reduced to 100 psi, and HI was first heated and evaporated to a thickness of 40 nm. N was heated and evaporated to a thickness of 5 nm, and then HT-1 was heated to a thickness of 15 nm. Next, HT-2 was heated and evaporated to a thickness of 10 nm. Next, a hole injection / transport layer was formed by dissolving the compound (2-1) and the compound (1-139). At the same time, the compound (2-1) was heated and evaporated to a thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the weight ratio of the compound (1-139) to the compound (1-139) was approximately 98:2. Next, ET-1 was heated and evaporated to a thickness of 5 nm to form an electron transport layer 1. ET-2 and Liq were simultaneously heated and evaporated to a thickness of 25 nm to form an electron transport layer 2. The deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50:50. The deposition rate for each layer was 0.01 to 1 nm / sec. After that, the liquid was heated to a thickness of 1 The deposition rate was 0.01 to 0.1 nm / sec to obtain a thickness of 1 nm. and silver are simultaneously heated and evaporated to a thickness of 100 nm to form a cathode. At this time, the ratio of magnesium to silver atoms was 10:1, and the thickness was 0.1 nm to 1. The deposition rate was adjusted between 0 nm / sec and 100 nm / sec.

[0387] A DC voltage was applied between the ITO electrode as the anode and the magnesium / silver electrode as the cathode, and the d / m 2 When the light-emitting characteristics were measured, blue light with a wavelength of 462 nm was obtained. The driving voltage was 4.1 V and the external quantum efficiency was 6.7%.

[0388] <Examples 2 to 12 and Comparative Example 1> The materials shown in Table 1 were selected as the materials for each layer, and an organic EL device was fabricated in the same manner as in Example 1. In Example 11, ET-1 and LIq were co-deposited to a thickness of 30 nm to form a single layer. The organic EL characteristics were evaluated in the same manner as in Example 1. (Table 1) All the devices emitted blue light.

[0389] As described above, some of the compounds according to the present invention are evaluated as materials for the light-emitting layer of organic EL devices. However, other compounds that have not been evaluated have the same basic structure, These compounds have similar structures as a whole, and those skilled in the art would recognize that they are similarly excellent compounds for use in an emitting layer. You can understand that it is a material. [Industrial Applicability]

[0390] According to a preferred embodiment of the present invention, a polycyclic aromatic compound represented by formula (1) and a compound thereof and a pyrene-based compound represented by formula (2) that can provide optimal light-emitting properties. By using a combination of these materials for the light-emitting layer to produce an organic EL element, In particular, an organic EL element exhibiting excellent luminous efficiency and well-balanced performance can be provided. do. [Explanation of symbols]

[0391] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A pyrene-based compound represented by the following general formula (2): 【Chemical 1】 In the above formula (2), s pyrene moieties and p Ar moieties are bonded to each other, and the Ar moieties are bonded to any of the positions marked with * on the pyrene moieties; At least one hydrogen atom in the pyrene moiety may be independently substituted with an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 4 carbon atoms; Ar's are each independently a group represented by any one of the following general formulas (Ar-1-2) to (Ar-1-10) and (Ar-1-12): 【Chemistry 4】 In the above formulas (Ar-1-2) to (Ar-1-10) and (Ar-1-12), R is an aryl having 6 to 10 carbon atoms, and R may be bonded to each other to form a spiro-bonded fluorene ring; In the above formula (2), the pyrene moiety is bonded to any position of the benzene ring represented by the above formulas (Ar-1-2) to (Ar-1-10) and (Ar-1-12), s and p each independently represent an integer of 1 or 2, and s and p cannot simultaneously represent 2; when s is 2, the two pyrene moieties may be structurally identical or different, including substituents; when p is 2, the two Ar moieties may be structurally identical or different, including substituents; and At least one hydrogen atom in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium.

2. The pyrene compound according to claim 1, wherein Ar is each independently a group represented by any one of the following general formulas (Ar-1-2) to (Ar-1-5), (Ar-1-7) to (Ar-1-10), and (Ar-1-12): 【Chemistry 5】

3. 2. The pyrene-based compound according to claim 1, wherein Ar is each independently a group represented by any one of the following general formulas (Ar-1-2) to (Ar-1-4) and (Ar-1-12): 【Chemistry 6】

4. The pyrene-based compound according to claim 1, which is represented by any one of the following structural formulas: 【Chemistry 7】

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