TW202017225A - Organic electroluminescent element - Google Patents

Abstract

Provided is an organic electroluminescent element having a pair of electrodes comprising a positive electrode and a negative electrode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains an anthracene compound and at least one of the polycyclic aromatic compounds represented by general formula (1) and multimers thereof. The organic electroluminescent element has optimum light emission characteristics. (In formula (1), rings A to C are aryl rings, etc., Y1 is B (boron), and X1 and X2 are > O or > N-R).

Description

Organic electric field light-emitting element, display device and lighting device

The invention relates to an organic electric field light-emitting element, a display device and a lighting device using the same.

Previously, display devices using light-emitting elements that emit light in an electric field have received various studies because they can achieve power saving or thinning. Furthermore, organic electric-field light-emitting elements containing organic materials (hereinafter, also referred to as "organic EL (Electroluminescence) elements" ) Actively researched because it is easy to lighten or enlarge. In particular, the development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and the combination of various materials that have the best light-emitting properties have been actively studied, regardless of polymer compounds and low-molecular compounds. .

The organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and including an organic compound. Among the layers containing organic compounds, there are a light-emitting layer, or a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (International Publication No. 2004/061047). In addition, as the hole transport material, for example, triphenylamine-based compounds have been developed (Japanese Patent Laid-Open No. 2001-172232). In addition, as an electron transport material, for example, an anthracene-based compound has been developed (Japanese Patent Laid-Open No. 2005-170911).

In addition, in recent years, there have been reported materials that improve triphenylamine derivatives (International Publication No. 2012/118164). This material is the following material, which is characterized by reference to the practical N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4, 4'-Diamine (TPD) connects the aromatic rings constituting triphenylamine to each other, thereby improving its planarity. This document evaluates, for example, the charge transport characteristics of NO-linked compounds (Compound 1 on page 63), but does not describe methods for producing materials other than NO-linked compounds. In addition, if the linked elements are different, the overall compound The electronic states are different, so the properties obtained from materials other than NO-linked compounds are still unknown. Examples of such compounds can also be found in other documents (International Publication No. 2011/107186). For example, a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and thus is useful as a blue light-emitting layer material. [Prior Art Literature] [Patent Literature]

[Patent Document 1] International Publication No. 2004/061047 [Patent Document 2] Japanese Patent Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2012/118164 [Patent Document 5] International Publication No. 2011/107186

[Problems to be solved by the invention] As described above, various materials have been developed as materials used in organic EL elements, but in order to increase the options for materials for organic EL elements, the development of materials containing compounds different from those in the past has been promoted, and an organic material with optimal light-emitting characteristics is desired Electric field light emitting element. [Means to solve the problem]

The inventors of the present invention conducted intensive studies to solve the above-mentioned problems, and found that an organic EL element can be obtained by arranging a light-emitting layer between a pair of electrodes to constitute an excellent organic EL element, thereby completing the present invention. The light-emitting layer contains at least one of polycyclic aromatic compounds and their polymers (hereinafter, also simply referred to as "polycyclic aromatic compounds") in which multiple aromatic rings are connected by boron atoms, oxygen atoms, or nitrogen atoms , And anthracene compounds.

In addition, in this specification, the chemical structure or substituent is sometimes indicated by the carbon number, and when the chemical structure is substituted with a substituent, or when the substituent is further substituted with a substituent, the carbon number refers to the chemical The carbon number of each structure or substituent does not mean the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, the so-called "substituent B substituted with carbon number X substituent A and carbon number Y" means that "substituent A with carbon number X" is substituted on "substituent B with carbon number Y". Y is not the total carbon number of substituent A and substituent B. In addition, for example, the so-called "substituent B of carbon number Y substituted with substituent A" means that "(substituent A without carbon number)" is substituted on "substituent B of carbon number Y" Y is not the total carbon number of substituent A and substituent B.

（所述式（1）中， A環、B環及C環分別獨立地為芳基環或雜芳基環，該些環中的至少一個氫可被取代， Y¹ 為B， X¹ 及X² 分別獨立地為＞O或＞N-R，所述＞N-R的R為可被取代的芳基、可被取代的雜芳基、可被取代的烷基或可被取代的環烷基，另外，所述＞N-R的R可經由連結基或單鍵而與所述A環、B環及C環中的至少一個鍵結，而且， 式（1）所表示的化合物或結構中的至少一個氫可由鹵素或氘取代）Item 1. An organic electric field light-emitting device having: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, and the light-emitting layer includes a plurality represented by the following general formula (1) At least one polymer of a ring aromatic compound and a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1), and an anthracene compound. [Chem 13]

(In the above formula (1), ring A, ring B and ring C are each independently an aryl ring or heteroaryl ring, at least one hydrogen in these rings may be substituted, Y ¹ is B, X ¹ and X ^{2 is} independently >O or >NR, and R of >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted, or a cycloalkyl group which may be substituted, in addition , The R> NR may be bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond, and at least one hydrogen in the compound or structure represented by formula (1) Can be replaced by halogen or deuterium)

Item 2. The organic electroluminescent element according to Item 1, wherein in the formula (1), the A ring, the B ring, and the C ring are each independently an aryl ring or a heteroaryl ring, and at least A hydrogen can be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamine, substituted or unsubstituted diheteroarylamine , Substituted or unsubstituted arylheteroarylamine, substituted or unsubstituted diarylboryl (two aryl groups can be bonded via a single bond or linking group), substituted or unsubstituted substituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted or a substituted aryloxy group. in addition, these rings comprising Y ¹ and having , The condensed bicyclic structure at the center of the formula of X ¹ and X ² shares a bonded 5-member ring or 6-member ring, Y ¹ is B, X ¹ and X ² are independently >O or >NR, the >R of NR is an aryl group that can be substituted by an alkyl group, a cycloalkyl group, a diarylamine group, or a diarylboryl group (two aryl groups can be bonded via a single bond or a linking group), an alkyl group, a ring Heteroaryl, alkyl or cycloalkyl substituted with alkyl, diarylamino, diarylboryl (two aryl groups can be bonded via a single bond or a linking group), in addition, R >NR It can be bonded to at least one of the A ring, B ring, and C ring via a linking group or a single bond selected from -O-, -S-, and -C(-R) ₂ -, the -C R of (-R) ₂ -is hydrogen, alkyl or cycloalkyl, and at least one hydrogen in the compound or structure represented by formula (1) may be substituted by halogen or deuterium, and, in the case of a polymer, is Dimer or trimer having 2 or 3 structures represented by formula (1).

（所述式（2）中， R¹ 、R² 、R³ 、R⁴ 、R⁵ 、R⁶ 、R⁷ 、R⁸ 、R⁹ 、R¹⁰ 及R¹¹ 分別獨立地為氫、芳基、雜芳基、二芳基胺基、二雜芳基胺基、芳基雜芳基胺基、二芳基硼基（兩個芳基可經由單鍵或連結基而鍵結）、烷基、環烷基、烷氧基或芳氧基，該些中的至少一個氫可由芳基、雜芳基、烷基或環烷基取代，另外，R¹ ～R¹¹ 中鄰接的基團彼此可鍵結並與a環、b環或c環一同形成芳基環或雜芳基環，所形成的環中的至少一個氫可由芳基、雜芳基、二芳基胺基、二雜芳基胺基、芳基雜芳基胺基、二芳基硼基（兩個芳基可經由單鍵或連結基而鍵結）、烷基、環烷基、烷氧基或芳氧基取代，該些中的至少一個氫可由芳基、雜芳基、烷基或環烷基取代， Y¹ 為B， X¹ 及X² 分別獨立地為＞O或＞N-R，所述＞N-R的R為可由烷基、環烷基、二芳基胺基或二芳基硼基（兩個芳基可經由單鍵或連結基而鍵結）取代的碳數6～12的芳基、可由烷基、環烷基、二芳基胺基或二芳基硼基（兩個芳基可經由單鍵或連結基而鍵結）取代的碳數2～15的雜芳基、碳數1～6的烷基或碳數3～14的環烷基，另外，所述＞N-R的R可經由選自-O-、-S-及-C(-R)₂ -中的連結基或單鍵而與所述a環、b環及c環中的至少一個鍵結，所述-C(-R)₂ -的R為碳數1～6的烷基或碳數3～14的環烷基， 式（2）所表示的化合物中的至少一個氫可由鹵素或氘取代）Item 3. The organic electroluminescent device according to Item 1, wherein the polycyclic aromatic compound and its multimer are polycyclic aromatic compounds represented by the following general formula (2) and have a plurality of A polymer of a polycyclic aromatic compound of the structure represented by formula (2). [化14]

(In the above formula (2), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups can be bonded via a single bond or linking group), alkyl, Cycloalkyl, alkoxy or aryloxy, at least one of which may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, and the adjacent groups in R ¹ to R ¹¹ may be bonded to each other Combined with a ring, b ring or c ring to form an aryl ring or heteroaryl ring, at least one hydrogen in the formed ring may be aryl, heteroaryl, diarylamino, diheteroarylamine Group, arylheteroarylamine group, diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, these At least one hydrogen in may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, Y ¹ is B, X ¹ and X ² are independently >O or >NR, and the R of >NR may be alkyl Group, cycloalkyl group, diarylamine group or diarylboryl group (two aryl groups may be bonded via a single bond or a linking group) substituted aryl group having 6 to 12 carbon atoms, which may be an alkyl group or a cycloalkane group Group, diarylamine group or diarylboryl group (two aryl groups may be bonded through a single bond or a linking group) substituted C 2-15 heteroaryl group, C 1-6 alkyl group or A cycloalkyl group having 3 to 14 carbon atoms, and the R>NR may be linked to the a through a linking group or a single bond selected from -O-, -S-, and -C(-R) _2- At least one of the ring, the ring b, and the ring c is bonded, and R in the -C(-R) ₂ -is a C 1-6 alkyl group or a C 3-14 cycloalkyl group, formula (2) At least one hydrogen in the represented compound may be replaced by halogen or deuterium)

Item 4. The organic electroluminescent element according to Item 3, wherein in the formula (2), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and a diarylamine group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms) ) Or a diarylboryl group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms, and two aryl groups may be bonded via a single bond or a linking group), and in addition, adjacent groups in R ¹ to R ¹¹ The groups may be bonded to each other and form a 9-16 aryl ring or a 6-15 heteroaryl ring together with a ring, b ring or c ring, at least one hydrogen in the formed ring may be diaryl Amine group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms) or diarylboron group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms, two aryl groups may be through a single bond or Substituted by a linking group, X ¹ and X ² are independently >O or >NR (wherein R of the NR is selected from alkyl, cycloalkyl, diarylamino or diarylboryl) (Two aryl groups may be bonded via a single bond or a linking group) substituted aryl groups having 6 to 10 carbon atoms), and at least one hydrogen in the compound represented by formula (2) may be substituted with halogen or deuterium.

Item 5. The organic electroluminescence element according to any one of items 1 to 4, wherein the polycyclic aromatic compound and its polymer have at least one deuterium.

Item 6. Item 5. The organic electroluminescence device according to item 5, wherein the total amount of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule in the polycyclic aromatic compound and its polymer is 100% The proportion of deuterium is 10% to 100%.

Item 7. Item 5. The organic electroluminescence device according to item 5, wherein the total amount of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule in the polycyclic aromatic compound and its polymer is 100% , The proportion of deuterium is 100%.

（所述各結構式中的「Me」表示甲基，「tBu」表示第三丁基，「tAm」表示第三戊基，「D」表示氘）Item 8. The organic electroluminescence device according to Item 1, wherein the polycyclic aromatic compound and its multimer are compounds having a structure represented by any of the following. [化15]

(“Me” in the above-mentioned structural formulas represents methyl, “tBu” represents third butyl, “tAm” represents third pentyl, and “D” represents deuterium)

（所述式（3）中， L為單鍵、碳數6～18的伸芳基、或碳數1～10的伸烷基，所述伸芳基及所述伸烷基中的至少一個氫可由芳基、雜芳基、烷基或環烷基取代， Ar⁴ 分別獨立地為氫、苯基、聯苯基、聯三苯基、萘基、由選自碳數1～4的烷基及碳數5～10的環烷基中的基團取代的矽烷基， n為0或1， X分別獨立地為所述式（3-X1）、式（3-X2）或式（3-X3）所表示的基團， 所述式（3-X1）、式（3-X2）或式（3-X3）中的*表示與式（3）中的蒽環的9位或10位的鍵結位置， Ar¹ 及Ar² 分別獨立地為氫、苯基、聯苯基、聯三苯基、聯四苯基、萘基、菲基、芴基、苯並芴基、䓛基、三伸苯基、芘基、咔唑基、苯並咔唑基、或苯基取代咔唑基、苯並呋喃基、二苯並呋喃基、萘並苯並呋喃基、苯並噻吩基、二苯並噻吩基、或萘並苯並噻吩基，該些基團中的至少一個氫可進而由碳數1～6的烷基、碳數3～14的環烷基、苯基、或萘基取代， Ar³ 為苯基、聯苯基、聯三苯基、聯四苯基、萘基、菲基、芴基、苯並芴基、䓛基、三伸苯基、芘基、咔唑基、苯並咔唑基、苯基取代咔唑基、苯並呋喃基、二苯並呋喃基、萘並苯並呋喃基、苯並噻吩基、二苯並噻吩基、或萘並苯並噻吩基，該些基團中的至少一個氫可進而由碳數1～6的烷基、碳數3～14的環烷基、經烷基或環烷基取代或未經取代的苯基、經烷基或環烷基取代或未經取代的聯苯基、經烷基或環烷基取代或未經取代的聯三苯基、經烷基或環烷基取代或未經取代的萘基、經烷基或環烷基取代或未經取代的菲基、經烷基或環烷基取代或未經取代的芴基、經烷基或環烷基取代或未經取代的苯並芴基、經烷基或環烷基取代或未經取代的䓛基、經烷基或環烷基取代或未經取代的三伸苯基、經烷基或環烷基取代或未經取代的芘基、經烷基或環烷基取代或未經取代的二苯並呋喃基、經烷基或環烷基取代或未經取代的二苯並噻吩基、經烷基或環烷基取代或未經取代的咔唑基、苯基取代咔唑基、經烷基或環烷基取代或未經取代的苯並呋喃基、經烷基或環烷基取代或未經取代的萘並苯並呋喃基、經烷基或環烷基取代或未經取代的苯並噻吩基、或者經烷基或環烷基取代或未經取代的萘並苯並噻吩基取代，而且， 式（3）所表示的化合物中的至少一個氫可由氘取代）Item 9. The organic electroluminescence element according to any one of Item 1 to Item 8, wherein the anthracene-based compound is a compound represented by the following general formula (3). [Chem 16]

(In the formula (3), L is a single bond, an aryl group having 6 to 18 carbon atoms, or an alkylene group having 1 to 10 carbon atoms, at least one of the aryl group and the alkylene group Hydrogen may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, Ar ^{4 is} independently hydrogen, phenyl, biphenyl, biphenyl, naphthyl, selected from the group consisting of C 1-4 alkyl Silyl group substituted by a group and a cycloalkyl group having 5 to 10 carbon atoms, n is 0 or 1, X is independently the above formula (3-X1), formula (3-X2) or formula (3 -X3), the * in the formula (3-X1), formula (3-X2) or formula (3-X3) represents the 9th or 10th position of the anthracene ring in the formula (3) The bonding position of Ar ¹ and Ar ² are independently hydrogen, phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzyl, Triphenylene, pyrenyl, carbazolyl, benzocarbazolyl, or phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, di Benzothienyl, or naphthobenzothienyl, at least one hydrogen in these groups can be further composed of C 1-6 alkyl, C 3-14 cycloalkyl, phenyl, or naphthyl Substitution, Ar ³ is phenyl, biphenyl, triphenylphenyl, tetratetraphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzyl, triphenylene, pyrenyl, carbazolyl , Benzocarbazolyl, phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, or naphthobenzothienyl , At least one hydrogen in these groups may be further substituted by C 1-6 alkyl, C 3-14 cycloalkyl, substituted or unsubstituted phenyl, alkyl Substituted or unsubstituted biphenyl, substituted or unsubstituted biphenyl substituted with alkyl or cycloalkyl, substituted or unsubstituted naphthyl substituted with alkyl or cycloalkyl, Alkyl or cycloalkyl substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl substituted with alkyl or cycloalkyl, alkyl or cycloalkyl substituted or unsubstituted benzofluorenyl, substituted Alkyl or cycloalkyl substituted or unsubstituted benzyl, tri-phenylene substituted or unsubstituted by alkyl or cycloalkyl, substituted or unsubstituted pyrenyl substituted by alkyl or cycloalkyl, Alkyl or cycloalkyl substituted or unsubstituted dibenzofuranyl, substituted with alkyl or cycloalkyl or unsubstituted dibenzothienyl, substituted with alkyl or cycloalkyl or unsubstituted Carbazolyl, phenyl substituted carbazolyl, alkyl or cycloalkyl substituted or unsubstituted benzofuranyl, alkyl or cycloalkyl substituted or unsubstituted naphthobenzofuranyl, Alkyl or cycloalkyl substituted or unsubstituted benzothienyl, or substituted by alkyl or cycloalkyl or unsubstituted naphthobenzothienyl, and, in the compound represented by formula (3) At least one hydrogen can be replaced by deuterium)

（所述式（3-X3-1）及式（3-X3-2）中， *表示與式（3）中的蒽環的9位或10位的鍵結位置， Ar⁵ 分別獨立地為氫、苯基、聯苯基、聯三苯基、萘基、菲基、芴基、䓛基、三伸苯基、芘基、二苯並呋喃基、二苯並噻吩基、咔唑基、苯基取代咔唑基、苯並呋喃基、萘並苯並呋喃基、苯並噻吩基、或萘並苯並噻吩基，該些的至少一個氫可進而由碳數1～6的烷基或碳數3～14的環烷基取代）Item 10. The organic electroluminescent device according to Item 9, wherein the group represented by the formula (3-X3) is a phenyl group, a phenanthrenyl group, and a group represented by the following formula (3-X3-1) Or a group represented by the following formula (3-X3-2), these may be further substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. [化17]

(In the above formula (3-X3-1) and formula (3-X3-2), * represents the bonding position to the 9th or 10th position of the anthracene ring in the formula (3), and Ar ^{5 is} independently Hydrogen, phenyl, biphenyl, triphenylphenyl, naphthyl, phenanthrenyl, fluorenyl, benzyl, triphenylene, pyrenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, Phenyl substituted carbazolyl, benzofuranyl, naphthobenzofuranyl, benzothienyl, or naphthobenzothienyl, at least one of these hydrogens can be further substituted by C 1-6 alkyl or (C3-C14 cycloalkyl substitution)

式（3-1-X）中， ϕ為與苯基鍵結的可由Ar¹ 及R取代的苯基、萘基、菲基或三伸苯基， Ar為可被取代的芳基，n為1或2，n為1時，Ar鍵結於x位及y位中的任一者，n為2時，Ar鍵結於x位及y位兩者，各自的結構可相同亦可不同， Ar¹ 為可被取代的芳基，m為0至ϕ上可取代的最大整數，m為2以上時，Ar¹ 的結構分別可相同亦可不同， R分別獨立地為烷基或環烷基，a為0～5的整數，b為0～3的整數且b+n為4以下，c為0至ϕ上可取代的最大整數且c+m為ϕ上可取代的最大整數以下，d為0～4的整數，而且， 式（3-1-X）所表示的化合物中的至少一個氫可由氘取代。Item 11. The organic electroluminescence element according to any one of Item 1 to Item 10, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X). [Chemical 18]

In formula (3-1-X), ϕ is a phenyl group, naphthyl group, phenanthryl group, or triphenylene group which may be substituted with Ar ¹ and R, and Ar is an aryl group which may be substituted, and n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or different, Ar ¹ is an aryl group that may be substituted, m is the largest integer that can be substituted from 0 to ϕ, and when m is 2 or more, the structure of Ar ¹ may be the same or different, and R is independently an alkyl group or a cycloalkyl group , A is an integer from 0 to 5, b is an integer from 0 to 3 and b+n is 4 or less, c is the largest integer replaceable from 0 to ϕ and c+m is the largest integer replaceable from ϕ, d It is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X) may be substituted with deuterium.

式（3-1-X1）中， Ar為可被取代的芳基，n為1或2，n為1時，Ar鍵結於x位及y位中的任一者，n為2時，Ar鍵結於x位及y位兩者，各自的結構可相同亦可不同， Ar¹ 為可被取代的芳基，m為0～5的整數，m為2以上時，Ar¹ 的結構分別可相同亦可不同， R分別獨立地為烷基或環烷基，a為0～5的整數，b為0～3的整數且b+n為4以下，c為0～5的整數且c+m為5以下，d為0～4的整數，而且， 式（3-1-X1）所表示的化合物中的至少一個氫可由氘取代。Item 12. The organic electroluminescence device according to Item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X1). [Chem 19]

In formula (3-1-X1), Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, and when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or different. Ar ¹ is an aryl group that may be substituted, m is an integer of 0 to 5, and when m is 2 or more, the structure of Ar ¹ is May be the same or different, R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 5 and c +m is 5 or less, d is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X1) may be substituted with deuterium.

式（3-1-X2）中， 式（3-1-X2）中所表示的萘環為與苯基鍵結的1-萘基或2-萘基， Ar為可被取代的芳基，n為1或2，n為1時，Ar鍵結於x位及y位中的任一者，n為2時，Ar鍵結於x位及y位兩者，各自的結構可相同亦可不同， Ar¹ 為可被取代的芳基，m為0～7的整數，m為2以上時，Ar¹ 的結構分別可相同亦可不同， R分別獨立地為烷基或環烷基，a為0～5的整數，b為0～3的整數且b+n為4以下，c為0～7的整數且c+m為7以下，d為0～4的整數，而且， 式（3-1-X2）所表示的化合物中的至少一個氫可由氘取代。Item 13. The organic electroluminescence device according to Item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X2). [化20]

In formula (3-1-X2), the naphthalene ring represented in formula (3-1-X2) is a 1-naphthyl group or a 2-naphthyl group bonded to a phenyl group, Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or Differently, Ar ¹ is an aryl group which may be substituted, m is an integer from 0 to 7, when m is 2 or more, the structure of Ar ¹ may be the same or different, and R is independently an alkyl group or a cycloalkyl group, a Is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 7 and c+m is 7 or less, d is an integer of 0 to 4, and, formula (3 -1-X2) At least one hydrogen in the compound represented by can be replaced by deuterium.

式（3-1-X3）中， 式（3-1-X3）中所表示的菲環為與苯基鍵結的1-菲基、2-菲基、3-菲基、4-菲基或9-菲基， Ar為可被取代的芳基，n為1或2，n為1時，Ar鍵結於x位及y位中的任一者，n為2時，Ar鍵結於x位及y位兩者，各自的結構可相同亦可不同， Ar¹ 為可被取代的芳基，m為0～9的整數，m為2以上時，Ar¹ 的結構分別可相同亦可不同， R分別獨立地為烷基或環烷基，a為0～5的整數，b為0～3的整數且b+n為4以下，c為0～9的整數且c+m為9以下，d為0～4的整數，而且， 式（3-1-X3）所表示的化合物中的至少一個氫可由氘取代。Item 14. The organic electroluminescence device according to Item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X3). [化21]

In formula (3-1-X3), the phenanthrene ring represented in formula (3-1-X3) is 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl bonded to phenyl Or 9-phenanthryl, Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and y position, when n is 2, Ar is bonded to The structure of each of the x position and the y position may be the same or different. Ar ¹ is an aryl group which may be substituted, m is an integer of 0-9, and when m is 2 or more, the structure of Ar ¹ may be the same or different Differently, R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 9 and c+m is 9 Hereinafter, d is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X3) may be substituted with deuterium.

式（3-1-X4）中， 式（3-1-X4）中所表示的三伸苯環為與苯基鍵結的1-三伸苯基或2-三伸苯基， Ar為可被取代的芳基，n為1或2，n為1時，Ar鍵結於x位及y位中的任一者，n為2時，Ar鍵結於x位及y位兩者，各自的結構可相同亦可不同， Ar¹ 為可被取代的芳基，m為0～11的整數，m為2以上時，Ar¹ 的結構分別可相同亦可不同， R分別獨立地為烷基或環烷基，a為0～5的整數，b為0～3的整數且b+n為4以下，c為0～11的整數且c+m為11以下，d為0～4的整數，而且， 式（3-1-X4）所表示的化合物中的至少一個氫可由氘取代。Item 15. The organic electroluminescence device according to Item 11, wherein the anthracene-based compound is a compound represented by the following general formula (3-1-X4). [化22]

In the formula (3-1-X4), the triphenylene ring represented in the formula (3-1-X4) is 1-triphenylene or 2-triphenylene bonded to phenyl, Ar is Substituted aryl, n is 1 or 2, when n is 1, Ar is bonded to either of the x position and y position, when n is 2, Ar is bonded to both the x position and y position, each The structures of may be the same or different, Ar ¹ is an aryl group which may be substituted, m is an integer of 0 to 11, when m is 2 or more, the structures of Ar ¹ may be the same or different, and R is independently an alkyl group Or cycloalkyl, a is an integer from 0 to 5, b is an integer from 0 to 3 and b+n is 4 or less, c is an integer from 0 to 11 and c+m is 11 or less, and d is an integer from 0 to 4 And, at least one hydrogen in the compound represented by the formula (3-1-X4) may be replaced by deuterium.

Item 16. The organic electric field light-emitting element according to any one of items 1 to 15, wherein the anthracene-based compound has at least one deuterium.

Item 17. Item 16. The organic electroluminescence device according to item 16, wherein in the anthracene-based compound, the proportion of deuterium relative to 100% of the total number of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule is 10%～100%.

Item 18. Item 16. The organic electroluminescence device according to item 16, wherein in the anthracene-based compound, the proportion of deuterium relative to 100% of the total number of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule is 100%.

（所述各結構式中的「D」表示氘）Item 19. The organic electroluminescence device according to Item 16, wherein the anthracene-based compound is a compound represented by any one of the following formulas. [化23]

("D" in the above structural formulas represents deuterium)

Item 20. The organic electroluminescence device according to any one of Item 1 to Item 15, wherein the anthracene-based compound is a compound represented by any one of the following. [化24]

Item 21. The organic electric field light-emitting element according to any one of items 1 to 20, wherein in the light-emitting layer, the polycyclic aromatic compound represented by the general formula (1) and a polymer thereof and the anthracene The content ratio of the compound [the polycyclic aromatic compound and its multimer/the anthracene compound] is 0.001/99.999 to 50/50 in terms of mass ratio.

Item 22. The organic electric field light-emitting element according to any one of items 1 to 21, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and the electron At least one of the transport layer and the electron injection layer contains a derivative selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, and pyrimidine derivatives Compounds, carbazole derivatives, triazine derivatives, benzimidazole derivatives, morpholine derivatives, and hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, thiazole derivatives, and oxazolines (Azoline) At least one of the group consisting of derivatives.

Item 23. Item 22. The organic electroluminescent device according to item 22, wherein at least one of the electron transport layer and the electron injection layer further contains an oxide selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metals, and alkali metal halides. Composed of oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals At least one of the group.

Item 24. A display device or a lighting device including the organic electric field light-emitting element according to any one of items 1 to 23. [Effect of invention]

The organic EL device according to the preferred embodiment of the present invention has the best light-emitting characteristics.

1. Characteristic light-emitting layer in an organic EL element The present invention is an organic EL device having: a pair of electrodes including an anode and a cathode; and a light emitting layer disposed between the pair of electrodes, and the light emitting layer includes a polycyclic aromatic compound represented by the general formula (1) At least one of a multi-group compound and a polymer of a polycyclic aromatic compound having a plurality of structures represented by the general formula (1), and the anthracene-based compound. In particular, the light-emitting layer included in the organic EL device of the present invention includes not only an anthracene-based compound but also a polycyclic aromatic compound represented by the general formula (1) and a plurality of the general formula (1) At least one of the polymers of the polycyclic aromatic compound of the structure can be an organic EL element with a narrow half-value width of light emission, a long life, and excellent quantum efficiency. Hereinafter, the polycyclic aromatic compound and its multimer and the anthracene-based compound included in the light-emitting layer will be described.

1-1. Polycyclic aromatic compounds and their polymers The polymers of polycyclic aromatic compounds represented by the general formula (1) and polycyclic aromatic compounds having a plurality of structures represented by the general formula (1) Basically function as a dopant. The polycyclic aromatic compound and its polymer are preferably a polycyclic aromatic compound represented by the following general formula (2), or a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2) Group of compounds. [化25]

Ring A, ring B and ring C in general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. The substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamine, substituted or unsubstituted diheteroaryl Amine groups, substituted or unsubstituted arylheteroarylamine groups (amine groups with aryl and heteroaryl groups), substituted or unsubstituted diarylboryl groups (two aryl groups can also be Bonded via a single bond or linker), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted Aryloxy. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the aryl ring or heteroaryl ring preferably has a condensed bicyclic structure with the center of the general formula (1) including Y ¹ , X ¹ and X ² (hereinafter, this structure is also referred to as a “D structure” ”) There are 5 or 6 member rings that are bonded together.

Here, the "condensed bicyclic structure (D structure)" refers to a structure formed by condensing two saturated hydrocarbon rings composed of Y ¹ , X ¹ and X ² shown in the center of the general formula (1). In addition, the "6-membered ring that shares a bond with the condensed bicyclic structure", for example, as shown in the general formula (2), refers to the a ring (benzene ring (6-membered ring) condensed in the D structure ring)). In addition, the "(A ring) aryl ring or heteroaryl ring has the 6-membered ring" means that the A-ring is formed only from the 6-membered ring, or the 6-membered ring is included in the 6-membered ring Furthermore, other rings and the like are condensed to form an A ring. In other words, the "aryl ring or heteroaryl ring having a 6-membered ring (A ring)" herein means that all or part of the 6-membered ring constituting the A ring is condensed in the D structure. The same applies to "B ring (b ring)", "C ring (c ring)" and "5 member ring".

Ring A (or ring B, ring C) in general formula (1) corresponds to ring a and its substituent R ¹ to substituent R ³ (or ring b and its substituent R ⁸ to substituent in general formula (2) R ¹¹ , ring c and its substituent R ⁴ to substituent R ⁷ ). That is, the general formula (2) corresponds to a formula in which "A ring to C ring having 6 member rings" is selected as the A ring to C ring in the general formula (1). In this sense, each ring of the general formula (2) is represented by lowercase letters a to c.

In the general formula (2), the adjacent groups of the substituents R ¹ to R ¹¹ of the a ring, b ring, and c ring may also be bonded to each other and form an aryl ring together with the a ring, b ring, or c ring Or heteroaryl ring, at least one hydrogen in the formed ring may also be composed of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (Two aryl groups may also be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these hydrogens may also be substituted by aryl, heteroaryl, Alkyl or cycloalkyl substitution. Therefore, the polycyclic aromatic compound represented by the general formula (2) is represented by the following formula (2-1) and formula (2-2) according to the mutual bonding form of the substituents in the a ring, b ring and c ring Shows that the ring structure of the compound changes. The A'ring, B'ring and C'ring in each formula correspond to the A ring, B ring and C ring in the general formula (1), respectively. In the following formula (2-1) and formula (2-2), the definition of each symbol is the same as the definition described above.

[化26]

If the general formula (2) is used, the A′ ring, the B′ ring and the C′ ring in the formula (2-1) and the formula (2-2) represent the substituent R ¹ to the substituent R ¹¹ Adjacent groups are bonded to each other and form an aryl ring or heteroaryl ring together with a ring, b ring and c ring (also can be called other ring structure condensed in a ring, b ring or c ring Of the condensation ring). In addition, although not shown by the formula, there are also compounds in which all of a ring, b ring and c ring are changed to A'ring, B'ring and C'ring. In addition, as can be seen from the above formula (2-1) and formula (2-2), for example, R ⁸ of the b ring and R ⁷ of the c ring, R ¹¹ of the b ring, and R ¹ and c of the a ring R ⁴ and R ^{3 of the} a ring do not correspond to "adjacent groups with each other", and these will not be bonded. That is, the so-called "adjacent groups" refer to groups adjacent to the same ring.

The compound represented by the formula (2-1) or the formula (2-2) has, for example, a benzene ring, an indan ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring. For the compound of A'ring (or B'ring or C'ring) formed by condensation of benzene ring which is a ring (or b ring or c ring), the condensed ring A'(or condensed ring B'or The condensed ring C') becomes a naphthalene ring, a fluorene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

For example, examples of the compound represented by the above formula (2-1) include compounds represented by the following general formula (2-1A) or general formula (2-1B). [化27]

The compound represented by the formula (2-1A) is an indane ring which is condensed with the benzene ring of both the b ring and the c ring in the formula (2-1) to form a fluorene ring, and then the fluorene ring A compound substituted with a group represented by -N(Ar ^x ) ₂ . In addition, the compound represented by the formula (2-1B) is an indane ring which is condensed with the benzene ring of only the b ring in the formula (2-1) to form a fluorene ring, which is further substituted on the fluorene ring A compound having a group represented by -N(Ar ^x ) ₂ . In the formula (2-1A) and the formula (2-1B), Y ¹ , X ¹ , X ² , R ¹ to R ⁸ and R ¹¹ have the same definitions as in the general formula (2).

R ^{x is} independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups can also be Bond or linking group), alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these hydrogens may also be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

R ^{y is} each independently an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group. p is independently an integer of 0 to 3.

Furthermore, the definitions of R ^x and R ^y correspond to the substitution of the adjacent groups of R ¹ to R ¹¹ in the formula (2) to form an aryl ring when forming an aryl ring. Of the relevant provisions of the substituents.

Ar ^{x is} independently an aryl group or a heteroaryl group, and at least one of these hydrogens may be substituted by an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group. Examples of the "aryl group" and "heteroaryl group" of Ar ^x include the monovalent "aryl ring" or "heteroaryl ring" that can be selected as the A ring, B ring, and C ring of the general formula (1) Group.

In the general formula (2-1A) and the general formula (2-1B), when Ar ^{x is} limited to phenyl, the following general formula (2-1A') and the following general formula (2-1B') The compound represented. [Chem 28]

In the formula (2-1A') and formula (2-1B'), Y ¹ , X ¹ , X ² , R ¹ to R ⁸ and R ¹¹ have the same definitions as in the general formula (2), R ^x , R ^y and p are the same as defined in the general formula (2-1A) and the general formula (2-1B). q is independently an integer of 0-5.

In the case of formula (2-1A ') and formula (2-1B'), the substituent R ^y with a fluorene structure diphenylamine structure adjacent substituent groups R ^y, which via a connecting group also these Or single bond and bond. The linking group is preferably -O-, -S- or -C(-R ^a ) ₂ -. Further, the "-C (-R ^a) ₂ -" is R ^a is hydrogen, alkyl or cycloalkyl.

Here, a substituted substituent group R ^y R ^y adjacent a fluorene structure and a so-called diphenylamine structure, as is, for example as follows, in the substituents R ^y Ar (phenyl) and N (nitrogen) In the case where the position adjacent to the bonding position of is substituted, and the substituent R ^y is substituted in the position adjacent to the bonding position of N (nitrogen) in the fluorene structure. That is, the two substituents R ^y may be bonded as follows. [Chem 29]

（所述式（1a）、式（1b）及式（1c）中，A環、B環及C環、以及Y¹ 與所述通式（1）中的定義相同）In the general formula (1) and the general formula (2), Y ¹ is B (boron), and X ¹ and X ² are independently >O or >NR. That is, the polycyclic aromatic compound represented by the general formula (1) and its multimer are represented by any one of the following general formula (1a), general formula (1b), and general formula (1c) Polycyclic aromatic compounds and their polymers. [化30]

(In the above formula (1a), formula (1b) and formula (1c), ring A, ring B and ring C, and Y ¹ are as defined in the general formula (1))

（所述式（2a）、式（2b）及式（2c）中，R¹ ～R¹¹ 、以及Y¹ 與所述通式（2）中的定義相同）Moreover, the polycyclic aromatic compound represented by the said general formula (2) and its multimer are represented by any one of the following general formula (2a), general formula (2b), and general formula (2c) Polycyclic aromatic compounds and their polymers. [化31]

(In the formula (2a), formula (2b) and formula (2c), R ¹ to R ¹¹ and Y ¹ have the same definition as in the general formula (2))

In the general formula (1) and the general formula (2), the R of >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted, or a cycloalkyl group which may be substituted , Preferably an aryl group substituted by an alkyl group, a cycloalkyl group, a diarylamine group or a diarylboryl group (two aryl groups can also be bonded via a single bond or a linking group), an alkyl group, a ring Heteroaryl, alkyl or cycloalkyl substituted with alkyl, diarylamino or diarylboryl (two aryl groups can also be bonded via a single bond or linking group). The R of >NR may be bonded to at least one of the A ring, B ring, and C ring via a linking group or a single bond. Here, the linking group is preferably -O-, -S- or -C(-R) ₂ -. Furthermore, R in the "-C(-R) ₂ -" is hydrogen, alkyl or cycloalkyl.

Here, the definition of "> R of NR is bonded to at least one of the A ring, the B ring, and the C ring via a linking group or a single bond" in the general formula (1) corresponds to the general formula (2) "> R of NR is bonded to at least one of the a ring, b ring, and c ring via a linking group or a single bond". This regulation can be expressed by a compound represented by the following formula (2-3-1) and having a ring structure in which X ¹ or X ² is introduced into the condensed ring B′ and the condensed ring C′. That is, for example, it is a B′ ring (or C′) formed by condensing a benzene ring which is a b ring (or c ring) in the general formula (2) with another ring to introduce X ¹ (or X ² ) Ring) compounds. In addition, the above-mentioned regulation can also be expressed by a compound represented by the following formula (2-3-2) or formula (2-3-3) and having at least one of X ¹ and X ² The ring structure introduced into the condensed ring A'. That is, for example, a compound having an A′ ring formed by condensing another ring with a benzene ring that is the a ring in the general formula (2) by introducing X ¹ (at least one of X ¹ and X ² ). In addition, R ¹ to R ¹¹ , Y ¹ , X ¹ and X ^{2 in} formula (2-3-1) to formula (2-3-3) have the same definitions as in formula (2).

[化32]

Examples of the "aryl ring" of the A ring, the B ring and the C ring of the general formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, and more preferably The aryl ring having 6 to 12 carbon atoms is more preferably an aryl ring having 6 to 10 carbon atoms. Furthermore, this "aryl ring" corresponds to the "aryl ring" which is defined by the general formula (2) and "adjacent groups in R ¹ to R ¹¹ are bonded to each other and formed together with a ring, b ring, or c ring""In addition, ring a (or ring b or ring c) already contains a benzene ring with a carbon number of 6, so the total carbon number of the condensed ring formed by condensing a 5-membered ring therein is 9 as the lower limit carbon number.

Specific "aryl rings" include: benzene ring as a monocyclic system; biphenyl ring as a bicyclic system; naphthalene ring as a condensed bicyclic system; biphenyl ring as a tricyclic system (interlinked Triphenyl, o-biphenyl, p-biphenyl); acenaphthene ring, fluorene ring, selenium ring, phenanthrene ring as condensed tricyclic ring system; triphenylene ring, pyrene ring, condensed four ring ring as condensed four ring system Benzene (naphthacene) ring; perylene ring as condensed five-ring system, pentacene ring, etc.

Examples of the "heteroaryl ring" of the A ring, the B ring and the C ring of the general formula (1) include a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, More preferred is a heteroaryl ring having 2 to 20 carbon atoms, further preferred is a heteroaryl ring having 2 to 15 carbon atoms, and particularly preferred is a heteroaryl ring having 2 to 10 carbon atoms. In addition, examples of the "heteroaryl ring" include a heterocyclic ring containing one to five hetero atoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon. In addition, this "heteroaryl ring" corresponds to the "heteroaryl group" which is defined by the general formula (2) and the adjacent groups in R ¹ to R ¹¹ are bonded to each other and formed together with a ring, b ring or c ring In addition, since the a ring (or b ring and c ring) already contains a benzene ring with a carbon number of 6, the total carbon number of the condensed ring formed by condensing a five-member ring therein is 6 as the lower limit carbon number.

Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, Tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole Ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine Ring, pyridine ring, carbazole ring, acridine ring, phenoxazine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazine ring (Phenazasiline) ring, indazine ring, furan ring, benzo Furan ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphorane (Benzophosphole) ring, dibenzophosphorene ring, benzophosphorene ring, dibenzophosphorene ring, furazan (furazan) ring, thio Anthracene ring, indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole ring, etc.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" may also be a substituted or unsubstituted "aryl" as a first substituent, a substituted or unsubstituted "heteroaryl" ", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", Substituted or unsubstituted "diarylboryl (two aryl groups can also be bonded via a single bond or linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "Cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy" as the first substituent of "aryl" or "heteroaryl" Aryl", "diarylamino" aryl, "diheteroarylamino" heteroaryl, "arylheteroarylamino" aryl and heteroaryl, "diarylboryl" The aryl group of "" or the aryl group of "aryloxy" includes the above-mentioned monovalent groups of "aryl ring" or "heteroaryl ring".

In addition, the “alkyl group” as the first substituent may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. The alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms) is preferred, and the alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms) is more preferred. It is an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms), particularly preferably an alkyl group having 1 to 5 carbon atoms (branched chain alkyl group having 3 to 5 carbon atoms). It is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms).

Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl, and neo Amyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2- Ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, third octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethyl Hexyl, 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-fifteen, n-hexadecyl, n-heptadecyl, n- Eighteen bases, twenty bases, etc. In addition, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl , 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-bis Methylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2- Tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl Group, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1- Methylbutyl, 1,1-dimethylhexyl, etc.

In addition, examples of the "cycloalkyl group" as the first substituent include cycloalkyl groups having 3 to 24 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, and 3 carbon atoms. Cycloalkyl of -14, cycloalkyl of 3-12 carbons, preferably cycloalkyl of 3-10 carbons or cycloalkyl of 5-10 carbons, more preferably carbon 3-8 or carbons The cycloalkyl group having 5 to 8 carbon atoms is more preferably a cycloalkyl group having 3 to 6 carbon atoms or 5 to 6 carbon atoms, and particularly preferably a cycloalkyl group having 5 carbon atoms.

Specific cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and at least one of these groups. Substitutions where hydrogen is substituted with C 1-5 alkyl groups (especially methyl), or norbornyl, 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, diadamantyl, decahydrogen Naphthyl (decahydronaphthalenyl) or decahydroazulenyl (decahydroazulenyl) etc.

In addition, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. Preferably, it is a C1-C18 alkoxy group (C3-C18 branched chain alkoxy group), More preferably, it is a C1-C12 alkoxy group (C3-C12 branched chain alkoxy group) ), further preferably C 1-6 alkoxy (C 3-6 branched chain alkoxy), particularly preferably C 1-5 alkoxy (C 3-5 branched alkane) Oxygen group), and may also be an alkoxy group having 1 to 4 carbon atoms (a branched chain alkoxy group having 3 to 4 carbon atoms).

Specific alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, second butoxy, third butoxy, and Tripentyloxy (t-amyloxy), n-pentyloxy, isopentyloxy, neopentyloxy, third pentyloxy (t-pentyloxy), n-hexyloxy, 1-methylpentyloxy, 4- Methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, third octyloxy Group, 1-methylheptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl- 4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-eicosyloxy, etc.

In addition, the "aryl group" in the "diarylboryl group" as the first substituent may refer to the description of the aryl group described above. In addition, the two aryl groups may be bonded via a single bond or a linking group (for example, >C(-R) ₂ , >O, >S, or >NR). Here, R for >C(-R) ₂ and >NR is aryl, heteroaryl, diarylamine, diheteroarylamine, arylheteroarylamine, alkyl, cycloalkyl , Alkoxy or aryloxy (above the first substituent), the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (above the second substituent) As specific examples of these groups, the description of the aryl group, heteroaryl group, diarylamine group, alkyl group, cycloalkyl group, alkoxy group or aryloxy group as the first substituent may be cited.

As the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted Substituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl" (two aryl groups can also pass through Single bond or linking group)), substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or As the substituted or unsubstituted "aryloxy group" is described as substituted or unsubstituted, at least one hydrogen in these groups may also be substituted by a second substituent. Examples of the second substituent include an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group. For specific examples of these, refer to the monovalent value of the "aryl ring" or "heteroaryl ring" described above. Description of the group and "alkyl" or "cycloalkyl" as the first substituent. In addition, in the aryl group or the heteroaryl group as the second substituent, at least one of these hydrogen atoms passes through an aryl group such as phenyl (specific examples are the groups described above) or an alkyl group such as methyl (specific examples Groups substituted with the above-mentioned groups) or cycloalkyl groups such as cyclohexyl groups (specific examples are the above-mentioned groups) are also included in the aryl group or heteroaryl group as the second substituent. As an example thereof, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl group such as phenyl or an alkyl group such as methyl or a cycloalkyl group such as cyclohexyl also includes In the heteroaryl group as the second substituent.

The aryl, heteroaryl, and diarylamino groups of R ¹ to R ¹¹ in the general formula (2), the heteroaryl group of the diheteroarylamino group, and the aromatic group of the arylheteroarylamino group Examples of the "aryl ring" or "heteroaryl ring" described in the general formula (1) include the aryl group and the heteroaryl group, the aryl group of the diarylboryl group, or the aryl group of the aryloxy group group. In addition, as the alkyl group, cycloalkyl group or alkoxy group in R ¹ to R ¹¹ , reference may be made to the “alkyl group” and “cycloalkyl group” as the first substituent in the description of the general formula (1) And the description of "alkoxy". Furthermore, the aryl group, heteroaryl group, alkyl group, or cycloalkyl group as a substituent to these groups is also the same. In addition, when the adjacent groups of R ¹ to R ¹¹ are bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, the heteroaryl group for the substituents of these rings, Diarylamine group, diheteroarylamine group, arylheteroarylamine group, diarylboron group (two aryl groups can also be bonded via a single bond or linking group), alkyl, cycloalkyl , Alkoxy or aryloxy, and aryl, heteroaryl, alkyl or cycloalkyl as further substituents are also the same.

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron-donating property and electron-withdrawing property of the structure of the first substituent, preferably a group represented by the following structural formula, more preferably a methyl group, a third Butyl, third pentyl, third octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2, 4,6-Methresyl, diphenylamino, di-p-tolylamino, bis(p-(third butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarba Oxazolyl, 3,6-di-tert-butylcarbazolyl and phenoxy, further preferably methyl, tert-butyl, tert-pentyl, tert-octyl, phenyl, o-tolyl, 2 ,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(third-butyl)phenyl)amino, carbazolyl , 3,6-dimethylcarbazolyl and 3,6-di-third butylcarbazolyl. From the viewpoint of ease of synthesis, the larger steric hindrance is preferred for selective synthesis, specifically, the third butyl group, the third pentyl group, the third octyl group, o-tolyl group, and p-toluene Base, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, bis-p-tolylamino, bis(p(p( Tributyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-third butylcarbazolyl.

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In the following structural formula, "Me" means methyl, "tBu" means third butyl, "tAm" means third pentyl, and "tOct" means third octyl. [化33]

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In X ¹ and X ² of the general formula (1), R of >NR is an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group that may be substituted with the second substituent described above, and the aryl group, the heteroaryl group Specific examples of the group, alkyl group or cycloalkyl group include the groups described above. Particularly preferred are aryl groups having 6 to 10 carbon atoms (for example, phenyl, naphthyl, etc.), heteroaryl groups having 2 to 15 carbon atoms (for example, carbazolyl, etc.), and alkyl groups having 1 to 5 carbon atoms (for example, methyl group). , Ethyl, etc.), cycloalkyl having 3 to 16 carbon atoms (such as bicyclooctyl or adamantyl, etc.). Furthermore, at least one hydrogen in the aryl group and heteroaryl group selected as R of >NR may be, for example, an alkyl group, a cycloalkyl group, a diarylamine group, or a diarylboryl group (two aryl groups may also be It is substituted by a single bond or a linking group). Specific examples of these alkyl groups, cycloalkyl groups, diarylamine groups, and diarylboryl groups include the groups described above. This description also applies to X ¹ and X ² in the general formula (2).

R in the "-C(-R) ₂ -" linking group in the general formula (1) is hydrogen, alkyl or cycloalkyl, and specific examples of the alkyl or cycloalkyl include the above Group. Particularly preferred is an alkyl group having 1 to 5 carbon atoms (for example, methyl, ethyl, etc.). This description also applies to "-C(-R) ₂ -" as a linking group in the general formula (2).

In addition, the light-emitting layer may also contain a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), and preferably includes a unit structure having a plurality of unit structures represented by the general formula (2) A polymer of polycyclic aromatic compounds. The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form having a plurality of the unit structures in one compound. For example, in addition to a single bond, a C1-C3 alkylene group, a phenyl group, a naphthyl group, etc. In addition to the form in which the unit structure is bonded (linked polymer), any ring (A ring, B ring, or C ring included in the unit structure may be shared by a plurality of unit structures, a A form in which the ring, b ring, or c ring is bonded (ring-shared polymer), or any ring (A ring, B ring, or C ring) included in the unit structure , A-ring, b-ring or c-ring) are condensed with each other (ring-condensed polymer), preferably ring-shared polymer and ring-condensed polymer, more preferably ring-shared Type polymer.

Examples of such polymers include the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula ( 2-5-4) or the multimeric compound represented by formula (2-6). The following formula (2-4) is a dimer compound, formula (2-4-1) is a dimer compound, formula (2-4-2) is a trimer compound, formula (2-5-1) Is a dimer compound, formula (2-5-2) is a dimer compound, formula (2-5-3) is a dimer compound, formula (2-5-4) is a trimer compound, formula ( 2-6) are dimer compounds. The multimeric compound represented by the following formula (2-4) is a compound having a plurality of units represented by the general formula (2) in a compound in the general formula (2) so as to share a benzene ring as the a ring Structured multimeric compounds (ring-shared polymers). The multimeric compound represented by the following formula (2-4-1) is represented by two general formulas (2) in a compound in the general formula (2) so as to share a benzene ring as the a ring The unit structure of the multimeric compound (ring-shared multimer). The multimeric compound represented by the following formula (2-4-2) is represented by the general formula (2) in the general formula (2) so as to share a benzene ring as the a ring, and has three general formula (2) in one compound The unit structure of the multimeric compound (ring-shared multimer). The multimeric compound represented by the following formula (2-5-1) to formula (2-5-4) is a system in which the benzene ring as the b ring (or c ring) is shared in the general formula (2), A multimeric compound (ring-shared polymer) having multiple unit structures represented by general formula (2) in one compound. In addition, the multimeric compound represented by the following formula (2-6) is represented by the benzene ring of b ring (or a ring, c ring) as a certain unit structure in general formula (2) and as a certain The unit structure of the b ring (or a ring, c ring) of the benzene ring is condensed, a compound having multiple unit structures represented by the general formula (2) in a compound (ring condensation polymer ). Furthermore, formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4) and formula (2- 6) R ¹ to R ¹¹ , Y ¹ , X ¹ and X ² have the same definitions as in formula (2).

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The multimeric compound may be a polymerized form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) and formula (2-5-1) to formula ( Any of 2-5-4) or the polymerized form represented by the formula (2-6) may be a combination of formula (2-5-1) to formula (2- 5-4) The polymerized form represented by any one of the polymerized forms and the polymerized form represented by the formula (2-6) may be a combination of formula (2-4) and formula (2-4-1) or formula (2-4-2) shows the multimerization form and any of formula (2-5-1) to formula (2-5-4). A polymer formed by combining a polymerized form with a polymerized form represented by formula (2-6).

In addition, all or part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or the general formula (2) and its multimer may be deuterium. That is, as with the compounds (2-2A-1) to (2-2A-248) described later, the polycyclic aromatic compound and its multimer represented by the general formula (1) or the general formula (2) may also be Compounds with at least one deuterium.

In the polycyclic aromatic compound represented by the general formula (1) or the general formula (2) and its multimer, 100% of the total amount of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule The ratio of deuterium is preferably 10% to 100%, more preferably 30% to 100%, still more preferably 50% to 100%, still more preferably 80% to 100%, and particularly preferably 100%.

Furthermore, the so-called "hydrogen and deuterium bonded to carbon (ring-forming carbon) constituting the aromatic ring in one molecule" refers to hydrogen and deuterium directly bonded to the ring-forming carbon, if formed with the ring Like hydrogen and deuterium in a carbon-bonded substituent, hydrogen and deuterium that form a carbon bond with a ring via a linking atom such as carbon or nitrogen cannot be included. For example, in the case of the following compound (2-2A-64), the number of "carbons forming an aromatic ring in one molecule (ring-forming carbon)" is 34, of which 18 are related to "deuterium (D )” bond, 5 bonds to “methyl (Me)”, and 0 hydrogens directly bond to the ring forming carbon. In addition, the hydrogen contained in the methyl group does not correspond to "hydrogen bonded to the carbon constituting the aromatic ring (ring-forming carbon)", so there is no need to consider it. Therefore, the "ratio of deuterium" in the compound (2-2A-64) becomes 100% (=18/(18+0)×100). [化39]

In addition, all or part of at least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by general formula (1) or general formula (2) and its multimer may be halogen. For example, in formula (1), ring A, ring B, ring C (rings A to C are the aforementioned aryl ring or heteroaryl ring), substituents for ring A to ring C, and as X ¹ and X ² of >NR in R (R is the alkyl, cycloalkyl or aryl group) at least one hydrogen may be substituted by halogen, these may include at least one of aryl or heteroaryl (All or a part) Hydrogen is substituted by halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably chlorine.

As specific examples of the polycyclic aromatic compound, the following compounds may be mentioned. Furthermore, in the following structural formula, "Me" represents methyl, "Et" represents ethyl, "tBu" represents third butyl, "tAm" represents third pentyl, and "D" represents deuterium.

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In addition, the polycyclic aromatic compound and its multimer are selected from at least one of A ring, B ring, and C ring (a ring, b ring, and c ring) relative to B (boron) as Y ¹ A phenyloxy group, a carbazolyl group, a diphenylamino group, or a diarylboryl group is introduced at the position, and an increase in T1 energy (about 0.01 eV to 0.1 eV increase) can be expected. In particular, by introducing a phenyloxy group to the para position with respect to B (boron) as Y ¹ , the highest on the benzene ring as the A ring, B ring and C ring (a ring, b ring and c ring) Occupied molecular orbital (Highest Occupied Molecular Orbital, HOMO) is further localized in the meta position relative to boron, and the lowest unoccupied molecular orbital (LUMO) is localized in the ortho and para position relative to boron Therefore, the increase in T1 energy can be particularly expected.

In addition, examples of the polycyclic aromatic compound include one or more phenyl groups in the compound or at least one hydrogen in one phenylene group through one or more alkyl groups having 1 to 5 carbon atoms and 5 to 10 carbon atoms. Compounds substituted with cycloalkyl, preferably C1-C3 alkyl (preferably one or more methyl groups), more preferably, hydrogen in the ortho position of one phenyl group (in both positions, Compounds substituted with methyl at both sites, preferably at any site) or hydrogen in the ortho position of one phenylene group (at most four sites, all at four sites, preferably at any site).

By substituting at least one hydrogen in the ortho position of the terminal phenyl group or p-phenylene group in the compound with a methyl group or the like, adjacent aromatic rings are easily orthogonal to each other and the conjugation becomes weaker, resulting in a triplet state excitation energy (E _T).

1-2. Method for producing polycyclic aromatic compounds and their polymers The polycyclic aromatic compounds and their polymers represented by general formula (1) or general formula (2) can be applied, for example, by International Publication No. 2015 It is synthesized by the method disclosed in /102118. That is, as shown in the following scheme, by using X ¹ or X ² to synthesize an intermediate formed by bonding A ring (a ring) with B ring (b ring) and C ring (c ring), and using a tandem type The Tandem Hetero-Friedel-Crafts Reaction (continuous aromatic electrophilic substitution reaction) cyclizes it to synthesize the desired polycyclic aromatic compounds and their polymers. In the following scheme, X represents halogen or hydrogen, and the definitions of other symbols are the same as those described above. [化101]

The intermediate before cyclization in the above process can also be synthesized by the method shown in International Publication No. 2015/102118 and the like. That is, it can be synthesized by appropriately combining the Buchwald-Hartwig reaction or the Suzuki coupling reaction, or an etherification reaction using a nucleophilic substitution reaction or a Ullmann reaction, etc. Intermediate with the desired substituent.

The cyclization using the tandem Zafried-Quaft reaction shown in the above procedure is introduced by bonding A ring (a ring), B ring (b ring) and C ring (c ring) B (boron) reaction. First, the hydrogen atom between X ¹ and X ² is ortho-metalized with n-butyl lithium, second butyl lithium, third butyl lithium, or the like. Then, add boron trichloride or boron tribromide, etc., and perform lithium-boron metal exchange, then add a Bronsted base such as N,N-diisopropylethylamine to carry out tandem boron Tandem Bora-Friedel-Crafts Reaction to obtain the target. Here, in order to promote the reaction, Lewis acid such as aluminum trichloride may also be added.

In addition to the method of introducing lithium to a desired position by ortho-metallization, it is also possible to introduce a halogen such as a bromine atom at a position where lithium is to be introduced, and to introduce lithium to a desired position by halogen-metal exchange.

In addition, the polycyclic aromatic compound or its multimer also contains a compound in which at least a part of hydrogen atoms are replaced by deuterium or a compound in which halogen is replaced by fluorine or chlorine, etc. Such compounds can be treated by using a desired site The deuterated, fluorinated or chlorinated raw materials are synthesized in the same manner as described above.

1-3. Anthracene compound Anthracene compound basically functions as a main body. The anthracene-based compound may be any compound having an anthracene structure, and examples thereof include compounds represented by the following general formula (3). [化102]

1-3-1. Anthracene compound represented by general formula (3) L in the general formula (3) is a single bond, an aryl group having 6 to 18 carbon atoms, or an alkylene group having 1 to 10 carbon atoms, at least one hydrogen in the aryl group and the alkylene group may also be Group, heteroaryl, alkyl or cycloalkyl (second substituent) substitution. In addition, the aryl, heteroaryl, alkyl and cycloalkyl which can be substituted on the aryl and alkylene as the second substituent can be cited as the "second substituent of the general formula (2) ”Relevant explanation.

As the arylene group, among the divalent groups represented by removing any two hydrogen atoms from the "aryl ring" described in the polycyclic aromatic compound, divalent groups having 6 to 18 carbon atoms can be mentioned. group.

Examples of the alkylene group include divalent groups represented by removing any one hydrogen atom from the "alkyl group" described in the polycyclic aromatic compound, and examples include divalent groups having 1 to 10 carbon atoms. It may be any of a linear chain and a branching difference, and examples thereof include methylene, ethylidene, propylidene, isopropylidene, butylidene, isobutylidene, and pentylidene.

Ar ⁴ in the general formula (3) is independently hydrogen, phenyl, biphenyl, triphenylphenyl, naphthyl, selected from the group consisting of C 1-4 alkyl groups and C 5-10 cycloalkanes A silane group substituted by a group in the group.

Examples of the alkyl group having 1 to 4 carbon atoms substituted on the silane group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, and third butyl groups. The three hydrogens in the silane group are independently substituted by these alkyl groups.

Specific "silyl groups substituted with alkyl groups having 1 to 4 carbon atoms" include trimethylsilyl groups, triethylsilyl groups, tripropylsilyl groups, triisopropylsilyl groups, and tributyl groups Silyl, tri-second butyl silane, tri-third butyl silane, ethyl dimethyl silane, propyl dimethyl silane, isopropyl dimethyl silane, butyl dimethyl Silane group, second butyl dimethyl silane group, third butyl dimethyl silane group, methyl diethyl silane group, propyl diethyl silane group, isopropyl diethyl silane group, butyl Diethylsilyl, second butyldiethylsilyl, third butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl , Second butyl dipropyl silane, third butyl dipropyl silane, methyl diisopropyl silane, ethyl diisopropyl silane, butyl diisopropyl silane, second Butyl diisopropyl silane, third butyl diisopropyl silane, etc.

Examples of cycloalkyl groups having 5 to 10 carbon atoms substituted on the silane group include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and 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, decahydrogen Naphthyl, decahydroazulyl, etc., the three hydrogens in the silane group are each independently substituted by these cycloalkyl groups.

Specific examples of the "silyl group substituted with a cycloalkyl group having 5 to 10 carbon atoms" include tricyclopentylsilyl group, tricyclohexylsilyl group, and the like.

As substituted silane groups, there are also dialkyl cycloalkyl silane groups substituted with two alkyl groups and one cycloalkyl group, and alkyl dicycloalkanes substituted with one alkyl group and two cycloalkyl groups As a specific example of the substituted alkyl group and cycloalkyl group, the silyl group may include the groups described above.

In the general formula (3), n is 0 or 1. That is, the compound represented by the general formula (3) is divided into the compound represented by the following general formula (3a) and the compound represented by the following general formula (3b). In the following formula (3a) and formula (3b), the definition of each symbol is the same as that of the general formula (3). [化103]

In the general formula (3), X is independently a group represented by the following formula (3-X1), formula (3-X2), or formula (3-X3). * In the following formula (3-X1), formula (3-X2), or formula (3-X3) represents the bonding position to the 9-position or 10-position of the anthracene ring in formula (3). [化104]

Ar ¹ and Ar ^{2 in} formula (3-X1) or formula (3-X2) are independently hydrogen, phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthrenyl, fluorene Group, benzofluorenyl, benzyl, triphenylene, pyrenyl, carbazolyl, benzocarbazolyl, phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzo Furyl, benzothienyl, dibenzothienyl, or naphthobenzothienyl, at least one of these hydrogens may be further substituted by aryl, heteroaryl, alkyl, or cycloalkyl, or by carbon number It is substituted with an alkyl group of 1 to 6, a cycloalkyl group having 3 to 14 carbon atoms, a phenyl group, or a naphthyl group.

Furthermore, examples of the C 1-6 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, and third butyl. , N-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, etc.

In addition, examples of the cycloalkyl group having 3 to 14 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, And the C 1-4 alkyl (especially methyl) substituents of these groups, or 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, diadamantyl, decahydronaphthyl, deca Hydrogen azulyl etc.

Ar ³ in formula (3-X3) is phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzyl, triphenylene, Pyrenyl, carbazolyl, benzocarbazolyl, phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, or Naphthobenzothienyl.

Furthermore, at least one hydrogen of these groups which may be selected as Ar ³ may be further substituted or unsubstituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an alkyl group or a cycloalkyl group Substituted phenyl, biphenyl substituted or unsubstituted with alkyl or cycloalkyl, biphenyl substituted or unsubstituted with alkyl or cycloalkyl, substituted with alkyl or cycloalkyl or Unsubstituted naphthyl, phenanthrenyl substituted or unsubstituted with alkyl or cycloalkyl, fluorenyl substituted or unsubstituted with alkyl or cycloalkyl, substituted or unsubstituted with alkyl or cycloalkyl Substituted benzyl, triphenylene substituted or unsubstituted with alkyl or cycloalkyl, pyrenyl substituted or unsubstituted with alkyl or cycloalkyl, substituted or unsubstituted with alkyl or cycloalkyl Substituted dibenzofuranyl, alkyl or cycloalkyl substituted or unsubstituted dibenzothienyl, alkyl or cycloalkyl substituted or unsubstituted carbazolyl, phenyl substituted carbazolyl , Benzofuranyl substituted or unsubstituted by alkyl or cycloalkyl, naphthobenzofuranyl substituted or unsubstituted by alkyl or cycloalkyl, substituted or unsubstituted by alkyl or cycloalkyl Substituted benzothienyl, or naphthobenzothienyl substituted with alkyl or cycloalkyl or unsubstituted. In addition, examples of the "alkyl" or "cycloalkyl" that may be further substituted on these substituents include the above-mentioned alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms.

The group represented by the formula (3-X3) is preferably a phenyl group, a phenanthrenyl group, a group represented by the following formula (3-X3-1), or a group represented by the following formula (3-X3-2) In the groups represented, at least one of these hydrogens may be substituted by the aryl group, heteroaryl group, alkyl group or cycloalkyl group as the second substituent, and may also be substituted by an alkyl group having 1 to 6 carbon atoms. * In the following formulas (3-X3-1) and (3-X3-2) represents the bonding position to the 9-position or 10-position of the anthracene ring in the general formula (3). [化105]

In addition, Ar ^{5 is} independently hydrogen, phenyl, biphenyl, triphenylphenyl, naphthyl, phenanthrenyl, fluorenyl, benzyl, triphenylene, pyrenyl, dibenzofuranyl, diphenyl Thiothienyl, carbazolyl, phenyl substituted carbazolyl, benzofuranyl, naphthobenzofuranyl, benzothienyl, or naphthobenzothienyl, at least one of these hydrogens can be further substituted by carbon It is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. In addition, at least one hydrogen of the group represented by the formula (3-X3-1) and the formula (3-X3-2) may be substituted by a C 1-6 alkyl group or a C 3 to C group The cycloalkyl group of 14 is as described above.

1-3-2. Anthracene-based compound represented by the general formula (3-1-X) In addition, as the anthracene-based compound, compounds represented by the following general formula (3-1-X) can also be mentioned. [化106]

In formula (3-1-X), ϕ is a phenyl group, a naphthyl group, a phenanthryl group, or a triphenylene group which may be substituted with Ar ¹ and R and bonded to a phenyl group. Therefore, the compound represented by the general formula (3-1-X) is classified as the compound represented by the following general formula (3-1-X1) (ϕ=phenyl which may be substituted by Ar ¹ and R), the following general The compound represented by the formula (3-1-X2) (ϕ=naphthyl group which may be substituted by Ar ¹ and R), and the compound represented by the following general formula (3-1-X3) (ϕ=may be substituted by Ar ¹ and R Phenanthrenyl group), and the compound represented by the following general formula (3-1-X4) (ϕ = triphenylene group which may be substituted by Ar ¹ and R).

[化107]

The compounds represented by general formula (3-1-X) and general formula (3-1-X1) to general formula (3-1-X4) are basically bonded to the 9-position and the 10-position by two phenyl groups In the anthracene compound, the specific aryl is based on the substitution of 2 and 5 positions, 3 and 4 positions, or 2 and 4 and 5 positions of one of the phenyl groups (bonded with anthracene at its 1 position) compound of. By selecting such a substitution position and an aryl structure, it can be a compound that achieves more excellent driving voltage, luminous efficiency, and device life as a material for a light-emitting layer.

In the general formula (3-1-X), Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, and n is 2 , Ar is bonded to both the x position and the y position, and the respective structures may be the same or different. That is, the general formula (3-1-X) is classified into the structure represented by the following formula (3-1-Xa), the structure represented by the formula (3-1-Xb), and the formula (3-1-Xc) ) Represents the structure.

[化108]

Examples of the "aryl group" as the "substitutable aryl group" of Ar in the general formula (3-1-X) include aryl groups having 6 to 30 carbon atoms. The preferred "aryl group" is an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, and further preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups" include phenyl as a monocyclic aryl group; (1-, 2-) naphthyl as a condensed bicyclic aryl group; acenaphthylene-( as a tricyclic aryl group) 1-, 3-, 4-, 5-) group, fluorene-(1-, 2-, 3-, 4-, 9-) group, 萉-(1-, 2-) group, (1-, 2 -, 3-, 4-, 9-) phenanthrenyl; triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, condensed as condensed tetracyclic aryl Tetraphenyl-(1-, 2-, 5-) group; Perylene-(1-, 2-, 3-) group as condensed pentacyclic aryl group, fused pentabenzene-(1-, 2-, 5- , 6-) group and so on.

As the "aryl group", among these, preferably, phenyl, naphthyl, phenanthrenyl, benzyl, or triphenylene, etc. are mentioned, and more preferably, phenyl, 1-naphthyl, 2-naphthyl are mentioned. Or phenanthrenyl, particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

The substituent for the "aryl group" is not particularly limited as long as the desired characteristics are obtained, and preferably includes an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or a carbon number 6 to 18 aryl groups.

The "alkyl group having 1 to 12 carbons" as the substituent may be either a straight chain or a branched chain. That is, it is a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 3 to 12 carbon atoms. More preferred is an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms), and further preferred is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl, neopentyl, Third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl or 2-ethylbutyl, etc., preferably methyl, ethyl Group, n-propyl, isopropyl, n-butyl, isobutyl, second butyl or third butyl, more preferably methyl, isopropyl or third butyl.

In addition, the "cycloalkyl group having 3 to 12 carbon atoms" as the substituents include, as specific examples, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, and cyclo Heptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl, etc. Among these, cyclopentyl or cyclohexyl is preferred.

The "aryl group having 6 to 18 carbon atoms" as the substituent is preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples are phenyl, (2-, 3-, 4-) biphenyl, (1-, 2-) naphthyl, (1-, 2-, 3-, 4-, 9-) phenanthryl, ( 1-, 2-) Tris phenyl, etc.

Regarding the substituent for "aryl", it is preferably unsubstituted, and in the presence of the substituent, the number thereof is, for example, the maximum number that can be substituted, preferably 1 to 3, more preferably 1 ~2, and more preferably 1.

In the general formula (3-1-X), Ar ¹ is an aryl group which may be substituted. Examples of the "aryl group" as the "aryl group which may be substituted" for Ar ¹ include aryl groups having 6 to 30 carbon atoms. The preferred "aryl group" is an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, and further preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups" include: phenyl groups as monocyclic aryl groups; (2-, 3-, 4-) biphenyl groups as bicyclic aryl groups; and those as condensed bicyclic aryl groups (1-, 2-) naphthyl; acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-) group, Cyan-(1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrenyl group; triphenylene-(1- as a condensed tetracyclic aryl group , 2-) group, pyrene-(1-, 2-, 4-) group, condensed tetraphenyl-(1-, 2-, 5-) group; perylene-(1-, 2-, 3-) groups, fused pentabenzene-(1-, 2-, 5-, 6-) groups, etc.

As the "aryl group", among these, preferably, phenyl, biphenyl, naphthyl, phenanthryl, benzyl, or triphenylene, etc., and more preferably, phenyl, 3-biphenyl , 4-biphenyl, 1-naphthyl, 2-naphthyl, phenanthrenyl or triphenylene, particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

The substituent for the "aryl group" is not particularly limited as long as the desired characteristics are obtained, and preferably includes an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or a carbon number 6 to 18 aryl groups.

As the "alkyl group having 1 to 12 carbon atoms" or "cycloalkyl group having 3 to 12 carbon atoms" as the substituent, the same groups as those described in the Ar column may be mentioned.

The "aryl group having 6 to 18 carbon atoms" as the substituent is preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples are phenyl, (1-, 2-)naphthyl, (1-, 2-, 3-, 4-, 9-)phenanthryl, and the like.

Regarding the substituent for "aryl", it is preferably unsubstituted, and in the presence of the substituent, the number thereof is, for example, the maximum number that can be substituted, preferably 1 to 3, more preferably 1 ~2, and more preferably 1.

The number m of substituents for Ar ¹ is 0 to the largest integer that can be substituted on ϕ. When m is 2 or more, the structure of Ar ¹ may be the same or different, preferably an integer of 0 to 2, and more preferably 0 or 1.

Examples of the "alkyl group" of R in the general formula (3-1-X) include an alkyl group having 1 to 12 carbon atoms, and the specific description can be referred to the description in the Ar column.

Examples of the “cycloalkyl group” of R in the general formula (3-1-X) include cycloalkyl groups having 3 to 12 carbon atoms, and the specific description can be referred to the description in the Ar column.

Regarding the number of substituents (a to d) of R, a is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is the largest integer that can be substituted on 0 to ϕ and c+m is Below the maximum integer that can be substituted on ϕ, d is an integer from 0 to 4. Preferably, a is an integer of 0 to 2, b is 0 or 1, and b+n is 4 or less, c is an integer of 0 to 2, and d is an integer of 0 to 2. Further preferably, a to d are 0.

In addition, hydrogen in the anthracene skeleton constituting the compound represented by the general formula (3-1-X), hydrogen in the phenyl group substituted at the 9-position or 10-position of anthracene, and hydrogen in Ar, Ar ¹ or R At least one of can also be replaced by deuterium.

1-3-3. Anthracene compounds represented by the general formula (3-1-X1) The general formula (3-1-X1) is classified into the structure represented by the following formula (3-1-X1a), the structure represented by the formula (3-1-X1b), and the formula (3-1-X1c) Represented structure.

[化109]

Examples of Ar, Ar ¹ and R in the general formula (3-1-X1) include those described in the general formula (3-1-X). In addition, the number m of substituents for Ar ¹ is an integer of 0 to 5, preferably an integer of 0 to 2, and more preferably 0 or 1. Regarding the number of substituents (a to d) of R, preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b+n is 4 or less), and c is an integer of 0 to 5 (c+m Is 5 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0-2, b is 0 or 1, c is an integer of 0-2, and d is an integer of 0-2. Further preferably, a to d are 0.

In addition, hydrogen in the anthracene skeleton constituting the compound represented by the general formula (3-1-X1), hydrogen in the phenyl group substituted at the 9-position or 10-position of anthracene, and hydrogen in Ar, Ar ¹ or R At least one of can also be replaced by deuterium.

1-3-4. Anthracene compounds represented by the general formula (3-1-X2) The general formula (3-1-X2) is classified into the structure represented by the following formula (3-1-X2a), the structure represented by the formula (3-1-X2b), and the formula (3-1-X2c) Represented structure. In each structure, the naphthalene ring is 1-naphthyl or 2-naphthyl.

[化110]

Examples of Ar, Ar ¹ and R in the general formula (3-1-X2) include those described in the general formula (3-1-X). In addition, the number m of substituents for Ar ¹ is an integer of 0 to 7, preferably an integer of 0 to 2, and more preferably 0 or 1. Regarding the number of substituents (a to d) of R, preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b+n is 4 or less), and c is an integer of 0 to 7 (c+m Is 7 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0-2, b is 0 or 1, c is an integer of 0-2, and d is an integer of 0-2. Further preferably, a to d are 0.

In addition, hydrogen in the anthracene skeleton constituting the compound represented by the general formula (3-1-X2), hydrogen in the phenyl group substituted at the 9-position or 10-position of anthracene, and hydrogen in Ar, Ar ¹ or R At least one of can also be replaced by deuterium.

1-3-5. Anthracene compounds represented by the general formula (3-1-X3) The general formula (3-1-X3) is classified into the structure represented by the following formula (3-1-X3a), the structure represented by the formula (3-1-X3b), and the formula (3-1-X3c) Represented structure. In each structure, the phenanthrene ring is 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, or 9-phenanthrenyl.

[化111]

Examples of Ar, Ar ¹ and R in the general formula (3-1-X3) include those described in the general formula (3-1-X). In addition, the number m of substituents for Ar ¹ is an integer of 0 to 9, preferably an integer of 0 to 2, and more preferably 0 or 1. Regarding the number of substituents (a to d) of R, preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b+n is 4 or less), and c is an integer of 0 to 9 (c+m Is 9 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0-2, b is 0 or 1, c is an integer of 0-2, and d is an integer of 0-2. Further preferably, a to d are 0.

In addition, hydrogen in the anthracene skeleton constituting the compound represented by the general formula (3-1-X3), hydrogen in the phenyl group substituted at the 9-position or 10-position of anthracene, and hydrogen in Ar, Ar ¹ or R At least one of can also be replaced by deuterium.

1-3-6. Anthracene compounds represented by the general formula (3-1-X4) The general formula (3-1-X4) is classified into the structure represented by the following formula (3-1-X4a), the structure represented by the formula (3-1-X4b), and the formula (3-1-X4c) Represented structure. In each structure, the triphenylene ring is 1-triphenylene or 2-triphenylene.

[化112]

Examples of Ar, Ar ¹ and R in the general formula (3-1-X4) include those described in the general formula (3-1-X). In addition, the number m of substituents for Ar ¹ is an integer of 0 to 11, preferably an integer of 0 to 2, and more preferably 0 or 1. Regarding the number of substituents (a to d) of R, preferably, a is an integer of 0 to 5, b is an integer of 0 to 3 (b+n is 4 or less), and c is an integer of 0 to 11 (c+m Is 11 or less), and d is an integer of 0 to 4. More preferably, a is an integer of 0-2, b is 0 or 1, c is an integer of 0-2, and d is an integer of 0-2. Further preferably, a to d are 0.

In addition, hydrogen in the anthracene skeleton constituting the compound represented by the general formula (3-1-X4), hydrogen in the phenyl group substituted at the 9-position or 10-position of anthracene, and hydrogen in Ar, Ar ¹ or R At least one of can also be replaced by deuterium.

1-3-7. Anthracene compounds with at least one deuterium In addition, at least one hydrogen in the compounds represented by general formula (3), general formula (3-1-X), and general formula (3-1-X1) to general formula (3-1-X4) may be substituted with deuterium . That is, like the compound (3-2-1) to the compound (2-2A-674) described later, the anthracene-based compound may be a compound having at least one deuterium.

In the anthracene-based compound, the proportion of deuterium is preferably 10% to 100%, and more preferably 30% to 100% of the total number of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule. 100%, more preferably 50% to 100%, still more preferably 80% to 100%, and particularly preferably 100%.

Furthermore, the so-called "hydrogen and deuterium bonded to carbon (ring-forming carbon) constituting the aromatic ring in one molecule" refers to hydrogen and deuterium directly bonded to the ring-forming carbon, if formed with the ring Like hydrogen and deuterium in a carbon-bonded substituent, hydrogen and deuterium that form a carbon bond with a ring via a linking atom such as carbon or nitrogen cannot be included. For example, in the case of the following compound (3-327), the number of "carbon constituting the aromatic ring in one molecule (ring-forming carbon)" is 36, of which 5 are related to "deuterium (D)" Bonded, 18 are bonded to "Hydrogen (H)". Therefore, the "ratio of deuterium" in compound (3-327) becomes approximately 21.7% (≒5/(5+18)×100). [化113]

In addition, for example, in the case of the following compound (3-2-59), the number of "carbons constituting an aromatic ring in one molecule (ring-forming carbon)" is 40, of which 25 are related to "deuterium (D)" is bonded, one is bonded to "methyl (Me)", and 0 hydrogen is directly bonded to the ring forming carbon. In addition, the hydrogen contained in the methyl group does not correspond to "hydrogen bonded to the carbon constituting the aromatic ring (ring-forming carbon)", so there is no need to consider it. Therefore, the "ratio of deuterium" in compound (3-2-59) becomes 100% (=25/(25+0)×100). [化114]

Specific examples of the anthracene-based compound include the compounds shown below. Furthermore, in the following structural formula, "Me" represents methyl, "Et" represents ethyl, "tBu" represents third butyl, "iPr" represents propyl, and "D" represents deuterium.

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2. Organic electroluminescent elements Hereinafter, the organic EL device of this embodiment will be described in detail based on the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL device of this embodiment.

<Structure of organic electroluminescent element> The organic EL element 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole transport layer 104 provided on the hole injection layer 103. The light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, the electron injection layer 107 provided on the electron transport layer 106, and the cathode 108 provided on the electron injection layer 107.

In addition, the organic EL element 100 may reverse the manufacturing order to form, for example, a structure including a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, and an electron The electron transport layer 106 on the injection layer 107, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, the hole injection layer 103 provided on the hole transport layer 104, And the anode 102 provided on the hole injection layer 103.

Not all of the above layers are necessary, and the minimum constitutional unit is configured to include the anode 102, the light emitting layer 105, and the cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are arbitrary Set layers. In addition, each of the layers may include a single layer or multiple layers.

As the form of the layer constituting the organic EL element, in addition to the form of the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", it may also be " "Substrate/anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light emitting 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/luminescent 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/hole injection layer/light emitting layer/electron transport layer/cathode", "substrate/anode /Light emitting layer/electron transport layer/cathode", "substrate/anode/light emitting layer/electron injection layer/cathode".

<Substrate in Organic Electroluminescence Element> The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, etc. are generally used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, a glass plate and a plate made of transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polystyrene are preferred. In the case of a glass substrate, soda lime glass, alkali-free glass, or the like may be used. In addition, the thickness may be a thickness sufficient to maintain mechanical strength. Therefore, for example, it may be 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, the less eluted ions derived from the glass, the better, so it is preferably alkali-free glass. Since soda lime glass with a barrier coating such as SiO _{2 is} also commercially available, the soda lime can be used glass. In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film may be provided on at least one side of the substrate 101. In particular, a board, film, or sheet made of a synthetic resin with low gas barrier properties is used as the substrate 101 In the case of, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescent element> The anode 102 functions to inject holes into the light emitting layer 105. Furthermore, when at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO)) , Indium-zinc oxide (Indium Zinc Oxide, IZO, etc.), halogenated metals (copper iodide, etc.), copper sulfide, carbon black, ITO glass or NESA glass, etc. Examples of the organic compound include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole, and polyaniline. In addition, it can be appropriately selected and used from among substances used as the anode of the organic EL element.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light-emitting element, but from the viewpoint of power consumption of the light-emitting element, low resistance is desirable. For example, if it is an ITO substrate of 300 Ω/□ or less, it functions as an element electrode. However, since a substrate of about 10 Ω/□ can also be supplied at present, it is particularly desirable to use, for example, 100 Ω/□ to 5 Ω/ □, preferably a low resistance product of 50 Ω/□ to 5 Ω/□. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 nm and 300 nm in most cases.

<The hole injection layer and hole transport layer in the organic electroluminescent element> The hole injection layer 103 functions to efficiently inject holes migrated from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 functions to efficiently transfer holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transmission layer 104 are formed by layering and mixing one or more of the hole injection and/or transmission materials, or by the hole injection and/or transmission materials and the polymer binder Mixture formed. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection and/or transport material to form a layer.

As the hole injection and/or transporting substance, it is necessary to efficiently inject and/or transport holes from the positive electrode between the electrodes to which the electric field is applied. Ideally, the hole injection efficiency is high and the injected holes are transported efficiently. Therefore, it is preferable that the free potential is small, the hole mobility is large, and the stability is excellent, and it is not likely to generate impurities that become traps during manufacturing and use.

As the material for forming the hole injection layer 103 and the hole transport layer 104, a hole injection layer and a compound of p-type semiconductors and organic EL elements that have been conventionally used as a charge transport material for holes in photoconductive materials, and Any known compound used in the hole transport layer is selected and used. Specific examples of these materials are carbazole derivatives such as carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) Compounds, triarylamine derivatives (polymers with aromatic tertiary amine groups on the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N '-Diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl- 4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diphenyl-1,1'-di amine, N, N'- two naphthyl -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 ,N ⁴ ,N ^4' , ⁴ N ^'- tetrakis [1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] -4,4'-diamine, 4,4', 4 '' - tris (3-Methylphenyl(phenyl)amino) triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (non-metallic, copper Phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (eg 1,4,5,8,9,12- Hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. In the polymer system, polycarbonate or styrene derivatives, polyvinylcarbazole, polysilane, etc. having the monomer on the side chain are preferred. The compound in which the anode is injected into the hole and can transmit the hole is not particularly limited.

In addition, it is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such an organic semiconductor matrix (matrix) substance contains a compound with good electron donation or a compound with good electron acceptability. For doping electron-donating substances, tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (2,3,5 ,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) and other strong electron acceptors (for example, refer to the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo (M. Pfeiffer, A. Beyer, T. Fritz, K. Leo), Appl. Phys. Lett., 73 (22), 3202-3204 (1998)" and the document "J. Blochwitz, M . Fife, T. Fritz, K. Leo (J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo), Appl. Phys. Lett., 73 (6) , 729-731 (1998)"). These generate so-called holes through the electron migration process of electron-donating basic substances (hole-transporting substances). The conductivity of basic substances varies considerably according to the number and mobility of holes. As a matrix substance having a hole-transporting property, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (4,4',4''-tri(N,N-diphenylamino group ) Triphenylamine (4,4',4''-tris(N,N-diphenylamino)triphenylamine, TDATA, etc.), or specific metal phthalocyanine (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Laid-Open 2005-167175).

<Light-emitting layer in organic electroluminescent element> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which the electric field is applied. The material for forming the light-emitting layer 105 may be a compound (luminescent compound) that is excited by recombination of holes and electrons (luminescent compound), and is preferably capable of forming a stable thin-film shape and exhibiting strong power in a solid state The luminescence (fluorescence) efficiency of the compound. In the present invention, as the material for the light-emitting layer, the polycyclic aromatic compound represented by the general formula (1) and the polycyclic aromatic compound having a plurality of structures represented by the general formula (1) can be used At least one of the polymers is used as a dopant material, and an anthracene compound is used as a host material.

The light-emitting layer may be a single layer or may include multiple layers, either of which may be formed of materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one kind or a combination of multiple kinds, and any one may be used. The dopant material may be included in the entire host material, or may be included in a part of the host material, either of which may be. As a doping method, it can be formed by a co-evaporation method with the host material, or it can be simultaneously vapor-deposited after mixing with the host material in advance.

The amount of the host material used differs according to the type of the host material, and it may be determined according to the characteristics of the host material. The standard of the amount of the host material used is preferably 50% to 99.999% by weight of the entire material for the light-emitting layer, more preferably 80% to 99.95% by weight, and still more preferably 90% to 99.9% by weight.

The amount of the dopant material used varies according to the type of dopant material, and it may be determined according to the characteristics of the dopant material. The standard of the amount of the dopant used is preferably 0.001 to 50% by weight of the entire material for the light-emitting layer, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight. If it is within the above range, it is preferable, for example, in that the concentration quenching phenomenon can be prevented.

Furthermore, the content ratio of the polycyclic aromatic compound and its multimer represented by the general formula (1) to the anthracene-based compound in the light-emitting layer [polycyclic aromatic compound and its multimer/anthracene-based compound] The mass ratio is preferably 0.001/99.999 to 50/50, more preferably 0.05/99.95 to 20/80, and even more preferably 0.1/99.9 to 10/90.

Examples of host materials that can be used in combination with anthracene compounds include condensed ring derivatives such as pyrene, which have been known as light emitters from the past, bisstyryl derivatives such as distyrylbenzene derivatives, and tetraphenylbutane Enene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, etc.

<Electron injection layer and electron transport layer in the organic electroluminescent element> The electron injection layer 107 functions to efficiently inject electrons transferred from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by stacking and mixing one or more types of electron transport and/or injection materials, respectively, or formed by a mixture of an electron transport and/or injection material and a polymer binder.

The electron injection and/or transport layer refers to the layer in charge of injecting electrons from the cathode and then transporting electrons. Ideally, the electron injection efficiency is high and the electrons injected are efficiently transported. Therefore, it is preferable to have a substance having a large electron affinity, a large electron mobility, and further excellent stability, and is unlikely to generate impurities that become traps during manufacturing and use. However, when considering the balance between the transmission of holes and electrons, in the case of mainly playing the role of effectively preventing the holes from the anode from flowing to the cathode side without recombination, even if the electron transport capacity is not so high, It also has the effect of improving the luminous efficiency as well as the material with high electron transmission ability. Therefore, the electron injection and/or transport layer in this embodiment may include a function of a layer that can effectively prevent hole migration.

As a material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic EL element can be used The known compounds used are arbitrarily selected and used.

As a material used in the electron transport layer or the electron injection layer, it is preferable to contain a metal compound selected from a compound containing an aromatic ring or a heteroaromatic ring, a pyrrole derivative and its condensed ring derivative, and an electron-accepting nitrogen At least one of the compounds, wherein the compound containing an aromatic ring or a heteroaromatic ring contains one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus. Specific examples include condensed ring-based aromatic ring derivatives such as naphthalene and anthracene, styryl-based aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, purple Cyclone derivatives, coumarin derivatives, naphthalene derivatives, quinone derivatives such as anthraquinone or biphenylquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, and tropolone. Metal complex, flavonol (flavonol) metal complex and benzoquinoline metal complex, etc. These materials can be used alone or mixed with different materials.

In addition, specific examples of other electron-transporting compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, morpholine derivatives, taxol derivatives, coumarin derivatives, and naphthalimide derivatives. Substances, anthraquinone derivatives, bifenone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-thirdbutylphenyl)1,3, 4-oxadiazolyl]benzene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives , Metal complexes of 8-hydroxyquinoline (oxine) derivatives, metal complexes of hydroxyquinoline series, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium Complexes, pyrazole derivatives, perfluorinated benzene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline-2 -Yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), Benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine and other oligopyridine 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, etc. ), aldehyde diazide derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, etc.

In addition, metal complexes having electron-accepting nitrogen can also be used, and examples thereof include hydroxyquinoline-based metal complexes and hydroxyphenyloxazole complexes such as hydroxyazole complexes and methylimine complexes. , Metal complex of cycloheptaphenone, metal complex of flavonol and metal complex of benzoquinoline, etc.

The materials can be used alone or mixed with different materials.

Among the materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives are preferred Compounds, triazine derivatives, benzimidazole derivatives, morpholine derivatives, and hydroxyquinoline metal complexes.

所述式（ETM-1）中，R¹¹ 及R¹² 分別獨立地為氫、烷基、環烷基、可被取代的芳基、經取代的矽烷基、可被取代的含氮雜環、或氰基中的至少一個，R¹³ ～R¹⁶ 分別獨立地為可被取代的烷基、可被取代的環烷基、或可被取代的芳基，X為可被取代的伸芳基，Y為可被取代的碳數16以下的芳基、經取代的硼基、或可被取代的咔唑基，而且，n分別獨立地為0～3的整數。另外，作為「可被取代」或「經取代」的情況下的取代基，可列舉：芳基、雜芳基、烷基或環烷基等。<Borane Derivatives> Borane derivatives are, for example, compounds represented by the following general formula (ETM-1), which are disclosed in detail in Japanese Patent Laid-Open No. 2007-27587. [化300]

In the formula (ETM-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silane group, nitrogen-containing heterocyclic ring which may be substituted, Or at least one of cyano groups, R ¹³ to R ¹⁶ are each independently an optionally substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl group, and X is an optionally substituted arylene group, Y is an aryl group having 16 or less carbon atoms which may be substituted, a substituted boron group, or a carbazolyl group which may be substituted, and n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group.

式（ETM-1-1）中，R¹¹ 及R¹² 分別獨立地為氫、烷基、環烷基、可被取代的芳基、經取代的矽烷基、可被取代的含氮雜環、或氰基中的至少一個，R¹³ ～R¹⁶ 分別獨立地為可被取代的烷基、可被取代的環烷基、或可被取代的芳基，R²¹ 及R²² 分別獨立地為氫、烷基、環烷基、可被取代的芳基、經取代的矽烷基、可被取代的含氮雜環、或氰基中的至少一個，X¹ 為可被取代的碳數20以下的伸芳基，n分別獨立地為0～3的整數，而且，m分別獨立地為0～4的整數。另外，作為「可被取代」或「經取代」的情況下的取代基，可列舉：芳基、雜芳基、烷基或環烷基等。 [化302]

式（ETM-1-2）中，R¹¹ 及R¹² 分別獨立地為氫、烷基、環烷基、可被取代的芳基、經取代的矽烷基、可被取代的含氮雜環、或氰基中的至少一個，R¹³ ～R¹⁶ 分別獨立地為可被取代的烷基、可被取代的環烷基、或可被取代的芳基，X¹ 為可被取代的碳數20以下的伸芳基，而且，n分別獨立地為0～3的整數。另外，作為「可被取代」或「經取代」的情況下的取代基，可列舉：芳基、雜芳基、烷基或環烷基等。Among the compounds represented by the general formula (ETM-1), the compounds represented by the following general formula (ETM-1-1) or the compounds represented by the following general formula (ETM-1-2) are preferred . [化301]

In formula (ETM-1-1), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silane group, nitrogen-containing heterocyclic ring which may be substituted, Or at least one of cyano groups, R ¹³ to R ¹⁶ are each independently an alkyl group that may be substituted, a cycloalkyl group that may be substituted, or an aryl group that may be substituted, and R ²¹ and R ²² are each independently hydrogen , An alkyl group, a cycloalkyl group, an aryl group that may be substituted, a substituted silane group, a nitrogen-containing heterocyclic ring that may be substituted, or a cyano group, X ¹ is a carbon number that can be substituted of 20 or less For arylene groups, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 4. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group. [化302]

In the formula (ETM-1-2), R ¹¹ and R ¹² are independently hydrogen, alkyl, cycloalkyl, aryl which may be substituted, substituted silane group, nitrogen-containing heterocyclic ring which may be substituted, Or at least one of cyano groups, R ¹³ to R ¹⁶ are each independently an optionally substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl group, and X ¹ is an optionally substituted carbon number 20 In the following arylene groups, n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "may be substituted" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group.

（各式中，R^a 分別獨立地為烷基、環烷基或可被取代的苯基）Specific examples of X ¹ include divalent groups represented by the following formula (X-1) to formula (X-9). [化303]

(In each formula, R ^{a is} independently an alkyl group, a cycloalkyl group, or a phenyl group which may be substituted)

As specific examples of the borane derivative, for example, the following compounds may be mentioned. [化304]

The borane derivative can be produced using well-known raw materials and well-known synthesis methods.

<Pyridine Derivative> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2). [化305]

ϕ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, sepal ring, phenanthrene ring or triphenylene ring), n is 1-4 Integer.

In the formula (ETM-2-1), R ¹¹ to R ¹⁸ are independently hydrogen, alkyl (preferably C 1-24 alkyl), and cycloalkyl (preferably C 3 ~ 12 cycloalkyl) or aryl (preferably an aryl group having 6 to 30 carbon atoms).

In the above formula (ETM-2-2), R ¹¹ and R ¹² are independently hydrogen, alkyl (preferably C 1-24 alkyl), cycloalkyl (preferably C 3 ~ 12 cycloalkyl) or aryl (preferably C 6-30 aryl), R ¹¹ and R ¹² may also be bonded to form a ring.

In each formula, the "pyridine-based substituent" is any one of the following formulas (Py-1) to (Py-15), and the pyridine-based substituents may each independently consist of a C1-C5 alkane It is substituted by a C5-10 cycloalkyl group. In addition, the pyridine-based substituent may be bonded to the ϕ, anthracene ring or fluorene ring in each formula via phenylene or naphthyl.

[化306]

[化308]

The pyridine-based substituent is any one of the formulas (Py-1) to (Py-15), and among these, the following formulas (Py-21) to (Py-44) are preferred Any one. [化307]

[化308]

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine-based substituents" in the formula (ETM-2-1) and formula (ETM-2-2) May be substituted by aryl.

The "alkyl" in R ¹¹ to R ¹⁸ may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. . The preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms). More preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms).

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl , Neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, third octyl (1,1,3,3-tetramethylbutyl), 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 , Positive eighteen bases, positive twenty bases, etc.

As the C 1-5 alkyl group substituted on the pyridine-based substituent, the description of the alkyl group can be cited.

Examples of the "cycloalkyl" in R ¹¹ to R ¹⁸ include cycloalkyl groups having 3 to 12 carbon atoms. The preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethyl ring Hexyl etc.

As the cycloalkyl group having 5 to 10 carbon atoms substituted on the pyridine-based substituent, the description of the cycloalkyl group can be cited.

As the "aryl group" in R ¹¹ to R ¹⁸ , a preferred aryl group is an aryl group having 6 to 30 carbon atoms, a more preferred aryl group is an aryl group having 6 to 18 carbon atoms, and more preferably a carbon atom having 6 to 6 carbon atoms The aryl group of 14 is particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include a phenyl group as a monocyclic aryl group; a (1-, 2-) naphthyl group as a condensed bicyclic aryl group; and a condensed tricyclic system Aromatic acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, 萉-(1-, 2-)yl , (1-, 2-, 3-, 4-, 9-) phenanthrenyl; triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-) group, condensed tetraphenyl-(1-, 2-, 5-) group; perylene-(1-, 2-, 3-) group, condensed pentabenzene-(1- , 2-, 5-, 6-) groups and so on.

Preferred "aryl groups having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthrenyl, benzyl, and triphenylene groups, and more preferred examples include phenyl, 1-naphthyl, and 2-naphthyl. Or phenanthrenyl, particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

R ¹¹ and R ^{12 in} the above formula (ETM-2-2) may be bonded to form a ring, and as a result, cyclobutane and cyclopentane may also be spiro-bonded to the 5-membered ring of the fluorene skeleton , Cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene.

As a specific example of this pyridine derivative, the following compounds are mentioned, for example. [化309]

The pyridine derivative can be produced using well-known raw materials and well-known synthesis methods.

<Fluoranthene Derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352. [化310]

In the formula (ETM-3), X ¹² to X ²¹ represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted Aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

As specific examples of the fluoranthene derivative, the following compounds may be mentioned, for example. [化311]

<BO derivative> The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4) Multimers of compounds. [化312]

R ¹ to R ¹¹ are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (both aryl groups are also May be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these hydrogens may also be substituted by aryl, heteroaryl, alkyl or cycloalkyl .

In addition, adjacent groups in R ¹ to R ¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with a ring, b ring or c ring, and at least one hydrogen in the formed ring may also be Group, heteroaryl group, diarylamine group, diheteroarylamine group, arylheteroarylamine group, diarylboryl group (two aryl groups can also be bonded via a single bond or linking group), Alkyl, cycloalkyl, alkoxy or aryloxy substitution, at least one of these hydrogens may also be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

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

For the description of the form of the substituent or ring formed in the formula (ETM-4) and the multimer formed by combining multiple structures of the formula (ETM-4), the general formula (1) or the general formula can be cited (2) Description of the represented polycyclic aromatic compound or its multimer.

As specific examples of this BO-based derivative, for example, the following compounds may be mentioned. [化313]

This BO-based derivative can be produced using well-known raw materials and well-known synthesis methods.

<Anthracene derivative> One of the anthracene derivatives is a compound represented by the following formula (ETM-5-1). [化314]

Ar is independently divalent benzene or naphthalene, and R ¹ to R ⁴ are independently hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, or C 6-20 aryl .

Ar may be independently selected from divalent benzene or naphthalene, and the two Ars may be different or the same. From the viewpoint of ease of synthesis of the anthracene derivative, it is preferably the same. Ar is bonded to pyridine to form a "site containing Ar and pyridine", and this site is bonded to anthracene as a group represented by any one of the following formula (Py-1) to formula (Py-12), for example .

[化315]

Among these groups, the group represented by any one of the formula (Py-1) to the formula (Py-9) is preferable, and the formula (Py-1) to the formula (Py) is more preferable -6) The group represented by any one of them. The structures bonded to the two "sites containing Ar and pyridine" of anthracene may be the same or different, and from the viewpoint of ease of synthesis of the anthracene derivative, the same structure is preferred. Among them, from the viewpoint of device characteristics, it is preferable that the structures of two "sites including Ar and pyridine" are the same or different.

The C 1-6 alkyl group in R ¹ to R ⁴ may be either a straight chain or a branched chain. That is, it is a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (branched chain alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl, neopentyl, T-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl or 2-ethylbutyl Group, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl or third butyl, more preferably methyl, ethyl or third butyl base.

Specific examples of C 3-6 cycloalkyl groups in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, and methyl Cyclohexyl, cyclooctyl or dimethylcyclohexyl, etc.

The C 6-20 aryl group in R ¹ to R ⁴ is preferably a C 6-16 aryl group, more preferably a C 6-12 aryl group, and particularly preferably a C 6-10 aryl group Aryl.

Specific examples of the "aryl group having 6 to 20 carbon atoms" include a phenyl group as a monocyclic aryl group, (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) cumene Group; (2-, 3-, 4-) biphenyl group as bicyclic aryl group; (1-, 2-) naphthyl group as condensed bicyclic system aryl group; biphenyl group as tricyclic system aryl group Phenyl (m-terphenyl-2'-yl, m-triphenyl-4'-yl, m-triphenyl-5'-yl, o-triphenyl-3'-yl, o-triphenyl-4' -Radical, para-triphenyl-2'-yl, meta-triphenyl-2-yl, meta-triphenyl-3-yl, meta-triphenyl-4-yl, o-biphenyl-2-yl, o-biphenyl Triphenyl-3-yl, o-biphenyl-4-yl, p-biphenyl-2-yl, p-biphenyl-3-yl, p-biphenyl-4-yl); anthracene as condensed tricyclic aryl -(1-, 2-, 9-) group, acenaphthene-(1-, 3-, 4-, 5-) group, fluorene-(1-, 2-, 3-, 4-, 9-) group, Cyan-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-) phenanthrenyl; triphenylene-(1-, 2-)yl as condensed tetracyclic aryl , Pyrene-(1-, 2-, 4-) group, condensed tetraphenyl-(1-, 2-, 5-) group; perylene-(1-, 2-, 3-) as a condensed pentacyclic aryl group ) Base etc.

The preferred "aryl group having 6 to 20 carbon atoms" is phenyl, biphenyl, triphenylphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or m- Biphenyl-5'-yl, further preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, most preferably phenyl.

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2). [化316]

Ar ^{1 is} independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene, or 萉.

Ar ^{2 is} each independently an aryl group having 6 to 20 carbon atoms, and the same description as the "aryl group having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. The aryl group having 6 to 16 carbon atoms is preferred, the aryl group having 6 to 12 carbon atoms is more preferred, and the aryl group having 6 to 10 carbon atoms is particularly preferred. Specific examples include: phenyl, biphenyl, naphthyl, triphenylphenyl, anthracenyl, acenaphthyl, fluorenyl, vulcanyl, phenanthrenyl, triphenylene, pyrenyl, fused tetraphenyl ( tetracenyl), perylene base, etc.

R ¹ to R ⁴ are independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the above formula (ETM-5-1 )instruction of.

Specific examples of these anthracene derivatives include, for example, the following compounds. [化317]

These anthracene derivatives can be produced using well-known raw materials and well-known synthesis methods.

<Benzofluorene Derivative> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [化318]

Ar ^{1 is} independently an aryl group having 6 to 20 carbon atoms, and the same description as the "aryl group having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. The aryl group having 6 to 16 carbon atoms is preferred, the aryl group having 6 to 12 carbon atoms is more preferred, and the aryl group having 6 to 10 carbon atoms is particularly preferred. Specific examples include: phenyl, biphenyl, naphthyl, triphenylphenyl, anthracenyl, acenaphthyl, fluorenyl, vulcanyl, phenanthrenyl, triphenylene, pyrenyl, fused tetraphenyl ( tetracenyl), perylene base, etc.

Ar ^{2 is} independently hydrogen, alkyl (preferably C 1-24 alkyl), cycloalkyl (preferably C 3-12 cycloalkyl) or aryl (preferably carbon number 6 to 30 aryl groups), two Ar ² may also be bonded to form a ring.

The "alkyl group" in Ar ² may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. The preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (branched chain alkyl group having 3 to 18 carbon atoms). More preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (branched chain alkyl group having 3 to 12 carbon atoms). A further preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (branched chain alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl group" is an alkyl group having 1 to 5 carbon atoms (branched chain alkyl group having 3 to 5 carbon atoms). Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl , Neopentyl, tert-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, etc.

Examples of the "cycloalkyl group" in Ar ² include cycloalkyl groups having 3 to 12 carbon atoms. The preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethyl ring Hexyl etc.

As the "aryl group" in Ar ² , a preferred aryl group is an aryl group having 6 to 30 carbon atoms, a more preferred aryl group is an aryl group having 6 to 18 carbon atoms, and more preferably an aryl group having 6 to 14 carbon atoms It is particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthyl, fluorenyl, vulcanyl, phenanthrenyl, triphenylene, pyrenyl, and naphthacenyl. , Perylene, thick pentaphenyl, etc.

Two Ar ² can also be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane can also be spiro-bonded to the 5-membered ring of the fluorene skeleton , Fluorene or indene.

As a specific example of this benzofluorene derivative, the following compounds are mentioned, for example. [化319]

The benzofluorene derivative can be produced using well-known raw materials and well-known synthesis methods.

R⁵ 為經取代或未經取代的碳數1～20的烷基、碳數3～20的環烷基、碳數6～20的芳基或碳數5～20的雜芳基， R⁶ 為CN、經取代或未經取代的、碳數1～20的烷基、碳數3～20的環烷基、碳數1～20的雜烷基、碳數6～20的芳基、碳數5～20的雜芳基、碳數1～20的烷氧基或碳數6～20的芳氧基， R⁷ 及R⁸ 分別獨立地為經取代或未經取代的碳數6～20的芳基或碳數5～20的雜芳基， R⁹ 為氧或硫， j為0或1，k為0或1，r為0～4的整數，q為1～3的整數。 此處，作為經取代的情況下的取代基，可列舉：芳基、雜芳基、烷基或環烷基等。<phosphine oxide derivative> 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. [化320]

R ⁵ is a substituted or unsubstituted C 1-20 alkyl group, a C 3-20 cycloalkyl group, a C 6-20 aryl group or a C 5-20 heteroaryl group, R ⁶ CN, substituted or unsubstituted, C 1-20 alkyl, C 3-20 cycloalkyl, C 1-20 heteroalkyl, C 6-20 aryl, carbon Heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms or aryloxy groups having 6 to 20 carbon atoms, and R ⁷ and R ⁸ are each independently substituted or unsubstituted carbon atoms having 6 to 20 carbon atoms Aryl group or heteroaryl group 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. Here, examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [化321]

R ¹ to R ³ may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aromatic Ether group, arylthio ether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, amine group, nitro group, silane group, and condensation formed between adjacent substituents ring.

Ar ¹ may be the same or different, and is arylene or heteroaryl. Ar ² may be the same or different, and is an aryl group or a heteroaryl group. Among them, at least one of Ar ¹ and Ar ² has a substituent, or a condensed ring is formed between the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structure part, and when n is 3, there is no R ¹ .

Among these substituents, the alkyl group means, for example, saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. The substituent in the case of substitution is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group. This aspect is also commonly used in the following description. In addition, the carbon number of the alkyl group is not particularly limited, and it is usually in the range of 1 to 20 in terms of ease of acquisition or cost.

In addition, the cycloalkyl group means, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl group, cyclohexyl group, norbornyl group, and adamantyl group, which may be unsubstituted or substituted. The number of carbons in the alkyl portion is not particularly limited, but is usually in the range of 3-20.

In addition, the aralkyl group means, for example, an aromatic hydrocarbon group such as a benzyl group and a phenylethyl group via an aliphatic hydrocarbon, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The carbon number of the aliphatic portion is not particularly limited, but is usually in the range of 1-20.

In addition, the alkenyl group means, for example, an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, and a butadienyl group, which may be unsubstituted or substituted. The carbon number of the alkenyl group is not particularly limited, but is usually in the range of 2-20.

In addition, the cycloalkenyl group means, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as cyclopentenyl group, cyclopentadienyl group, and cyclohexenyl group, which may be unsubstituted or substituted.

The alkynyl group means, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as ethynyl group, which may be unsubstituted or substituted. The carbon number of the alkynyl group is not particularly limited, but it is usually in the range of 2-20.

In addition, the alkoxy group means, for example, an aliphatic hydrocarbon group such as a methoxy group via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The carbon number of the alkoxy group is not particularly limited, but it is usually in the range of 1-20.

In addition, the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is replaced with a sulfur atom.

In addition, the cycloalkylthio group is a group in which the oxygen atom of the ether bond of the cycloalkoxy group is replaced with a sulfur atom.

In addition, the aryl ether group means, for example, an aromatic hydrocarbon group such as a phenoxy group via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The carbon number of the aryl ether group is not particularly limited, but it is usually in the range of 6 to 40.

In addition, the arylthio ether group is a group in which the oxygen atom of the ether bond of the aryl ether group is replaced with a sulfur atom.

In addition, the aryl group means, for example, aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthrenyl, triphenylphenyl, and pyrenyl. The aryl group may be unsubstituted or substituted. The carbon number of the aryl group is not particularly limited, but is usually in the range of 6 to 40.

In addition, the heterocyclic group means, for example, a cyclic structure group having an atom other than carbon, such as furyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, which may be unsubstituted or substituted . The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2-30.

The so-called halogen means fluorine, chlorine, bromine and iodine.

The aldehyde group, carbonyl group, and amine group can also contain groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be unsubstituted or substituted.

The silane group refers to a silicon compound group such as trimethylsilyl group, which may be unsubstituted or substituted. The carbon number of the silane group is not particularly limited, but is usually in the range of 3-20. In addition, the silicon number is usually 1 to 6.

The condensed ring formed between adjacent substituents is, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , Ar ¹ and A conjugated or non-conjugated condensed ring formed between Ar ² and the like. Here, when n is 1, two R ¹ may form a conjugated or non-conjugated condensed ring with each other. These condensed rings may contain nitrogen atoms, oxygen atoms, and sulfur atoms in the ring structure, and may also be condensed with other rings.

As specific examples of the phosphine oxide derivative, for example, the following compounds may be mentioned. [化322]

The phosphine oxide derivative can be produced using well-known raw materials and well-known synthesis methods.

<Pyrimidine Derivative> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). The details are also described in International Publication No. 2011/021689. [化323]

Ar is independently an aryl group which may be substituted, or a heteroaryl group which may be substituted. n is an integer of 1-4, Preferably it is an integer of 1-3, More preferably, it is 2 or 3.

Examples of the "aryl group" of the "optionally substituted aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. It is further preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups" include: phenyl groups as monocyclic aryl groups; (2-, 3-, 4-) biphenyl groups as bicyclic aryl groups; and those as condensed bicyclic aryl groups (1-, 2-) naphthyl; triphenylphenyl (triphenyl-2'-yl, metatriphenyl-4'-yl, metatriphenyl-5'- Base, o-biphenyl-3'-yl, o-biphenyl-4'-yl, p-biphenyl-2'-yl, m-biphenyl-2-yl, m-biphenyl-3-yl, m- Biphenyl-4-yl, o-biphenyl-2-yl, o-biphenyl-3-yl, o-biphenyl-4-yl, p-biphenyl-2-yl, p-biphenyl-3-yl , P-biphenyl-4-yl); acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-) group, 萉-(1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrenyl; bitetraphenyl (5'- Phenyl-m-triphenyl-2-yl, 5'-phenyl-m-triphenyl-3-yl, 5'-phenyl-m-triphenyl-4-yl, m-tetraphenyl); as Triphenylene-(1-, 2-) groups, pyrene-(1-, 2-, 4-) groups, condensed tetraphenyl-(1-, 2-, 5-) groups of condensed tetracyclic aryl groups; Perylene-(1-, 2-, 3-) groups, condensed pentabenzene-(1-, 2-, 5-, 6-) groups as condensed pentacyclic aryl groups.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, and more preferably 2 to 2 carbon atoms. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. In addition, as the heteroaryl group, for example, a heterocyclic ring containing one to five hetero atoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms, etc. can be mentioned.

Examples of specific heteroaryl groups include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, and tetrazolyl. , Pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzene Thiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pyridinyl, Carbazolyl, acridinyl, phenoxyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl group, indazinyl, furanyl, benzofuranyl, isobenzene Benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl , Monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, furyl, thioanthryl, indole Carbazolyl, benzoindolocarbazolyl, benzobenzolocarbazolyl and the like.

In addition, at least one hydrogen in the aryl group and the heteroaryl group may be substituted, or may be substituted with, for example, the aryl group or the heteroaryl group, respectively.

As specific examples of the pyrimidine derivative, for example, the following compounds may be mentioned. [化324]

This pyrimidine derivative can be produced using well-known raw materials and well-known synthesis methods.

<Carbazole Derivative> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9) or a polymer obtained by bonding a plurality of them with a single bond or the like. The details are described in US Publication No. 2014/0197386. [化325]

Ar is independently an aryl group which may be substituted, or a heteroaryl group which may be substituted. n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

Examples of the "aryl group" of the "optionally substituted aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. It is further preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups" include: phenyl groups as monocyclic aryl groups; (2-, 3-, 4-) biphenyl groups as bicyclic aryl groups; and those as condensed bicyclic aryl groups (1-, 2-) naphthyl; triphenylphenyl (triphenyl-2'-yl, metatriphenyl-4'-yl, metatriphenyl-5'- Base, o-biphenyl-3'-yl, o-biphenyl-4'-yl, p-biphenyl-2'-yl, m-biphenyl-2-yl, m-biphenyl-3-yl, m- Biphenyl-4-yl, o-biphenyl-2-yl, o-biphenyl-3-yl, o-biphenyl-4-yl, p-biphenyl-2-yl, p-biphenyl-3-yl , P-biphenyl-4-yl); acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-) group, 萉-(1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrenyl; bitetraphenyl (5'- Phenyl-m-triphenyl-2-yl, 5'-phenyl-m-triphenyl-3-yl, 5'-phenyl-m-triphenyl-4-yl, m-tetraphenyl); as Triphenylene-(1-, 2-) groups, pyrene-(1-, 2-, 4-) groups, condensed tetraphenyl-(1-, 2-, 5-) groups of condensed tetracyclic aryl groups; Perylene-(1-, 2-, 3-) groups, condensed pentabenzene-(1-, 2-, 5-, 6-) groups as condensed pentacyclic aryl groups.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, and more preferably 2 to 2 carbon atoms. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. In addition, as the heteroaryl group, for example, a heterocyclic ring containing one to five hetero atoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms, etc. can be mentioned.

Examples of specific heteroaryl groups include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, and tetrazolyl. , Pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzene Thiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pyridinyl, Carbazolyl, acridinyl, phenoxyl, phenoxazinyl, phenothiazine, phenazinyl, phenazinyl, indazinyl, furanyl, benzofuranyl, isobenzofuranyl, Dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphoryl Monovalent group of heterocyclopentadiene oxide ring, monovalent group of dibenzophosphorus heterocyclopentadiene oxide ring, furyl, thianthryl, indolocarbazolyl, benzoindene Indolocarbazolyl and benzobenzoindolocarbazolyl.

In addition, at least one hydrogen in the aryl group and the heteroaryl group may be substituted, or may be substituted with, for example, the aryl group or the heteroaryl group, respectively.

The carbazole derivative may be a polymer in which a plurality of compounds represented by the formula (ETM-9) are bonded by a single bond or the like. In this case, in addition to a single bond, an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phlebene ring, phenanthrene ring, or triphenylene ring) ) For bonding.

As specific examples of the carbazole derivative, for example, the following compounds may be mentioned. [化326]

The carbazole derivative can be produced using well-known raw materials and well-known synthesis methods.

<Triazine derivative> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). The details are described in US Publication No. 2011/0156013. [化327]

Ar is independently an aryl group which may be substituted, or a heteroaryl group which may be substituted. n is an integer of 1 to 3, preferably 2 or 3.

Examples of the "aryl group" of the "optionally substituted aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. It is further preferably an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups" include: phenyl groups as monocyclic aryl groups; (2-, 3-, 4-) biphenyl groups as bicyclic aryl groups; and those as condensed bicyclic aryl groups (1-, 2-) naphthyl; triphenylphenyl (triphenyl-2'-yl, metatriphenyl-4'-yl, metatriphenyl-5'- Base, o-biphenyl-3'-yl, o-biphenyl-4'-yl, p-biphenyl-2'-yl, m-biphenyl-2-yl, m-biphenyl-3-yl, m- Biphenyl-4-yl, o-biphenyl-2-yl, o-biphenyl-3-yl, o-biphenyl-4-yl, p-biphenyl-2-yl, p-biphenyl-3-yl , P-biphenyl-4-yl); acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-) group, 萉-(1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrenyl; bitetraphenyl (5'- Phenyl-m-triphenyl-2-yl, 5'-phenyl-m-triphenyl-3-yl, 5'-phenyl-m-triphenyl-4-yl, m-tetraphenyl); as Triphenylene-(1-, 2-) groups, pyrene-(1-, 2-, 4-) groups, condensed tetraphenyl-(1-, 2-, 5-) groups of condensed tetracyclic aryl groups; Perylene-(1-, 2-, 3-) groups, condensed pentabenzene-(1-, 2-, 5-, 6-) groups as condensed pentacyclic aryl groups.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, and more preferably 2 to 2 carbon atoms. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. In addition, as the heteroaryl group, for example, a heterocyclic ring containing one to five hetero atoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms, etc. can be mentioned.

Examples of specific heteroaryl groups include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, and tetrazolyl. , Pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzene Thiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pyridinyl, Carbazolyl, acridinyl, phenoxyl, phenoxazinyl, phenothiazine, phenazinyl, phenazinyl, indazinyl, furanyl, benzofuranyl, isobenzofuranyl, Dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphoryl Monovalent group of heterocyclopentadiene oxide ring, monovalent group of dibenzophosphorus heterocyclopentadiene oxide ring, furyl, thianthryl, indolocarbazolyl, benzoindene Indolocarbazolyl and benzobenzoindolocarbazolyl.

In addition, at least one hydrogen in the aryl group and the heteroaryl group may be substituted, or may be substituted with, for example, the aryl group or the heteroaryl group, respectively.

As a specific example of this triazine derivative, the following compounds are mentioned, for example. [化328]

The triazine derivative can be produced using well-known raw materials and well-known synthesis methods.

<Benzimidazole derivative> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [化329]

ϕ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, sepal ring, phenanthrene ring or triphenylene ring), n is 1 to 4 Integer, "benzimidazole-based substituent" is the pyridyl group in the "pyridine-based substituent" of the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced by In the benzimidazolyl substituent, at least one hydrogen in the benzimidazole derivative may also be substituted by deuterium. [化330]

R ¹¹ in the benzimidazolyl group is hydrogen, a C 1-24 alkyl group, a C 3-12 cycloalkyl group or a C 6-30 aryl group, and the formula (ETM-2 -1) and R ¹¹ in the formula (ETM-2-2).

ϕ It is further preferably an anthracene ring or a fluorene ring. The structure in this case can be referred to the description in the above formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ^{18 in each} formula can be Refer to the description in the formula (ETM-2-1) or formula (ETM-2-2). In addition, the above formula (ETM-2-1) or formula (ETM-2-2) has been described in a form in which two pyridine-based substituents are bonded, but these are substituted as benzimidazole-based substituents In this case, two pyridine-based substituents may be substituted by benzimidazole-based substituents (that is, n=2), or any one pyridine-based substituent may be substituted by a benzimidazole-based substituent, and another pyridine-based substituent may be substituted by R ¹¹ to R ¹⁸ Substituent (ie n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) may be substituted with a benzimidazole-based substituent and the “pyridine-based substituent” may be substituted with R ¹¹ to R ¹⁸ .

Specific examples of the benzimidazole derivatives include, for example, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benz[d]imidazole, 2 -(4-(10-(naphthalen-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2 -Yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracene-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalen-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d] Imidazole, 2-(4-(9,10-bis(naphthalen-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-( 9,10-bis(naphthalen-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-bis(naphthalen-2-yl )Anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole and the like. [化331]

The benzimidazole derivative can be produced using well-known raw materials and well-known synthesis methods.

<Porphyrin Derivatives> Porphyrin derivatives are, for example, compounds represented by the following formula (ETM-12) or formula (ETM-12-1). The details are described in International Publication 2006/021982. [化332]

ϕ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, sepal ring, phenanthrene ring or triphenylene ring), n is 1-4 Integer.

R ¹¹ to R ^{18 in} each ^formula are independently hydrogen, alkyl (preferably C 1-24 alkyl), cycloalkyl (preferably C 3-12 cycloalkyl) or aryl (Preferably an aryl group having 6 to 30 carbon atoms). In addition, in the above formula (ETM-12-1), any one of R ¹¹ to R ¹⁸ is bonded to ϕ which is an aryl ring.

At least one hydrogen in each morpholine derivative may also be substituted with deuterium.

As R ¹¹ ~ R ¹⁸ is alkyl, cycloalkyl, and aryl groups, may be explained by reference (ETM-2) of the formula R ¹¹ ~ R ¹⁸ is. In addition to ϕ, in addition to the above-mentioned examples, for example, the following structural formulas may be cited. Furthermore, R in the following structural formula is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl or biphenyl . [化333]

Specific examples of this morpholine derivative include, for example, 4,7-diphenyl-1,10-morpholine and 2,9-dimethyl-4,7-diphenyl-1,10-morphine Porphyrin, 9,10-bis(1,10-morpholin-2-yl)anthracene, 2,6-bis(1,10-morpholin-5-yl)pyridine, 1,3,5-tris(1, 10-morpholin-5-yl)benzene, 9,9'-difluoro-bi(1,10-morpholin-5-yl), 2,9-dimethyl-4,7-biphenyl-1, 10-phenoline (bathocuproine) or 1,3-bis(2-phenyl-1,10-morpholine-9-yl)benzene, etc. [化334]

This morpholine derivative can be produced using well-known raw materials and well-known synthesis methods.

式中，R¹ ～R⁶ 分別獨立地為氫、氟、烷基、環烷基、芳烷基、烯基、氰基、烷氧基或芳基，M為Li、Al、Ga、Be或Zn，n為1～3的整數。<Hydroxyquinoline-based metal complex> The hydroxyquinoline-based metal complex is, for example, a compound represented by the following general formula (ETM-13). [化335]

In the formula, R ¹ to R ⁶ are independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, Ga, Be or Zn, n is an integer of 1-3.

Specific examples of the hydroxyquinoline-based metal complex include lithium 8-hydroxyquinoline, tris(8-hydroxyquinoline) aluminum, tris(4-methyl-8-hydroxyquinoline) aluminum, and tri( 5-methyl-8-hydroxyquinoline) aluminum, tris(3,4-dimethyl-8-hydroxyquinoline) aluminum, tris(4,5-dimethyl-8-hydroxyquinoline) aluminum, tris (4,6-dimethyl-8-hydroxyquinoline) aluminum, bis(2-methyl-8-hydroxyquinoline) (phenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (2 -Methylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (3-methylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (4-methylphenol) aluminum , Bis(2-methyl-8-hydroxyquinoline) (2-phenylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (3-phenylphenol) aluminum, bis(2-methyl Yl-8-hydroxyquinoline) (4-phenylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (2,3-dimethylphenol) aluminum, bis(2-methyl-8 -Hydroxyquinoline) (2,6-dimethylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (3,4-dimethylphenol) aluminum, bis(2-methyl-8 -Hydroxyquinoline) (3,5-dimethylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (3,5-di-third butylphenol) aluminum, bis(2-methyl Yl-8-hydroxyquinoline) (2,6-diphenylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (2,4,6-triphenylphenol) aluminum, bis(2 -Methyl-8-hydroxyquinoline) (2,4,6-trimethylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) (2,4,5,6-tetramethylphenol ) Aluminum, bis(2-methyl-8-hydroxyquinoline) (1-naphthol) aluminum, bis(2-methyl-8-hydroxyquinoline) (2-naphthol) aluminum, bis(2,4 -Dimethyl-8-hydroxyquinoline) (2-phenylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) (3-phenylphenol) aluminum, bis (2,4 -Dimethyl-8-hydroxyquinoline) (4-phenylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) (3,5-dimethylphenol) aluminum, bis ( 2,4-Dimethyl-8-hydroxyquinoline) (3,5-di-tert-butylphenol) aluminum, bis(2-methyl-8-hydroxyquinoline) aluminum-μ-oxo-bis (2-methyl-8-hydroxyquinoline) aluminum, bis(2,4-dimethyl-8-hydroxyquinoline) aluminum-μ-oxo-bis(2,4-dimethyl-8-hydroxyl Quinoline) aluminum, bis(2-methyl-4-ethyl-8-hydroxyquinoline) aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline) aluminum, Bis(2-methyl-4-methoxy-8-hydroxyquinoline) aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline) aluminum, bis(2 -Methyl-5-cyano-8-hydroxyquinoline) aluminum-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline) aluminum, bis(2-methyl-5 -Trifluoromethyl-8-hydroxyquinoline) aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl- 8-hydroxyquinoline) aluminum, bis(10-hydroxybenzo[h]quinoline) beryllium, etc.

The hydroxyquinoline-based metal complex can be produced using well-known raw materials and well-known synthesis methods.

苯並噻唑衍生物例如為下述式（ETM-14-2）所表示的化合物。 [化337]

<thiazole derivative and benzothiazole derivative> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [化336]

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [化337]

Φ of each formula is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, selenium ring, phenanthrene ring or triphenylene ring), n is 1 Integer of ~4, "thiazole-based substituent" or "benzothiazole-based substituent" is "pyridine" of the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) The pyridyl group in the "substituent substituent" is substituted with a thiazolyl group or a benzothiazolyl group. At least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with deuterium. [化338]

ϕ It is further preferably an anthracene ring or a fluorene ring. The structure in this case can be referred to the description in the above formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ^{18 in each} formula can be Refer to the description in the formula (ETM-2-1) or formula (ETM-2-2). In addition, the above formula (ETM-2-1) or formula (ETM-2-2) has been described in a form in which two pyridine-based substituents are bonded, but these are substituted as thiazole-based substituents (or Benzothiazole-based substituents), two pyridine-based substituents (ie n=2) may be substituted by thiazole-based substituents (or benzothiazole-based substituents), or may be substituted by thiazole-based substituents (or benzothiazole-based substituents) Group) replaces any pyridine-based substituent and substitutes R ¹¹ to R ¹⁸ for another pyridine-based substituent (ie n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1) may be substituted by a thiazole-based substituent (or benzothiazole-based substituent) and substituted by R ¹¹ to R ¹⁸ Substituent."

These thiazole derivatives or benzothiazole derivatives can be produced using known materials and known synthesis methods.

<Sirole Derivative> The silole derivative is, for example, a compound represented by the following formula (ETM-15). The details are described in Japanese Patent Laid-Open No. 9-194487. [化339]

X and Y are independently an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an aryl group, and a heteroaryl group, and these may be substituted. For details of these groups, the description in the formula (2) can be cited, and further the description in the formula (ETM-7-2) can be cited. In addition, the alkenyloxy group and the alkynyloxy group are each a group in which the alkyl part of the alkoxy group is substituted with an alkenyl group or an alkynyl group. For details of the alkenyl group and alkynyl group, the above formula ( ETM-7-2). In addition, X and Y may be bonded to form a cycloalkyl ring (and a part of which becomes unsaturated). For details of the cycloalkyl ring, refer to the description of the cycloalkyl group in the above formula (2) .

R ¹ to R ⁴ are independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amine, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, or even Nitrogen, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfonyl, sulfanyl, silane Group, amine formyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate Ester, isothiocyanate, or cyano group, these may also be substituted by alkyl, cycloalkyl, aryl, or halogen, and may also form a condensed ring between adjacent substituents.

For details of the halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amine, aryl, heteroaryl, alkenyl and alkynyl groups in R ¹ to R ⁴ , the above formula ( 2).

About alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy in R ¹ to R ⁴ For details of the alkyl group, aryl group and alkoxy group in the group, the description in the above formula (2) can be cited.

Examples of the silane group include a group in which at least one of the three hydrogens of the silane group and the silane group is independently substituted by an aryl group, an alkyl group, or a cycloalkyl group, preferably a tri-substituted silane group. List: triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, etc. For details of the aryl group, alkyl group, and cycloalkyl group in these, the description in the above formula (2) can be cited.

The condensed ring formed between adjacent substituents is, for example, a conjugated or non-conjugated condensed ring formed between R ¹ and R ² , R ² and R ³ , R ³ and R ^4, and the like. These condensed rings may contain nitrogen atoms, oxygen atoms, and sulfur atoms in the ring structure, and may also be condensed with other rings.

Among them, it is preferred that when R ¹ and R ⁴ are phenyl groups, X and Y are not alkyl groups or phenyl groups. In addition, it is preferred that when R ¹ and R ⁴ are thienyl groups, X and Y do not simultaneously satisfy an alkyl group, and R ² and R ³ do not simultaneously satisfy an alkyl group, an aryl group, an alkenyl group, or R ² and R ³ The structure of a cycloalkyl group bonded to form a ring. In addition, it is preferable that when R ¹ and R ⁴ are silane groups, R ² , R ³ , X, and Y are each independently hydrogen or an alkyl group having 1 to 6 carbon atoms. In addition, in the case of a structure in which a benzene ring is condensed on R ¹ and R ² , it is preferable that X and Y are not an alkyl group or a phenyl group.

These thiazole derivatives can be produced using well-known raw materials and well-known synthesis methods.

<oxazoline derivative> The oxazoline derivative is, for example, a compound represented by the following formula (ETM-16). The details are described in International Publication No. 2017/014226. [化340]

式（L-1）中，X¹ ～X⁶ 分別獨立地為=CR⁶ -或=N-，X¹ ～X⁶ 中的至少兩個為=CR⁶ -，X¹ ～X⁶ 中的兩個=CR⁶ -中的R⁶ 為與ϕ或唑啉環鍵結的部位，其以外的=CR⁶ -中的R⁶ 為氫， 式（L-2）中，X⁷ ～X¹⁴ 分別獨立地為=CR⁶ -或=N-，X⁷ ～X¹⁴ 中的至少兩個為=CR⁶ -，X⁷ ～X¹⁴ 中的兩個=CR⁶ -中的R⁶ 為與ϕ或唑啉環鍵結的部位，其以外的=CR⁶ -中的R⁶ 為氫， L的至少一個氫亦可由碳數1～4的烷基、碳數5～10的環烷基、碳數6～10的芳基或碳數2～10的雜芳基取代， m為1～4的整數，當m為2～4時，由唑啉環與L形成的基團可相同亦可不同，而且， 式（ETM-16）所表示的化合物中的至少一個氫亦可由氘取代。In formula (ETM-16), ϕ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen It may also be substituted by a C 1-6 alkyl group, a C 3-14 cycloalkyl group, a C 6-18 aryl group or a C 2-18 heteroaryl group, and Y is independently -O-, -S- or >N-Ar, Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and at least one hydrogen of Ar may be selected from an alkyl group having 1 to 4 carbon atoms and a carbon atom having 5 to 5 carbon atoms 10 cycloalkyl group, C 6-12 aryl group or C 2-12 heteroaryl group substitution, R ¹ to R ⁵ are each independently hydrogen, C 1 to 4 alkyl group or C 5 to A cycloalkyl group of 10, wherein Ar in the >N-Ar and any one of the R ¹ to R ⁵ is a site bonded to L, and L is independently selected from the following formula (L-1 ) Represented by the divalent group and the divalent group represented by the following formula (L-2), [化341]

In formula (L-1), X ¹ to X ⁶ are independently =CR ⁶ -or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, two of X ¹ to X ⁶ R ⁶ in =CR ⁶ -is a site bonded to ϕ or an oxazoline ring, and R ⁶ in other = CR ⁶ -is hydrogen. In formula (L-2), X ⁷ to X ¹⁴ are independently The ground is =CR ⁶ -or =N-, at least two of X ⁷ ～X ¹⁴ are =CR ⁶ -, two of X ⁷ ～X ¹⁴ =CR ⁶ -R ^{6 in} is ϕ or oxazoline In the ring bonding site, R ⁶ in other =CR ⁶ -is hydrogen, and at least one hydrogen of L may be selected from C 1-4 alkyl groups, C 5-10 cycloalkyl groups, and C 6-6 carbon atoms. Substituted by an aryl group of 10 or a heteroaryl group having 2 to 10 carbon atoms, m is an integer of 1 to 4, when m is 2 to 4, the group formed by the oxazoline ring and L may be the same or different, and, At least one hydrogen in the compound represented by the formula (ETM-16) may be replaced by deuterium.

式（ETM-16-1）及式（ETM-16-2）中， ϕ為源自碳數6～40的芳香族烴的m價基團或源自碳數2～40的芳香族雜環的m價基團，ϕ的至少一個氫亦可由碳數1～6的烷基、碳數3～14的環烷基、碳數6～18的芳基或碳數2～18的雜芳基取代， 式（ETM-16-1）中，Y分別獨立地為-O-、-S-或＞N-Ar，Ar為碳數6～12的芳基或碳數2～12的雜芳基，Ar的至少一個氫亦可由碳數1～4的烷基、碳數5～10的環烷基、碳數6～12的芳基或碳數2～12的雜芳基取代， 式（ETM-16-1）中，R¹ ～R⁴ 分別獨立地為氫、碳數1～4的烷基或碳數5～10的環烷基，其中，R¹ 與R² 相同，另外R³ 與R⁴ 相同， 式（ETM-16-2）中，R¹ ～R⁵ 分別獨立地為氫、碳數1～4的烷基或碳數5～10的環烷基，其中，R¹ 與R² 相同，另外R³ 與R⁴ 相同， 式（ETM-16-1）及式（ETM-16-2）中， L分別獨立地選自由下述式（L-1）所表示的二價基團、及下述式（L-2）所表示的二價基團所組成的群組中， [化343]

式（L-1）中，X¹ ～X⁶ 分別獨立地為=CR⁶ -或=N-，X¹ ～X⁶ 中的至少兩個為=CR⁶ -，X¹ ～X⁶ 中的兩個=CR⁶ -中的R⁶ 為與ϕ或唑啉環鍵結的部位，其以外的=CR⁶ -中的R⁶ 為氫， 式（L-2）中，X⁷ ～X¹⁴ 分別獨立地為=CR⁶ -或=N-，X⁷ ～X¹⁴ 中的至少兩個為=CR⁶ -，X⁷ ～X¹⁴ 中的兩個=CR⁶ -中的R⁶ 為與ϕ或唑啉環鍵結的部位，其以外的=CR⁶ -中的R⁶ 為氫， L的至少一個氫亦可由碳數1～4的烷基、碳數5～10的環烷基、碳數6～10的芳基或碳數2～10的雜芳基取代， m為1～4的整數，當m為2～4時，由唑啉環與L形成的基團可相同亦可不同，而且， 式（ETM-16-1）或式（ETM-16-2）所表示的化合物中的至少一個氫亦可由氘取代。Specific oxazoline derivatives are compounds represented by the following general formula (ETM-16-1) or general formula (ETM-16-2). [化342]

In formulas (ETM-16-1) and (ETM-16-2), ϕ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an aromatic heterocyclic ring derived from 2 to 40 carbon atoms The m-valent group of ϕ, at least one hydrogen of ϕ may also be composed of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 2 to 18 carbon atoms. Substitution, in formula (ETM-16-1), Y is independently -O-, -S- or >N-Ar, Ar is C 6-12 aryl or C 2-12 heteroaryl , At least one hydrogen of Ar may also be substituted by a C 1-4 alkyl group, a C 5-10 cycloalkyl group, a C 6-12 aryl group or a C 2-12 heteroaryl group, formula (ETM -16-1), R ¹ to R ⁴ are independently hydrogen, C 1-4 alkyl or C 5-10 cycloalkyl, wherein R ¹ and R ^{2 are the} same, and R ³ is R ^{4 is the} same, and in formula (ETM-16-2), R ¹ to R ⁵ are independently hydrogen, C 1-4 alkyl or C 5-10 cycloalkyl, wherein R ¹ and R ^{2 is the} same, and R ³ and R ^{4 are the} same. In formula (ETM-16-1) and formula (ETM-16-2), L is independently selected from the divalent groups represented by the following formula (L-1) In the group consisting of a group, and a divalent group represented by the following formula (L-2), [化343]

In formula (L-1), X ¹ to X ⁶ are independently =CR ⁶ -or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, two of X ¹ to X ⁶ R ⁶ in =CR ⁶ -is a site bonded to ϕ or an oxazoline ring, and R ⁶ in other = CR ⁶ -is hydrogen. In formula (L-2), X ⁷ to X ¹⁴ are independently The ground is =CR ⁶ -or =N-, at least two of X ⁷ ～X ¹⁴ are =CR ⁶ -, two of X ⁷ ～X ¹⁴ =CR ⁶ -R ^{6 in} is ϕ or oxazoline In the ring bonding site, R ⁶ in other =CR ⁶ -is hydrogen, and at least one hydrogen of L may be selected from C 1-4 alkyl groups, C 5-10 cycloalkyl groups, and C 6-6 carbon atoms. Substituted by an aryl group of 10 or a heteroaryl group having 2 to 10 carbon atoms, m is an integer of 1 to 4, when m is 2 to 4, the group formed by the oxazoline ring and L may be the same or different, and, At least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[化345]

[化346]

所述式中的Z為＞CR₂ 、＞N-Ar、＞N-L、-O-或-S-，＞CR₂ 中的R分別獨立地為碳數1～4的烷基、碳數5～10的環烷基、碳數6～12的芳基或碳數2～12的雜芳基，R亦可相互鍵結而形成環，＞N-Ar中的Ar為碳數6～12的芳基或碳數2～12的雜芳基，＞N-L中的L為所述通式（ETM-16）、式（ETM-16-1）或通式（ETM-16-2）中的L。Preferably, ϕ is selected from a monovalent group represented by the following formula (ϕ1-1) to formula (ϕ1-18), and a divalent group represented by the following formula (ϕ2-1) to formula (ϕ2-34) Groups, trivalent groups represented by the following formula (ϕ3-1) to formula (ϕ3-3), and tetravalent groups represented by the following formula (ϕ4-1) to formula (ϕ4-2) In the group consisting of, at least one hydrogen of ϕ may also be composed of a C 1-6 alkyl group, a C 3-14 cycloalkyl group, a C 6-18 aryl group or a C 2-18 heteroaryl group replace. [化344]

[化345]

[化346]

Z in the formula is >CR ₂ , >N-Ar, >NL, -O- or -S-, and R in >CR ₂ is independently an alkyl group having 1 to 4 carbon atoms and 5 to 5 carbon atoms 10 cycloalkyl group, C 6-12 aryl group or C 2-12 heteroaryl group, R may also be bonded to each other to form a ring,> Ar in N-Ar is C 6-12 aryl Group or heteroaryl group having 2 to 12 carbon atoms, L in >NL is L in the above general formula (ETM-16), formula (ETM-16-1) or general formula (ETM-16-2).

Preferably, L is selected from benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline ), and the divalent group of the ring in the group consisting of pyridine, at least one hydrogen of L may also be a C 1-4 alkyl group, a C 5-10 cycloalkyl group, a C 6-10 Substituted by an aryl group or a heteroaryl group having 2 to 10 carbon atoms.

Preferably, Ar in Y>Z>N-Ar is selected from phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl , Naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pyridinyl, at least one hydrogen of Ar in Y>N-Ar may also be composed of It is substituted with a C 1-4 alkyl group, a C 5-10 cycloalkyl group or a C 6-10 aryl group.

Preferably, R ¹ to R ⁴ are independently hydrogen, a C 1-4 alkyl group or a C 5-10 cycloalkyl group, wherein R ¹ and R ^{2 are the} same and R ³ and R ^{4 are the} same, In addition, all of R ¹ to R ⁴ do not simultaneously become hydrogen, and m is 1 or 2, and when m is 2, the group formed by the oxazoline ring and L is the same.

[化348]

Specific examples of oxazoline derivatives include the following compounds. In addition, "Me" in the structural formula represents a methyl group. [化347]

[化348]

L為選自由苯、吡啶、吡嗪、嘧啶、噠嗪、及三嗪所組成的群組中的環的二價基團，L的至少一個氫亦可由碳數1～5的烷基、碳數5～10的環烷基、碳數6～10的芳基或碳數2～14的雜芳基取代， 作為Y的＞N-Ar中的Ar選自由苯基、吡啶基、吡嗪基、嘧啶基、噠嗪基、及三嗪基所組成的群組中，該Ar的至少一個氫亦可由碳數1～5的烷基、碳數5～10的環烷基或碳數6～10的芳基取代， R¹ ～R⁴ 分別獨立地為氫、碳數1～4的烷基或碳數5～10的環烷基，其中，R¹ 與R² 相同，R³ 與R⁴ 相同，另外R¹ ～R⁴ 的全部不會同時成為氫，而且， m為2，由唑啉環與L形成的基團相同。More preferably, ϕ is selected from divalent groups represented by the following formula (ϕ2-1), formula (ϕ2-31), formula (ϕ2-32), formula (ϕ2-33) and formula (ϕ2-34) In the group formed, at least one hydrogen of ϕ may also be substituted by an aryl group having 6 to 18 carbon atoms, [Chem. 349]

L is a bivalent group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L may be selected from the group consisting of C 1-5 alkyl, carbon Substitution of cycloalkyl group having 5-10 carbon atoms, aryl group having 6-10 carbon atoms, or heteroaryl group having 2-14 carbon atoms. Ar in N>Ar as Y is selected from phenyl, pyridyl, pyrazinyl In the group consisting of pyrimidinyl, pyridazinyl, and triazinyl, at least one hydrogen of the Ar may also be an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or 6 to 6 carbon atoms. Aryl substitution of 10, R ¹ to R ⁴ are each independently hydrogen, C 1-4 alkyl or C 5-10 cycloalkyl, wherein R ¹ and R ^{2 are the} same, R ³ and R ⁴ It is the same, and all of R ¹ to R ⁴ do not simultaneously become hydrogen, and m is 2, and the group formed by the oxazoline ring and L is the same.

As other specific examples of the oxazoline derivatives, for example, the following compounds may be mentioned. In addition, "Me" in the structural formula represents a methyl group. [化350]

For the details of the alkyl group, cycloalkyl group, aryl group or heteroaryl group in the respective formulas specifying the oxazoline derivative, the description in the general formula (2) can be cited.

This oxazoline derivative can be produced using well-known raw materials and well-known synthesis methods.

The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As long as the reducing substance is a substance having a certain degree of reduction, various substances can be used. For example, selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, and alkaline earth metals Oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one of them.

Examples of preferred reducing materials include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV). Or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV to 2.5 eV) or Ba (work function 2.52 eV), especially those with a work function 2.9 eV or less. Among these, the more preferable reducing substance is the alkali metal of K, Rb or Cs, further preferably Rb or Cs, and most preferably Cs. The reduction ability of these alkali metals is particularly high, and by adding a relatively small amount of these alkali metals to the material forming the electron transport layer or the electron injection layer, it is possible to improve the emission luminance of the organic EL device or extend the life. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of the above-mentioned alkali metals is also preferable, and a combination containing Cs is particularly preferable, for example, Cs and Na, Cs and K, Cs and Rb, Or a combination of Cs and Na and K. By including Cs, the reduction ability can be efficiently exhibited, and by adding to the material forming the electron transport layer or the electron injection layer, the emission luminance in the organic EL device can be improved or the life span can be increased.

<Cathode in organic electroluminescent elements> The cathode 108 functions to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same material as that for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium or alloys of these (magnesium-silver alloy) are preferred , Magnesium-indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum, etc.). In order to improve the efficiency of electron injection to improve device characteristics, it is effective to use lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals. However, these low work function metals are usually unstable in the atmosphere in most cases. In order to improve this aspect, for example, a method of doping a small amount of lithium, cesium, or magnesium into an organic layer and using an electrode with high stability is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. But it is not limited to these.

Furthermore, the following preferred examples may be mentioned: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, silicon dioxide, titanium dioxide, and nitrogen are used to protect the electrodes Inorganic materials such as silicon oxide, polyvinyl alcohol, vinyl chloride, and hydrocarbon-based polymer compounds are laminated. The manufacturing method of these electrodes is also not particularly limited as long as it can achieve conduction through resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

<Adhesives that can be used in each layer> The materials used in the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can be formed separately, and can also be dispersed in polyvinyl chloride and polycarbonate as a polymer binder , Polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, poly ash, polyphenylene oxide (polyphenylene oxide), polybutadiene, hydrocarbon resin, Soluble in ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile butadiene styrene (ABS) resin, polyurethane resin, etc. Resin, or curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. are used.

<Manufacturing method of organic electroluminescent element> Each layer constituting the organic EL element can be formed by using vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular deposition method, printing method, spin coating method or casting method, The coating method and the like form the materials that should constitute the layers into thin films. The film thickness of each layer formed in the above-mentioned manner is not particularly limited and can be appropriately set according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. In the case of using a vapor deposition method for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystal structure and the associated structure of the film, and the like. The deposition conditions are usually preferably at a boat heating temperature of +50°C to +400°C, a vacuum degree of 10 ^-6 Pa to 10 ^-3 Pa, a deposition rate of 0.01 nm/sec to 50 nm/sec, and a substrate temperature of -150°C It is appropriately set within a range of ~+300°C and a film thickness of 2 nm to 5 μm.

Then, as an example of a method of manufacturing an organic EL element, an organic EL including an anode/hole injection layer/hole transport layer/a light-emitting layer including a host material and a dopant material/electron transport layer/electron injection layer/cathode The manufacturing method of the component will be described. After forming an anode on a suitable substrate by forming a thin film of an anode material using a vapor deposition method or the like, a thin film of a hole injection layer and a hole transport layer is formed on the anode. On this, the host material and the dopant material are co-evaporated to form a thin film as a light-emitting layer, and an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film containing a cathode material is formed by evaporation or the like As a cathode, thereby obtaining the target organic EL element. In addition, in the production of the organic EL device, the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.

In the case of applying a DC voltage to the organic EL element obtained as described above, it is sufficient to apply the anode as the polarity of + and the cathode as the polarity of -, if a voltage of about 2 V to 40 V is applied, Luminescence was observed from the transparent or translucent electrode side (anode or cathode, and both). In addition, the organic EL element emits light even when pulse current or alternating current is applied. Furthermore, the waveform of the applied AC may be arbitrary.

<Application examples of organic electroluminescent elements> In addition, the present invention can also be applied to a display device provided with an organic EL element, a lighting device provided with an organic EL element, or the like. A display device or a lighting device provided with an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known drive device, and known drives such as DC drive, pulse drive, and AC drive can be appropriately used Method to drive.

Examples of the display device include panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescence (EL) displays, etc. (for example, refer to Japanese Patent Laid-Open No. 10-335066, Japanese Patent Laid-Open No. 2003- 321546, Japanese Patent Laid-Open No. 2004-281086, etc.). In addition, examples of the display method of the display include at least one of a matrix method and a segment method. Furthermore, matrix display and segmented display can also coexist in the same panel.

In the matrix, pixels for display are two-dimensionally arranged in a lattice or mosaic, etc., and characters or images are displayed using a set of pixels. The shape or size of the pixel is determined according to the application. For example, in the display of images and characters on personal computers, monitors, and televisions, pixels with a rectangular shape with a side of 300 μm or less are generally used. In addition, in the case of large displays such as display panels, one side is used with a mm level Pixels. In the case of monochrome display, it is only necessary to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are displayed side by side. In this case, a delta type and a stripe type are typical. Moreover, as a driving method of the matrix, it may be any of a line-sequential driving method or an active matrix. The line-sequential drive has the advantage of simple structure, but in consideration of the operating characteristics, sometimes the active matrix is better, so the drive method also needs to be used according to the purpose.

In the segmentation method (type), a pattern is formed in a manner of displaying information determined in advance, and the determined area is illuminated. For example, the time or temperature display on a digital clock or thermometer, the operating status display of audio equipment, induction cookers, etc., and the panel display of automobiles, etc. can be cited.

Examples of the lighting device include a lighting device such as indoor lighting and a backlight of a liquid crystal display device (for example, refer to Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, and Japanese Patent Japanese Patent Laid-Open No. 2004-119211, etc.). The backlight is mainly used to improve the visibility of a display device that does not perform self-luminescence, and is used in liquid crystal display devices, clocks, audio devices, automobile panels, display panels, and signs. In particular, as a backlight for a liquid crystal display device, in which thinning is a problem for personal computers, if the conventional method is difficult to reduce the thickness due to the inclusion of fluorescent lamps or light guide plates, the backlight using the light-emitting element of this embodiment is used It has the characteristics of thin and light weight.

In addition, we are actively researching the application of multi-colorization technology based on color conversion methods to liquid crystal displays, organic EL displays, and lighting. The so-called color conversion is to convert the light emitted from the luminous body into light with a longer wavelength (wavelength conversion), for example, to convert blue light into green light or red light. By filming the composition having the wavelength conversion function, for example, in combination with a blue light source, the three primary colors of blue, green, and red can be extracted from the blue light source, that is, white light can be extracted. A white light source formed by combining such a blue light source with a film having a wavelength conversion function is used as a light source unit, and is combined with a liquid crystal driving part and a color filter, thereby making it possible to produce a full color display. In addition, if there is no liquid crystal driving part, it can be directly used as a white light source, for example, as a white light source for light-emitting diode (LED) lighting. In addition, by using a blue organic EL element as a light source and combining it with a film converted to green and red, a full-color organic EL display without a metal mask can be produced. Furthermore, by using blue micro-LEDs as light sources and using them in combination with green and red films, it is possible to produce low-cost full-color micro-LED displays. The polycyclic aromatic compound represented by the general formula (1) is useful as a fluorescent material that imparts blue light emission or green light emission with high color purity by excitation light, and can also be used as having such a wavelength conversion function s material. Specifically, the polycyclic aromatic compound of formula (1) can be used as, for example, a light having a wavelength of 300 nm to 449 nm and a narrow half-value width (below 25 nm or less) having a maximum value at 450 nm to 500 nm. It is used for wavelength conversion materials that emit blue light below 20 nm. In addition, for example, it can be used as a wavelength conversion material that converts light with a wavelength of 300 nm to 499 nm into green light emission with a narrow half-value width (25 nm or less, and further 20 nm or less) having a maximum value at 500 nm to 570 nm. To use. [Example]

Hereinafter, in order to explain the present invention in more detail, examples of an organic EL device using the compound of the present invention are shown, but the present invention is not limited to these examples.

Synthesis Example (D-1) Compound (2-1A-114): (16,16,19,19-tetramethyl-N ² ,N ² ,N ¹⁴ ,N ¹⁴ -tetraphenyl-16,19-di Hydrogen-6,10-dioxa-17b-boraindeno[1,2-b]indeno[1',2':6,7]naphtho[1,2,3-fg]anthracene-2 ,14-diamine) Synthesis [Chem351]

Under a nitrogen atmosphere, the flask containing methyl 4-methoxysalicylate (50.0 g) and pyridine (dehydration) (350 ml) was cooled in an ice bath. Then, trifluoromethanesulfonic anhydride (154.9 g) was added dropwise to the solution. After the dropwise addition, the ice bath was removed and stirred at room temperature for 2 hours, and water was added to stop the reaction. After adding toluene to perform liquid separation, the silica gel short-path column (dissolved liquid: toluene) was used for purification, thereby obtaining 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoic acid Methyl ester (86.0 g). [化352]

Under a nitrogen atmosphere, to 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoic acid methyl ester (23.0 g), (4-(diphenylamino)phenyl ) Pd(PPh ₃ ) ₄ (2.5 g) was added to the suspension solution of boric acid (25.4 g), tripotassium phosphate (31.1 g), toluene (184 ml), ethanol (27.6 ml) and water (27.6 ml), and Stir at reflux temperature for 3 hours. The reaction liquid was cooled to room temperature, water and toluene were added to perform liquid separation, and the solvent of the organic layer was distilled off under reduced pressure. The obtained solid was refined using a silicone column (dissolved solution: heptane/toluene mixed solvent) to obtain 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl Methyl]-2-carboxylate (29.7 g). At this time, referring to the "Introduction to Organic Chemistry Experiments (1)-Substance Treatment Method and Separation and Refining Method -" published by Tongjin Co., Ltd., page 94, slowly increase the ratio of toluene in the dissolution solution to achieve the goal The substance dissolves. [化353]

In a nitrogen atmosphere, use a water bath to dissolve 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylic acid methyl ester (11.4 g) in tetrahydrofuran (THF (Tetrahydrofuran), 111.4 ml) solution was cooled, and a THF solution (1.0 M, 295 ml) of methylmagnesium bromide was added dropwise to the solution. After the dropwise addition, the water bath was removed and the temperature was raised to reflux temperature, and the mixture was stirred for 4 hours. After that, it was cooled with an ice bath, an ammonium chloride aqueous solution was added to stop the reaction, and ethyl acetate was added to perform liquid separation, and then the solvent was distilled off under reduced pressure. The obtained solid was purified using a silicone column (dissolved solution: toluene) to obtain 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]- 2-yl)propane-2-ol (8.3 g). [化354]

Under a nitrogen atmosphere, and at reflux temperature, put 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propane- The flask of 2-alcohol (27.0 g), TAYCACURE-15 (trade name, Tayca Co., Ltd.) (13.5 g) and toluene (162 ml) as a catalyst was stirred for 2 hours. The reaction solution was cooled to room temperature, and passed through a silica gel short-path column (dissolved solution: toluene), thereby removing TAYCACURE-15, and then the solvent was distilled off under reduced pressure to obtain 6-methyl Oxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.8 g). [化355]

Under a nitrogen atmosphere and at reflux temperature, put 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.0 g), pyridine The flask of hydrochloride (36.9 g) and N-Methyl-2-Pyrrolidone (NMP) (22.5 ml) was stirred for 6 hours. The reaction liquid was cooled to room temperature, and water and ethyl acetate were added to perform liquid separation. After distilling off the solvent under reduced pressure, the silica gel column (dissolving solution: toluene) was used for purification to obtain 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (22.0 g). [化356]

Under a nitrogen atmosphere, and at reflux temperature, 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (14.1 g), 2-bromo-1 , 3-Difluorobenzene (3.6 g), potassium carbonate (12.9 g) and NMP (30 ml) flasks were heated and stirred for 5 hours. After the reaction was stopped, the reaction liquid was cooled to room temperature, water was added, and the deposited precipitate was extracted by suction filtration. After sequentially cleaning the obtained precipitate with water and methanol, it was purified using a silica gel column (eluent: heptane/toluene mixed solvent) to obtain 6,6'-((2-bromo-1,3- Phenyl)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (12.6 g). At this time, the ratio of toluene in the dissolved solution is gradually increased to elute the target substance. [化357]

Under a nitrogen atmosphere, place 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl (9-9H-fluoren-2-amine) (11.0 g) and xylene (60.5 ml) were cooled to -40°C, and a 2.6 M solution of n-butyl lithium in hexane (5.1 ml) was added dropwise. After the dropwise addition, the mixture was stirred at -40°C for 0.5 hours, and then heated to 60°C and stirred for 3 hours. After that, the reaction solution was decompressed to distill off the low-boiling components, then cooled to -40°C and boron tribromide (4.3 g) was added. After warming to room temperature and stirring for 0.5 hours, it was cooled to 0°C and N-ethyl-N-isopropylpropan-2-amine (3.8 g) was added, and the mixture was heated and stirred at 125°C for 8 hours. The reaction liquid was cooled to room temperature, and after adding sodium acetate aqueous solution to stop the reaction, toluene was added to perform liquid separation. The organic layer was refined by using a silicone short-range column, a silicone column (dissolved solution: heptane/toluene = 4/1 (mixed solution of volume ratio)), and an activated carbon column (dissolved solution: toluene) in turn. 1.2 g of compound (2-1A-114) was obtained. [化358]

The structure of the obtained compound (2-1A-114) was confirmed by nuclear magnetic resonance (NMR) measurement. ¹ H-NMR (400 MHz, CDCl ₃ ): 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).

In addition, the compound (2-1A-114) was also synthesized from the compound (XD-10) using the same method as the synthesis example (D-10) described below and the following procedure. [化359]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (400 MHz, CDCl ₃ ): 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).

Synthesis Example (D-2) <Synthesis of Compound (2-1A-54)> Under a nitrogen atmosphere and at 90°C, put N ¹ ,N ¹ ,N ³ -triphenylbenzene-1,3 -Diamine (51.7 g), 1-bromo-2,3-dichlorobenzene (35.0 g), Pd-132 (0.6 g), NaOtBu (22.4 g) and xylene (350 ml) flasks were heated and stirred for 2 hours . After cooling the reaction liquid to room temperature, water and ethyl acetate were added to perform liquid separation. Then, the silica gel column chromatography (dissolved solution: toluene/heptane=5/5 (volume ratio)) was used for purification, thereby obtaining N ¹ -(2,3-dichlorophenyl)-N ¹ ,N ³ ,N ³ -triphenylbenzene-1,3-diamine (61.8 g). [化360]

Under a nitrogen atmosphere and at 120°C, N ¹ -(2,3-dichlorophenyl)-N ¹ ,N ³ ,N ³ -triphenylbenzene-1,3-diamine (15.0 g), bis([1,1'-biphenyl]-4-yl)amine (10.0 g), Pd-132 (0.2 g), NaOtBu (4.5 g) and xylene (70 ml) are heated and stirred 1 hour. After cooling the reaction liquid to room temperature, water and toluene were added to perform liquid separation. Then, the silica gel short-range column (dissolved solution: toluene) was used for purification. The obtained oily substance was reprecipitated with ethyl acetate/heptane mixed solvent, thereby obtaining N ¹ ,N ¹ -bis([1,1′-biphenyl] as the following compound (XD-1) -4-yl)-2-chloro-N ³ -(3-(diphenylamino)phenyl)-N ³ -phenylbenzene-1,3-diamine (18.5 g). [化361]

Under a nitrogen atmosphere, while cooling with an ice bath, put N ¹ ,N ¹ -bis([1,1′-biphenyl]-4-yl)- as the following compound (XD-1) on the side 2-chloro-N ³ -(3-(diphenylamino)phenyl)-N ³ -phenylbenzene-1,3-diamine (18.0 g) and tert-butylbenzene (130 ml) flask Add 1.7 M of a third butyllithium pentane solution (27.6 ml). After the dropwise addition was completed, the temperature was raised to 60°C and the mixture was stirred for 3 hours, and the component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50°C and add boron tribromide (4.5 ml), warm to room temperature and stir for 0.5 hour. Thereafter, it was cooled again with an ice bath and N,N-diisopropylethylamine (8.2 ml) was added. After stirring at room temperature until the end of heat generation, the temperature was raised to 120°C and the mixture was heated and stirred for 1 hour. The reaction liquid was cooled to room temperature, and sodium acetate aqueous solution cooled with an ice bath and ethyl acetate were sequentially added to perform liquid separation. Then, it was dissolved in heated chlorobenzene and purified using a silica gel short-path column (dissolved liquid: heated toluene). Furthermore, it recrystallized from chlorobenzene, and the compound (2-1A-54) (3.0 g) was obtained. [化362]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (400 MHz, CDCl ₃ ): δ = 9.09 (m, 1H), 8.79 (d, 1H), 7.93 (d, 2H), 7.75 (d, 2H), 7.72 (d, 2H), 7.67 (m, 1H), 7.52 (t, 2H), 7.40-7.50 (m, 7H), 7.27-7.38 (m, 2H), 7.19-7.26 (m, 7H), 7.11 (m, 4H), 7.03 (t , 2H), 6.96 (dd, 1H), 6.90 (d, 1H), 6.21 (m, 2H), 6.12 (d, 1H).

Synthesis Example (D-3) <Synthesis of Compound (2-1A-7)> Using the same method as Synthesis Example (D-2), Compound (2-1A-7) was synthesized from the following compound (XD-2) . [化363]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (500 MHz, CDCl ₃ ): 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).

Synthesis Example (D-4) <Synthesis of Compound (2-1A-69)> Using the same method as Synthesis Example (D-2), compound (2-1A-69) was synthesized from the following compound (XD-3) . [化364]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 1.20 (s, 9H), 1.37 (s, 18H), 1.46 (s, 9H), 1.47 (s, 9H), 2.18 (s, 3H), 5.97 (s, 1H), 6.08 (d, 1H), 6.63 (d, 1H), 6.66 (d, 1H), 7.20 (d, 2H), 7.27 (d, 2H), 7.32 (dd, 1H), 7.48 (dd, 1H ), 7.61 (t, 1H), 7.67 (d, 2H), 8.84 (d, 1H), 8.94 (d, 1H).

Synthesis Example (D-5) <Synthesis of Compound (2-1A-202)> Using the same method as Synthesis Example (D-2), Compound (2-1A-202) was synthesized from the following compound (XD-4) . [化365]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR: δ = 1.1 (s, 9H), 1.4 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 1.5 (s, 9H), 2.2 (s, 3H), 5.9 (s, 1H), 6.1 (s, 1H), 6.7 (m, 2H), 7.0 (d, 2H), 7.1 (d, 2H), 7.2 (d, 1H), 7.3 (m, 2H), 7.4 ( m, 1H), 7.5 (m, 1H), 7.6 (dd, 1H), 7.7 (m, 3H), 8.9 (d, 1H), 8.9 (d, 1H).

Synthesis Example (D-6) <Synthesis of Compound (2-1A-215)> Using the same method as Synthesis Example (D-2), Compound (2-1A-215) was synthesized from the following compound (XD-5) . [化366]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 1.21 (s, 18H), 1.36 (s, 36H), 1.48-1.66 (m, 12H), 1.89 (s, 3H), 6.18 (s, 2H), 6.78 ( s, 2H), 7.22 (d, 4H), 7.25-7.28 (m, 2H), 7.59 (t, 2H), 8.86 (d, 2H)

Synthesis Example (D-7) <Synthesis of Compound (2-1A-201)> Using the same method as Synthesis Example (D-2), Compound (2-1A-201) was synthesized from the following compound (XD-6) . [化367]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 0.62 (t, 6H), 0.75 (t, 6H), 1.29 (s, 12H), 1.43 (s, 12H), 1.62 (q, 4H), 1.75 (q, 4H), 5.63 (s, 2H), 6.70 (d, 2H), 6.86 (m, 2H), 6.92 (d, 4H), 7.05 (m, 4H), 7.14 (d, 4H), 7.38 (m, 6H ), 8.85 (d, 2H).

Synthesis Example (D-8) <Synthesis of Compound (2-2A-218)> Using the same method as Synthesis Example (D-2), compound (2-2A-218) was synthesized from the following compound (XD-7) . [化368]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 1.32 (s, 18H), 1.46 (s, 18H), 5.55 (s, 2H)

Synthesis Example (D-9) <Synthesis of Compound (2-1A-206)> Using the same method as Synthesis Example (D-2), Compound (2-1A-206) was synthesized from the following compound (XD-8) . [化369]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 1.08 (s, 6H), 1.27 (s, 6H), 1.42 (s, 6H), 1.46 (s, 9H), 1.47 (s, 9H), 1.48 (s, 6H), 1.69-1.81 (m, 8H), 2.18 (s, 3H), 5.97 (s, 1H), 6.06 (s, 1H), 6.52 (s, 1H), 6.67 (d, 1H), 7.08 (dd , 1H), 7.25-7.29 (m, 3H), 7.48 (dd, 1H), 7.59 (d, 1H), 7.67 (d, 2H), 8.89 (s, 1H), 8.97 (d, 1H).

Synthesis example (D-10) <Synthesis of Compound (X-D-9)> Under a nitrogen atmosphere, the flask containing intermediate 1 (15 g) and toluene (300 ml) was heated to 70°C to completely dissolve intermediate 1. After the flask was cooled to -20°C, a mixed solution of tetramethylethylenediamine (20.8 g) and 1.00 M of cyclohexane and n-hexane of second butyllithium (89 ml) was added. After warming to 0°C and stirring for 3 hours, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (33.3 g) was added and carried out 1 Hour reflux. Water and toluene were added to perform liquid separation, and the solvent of the organic layer was distilled off under reduced pressure. The obtained solid was washed with Solmix A-11 (trade name: Japan Alcohol Co., Ltd.), dissolved in toluene, and left at 0°C for 1 hour. The deposited precipitate was filtered and separated, and the filtrate was passed into a silica gel column (dissolved solution: toluene/heptane=1/5 mixed solvent (capacity ratio)). After distilling off the solvent under reduced pressure, reprecipitation was performed using a mixed solvent of ethyl acetate and Solmix A-11, thereby obtaining the following compound (X-D-9) (9.5 g) in the form of a white solid

[化370]

<Synthesis of Compound (2-1A-18)> Under a nitrogen atmosphere and at 120°C, compound (XD-9) (8.7 g), aluminum chloride (12.5 g), N,N-diisopropylethylamine (N,N-diisopropylethylamine, DIPEA) (6.0 g) and chlorobenzene (44 ml) were stirred for 1 hour. The reaction mixture cooled to room temperature was poured into ice water (200 ml), and toluene was added to extract the organic layer. The solid obtained by distilling off the solvent of the organic layer under reduced pressure was dissolved in chloroform, and passed into a silica gel short-path column (dissolved solution: toluene). The crude refined product obtained by distilling off the solvent under reduced pressure was reprecipitated with cyclopentyl methyl ether and Solmix A-11, thereby obtaining the compound (2-1A-18) as a yellow solid (6.2 g, yield 70%).

[化371]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (400 MHz, CDCl ₃ ): δ = 8.95 (d, 2H), 7.45 (dd, 6H), 7.13 (d, 4H), 7.08-7.04 (m, 4H), 6.95-6.88 (m, 6H), 6.75 (d, 2H), 5.56 (s, 2H), 1.46 (s, 18H), 1.33 (s, 18H).

Synthesis Example (D-11) <Synthesis of Compound (2-1A-155)> Under a nitrogen atmosphere and at reflux temperature, 7-(diphenylamino)-9,9'-dimethyl The flask of N-9H-fluoren-3-ol (9.0 g), 1,2-dibromo-3-fluorobenzene (7.9 g), potassium carbonate (8.2 g) and NMP (45 ml) was heated and stirred for 2 hours. After the reaction was stopped, the reaction liquid was cooled to room temperature, water was added, and the deposited precipitate was extracted by suction filtration. After sequentially cleaning the obtained precipitate with water and Solmix, it was purified by silica gel column chromatography (dissolved solution: heptane/toluene=3/1 (volume ratio)), thereby 12.4 g of 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine was obtained (yield: 84.8%). [化372]

Under a nitrogen atmosphere, and at 80 ℃ will be placed 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2- Amine (10.0 g), di([1,1'-biphenyl]-4-yl)amine (5.3 g), palladium acetate (0.15 g), dicyclohexyl (2',6'-diisopropoxy -A flask of [1,1'-biphenyl]-2-yl)phosphane (0.61 g), NaOtBu (2.4 g) and toluene (35 ml) was heated for 6 hours. After cooling the reaction liquid to room temperature, water and toluene were added to perform liquid separation. Furthermore, it was purified by silica gel column chromatography (dissolved solution: heptane/toluene=2/1 (volume ratio)) to obtain 6-(2-bromo-3-(di([1,1'-linked Benzene]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine 7.4 g (yield: 53.1%). [化373]

Under a nitrogen atmosphere, combine 6-(2-bromo-3-(bis([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N, Put N-diphenyl-9H-fluoren-2-amine (7.9 g) and tetrahydrofuran (42 ml) in a flask, cool to -40°C, and add 1.6 M n-butyllithium hexane solution (6 ml). After the dropwise addition was completed, after stirring at this temperature for 1 hour, trimethylborate (1.7 g) was added. Warm to room temperature and stir for 2 hours. Thereafter, water (100 ml) was slowly added dropwise. Then, the reaction mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the desiccant was removed to obtain dimethyl(2-(di([1,1'-biphenyl]-4-yl)amine Group)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronic acid ester 7.0 g (yield: 100% ). [化374]

Under a nitrogen atmosphere, combine dimethyl(2-(bis([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9 -Dimethyl-9H-fluoren-3-yl)oxy)phenyl)boronic acid ester (6.5 g), aluminum chloride (10.3 g) and toluene (39 ml) were put into the flask and stirred for 3 minutes . Thereafter, N-ethyl-N-isopropylpropane-2-amine (2.5 g) was added, and the mixture was heated and stirred at 105°C for 1 hour. After heating, the reaction solution was cooled, and ice water (20 ml) was added. After that, the reaction mixture was extracted with toluene, followed by a short-range silica gel column (dissolved solution: toluene) and a silica gel column chromatography (dissolved solution: heptane/toluene=3/1 (volume ratio)) against organic After the layer was purified, reprecipitation was performed using heptane, and further purification was performed using a column (solvent: heptane/toluene=1/1 (capacity ratio)) using NH2 silica gel. Finally, sublimation purification was performed to obtain compound (2-1A-155) (0.74 g, yield: 12.3%). [化375]

The structure of the obtained compound was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 9.22 (s, 1H), 8.78 (s, 1H), 7.96 (d, 2H), 7.80～7.77 (m, 6H), 7.71 (d, 1H), 7.59～ 7.44 (m, 8H), 7.39 (t, 1H), 7.32～7.29 (m, 4H), 7.71 (d, 1H), 7.19 (dd, 4H), 7.12～7.06 (m, 4H), 7.00 (d, 1H), 6.45 (d, 1H), 1.57 (s, 6H).

Synthesis Example (D-12) <Synthesis of Compound (2-1A-254)> Using the same method as Synthesis Example (D-2), Compound (2-1A-254) was synthesized from the following compound (XD-11) . Electron ionization mass spectrometry (EI-MS): m/z=756. [化376]

Synthesis Example (D-13) <Synthesis of Compound (2-1A-263)> Using the same method as Synthesis Example (D-2), Compound (2-1A-263) was synthesized from the following compound (XD-12) . EI-MS: m/z=790. [化377]

Synthesis Example (H-1) <Synthesis of Compound (3-45) and Compound (3-2-43)> (1) Synthesis of [2,2'-binaphthalene]-7-yl trifluoromethanesulfonate Under a nitrogen atmosphere, 31.8 g of naphthalene-2,7-diylbis(trifluoromethanesulfonate), 12.9 g of 2-naphthaleneboronic acid, and palladium(0) tetrakis(triphenylphosphine)(Pd(PPh ₃ ) ₄ ) 1.73 g, potassium phosphate 31.8 g, and a mixed solvent of tetrahydrofuran (THF) and isopropyl alcohol (IPA) 300 ml (THF/IPA=4/1 (volume ratio)) are put into the flask, and refluxed for 5 hours . After heating, the reaction solution was cooled, water was added, and the target component was extracted with toluene. Furthermore, the crude product obtained by concentrating the organic layer under reduced pressure was subjected to column refining (solvent: heptane) using silicone rubber to obtain [2,2'-binaphthalene]-7-yl trifluoromethanesulfonate 13.4 g ( Yield: 44%).

[化378]

(2) Synthesis of compound (3-45) Under a nitrogen atmosphere, [2,2'-binaphthalene]-7-yl trifluoromethanesulfonate 10 g, (10-phenylanthracene-9-yl) Boric acid 7.4 g, tetrakis (triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) 0.57 g, potassium phosphate 10.55 g, and mixed solvent of toluene and ethanol 100 ml (toluene/ethanol = 4/1 (capacity Ratio)) Put into the flask and stir for 5 minutes. Thereafter, 10 ml of water was added and refluxed for 3 hours. After heating, the reaction solution was cooled, 60 ml of methanol was added, and Shendian was filtered. Furthermore, Shendian was washed with methanol and water to obtain 6.6 g (yield: 53%) of compound (3-45).

[化379]

(3) Synthesis of compound (3-2-43) Under an argon atmosphere, the compound (3-45) (1 g), 5% platinum-carbon (5%Pt/C, 300 mg), deuterium (40 mL), cyclohexane (cHex, 20 mL), And isopropanol (IPA, 5 mL) was put into the flask and heated at 100°C. After the reaction, water and chloroform were added and subjected to liquid extraction, and the organic layer was dried with magnesium sulfate and filtered, and then the crude product obtained by concentrating the organic layer was recrystallized to obtain the target compound (3-2-43) . EI-MS: m/z=532.

[化380]

Synthesis Example (H-2) <Synthesis of compound (3-559) and compound (3-2-593)> The following compound (3-559) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-593) was synthesized from the following compound (3-559). EI-MS: m/z=532.

[化381]

Synthesis Example (H-3) <Synthesis of Compound (3-562) and Compound (3-2-597)> The following compound (3-562) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-597) was synthesized from the following compound (3-562). EI-MS: m/z=480.

[化382]

Synthesis Example (H-4) <Synthesis of Compound (3-560) and Compound (3-2-596)> The following compound (3-560) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-596) was synthesized from the following compound (3-560). EI-MS: m/z=480.

[化383]

Synthesis example (H-5) <Synthesis of Compound (3-571) and Compound (3-2-600)> The following compound (3-571) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-600) was synthesized from the following compound (3-571). EI-MS: m/z=440.

[化384]

Synthesis example (H-6) <Synthesis of Compound (3-555) and Compound (3-2-589)> The following compound (3-555) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-589) was synthesized from the following compound (3-555). EI-MS: m/z=492.

[化385]

Synthesis Example (H-7) <Synthesis of Compound (3-629) and Compound (3-2-656)> The following compound (3-629) was synthesized using the same method as Synthesis Example (H-1), and the following compound (3-2-656) was synthesized from the following compound (3-629). EI-MS: m/z=520.

[化386]

Synthesis Example (H-8) <Synthesis of Compound (3-1-1)> In a nitrogen atmosphere, 15 g of 2-bromo-1,4-dichlorobenzene, (10-phenylanthracene-9-yl) Boric acid 19.8 g, tetrakis(triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) 1.53 g, potassium phosphate 28.19 g, and mixed solvent of toluene and ethanol 260 ml (toluene/ethanol=4/1 (capacity Ratio)) Put into the flask and stir for 5 minutes. Thereafter, 26 ml of water was added and refluxed for 15 hours. After heating, the reaction solution was cooled, and 50 ml of water was added. After that, the reaction mixture was extracted with toluene, dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained crude product was subjected to short column purification using silica gel (solvent: toluene). Furthermore, reprecipitation was carried out with methanol to obtain 18 g of 9-(2,5-dichlorophenyl)-10-phenylanthracene as an intermediate compound (yield: 68%).

[化387]

Under a nitrogen atmosphere, 5 g of 9-(2,5-dichlorophenyl)-10-phenylanthracene, 4.55 g of phenylboronic acid, and bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ ) 0.719 g, tricyclohexylphosphine (PCy ₃ ) 0.526 g, potassium phosphate 10.61 g, and toluene 50 ml were put into the flask and stirred for 5 minutes. Thereafter, 10 ml of water was added and refluxed for 15 hours. After the heating was completed, the reaction liquid was cooled, water was added, and filtration was performed, and the solid part was designated as crude product 1. The organic layer in the filtrate portion was separated and dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained solid was regarded as crude product 2. Then, the crude product 1 and the crude product 2 are combined together, and a short column refining (solvent: toluene) is performed using silicone rubber. Thereafter, methanol was used for washing, toluene was used for recrystallization, and sublimation purification was performed to obtain 2.63 g of compound (3-1-1) (yield: 44%).

[化388]

The structure of compound (3-1-1) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.90～7.88 (dd, 1H), 7.77～7.70 (m, 6H), 7.62～7.51 (m, 5H), 7.45～7.40 (m, 4H), 7.36～7.24 (m, 5H), 7.06～7.04 (m, 2H), 6.92～6.87 (m, 3H).

In addition, the glass transition temperature (Tg) of the compound (3-1-1) was 97.3°C. In addition, in this specification, the glass transition temperature is measured using a device: Diamond differential scanning calorimeter (DSC) (manufactured by PERKIN-ELMER) at a cooling rate of 200°C/ The measured value was measured at 10 minutes/minute and a temperature increase rate of 10°C/minute, and the glass transition temperature of subsequent compounds was measured in the same manner.

Synthesis Example (H-9) <Synthesis of Compound (3-1-301)> In a nitrogen atmosphere, 15.8 g of 4-bromo-1,2-dichlorobenzene, (10-phenylanthracene-9-yl) Boric acid 20.9 g, tetrakis(triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) 1.62 g, potassium phosphate 29.7 g, and toluene and ethanol mixed solvent 280 ml (toluene/ethanol=9/1 (capacity Ratio)) Put into the flask and stir for 5 minutes. Thereafter, 28 ml of water was added and refluxed for 5 hours. After heating, the reaction solution was cooled, and 100 ml of water was added. After that, the reaction mixture was extracted with toluene, dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained crude product was subjected to short column purification using silica gel (solvent: toluene). Furthermore, reprecipitation was carried out with methanol to obtain 12 g of 9-(3,4-dichlorophenyl)-10-phenylanthracene as an intermediate compound (yield: 43%).

[化389]

Under a nitrogen atmosphere, 5 g of 9-(3,4-dichlorophenyl)-10-phenylanthracene, 4.55 g of phenylboronic acid, and bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ ) 0.719 g, tricyclohexylphosphine (PCy ₃ ) 0.526 g, potassium phosphate 10.61 g, and toluene 50 ml were put into the flask and stirred for 5 minutes. Thereafter, 5 ml of water was added and refluxed for 5 hours. After heating, the reaction solution was cooled, 50 ml of methanol was added, and Shendian was filtered. Furthermore, methanol and water are used to clean Shendian to obtain crude products. After refining the crude product with silica gel in a short column (solvent: toluene), it was recrystallized with toluene, and then sublimation purification was performed to obtain 4.59 g (yield: 76%) of compound (3-1-301).

[化390]

The structure of compound (3-1-301) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.91～7.89 (m, 2H), 7.72～7.70 (m, 2H), 7.66 (d, 1H), 7.63～7.47 (m, 7H), 7.40～7.18 (m , 14H). In addition, the compound (3-1-301) has a glass transition temperature (Tg) of 110.1°C.

Synthesis Example (H-10) <Synthesis of Compound (3-1-307)> In a nitrogen atmosphere, 9-(3,4-dichlorophenyl)-10-phenylanthracene 3.99 g was used as an intermediate compound , 4- (naphthalen-1-yl) phenylboronic acid 5.46 g, bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) 0.575 g, tricyclohexylphosphine (PCy ₃ ) 0.421 g, phosphoric acid 8.49 g of potassium and 50 ml of toluene were put into the flask and stirred for 5 minutes. Thereafter, 5 ml of water was added and refluxed for 5 hours. After heating, the reaction solution was cooled, 50 ml of methanol was added, and Shendian was filtered. Further, Shen Dian was washed with methanol and water to obtain a crude product of the target compound represented by formula (1-307). After the crude product was subjected to short-column refining (solvent: toluene) with silicone rubber, it was recrystallized with toluene, and then sublimated and refined, thereby obtaining 5.1 g (yield: 69.4%) of compound (3-1-307).

[化391]

The structure of the compound (3-1-307) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.99～7.97 (m, 3H), 7.92 (d, 1H), 7.88 (d, 3H), 7.84 (d, 2H), 7.75～7.73 (m, 3H), 7.64 to 7.61 (m, 3H), 7.58 to 7.32 (m, 23H). In addition, the glass transition temperature (Tg) of the compound (3-1-307) is 147.6°C.

Synthesis Example (H-11) <Synthesis of Compound (3-1-3)> In a nitrogen atmosphere, 9-(2,5-dichlorophenyl)-10-phenylanthracene 2 g as an intermediate compound , 2.98 g of 3-biphenylboronic acid, 0.11 g of palladium (II) acetate (Pd(OAc) ₂ ), 0.31 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, triphosphate Potassium 4.25 g, and mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 23 ml (1,2,4-trimethylbenzene/tertiary butanol = 10/1 (capacity ratio)) Put into the flask and stir for 5 minutes. Thereafter, 3 ml of water was added and refluxed for 8 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, and the organic layer is subjected to a short column refining (solvent: toluene) using silicone rubber. Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.83 g of compound (3-1-3) (yield: 57.5%).

[化392]

The structure of compound (3-1-3) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.98 (dd, 1H), 7.94 (d, 1H), 7.87 (d, 1H), 7.83～7.79 (m, 3H), 7.73～7.72 (m, 1H), 7.66～7.42 (m, 12H), 7.36～7.23 (m, 7H), 7.16～7.08 (m, 6H), 6.68～6.65 (m, 2H). In addition, the glass transition temperature of compound (3-1-3) (Tg) is 104.1°C.

Synthesis Example (H-12) <Synthesis of Compound (3-1-23)> Under nitrogen atmosphere, (5-chloro-2-methoxyphenyl)boronic acid 12.59 g, 9-bromo-10-phenyl Anthracene 15 g, tetrakis (triphenylphosphine) palladium (0) (Pd(PPh ₃ ) ₄ ) 1.56 g, tripotassium phosphate 19.11 g, and a mixture of 1,2,4-trimethylbenzene and third butanol 182 ml of solvent (1,2,4-trimethylbenzene/third butanol=10/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 17 ml of water was added and refluxed for 15 hours. After heating, the reaction solution was cooled, and 100 ml of water was added. After that, filtration was performed, and the solid part was set as the crude product 1. The organic layer in the filtrate portion was separated and dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained solid was regarded as crude product 2. After that, the crude product 1 and the crude product 2 are combined, and a short column refining (solvent: toluene) is performed using silicone rubber. Furthermore, reprecipitation was performed with heptane to obtain 16.5 g of 9-(5-chloro-2-methoxyphenyl)-10-phenylanthracene as an intermediate compound (yield: 93%).

[化393]

Under a nitrogen atmosphere, 5 g of 9-(5-chloro-2-methoxyphenyl)-10-phenylanthracene as an intermediate compound, 3.01 g of 3-biphenylboronic acid, and bis(dibenzylidene) Acetone) palladium (0) (Pd(dba) ₂ ) 0.36 g, tricyclohexylphosphine (PCy ₃ ) 0.27 g, tripotassium phosphate 5.38 g, and o-xylene 50 ml were put into the flask and stirred for 5 minutes. Thereafter, 5 ml of water was added and refluxed for 8 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, dried with anhydrous sodium sulfate, the desiccant is removed, the solvent is distilled off under reduced pressure, and the obtained solid is subjected to column purification using silica gel (solvent: Heptane/toluene = 2/1 (volume ratio)), thereby obtaining 9-(4-methoxy-[1,1':3',1''-terphenyl)-3- Base)-10-phenylanthracene 6.3 g (yield: 97%).

[化394]

Under a nitrogen atmosphere, 9-(4-methoxy-[1,1':3',1''-biphenyl]-3-yl)-10-phenylanthracene as an intermediate compound 6.3 g , 7.1 g of pyridine hydrochloride, and 6 ml of 1-methyl-2-pyrrolidone were placed in a flask and heated at 175°C for 4 hours. After the heating, the reaction solution was cooled, 100 ml of water was added, and Shendian was filtered. Furthermore, Shen Dian was washed with water, and the obtained crude product was subjected to short column refining using silica gel (solvent: toluene/ethyl acetate = 2/1 (volume ratio)), thereby obtaining 3-(10 as an intermediate compound -Phenylanthracene-9-yl)-[1,1':3',1"-biphenyl]-4-ol 6.1 g (yield: 99%).

[化395]

Under a nitrogen atmosphere, 6.1 g of 3-(10-phenylanthracene-9-yl)-[1,1':3',1''-biphenyl)-4-ol and pyridine as intermediate compounds 33 ml was placed in a flask, and after cooling to 0°C, 6.9 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0°C for 30 minutes and at room temperature for 2 hours. Then, water was added to the reaction liquid, and Shendian was filtered. After refining the obtained crude product with silica gel in a short column (solvent: toluene) and washing with heptane, 3-(10-phenylanthracene-9-yl)-[1, 1': 3', 1''-terphenyl)-4-yl trifluoromethanesulfonate 7.67 g (yield: 99%).

[化396]

Under a nitrogen atmosphere, use 3-(10-phenylanthracene-9-yl)-[1,1':3',1''-biphenyl]-4-yltrifluoromethanesulfonate as an intermediate compound Ester 1.4 g, phenylboronic acid 0.41 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.05 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.14 g, phosphoric acid Tripotassium 0.94 g, potassium bromide 0.53 g, and mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 14 ml (1,2,4-trimethylbenzene/tertiary butanol=10 /1 (volume ratio)) into the flask and stir for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 6 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was performed to obtain 0.57 g (yield: 46%) of compound (3-1-23).

[化397]

The structure of compound (3-1-23) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.96 (dd, 1H), 7.91 (t, 1H), 7.78～7.74 (m, 4H), 7.71～7.69 (m, 1H), 7.64～7.50 (m, 9H ), 7.45～7.40 (m, 4H), 7.36～7.25 (m, 5H), 7.07～7.05 (m, 2H), 6.95～6.88 (m, 3H). In addition, the glass of compound (3-1-23) The transition temperature (Tg) is 102.9°C.

Synthesis Example (H-13) <Synthesis of Compound (3-1-53)> In a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1' as an intermediate compound: 3',1''-terphenyl)-4-yl trifluoromethanesulfonate 3.2 g, 1-naphthaleneboronic acid 1.31 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.11 g, 2-bicyclo 0.31 g of hexylphosphino-2',6'-dimethoxybiphenyl, 2.15 g of tripotassium phosphate, 1.21 g of potassium bromide, and a mixed solvent of 1,2,4-trimethylbenzene and third butanol 24 ml (1,2,4-trimethylbenzene/third butanol=5/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 4 ml of water was added and refluxed for 8 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, and the organic layer is subjected to a short column refining (solvent: toluene) using silicone rubber. After that, it was washed with methanol, recrystallized with ethyl acetate, and further subjected to column purification using silica gel (solvent: toluene/heptane=1/5 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.42 g (yield: 46%) of compound (3-1-53).

[化398]

The structure of compound (3-1-53) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.13 (d, 1H), 8.02～7.97 (m, 3H), 7.92 (d, 1H), 7.78～7.75 (m, 3H), 7.66～7.27 (m, 20H ), 7.03 to 6.93 (m, 3H), 6.87 to 6.84 (t, 1H). In addition, the glass transition temperature (Tg) of the compound (3-1-53) was 122.8°C.

Synthesis Example (H-14) <Synthesis of Compound (3-1-83)> Under a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1' as an intermediate compound: 3',1''-terphenyl)-4-yl trifluoromethanesulfonate 1.4 g, 2-naphthaleneboronic acid 0.57 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.05 g, 2-bicyclo Hexylphosphino-2',6'-dimethoxybiphenyl 0.14 g, tripotassium phosphate 0.94 g, potassium bromide 0.53 g, and a mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 14 ml (1,2,4-trimethylbenzene/third butanol=10/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 6 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, and the organic layer is subjected to a short column refining (solvent: toluene) using silicone rubber. After that, it was washed with methanol, recrystallized with ethyl acetate, and further subjected to column purification using silica gel (solvent: toluene/heptane=1/5 (capacity ratio)). Finally, sublimation purification was performed to obtain 0.67 g (yield: 50%) of compound (3-1-83).

[化399]

The structure of compound (3-1-83) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.99 (dd, 1H), 7.94 (t, 1H), 7.85～7.82 (m, 4H), 7.73 (tt, 1H), 7.65～7.50 (m, 11H), 7.46 to 7.43 (m, 4H), 7.37 to 7.23 (m, 9H), 7.15 (dd, 1H). In addition, the glass transition temperature (Tg) of the compound (3-1-83) is 110.2°C.

Synthesis Example (H-15) <Synthesis of Compound (3-1-252)> In a nitrogen atmosphere, use 9-(5-chloro-2-methoxyphenyl)-10-phenyl as an intermediate compound Anthracene 36.7 g, phenylboronic acid 17 g, bis(dibenzylideneacetone)palladium(0)(Pd(dba) ₂ )1.6 g, tricyclohexylphosphine (PCy ₃ )1.2 g, tripotassium phosphate 39.5 g, and 400 ml of o-xylene was put into the flask and refluxed for 10 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, dried with anhydrous sodium sulfate, the desiccant is removed, the solvent is distilled off under reduced pressure, and the obtained solid is subjected to column purification using silica gel (solvent: Heptane/toluene=1/1 (volume ratio)), thereby obtaining 9-(4-methoxy-[1,1'-biphenyl]-3-yl)-10-phenylanthracene as an intermediate compound 40.5 g (yield: 100%).

[化400]

Under a nitrogen atmosphere, 40.5 g of 9-(4-methoxy-[1,1′-biphenyl]-3-yl)-10-phenylanthracene, 53.6 g of pyridine hydrochloride as an intermediate compound, And 40 ml of 1-methyl-2-pyrrolidone was put into the flask and heated at 175°C for 3 hours. After heating, the reaction solution was cooled, 500 ml of water was added, and Shendian was filtered. Furthermore, Shen Dian was washed with water, and the obtained crude product was subjected to short column refining using silica gel (solvent: toluene/ethyl acetate = 2/1 (volume ratio)), thereby obtaining 3-(10 as an intermediate compound -Phenylanthracene-9-yl)-[1,1'-biphenyl]-4-ol 40 g (yield: 100%).

[化401]

Under a nitrogen atmosphere, put 40 g of 3-(10-phenylanthracene-9-yl)-[1,1'-biphenyl]-4-ol and 450 ml of pyridine as intermediate compounds into a flask, After cooling to 0°C, 54 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0°C for 30 minutes and at room temperature for 2 hours. Then, water was added to the reaction liquid, and Shendian was filtered. After the obtained crude product was subjected to short-column refining with silica gel (solvent: toluene/heptane=3/1 (capacity ratio)), it was washed with heptane to obtain 3-(10-benzene as an intermediate compound Anthracene-9-yl)-[1,1'-biphenyl]-4-yl trifluoromethanesulfonate 50 g (yield: 93%).

[化402]

Under a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1'-biphenyl]-4-yltrifluoromethanesulfonate 3 g, 2-naphthalene Boric acid 1.4 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.12 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.33 g, tripotassium phosphate 2.3 g, brominated Potassium 1.29 g, and mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 26 ml (1,2,4-trimethylbenzene/tertiary butanol = 10/1 (capacity ratio)) Put into the flask and stir for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 5 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.25 g (yield: 44%) of compound (3-1-252).

[化403]

The structure of compound (3-1-252) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.92 (dd, 1H), 7.83～7.81 (m, 3H), 7.76～7.72 (m, 3H), 7.61～7.49 (m, 7H), 7.46～7.42 (m , 4H), 7.37～7.22 (m, 9H), 7.14 (dd, 1H). In addition, the glass transition temperature (Tg) of compound (3-1-252) is 107.8℃.

Synthesis Example (H-16) <Synthesis of Compound (3-1-255)> Under a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1'- Biphenyl]-4-yl trifluoromethanesulfonate 3 g, 2-([1,2'-binaphthalene]-4-yl)-4,4,5,5-tetramethyl-1,3, 2-dioxaborolane 2.5 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.04 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.10 g, triphosphate Potassium 2.3 g, potassium bromide 1.3 g, and mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 33 ml (1,2,4-trimethylbenzene/tertiary butanol=10/ 1 (Volume ratio)) Put into the flask and stir for 5 minutes. Thereafter, 3 ml of water was added and refluxed for 15 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and sublimation purification was performed to obtain 0.1 g of compound (3-1-255) (yield: 3%).

[化404]

The structure of compound (3-1-255) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.20 (d, 1H), 8.03 (d, 1H), 7.95 (dd, 1H), 7.88 (d, 1H), 7.86～7.72 (m, 9H), 7.64 ( d, 1H), 7.56～7.27 (m, 16H), 7.11～7.01 (m, 3H), 6.91 (d, 1H). In addition, the glass transition temperature (Tg) of compound (3-1-255) is 150.3℃ .

Synthesis Example (H-17) <Synthesis of Compound (3-1-261)> Under a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1'- Biphenyl]-4-yltrifluoromethanesulfonate 3 g, 9-phenanthroboronic acid 1.8 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.12 g, 2-dicyclohexylphosphino-2',6 0.33 g of'-dimethoxybiphenyl, 2.3 g of tripotassium phosphate, 1.3 g of potassium bromide, and a mixed solvent of 1,2,4-trimethylbenzene and third butanol 26 ml (1,2,4 -Trimethylbenzene/third butanol = 10/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 6 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was performed to obtain 0.57 g (yield: 18%) of compound (3-1-261).

[化405]

The structure of compound (3-1-261) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.49 (d, 1H), 8.43 (d, 1H), 8.16 (d, 1H), 8.07 (d, 1H), 7.95 (dd, 1H), 7.90 (d, 1H), 7.83～7.77 (m, 4H), 7.58 (d, 1H), 7.51～7.29 (m, 15H), 7.18～7.12 (m, 2H), 7.03～7.00 (m, 2H). In addition, the compound ( 3-1-261) The glass transition temperature (Tg) is 136.0°C.

Synthesis Example (H-18) <Synthesis of Compound (3-1-262)> Under a nitrogen atmosphere, 3-(10-phenylanthracene-9-yl)-[1,1'- Biphenyl]-4-yltrifluoromethanesulfonate 3 g, 2-triphenyleneboronic acid 1.8 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.04 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.10 g, tripotassium phosphate 2.3 g, potassium bromide 1.3 g, and a mixed solvent of 1,2,4-trimethylbenzene and third butanol 33 ml (1,2 ,4-trimethylbenzene/third butanol=10/1 (volume ratio)) into the flask and stir for 5 minutes. Thereafter, 3 ml of water was added and refluxed for 28 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and sublimation purification was performed to obtain 0.75 g of compound (3-1-262) (yield: 22%).

[化406]

The structure of compound (3-1-262) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.49～8.40 (m, 3H), 8.30 (d, 1H), 8.08 (d, 1H), 8.00～7.88 (m, 5H), 7.78 (d, 2H), 7.60～7.27 (m, 17H), 7.20 (t, 1H), 6.98 (d, 1H), 6.80 (d, 1H). In addition, the glass transition temperature (Tg) of the compound (3-1-262) is 148.4℃ .

Synthesis Example (H-19) <Synthesis of Compound (3-1-283)> In a nitrogen atmosphere, 2 g of 9-(2,5-dichlorophenyl)-10-phenylanthracene as an intermediate compound , [1,1':3',1"-tri]-5'-ylphenylboronic acid 4.12 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.11 g, 2-dicyclohexylphosphino- 2',6'-dimethoxybiphenyl 0.31 g, tripotassium phosphate 4.25 g, and a mixed solvent of 1,2,4-trimethylbenzene and third butanol 23 ml (1,2,4-tri Methylbenzene/third butanol = 10/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 3 ml of water was added and refluxed for 12 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, and the organic layer is subjected to a short column refining (solvent: toluene) using silicone rubber. Thereafter, methanol was used for reprecipitation, and the silica gel was used for column purification (solvent: toluene/heptane=1/4 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.90 g (yield: 48%) of compound (3-1-283).

[化407]

The structure of compound (3-1-283) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.08 (dd, 1H), 7.99 (d, 1H), 7.95 (d, 2H), 7.93 (d, 1H), 7.85 (d, 2H), 7.82 (t, 1H), 7.73～7.67 (m, 6H), 7.61～7.59 (m, 1H), 7.55～7.46 (m, 7H), 7.40～7.25 (m, 16H), 7.02～7.01 (m, 4H). In addition, The glass transition temperature (Tg) of the compound (3-1-283) was 145.3°C.

Synthesis Example (H-20) <Synthesis of Compound (3-1-559)> Under a nitrogen atmosphere, 9 g of 4-bromo-2-chlorophenol and 12.93 g of (10-phenylanthracene-9-yl)boronic acid , Bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ ) 0.75 g, tricyclohexylphosphine (PCy ₃ ) 0.55 g, tripotassium phosphate 18.42 g, and a mixed solvent of toluene and ethanol 180 ml ( Toluene/ethanol=4/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 18 ml of water was added and refluxed for 15 hours. After heating, the reaction solution was cooled, and 100 ml of water was added. After that, the reaction mixture was extracted with toluene, dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained crude product was subjected to column purification using silica gel (solvent: heptane/toluene= 1/2 (capacity ratio)), thereby obtaining 8.3 g of 2-chloro-4-(10-phenylanthracene-9-yl)phenol as an intermediate compound (yield: 50%).

[化408]

Under a nitrogen atmosphere, 7.9 g of 2-chloro-4-(10-phenylanthracene-9-yl)phenol as an intermediate compound, 3.79 g of phenylboronic acid, and bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ ) 0.6 g, tricyclohexylphosphine (PCy ₃ ) 0.44 g, tripotassium phosphate 8.81 g, and o-xylene 80 ml were put into the flask and stirred for 5 minutes. Thereafter, 8 ml of water was added and refluxed for 5 hours. After heating, the reaction solution was cooled, and water was added. After that, filtration was performed, and the solid part was set as the crude product 1. The organic layer in the filtrate portion was separated and dried with anhydrous sodium sulfate, the desiccant was removed, the solvent was distilled off under reduced pressure, and the obtained solid was regarded as crude product 2. After that, the crude product 1 and the crude product 2 are combined, and a short column refining (solvent: toluene) is performed using silicone rubber. Furthermore, reprecipitation was carried out with heptane to obtain 8.4 g of 5-(10-phenylanthracene-9-yl)-[1,1′-biphenyl]-2-ol as an intermediate compound (yield: 95.9 %).

[化409]

Under a nitrogen atmosphere, put 8.4 g of 5-(10-phenylanthracene-9-yl)-[1,1'-biphenyl]-2-ol and 80 ml of pyridine as intermediate compounds into a flask, After cooling to 0°C, 11.2 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0°C for 30 minutes and at room temperature for 2 hours. Then, water was added to the reaction liquid, and Shendian was filtered. After refining the obtained crude product with silicone rubber in a short column (solvent: toluene) and washing with heptane, 5-(10-phenylanthracene-9-yl)-[1, 1'-biphenyl]-2-yltrifluoromethanesulfonate 11 g (yield: 100%).

[化410]

Under a nitrogen atmosphere, the intermediate compound 5-(10-phenylanthracene-9-yl)-[1,1'-biphenyl]-2-yltrifluoromethanesulfonate 2.6 g, 1-naphthalene Boric acid 1.21 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.11 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.29 g, tripotassium phosphate 1.99 g, brominated Potassium 1.12 g, and mixed solvent of 1,2,4-trimethylbenzene and tertiary butanol 20 ml (1,2,4-trimethylbenzene/tertiary butanol = 10/1 (capacity ratio)) Put into the flask and stir for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 6 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was carried out to obtain 1.2 g (yield: 48%) of compound (3-1-559).

[化411]

The structure of compound (3-1-559) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.97 (q, 2H), 7.94～7.92 (m, 1H), 7.89～7.87 (m, 1H), 7.81 (d, 1H), 7.73 (d, 2H), 7.71 (d, 1H), 7.67 (d, 1H), 7.64～7.55 (m, 4H), 7.52～7.35 (m, 10H), 7.16～7.14 (m, 2H), 7.03～7.01 (m, 3H). In addition, the glass transition temperature (Tg) of the compound (3-1-559) was 126.6°C.

Synthesis Example (H-21) <Synthesis of Compound (3-1-560)> Under a nitrogen atmosphere, 5-(10-phenylanthracene-9-yl)-[1,1'- Biphenyl]-2-yltrifluoromethanesulfonate 2.6 g, 2-naphthaleneboronic acid 1.21 g, palladium (II) acetate (Pd(OAc) ₂ ) 0.11 g, 2-dicyclohexylphosphino-2',6 '-Dimethoxybiphenyl 0.29 g, tripotassium phosphate 1.99 g, potassium bromide 1.12 g, and a mixed solvent of 1,2,4-trimethylbenzene and third butanol 20 ml (1,2,4 -Trimethylbenzene/third butanol = 10/1 (volume ratio)) was put into the flask and stirred for 5 minutes. Thereafter, 2 ml of water was added and refluxed for 6 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for washing, ethyl acetate was used for recrystallization, and silica gel was used for column purification (solvent: toluene/heptane = 1/3 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.4 g (yield: 56%) of compound (3-1-560).

[化412]

The structure of compound (3-1-560) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 7.96 (s, 1H), 7.92 (d, 2H), 7.85～7.81 (m, 2H), 7.78 (d, 1H), 7.73～7.68 (m, 3H), 7.63～7.54 (m, 5H), 7.51～7.47 (m, 4H), 7.42～7.28 (m, 7H), 7.18～7.16 (m, 3H). In addition, the glass transition temperature of compound (3-1-560) (Tg) is 116.6°C.

Synthesis Example (H-22) <Synthesis of Compound (3-1-2-1)> In a nitrogen atmosphere, 9-(5-chloro-2-methoxyphenyl)-10- as an intermediate compound 6 g of phenylanthracene, 3.14 g of 1-naphthaleneboronic acid, 0.26 g of bis(dibenzylideneacetone) palladium (0) (Pd(dba) ₂ ), 0.19 g of tricyclohexylphosphine (PCy ₃ ), 6.45 g of tripotassium phosphate g, and 50 ml of xylene were put into the flask and stirred for 5 minutes. Thereafter, 5 ml of water was added and refluxed for 14 hours. After the heating is completed, the reaction solution is cooled, water is added, the organic layer is separated, dried with anhydrous sodium sulfate, the desiccant is removed, the solvent is distilled off under reduced pressure, and the obtained solid is subjected to column purification using silica gel (solvent: Heptane/toluene=2/1 (volume ratio)), thereby obtaining 9-(2-methoxy-5(naphthalen-1-yl)phenyl)-10-phenylanthracene 5.3 g as an intermediate compound ( Yield: 71.7%).

[化413]

Under a nitrogen atmosphere, 9-(2-methoxy-5(naphthalene-1-yl)phenyl)-10-phenylanthracene 5.3 g, pyridine hydrochloride 6.3 g, and 1- 5 ml of methyl-2-pyrrolidone was put into a flask and heated at 175°C for 4 hours. After the heating, the reaction solution was cooled, 100 ml of water was added, and Shendian was filtered. Furthermore, Shen Dian was washed with water, and the obtained crude product was subjected to short column refining with silica gel (solvent: toluene/ethyl acetate = 2/1 (volume ratio)) to obtain 4-(naphthalene as an intermediate compound -1-yl)-2-(10-phenylanthracene-9-yl)phenol 4.6 g (yield: 89%).

[化414]

Under a nitrogen atmosphere, put 4.6 g of 4-(naphthalene-1-yl)-2-(10-phenylanthracene-9-yl)phenol and 25 ml of pyridine as intermediate compounds into a flask, and cool to 0 After ℃, 5.5 g of trifluoromethanesulfonic anhydride was slowly added dropwise. Thereafter, the reaction solution was stirred at 0°C for 30 minutes and at room temperature for 2 hours. Then, water was added to the reaction liquid, and Shendian was filtered. After the obtained crude product was subjected to short-column refining (solvent: toluene) with silicone rubber, it was washed with heptane to obtain 4-(naphthalen-1-yl)-2-(10-phenyl as an intermediate compound Anthracene-9-yl)phenyl triflate 5.95 g (yield: 100%).

[化415]

Under a nitrogen atmosphere, 4.7 g of 4-(naphthalene-1-yl)-2-(10-phenylanthracene-9-yl)phenyl triflate and 1.42 g of phenylboronic acid as intermediate compounds , Palladium(II) acetate (Pd(OAc) ₂ ) 0.09 g, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl 0.27 g, tripotassium phosphate 1.65 g, sodium bromide 0.80 g And 33 ml of 1,2,4-trimethylbenzene were placed in the flask and stirred for 5 minutes. Thereafter, 3 ml of water was added and refluxed for 8 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, and the organic layer is subjected to a short column refining using silica gel (solvent: toluene). Thereafter, methanol was used for reprecipitation, and silica gel was used for column refining (solvent: toluene/heptane = 1/6 (capacity ratio)). Finally, sublimation purification was performed to obtain 1.68 g (yield: 40.5%) of compound (3-1-2-1).

[化416]

The structure of the compound (3-1-2-1) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.21～8.19 (m, 1H), 7.91～7.84 (m, 4H), 7.79 (q, 2H), 7.62～7.46 (m, 10H), 7.41～7.38 (m , 2H), 7.35～7.32 (m, 2H), 7.27～7.24 (m, 2H), 7.11 (dd, 2H), 6.95～6.93 (m, 3H).

Synthesis Example (H-23) <Synthesis of Compound (3-1-3-1)> First, under a nitrogen atmosphere, 5 g of 9-(2,5-dichlorophenyl)-10-phenylanthracene, Phenanthrene-9-ylboronic acid (3.61 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ , 0.72 g), tricyclohexylphosphine (PCy ₃ , 0.70 g), potassium phosphate (7.97 g), tetrabutylammonium bromide (TBAB (0.20 g), and toluene (40 ml) are put into the flask and stirred for 5 minutes. Thereafter, water (5 ml) was added and refluxed for 8 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, followed by a silica gel short-path column and a silica gel column chromatography method (developing solution: toluene/heptane=1/4 (capacity ratio)) to the organic layer Refined. Furthermore, reprecipitation was carried out with methanol to obtain 3.5 g of 9-(2-chloro-5-(phenanthrene-9-yl)phenyl)-10-phenylanthracene as an intermediate compound (yield: 52%).

[化417]

Then, under a nitrogen atmosphere, 9-(2-chloro-5-(phenanthrene-9-yl)phenyl)-10-phenylanthracene (3.0 g) and phenylboronic acid (1.22 g), Pd-132 (Johnson Matthey, 0.20 g), potassium carbonate (2.30 g), tetrabutylammonium bromide (TBAB, 0.09 g), and toluene (24 ml) are put into the flask Medium and stir for 5 minutes. Thereafter, water (3 ml) was added and refluxed for 9 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, followed by a silica gel short-path column and a silica gel column chromatography (developing solution: toluene/heptane = 1/3 (capacity ratio)) to the organic layer Refined. After that, it was reprecipitated several times with Solmix, followed by sublimation purification to obtain 1.88 g (yield: 58%) of compound (3-1-3-1).

[化418]

The structure of the compound (3-1-3-1) was confirmed by NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.78 (d, 1H), 8.72 (d, 1H), 8.24 (dd, 1H), 7.91～7.79 (m, 6H), 7.69～7.50 (m, 10H), 7.42～7.34 (m, 4H), 7.29～7.26 (m, 2H), 7.14～7.12 (m, 2H), 6.98～6.92 (m, 3H).

Synthesis Example (H-24) <Synthesis of Compound (3-1-4-1)> First, under a nitrogen atmosphere, 5 g of 9-(2,5-dichlorophenyl)-10-phenylanthracene, Tribenzyl-2-ylboronic acid (4.43 g), bis(dibenzylideneacetone) palladium(0) (Pd(dba) ₂ , 0.72 g), tricyclohexylphosphine (PCy ₃ , 0.70 g), potassium phosphate (7.97 g), tetrabutylammonium bromide (TBAB, 0.20 g), and toluene (40 ml) were put into the flask and stirred for 5 minutes. Thereafter, water (5 ml) was added and refluxed for 9 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, followed by a silica gel short-path column and a silica gel column chromatography method (developing solution: toluene/heptane=1/4 (capacity ratio)) to the organic layer Refined. Furthermore, by reprecipitation using Solmix, 9-(2-chloro-5-(triphenyl-2-yl)phenyl)-10-phenylanthracene 3.7 was obtained as an intermediate compound g (yield: 50%).

[化419]

Then, under a nitrogen atmosphere, 9-(2-chloro-5-(triphenyl-2-yl)phenyl)-10-phenylanthracene (3.0 g), phenylboronic acid as the intermediate compound (1.24 g), Pd-132 (Johnson Matthey, 0.15 g), potassium carbonate (2.10 g), tetrabutylammonium bromide (TBAB, 0.16 g), and toluene (24 ml) Into the flask and stir for 5 minutes. Thereafter, water (3 ml) was added and refluxed for 18 hours. After the heating is completed, the reaction solution is cooled, water is added, and the organic layer is separated, followed by a silica gel short-path column and a silica gel column chromatography (developing solution: toluene/heptane = 1/3 (capacity ratio)) to the organic layer Refined. After that, it was reprecipitated several times with Solmix, followed by sublimation purification to obtain 0.93 g (yield: 29%) of compound (3-1-4-1).

[化420]

The structure of the compound (3-1-4-1) was confirmed by MS spectrum and NMR measurement. ¹ H-NMR (CDCl ₃ ): δ = 8.96 (s, 1H), 8.72～8.63 (m, 5H), 8.11 (dd, 1H), 7.99 (dd, 1H), 7.94 (s, 1H), 7.86～ 7.81 (m, 3H), 7.66～7.43 (m, 11H), 7.36～7.27 (m, 4H), 7.12～7.10 (m, 2H), 6.97～6.91 (m, 3H).

Synthesis example (H-25) <Synthesis of Compound (3-2-670)> Compound (3-1-3-1) was deuterated using the same method as Synthesis Example (H-1) to obtain compound (3-2-673). EI-MS: m/z=611.

[化421]

Synthesis example (H-26) <Synthesis of Compound (3-2-673)> Compound (3-1-4-1) was deuterated using the same method as Synthesis Example (H-1) to obtain compound (3-2-673). EI-MS: m/z=663.

[化422]

By appropriately changing the compound of the raw material, other polycyclic aromatic compounds of the present invention can be synthesized by the method according to the above synthesis example.

Hereinafter, in order to explain the present invention in more detail, examples of organic EL devices using the compound of the present invention are shown, but the present invention is not limited to these examples.

Organic EL devices were fabricated in the following examples, respectively, for the characteristics of the driving voltage (V), the emission wavelength (nm), the color of the Commission Internationale de L'Eclairage (CIE) color when emitting light from 1000 cd/m ² The characteristics selected from the degree (x, y), the external quantum efficiency (%), and the time to maintain the brightness of 90% or more of the initial brightness (hereinafter, also simply referred to as "90% lifetime") are measured.

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency. The internal quantum efficiency indicates a ratio in which external energy injected into the light-emitting layer of the light-emitting element as electrons (or holes) is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of this photon released to the outside of the light-emitting element, and part of the photons generated in the light-emitting layer is absorbed or continuously reflected inside the light-emitting element without being released to the outside of the light-emitting element, so The external quantum efficiency is lower than the internal quantum efficiency.

The measurement method of external quantum efficiency is as follows. A voltage/current generator R6144 manufactured by Advantest Co., Ltd. was used to apply a voltage to make the brightness of the device reach 1000 cd/m ² to make the device emit light. The spectroscopic radiance meter SR-3AR manufactured by TOPCON was used to measure the spectral radiance in the visible light region from the direction perpendicular to the light emitting surface. Assuming that the light-emitting surface is a completely diffused surface, the value of the measured spectral radiance of each wavelength component is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Then, the number of photons is accumulated in the observed full wavelength region, and set as the total number of photons released from the element. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the total number of photons released from the device is divided by the number of carriers injected into the device The value of is the external quantum efficiency.

The material of each layer in the organic EL device produced in the following examples is shown. "HI" (a hole injection layer material) of N ^4, N ^{4 '-} diphenyl -N ^4, N ^4' - bis (9-phenyl -9H- carbazol-3-yl) - [1, 1'-biphenyl]-4,4'-diamine, "HAT-CN" (hole injection layer 2 material) is 1,4,5,8,9,12-hexaazatrisphthalene nitrile , "HT-1" (hole transport layer 1 material) is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-benzene Yl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, "HT-2" (hole transport layer 2 material) is N,N-bis(4-(dibenzo[ b,d]furan-4-yl)phenyl)-[1,1': 4',1"-biphenyl]-4-amine. In addition, as the electron transmission material, "ET-1" (electronics) selected from "ET-1", "ET-2", "ET-3", and "Liq" represented by the following formula is used The material of the transmission layer) is 4-(3-(4-(10-phenylanthracene-9-yl)naphthalen-1-yl)phenyl)pyridine, and "ET-2" is 9,9'-(5-( 6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole), "ET-3" is 3,3'-[(2-phenylanthracene-9,10-diyl)diphenyl-4,1-diyl]dipyridine. The chemical structure is shown below together with "Liq" and "Compound (3-15)" used as a host in Example 1.

[化423]

<Example 1> <Elements with compound (3-15) as the main body and compound (2-1A-114) as the dopant> A glass substrate (manufactured by Opto Science Co., Ltd.) of 26 mm×28 mm×0.7 mm in which ITO film formed by sputtering with a thickness of 180 nm was polished to 150 nm was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Cheung Chau Industries Co., Ltd.), and mounted with HI, HAT-CN, HT-1, HT-2, compound 15) Compound (2-1A-114) and ET-1 tantalum vapor deposition boat, aluminum nitride vapor deposition boat containing Liq, magnesium and silver, respectively.

The following layers are sequentially formed on the ITO film of the transparent supporting substrate. The vacuum chamber was decompressed to 5×10 ^-4 Pa. First, the HI was heated, and vapor deposition was performed so that the film thickness became 40 nm, thereby forming the hole injection layer 1. Then, the HAT-CN was heated, and vapor deposition was performed so that the film thickness became 5 nm, thereby forming the hole injection layer 2. Then, HT-1 was heated, and vapor deposition was performed so that the film thickness became 15 nm, thereby forming the hole transport layer 1. Then, HT-2 was heated, and vapor deposition was performed so that the film thickness became 10 nm, thereby forming the hole transport layer 2. Then, the compound (3-15) and the compound (2-1A-114) synthesized as described above were simultaneously heated and vapor-deposited so that the film thickness became 20 nm, thereby forming a light-emitting layer. The evaporation rate was adjusted so that the mass ratio of the compound (3-15) to the compound (2-1A-114) became about 98 to 2. Then, ET-1 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25 nm, thereby forming an electron transport layer. The vapor deposition rate was adjusted so that the mass ratio of ET-1 to Liq became about 50 to 50. The evaporation rate of each layer is 0.01 nm/sec to 1 nm/sec. After that, Liq is heated to be deposited at a deposition rate of 0.01 nm/sec to 0.1 nm/sec so that the film thickness becomes 1 nm, and then, magnesium and silver are simultaneously heated to a film thickness of 100 nm To form a cathode by evaporation to obtain an organic EL element. At this time, the vapor deposition rate was adjusted between 0.1 nm/sec and 10 nm/sec so that the atomic ratio of magnesium to silver became 10 to 1.

Using an ITO electrode as the anode and a magnesium/silver electrode as the cathode, applying a DC voltage, and measuring the characteristics at 1000 cd/m ² when emitting light, the result was that the wavelength was 460 nm, and the CIE chromaticity (x, y) = (0.133, 0.101) Blue glow. In addition, the driving voltage is 3.7 V and the external quantum efficiency is 7.3%.

<Example 2 to Example 66> Using the compound obtained in the above synthesis example, an organic EL device was produced in the following order. A glass substrate (manufactured by Opto Science Co., Ltd.) of 26 mm×28 mm×0.7 mm in which ITO film formed by sputtering has a thickness of 180 nm and polished to 150 nm was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and installed with HI, HAT-CN, HT-1, HT-2, BH-1, The main body and dopant, ET-2, and ET-3 described in Tables 1 to 4 are molybdenum deposition boats made of molybdenum, aluminum nitride deposition boats made of Liq, LiF, and aluminum .

The following layers are sequentially formed on the ITO film of the transparent supporting substrate. The vacuum chamber was decompressed to 5×10 ^-4 Pa. First, the HI was heated, and vapor deposition was performed so that the film thickness became 40 nm, thereby forming the hole injection layer 1. Then, the HAT-CN was heated, and vapor deposition was performed so that the film thickness became 5 nm, thereby forming the hole injection layer 2. Then, HT-1 was heated, and vapor deposition was performed so that the film thickness became 45 nm, thereby forming the hole transport layer 1. Then, HT-2 was heated, and vapor deposition was performed so that the film thickness became 10 nm, thereby forming the hole transport layer 2. Next, the host described in Tables 1 to 4 and the dopant were simultaneously heated and vapor-deposited so that the film thickness became 25 nm, thereby forming a light-emitting layer. The vapor deposition rate was adjusted so that the mass ratio of the main body to the dopant became about 98 to 2. Then, ET-2 was heated and vapor-deposited so that the film thickness became 5 nm to form the electron transport layer 1, and then, ET-2 and Liq were simultaneously heated and vaporized so that the film thickness became 25 nm Plating to form the electron transport layer 2. Furthermore, the vapor deposition rate was adjusted so that the mass ratio of ET-2 to Liq became about 50 to 50. The evaporation rate of each layer is 0.01 nm/sec to 1 nm/sec. After that, LiF was heated to be vapor-deposited at a deposition rate of 0.01 nm/sec to 0.1 nm/sec so that the film thickness became 1 nm, and then, aluminum was heated so that the film thickness became 100 nm The cathode is formed by vapor deposition to obtain organic EL elements, respectively. Hereinafter, as Tables 1 to 4, the materials of the layers of the organic EL devices produced in Examples 2 to 66 are shown.

[Table 1]

[Table 2]

[table 3]

[Table 4]

Regarding the organic EL devices produced in Examples 2 to 66, an ITO electrode was used as the anode and a LiF/aluminum electrode was used as the cathode, a DC voltage was applied, and the characteristics at 1000 cd/m ² when emitting light were measured. In addition, the measurement retention The time of the brightness above 90% of the initial brightness. The results are shown in Table 5 to Table 8.

[table 5]

[Table 6]

[Table 7]

[產業上之可利用性][Table 8]

[Industry availability]

According to a preferred embodiment of the present invention, by manufacturing an organic EL element including a light-emitting layer, it is possible to provide an organic EL element with a narrow half-value width, low driving voltage, and excellent quantum efficiency. Ring aromatic compounds and anthracene compounds. By using especially deuterated anthracene compounds, a long-life device can be obtained.

100: Organic electric field light emitting element 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

FIG. 1 is a schematic cross-sectional view showing an organic EL device of this embodiment.

100: Organic electric field light emitting element

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 (24)

An organic electric field light-emitting device comprising: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, and the light-emitting layer includes a polycyclic aromatic compound represented by the following general formula (1) At least one of a compound and a polymer of a plurality of polycyclic aromatic compounds having a structure represented by the following general formula (1), and an anthracene-based compound;

In the formula (1), the A ring, the B ring and the C ring are each independently an aryl ring or a heteroaryl ring, at least one hydrogen in these rings may be substituted, Y ¹ is B, X ¹ and X ² are independently >O or >NR, and the R of >NR is an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkyl group which may be substituted, or a cycloalkyl group which may be substituted, in addition, The R> NR may be bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond, and at least one hydrogen in the compound or structure represented by formula (1) may be Halogen or deuterium substitution. The organic electroluminescent element as described in item 1 of the patent application scope, wherein in the formula (1), the A ring, the B ring and the C ring are independently an aryl ring or a heteroaryl ring, and among these rings At least one hydrogen may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamine, substituted or unsubstituted diheteroarylamine Group, substituted or unsubstituted arylheteroarylamine group, substituted or unsubstituted diarylboryl group (two aryl groups can be bonded via a single bond or linking group), substituted or unsubstituted Substituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryloxy substitution, in addition, these rings have ¹ , the condensed bicyclic structure at the center of the formula of X ¹ and X ² shares a 5-membered ring or 6-membered ring bonded together, Y ¹ is B, X ¹ and X ² are independently >O or >NR, so Said >NR, R is an aryl group which may be substituted by an alkyl group, a cycloalkyl group, a diarylamine group or a diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), may be an alkyl group, Heteroaryl, alkyl or cycloalkyl substituted with cycloalkyl, diarylamine or diarylboryl (two aryl groups can be bonded via a single bond or a linking group), in addition, said>NR R may be bonded to at least one of the A ring, B ring and C ring via a linking group or a single bond selected from -O-, -S- and -C(-R) ₂ -, the -C(-R) ₂ -where R is hydrogen, alkyl or cycloalkyl, at least one hydrogen in the compound or structure represented by formula (1) may be substituted by halogen or deuterium, and, in the case of multimer , Is a dimer or trimer having two or three structures represented by formula (1). The organic electroluminescent device as described in item 1 of the patent application range, wherein the polycyclic aromatic compound and its multimer are polycyclic aromatic compounds represented by the following general formula (2) and have a plurality of the following Polymers of polycyclic aromatic compounds of the structure represented by general formula (2);

In the formula (2), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, aryl, hetero Aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups can be bonded via a single bond or linking group), alkyl, ring Alkyl, alkoxy or aryloxy, at least one of these hydrogens may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, in addition, adjacent groups in R ¹ to R ¹¹ may be bonded to each other Together with a ring, b ring or c ring to form an aryl ring or heteroaryl ring, at least one hydrogen in the formed ring may be aryl, heteroaryl, diarylamino, diheteroarylamino , Arylheteroarylamino, diarylboryl (two aryl groups can be bonded via a single bond or linking group), alkyl, cycloalkyl, alkoxy or aryloxy substituted, these At least one hydrogen of may be substituted by aryl, heteroaryl, alkyl or cycloalkyl, Y ¹ is B, X ¹ and X ² are independently >O or >NR, and R of >NR may be alkyl , Cycloalkyl, diarylamino or diarylboryl (two aryl groups can be bonded via a single bond or a linking group) substituted aryl group of 6 to 12 carbon atoms, which can be alkyl, cycloalkyl , Diarylamino or diarylboryl (two aryl groups can be bonded via a single bond or a linking group) substituted C 2-15 heteroaryl, C 1-6 alkyl or carbon The cycloalkyl group of 3 to 14, and the R> NR may be linked to the a ring via a linking group or a single bond selected from -O-, -S- and -C(-R) _2- , At least one of ring b and ring c is bonded, and R in -C(-R) ₂ -is a C 1-6 alkyl group or a C 3-14 cycloalkyl group, represented by formula (2) At least one hydrogen in the compound represented may be substituted by halogen or deuterium. The organic electroluminescent element as described in item 3 of the patent application scope, wherein in the formula (2), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ are independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and a diarylamine group (wherein each aryl group is an aromatic group having 6 to 12 carbon atoms) Group) or a diarylboryl group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms, and two aryl groups may be bonded via a single bond or a linking group); in addition, adjacent ones of R ¹ to R ¹¹ The groups may be bonded to each other and together with a ring, b ring or c ring to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, at least one hydrogen in the formed ring may be replaced by two Arylamino group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms) or diarylboron group (wherein each aryl group is an aryl group having 6 to 12 carbon atoms, two aryl groups may be through a single bond Or a linking group for bonding), X ¹ and X ² are independently >O or >NR (wherein R of the NR is selected from alkyl, cycloalkyl, diarylamino or diarylboron) A C6-10 aryl group substituted with a group (two aryl groups may be bonded via a single bond or a linking group), and at least one hydrogen in the compound represented by formula (2) may be substituted with halogen or deuterium. The organic electric field light-emitting element according to any one of claims 1 to 4, wherein the polycyclic aromatic compound and its polymer have at least one deuterium. The organic electroluminescent element as described in item 5 of the patent application range, wherein in the polycyclic aromatic compound and its multimer, relative to hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule The total amount is 100%, and the proportion of deuterium is 10% to 100%. The organic electroluminescent element as described in item 5 of the patent application range, wherein in the polycyclic aromatic compound and its multimer, relative to hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule The total amount is 100%, and the proportion of deuterium is 100%. The organic electroluminescent element as described in item 1 of the patent application range, wherein the polycyclic aromatic compound and its multimer are compounds having a structure represented by any of the following;

In the above structural formulas, "Me" represents a methyl group, "tBu" represents a third butyl group, "tAm" represents a third pentyl group, and "D" represents deuterium. The organic electric field light-emitting device according to any one of items 1 to 8 of the patent application range, wherein the anthracene compound is a compound represented by the following general formula (3);

In the formula (3), L is a single bond, an aryl group having 6 to 18 carbon atoms, or an alkylene group having 1 to 10 carbon atoms, and at least one hydrogen in the aryl group and the alkylene group May be substituted by aryl, heteroaryl, alkyl or cycloalkyl, Ar ^{4 is} independently hydrogen, phenyl, biphenyl, biphenyl, naphthyl, selected from the group consisting of C 1-4 alkyl And a silane group substituted with a group in a cycloalkyl group having 5 to 10 carbon atoms, n is 0 or 1, and X is independently the above formula (3-X1), formula (3-X2) or formula (3- The group represented by X3), the * in the formula (3-X1), formula (3-X2) or formula (3-X3) represents the 9-position or 10-position of the anthracene ring in the formula (3) Bonding position, Ar ¹ and Ar ² are independently hydrogen, phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzyl, triphenyl Phenyl, pyrenyl, carbazolyl, benzocarbazolyl, phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzo Thienyl, or naphthobenzothienyl, at least one hydrogen in these groups may be further substituted by C 1-6 alkyl, C 3-14 cycloalkyl, phenyl, or naphthyl, Ar ³ is phenyl, biphenyl, triphenylphenyl, tetratetraphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzyl, triphenylene, pyrenyl, carbazolyl, benzene Carbazolyl, phenyl substituted carbazolyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, or naphthobenzothienyl, the At least one hydrogen in these groups may be further substituted by C 1-6 alkyl, C 3-14 cycloalkyl, substituted or unsubstituted phenyl, alkyl or Cycloalkyl substituted or unsubstituted biphenyl, biphenyl substituted or unsubstituted with alkyl or cycloalkyl, naphthyl substituted or unsubstituted with alkyl or cycloalkyl, alkyl Or cycloalkyl substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl substituted with alkyl or cycloalkyl, alkyl or cycloalkyl substituted or unsubstituted benzofluorenyl, substituted alkyl Or cycloalkyl substituted or unsubstituted benzyl, trialkylene substituted or unsubstituted by alkyl or cycloalkyl, pyrene and unsubstituted pyrene, substituted by alkyl or cycloalkyl Or cycloalkyl substituted or unsubstituted dibenzofuranyl, alkyl or cycloalkyl substituted or unsubstituted dibenzothienyl, alkyl or cycloalkyl substituted or unsubstituted carbazole Group, phenyl substituted carbazolyl, alkyl or cycloalkyl substituted or unsubstituted benzofuranyl, alkyl or cycloalkyl substituted or unsubstituted naphthobenzofuranyl, alkyl Or a cycloalkyl substituted or unsubstituted benzothienyl group, or an alkyl or cycloalkyl substituted or unsubstituted naphthobenzothienyl group, and at least one of the compounds represented by formula (3) One hydrogen can be replaced by deuterium. The organic electroluminescent element as described in item 9 of the patent application, wherein the groups represented by the formula (3-X3) are phenyl, phenanthrenyl, and groups represented by the following formula (3-X3-1) Group or a group represented by the following formula (3-X3-2), these may be further substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms;

In the above formula (3-X3-1) and formula (3-X3-2), * represents the bonding position with the 9th or 10th position of the anthracene ring in the formula (3), and Ar ^{5 is} independently hydrogen , Phenyl, biphenyl, triphenylphenyl, naphthyl, phenanthrenyl, fluorenyl, benzyl, triphenylene, pyrenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzene Substituted carbazolyl, benzofuranyl, naphthobenzofuranyl, benzothienyl, or naphthobenzothienyl, at least one of these hydrogens can be further substituted by an alkyl or carbon having 1 to 6 carbon atoms Cycloalkyl substitution of the number 3-14. The organic electric field light-emitting device according to any one of claims 1 to 10, wherein the anthracene compound is a compound represented by the following general formula (3-1-X);

In formula (3-1-X), ϕ is a phenyl group, naphthyl group, phenanthryl group, or triphenylene group which may be substituted with Ar ¹ and R, and Ar is an aryl group which may be substituted, and n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or different, Ar ¹ is an aryl group that may be substituted, m is the largest integer that can be substituted from 0 to ϕ, and when m is 2 or more, the structure of Ar ¹ may be the same or different, and R is independently an alkyl group or a cycloalkyl group , A is an integer from 0 to 5, b is an integer from 0 to 3 and b+n is 4 or less, c is the largest integer replaceable from 0 to ϕ and c+m is the largest integer replaceable from ϕ, d It is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X) may be substituted with deuterium. The organic electroluminescent element as described in item 11 of the patent application range, wherein the anthracene compound is a compound represented by the following general formula (3-1-X1);

In formula (3-1-X1), Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, and when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or different. Ar ¹ is an aryl group that may be substituted, m is an integer of 0 to 5, and when m is 2 or more, the structure of Ar ¹ is May be the same or different, R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 5 and c +m is 5 or less, d is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X1) may be substituted with deuterium. The organic electroluminescent device as described in item 11 of the patent application range, wherein the anthracene compound is a compound represented by the following general formula (3-1-X2);

In formula (3-1-X2), the naphthalene ring represented in formula (3-1-X2) is a 1-naphthyl group or a 2-naphthyl group bonded to a phenyl group, Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and the y position, when n is 2, Ar is bonded to both the x position and the y position, and their respective structures may be the same or Differently, Ar ¹ is an aryl group which may be substituted, m is an integer from 0 to 7, when m is 2 or more, the structure of Ar ¹ may be the same or different, and R is independently an alkyl group or a cycloalkyl group, a Is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 7 and c+m is 7 or less, d is an integer of 0 to 4, and, formula (3 -1-X2) At least one hydrogen in the compound represented by can be replaced by deuterium. The organic electroluminescence device as described in item 11 of the patent application range, wherein the anthracene compound is a compound represented by the following general formula (3-1-X3);

In formula (3-1-X3), the phenanthrene ring represented in formula (3-1-X3) is 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl bonded to phenyl Or 9-phenanthryl, Ar is an aryl group which may be substituted, n is 1 or 2, when n is 1, Ar is bonded to any one of the x position and y position, when n is 2, Ar is bonded to The structure of each of the x position and the y position may be the same or different. Ar ¹ is an aryl group which may be substituted, m is an integer of 0-9, and when m is 2 or more, the structure of Ar ¹ may be the same or different Differently, R is independently alkyl or cycloalkyl, a is an integer of 0 to 5, b is an integer of 0 to 3 and b+n is 4 or less, c is an integer of 0 to 9 and c+m is 9 Hereinafter, d is an integer of 0 to 4, and at least one hydrogen in the compound represented by formula (3-1-X3) may be substituted with deuterium. The organic electroluminescence device as described in item 11 of the patent application range, wherein the anthracene compound is a compound represented by the following general formula (3-1-X4);

In the formula (3-1-X4), the triphenylene ring represented in the formula (3-1-X4) is 1-triphenylene or 2-triphenylene bonded to phenyl, Ar is Substituted aryl, n is 1 or 2, when n is 1, Ar is bonded to either of the x position and y position, when n is 2, Ar is bonded to both the x position and y position, each The structures of may be the same or different, Ar ¹ is an aryl group which may be substituted, m is an integer of 0 to 11, when m is 2 or more, the structures of Ar ¹ may be the same or different, and R is independently an alkyl group Or cycloalkyl, a is an integer from 0 to 5, b is an integer from 0 to 3 and b+n is 4 or less, c is an integer from 0 to 11 and c+m is 11 or less, and d is an integer from 0 to 4 And, at least one hydrogen in the compound represented by the formula (3-1-X4) may be replaced by deuterium. The organic electric field light-emitting element according to any one of claims 1 to 15, wherein the anthracene compound has at least one deuterium. The organic electroluminescent device as described in claim 16 of the patent application range, wherein the anthracene compound contains 100% of the total amount of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule. The proportion is from 10% to 100%. The organic electroluminescent device as described in claim 16 of the patent application range, wherein the anthracene compound contains 100% of the total amount of hydrogen and deuterium bonded to the carbon constituting the aromatic ring in one molecule. The proportion is 100%. The organic electroluminescence device as described in Item 16 of the patent application range, wherein the anthracene compound is a compound represented by any one of the following formulas;

"D" in each of the above structural formulas represents deuterium. The organic electric field light-emitting device according to any one of claims 1 to 15, wherein the anthracene compound is a compound represented by any of the following;

. The organic electric field light-emitting device according to any one of claims 1 to 20, wherein in the light-emitting layer, the polycyclic aromatic compound represented by the general formula (1) and its polymerization The content ratio of the compound to the anthracene-based compound [the polycyclic aromatic compound and its multimer/the anthracene-based compound] is 0.001/99.999 to 50/50 in terms of mass ratio. The organic electric field light-emitting element according to any one of claims 1 to 21, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer , And at least one of the electron transport layer and the electron injection layer contains a borane derivative, pyridine derivative, fluoranthene derivative, BO derivative, anthracene derivative, benzofluorene derivative, phosphine oxide Derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, morpholine derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, thiazole derivatives At least one of the group consisting of compounds and oxazoline derivatives. The organic electroluminescent device as described in Item 22 of the patent application range, wherein at least one of the electron transport layer and the electron injection layer further contains an oxide selected from an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal, an alkali metal Halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes At least one of the group of objects. A display device or a lighting device, comprising the organic electric field light-emitting element as described in any one of claims 1 to 23.

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