KR20220058824A - Polycyclic aromatic compound - Google Patents

Abstract

Provided are a novel polycyclic aromatic compound and an organic EL device using the same. The organic EL device using the novel polycyclic aromatic compound as, for example, a dopant material is manufactured so that an organic EL device with a narrow half-width of an emission spectrum and excellent color purity, and furthermore, an organic EL device with excellent quantum efficiency and device lifetime are provided.

Description

Polycyclic aromatic compound {POLYCYCLIC AROMATIC COMPOUND}

The present invention relates to a polycyclic aromatic compound, an organic electroluminescent device using the same, an organic field effect transistor, an organic thin film solar cell, an organic device such as a wavelength conversion filter, and a display device and a lighting device. In addition, in this specification, "organic electroluminescent element" may be described as "organic EL element" or simply "element".

Conventionally, a display device using a light emitting device that emits electroluminescence has been studied in various ways because it is possible to reduce power and thickness, and further, an organic electroluminescent device made of an organic material has been actively studied because it is easy to reduce the weight or increase in size. In particular, with respect to the development of organic materials having luminescent properties such as blue or green, which are one of the three primary colors of light, and the development of organic materials having charge transport capability (possible to become semiconductors or superconductors) such as holes and electrons, polymers Regardless of compound or low molecular weight compound, it has been actively studied until now.

The organic EL device has a structure consisting of a pair of electrodes comprising an anode and a cathode, disposed between the pair of electrodes, and including one or more layers containing an organic compound. The layer containing the organic compound includes a light emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers are being developed.

As a material for a light emitting layer, three types are currently used: a fluorescent material, a phosphorescent material, and a thermally activated delayed fluorescence (TADF) material. For example, in fluorescent materials, benzofluorene-based compounds are being developed (International Publication No. 2004/061047), and in phosphorescent materials, noble metal complexes having a polydentate ligand have been developed (Japanese Patent Laid-Open No. 2014-239225). report).

In addition, recently, materials obtained by improving azaborine derivatives have also been reported (International Publication No. 2015/102118). A compound having a narrow luminescence half width at a single peak and a conjugated structure with a small energy difference (ΔS ¹ T ¹ ) between singlet energy (S ¹ ) and triplet energy (T ¹ ) has high color purity and thermally activated delayed fluorescence ( Since high efficiency by TADF) is obtained, it is advantageous as a blue or green light emitting layer material. Moreover, the compound which has a novel conjugated structure with a large triplet energy (T ¹ ) is calculated|required also as an electron transport material or a hole transport material with the light emitting layer interposed therebetween.

However, there is a problem in that fluorescent materials have low luminous efficiency, and phosphorescent materials and TADF materials have high luminous efficiency, but have a wide luminescence spectrum at half maximum and low color purity of luminescence. Furthermore, phosphorescent materials contain precious metals. Therefore, there was a problem that it is expensive (Nature Vol.49213 December 2012, Applied Physics Letters 75, 4 (1999)).

Patent Document 1: International Publication No. 2004/061047 Patent Document 2: Japanese Patent Laid-Open No. 2014-239225 Patent Document 3: International Publication No. 2015/102118

Non-Patent Document 1: Nature Vol.49213 December 2012 Non-Patent Document 2: Applied Physics Letters 75, 4 (1999)

As described above, various materials have been developed as materials for use in organic EL devices. In order to increase the selection of materials for organic EL devices, development of materials made of compounds different from those in the prior art is desired. Further, in Patent Document 3, a polycyclic aromatic compound containing boron and an organic EL device using the same are reported, but in order to further improve device characteristics, a material for a light emitting layer that can improve color purity, luminous efficiency and device lifetime, particularly Dopant materials are in demand. In addition, as shown in Non-Patent Documents 1 and 2, thermally activated delayed fluorescent materials or phosphorescent light emitting materials utilizing the heavy atom effect have a wide luminescence spectrum at half maximum, and there is a problem in that color purity is improved.

In addition, as a method of forming an organic layer constituting an organic EL device, a wet film forming method is currently used in addition to the vacuum vapor deposition method. In particular, the development of an ink material for wet film formation for forming a hole injection layer, a hole transport layer and a light emitting layer is actively pursued. It is being done, and it is also beneficial to search for such an ink material.

As a result of intensive studies to solve the above problems, the present inventors have succeeded in preparing a novel polycyclic aromatic compound, and furthermore, that this compound is effective as a material with a small difference between singlet energy and triplet energy required for thermally activated delayed fluorescence. found something Then, for example, by using such a polycyclic aromatic compound as a dopant material and a light emitting layer using a compound having a larger triplet energy as a host material between a pair of electrodes to constitute an organic EL device, excellent thermal activation delay It found that a fluorescent type organic EL element was obtained, and completed this invention.

In addition, in the present specification, a chemical structure or a substituent is sometimes expressed by the number of carbon atoms, and the number of carbon atoms in the case where a substituent is substituted in the chemical structure or when a substituent is further substituted in the chemical structure means the number of carbon atoms in the chemical structure or each of the substituents. and does not mean the total number of carbon atoms of the chemical structure and the substituent or the total number of carbon atoms of the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent group A of carbon number X" is substituted for "substituent group B of carbon number Y", and carbon number Y is substituent A and substituent It is not the number of carbons in the sum of B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent A (without limitation in number of carbon atoms)" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and It is not the total number of carbon atoms of the substituent B.

Section 1.

A polycyclic aromatic compound represented by the following general formula (1A) or (1B).

[Formula 8]

In the above formula (1A) or (1B),

R ^a is hydrogen or a substituent, and "-C(-R ^a )=" in ring a may be substituted with "-N=",

Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;

Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > Each R of Ge(-R)- is independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl;

X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cyclo alkyl, wherein at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ may be bonded by a single bond or a linking group;

R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ may be bonded to at least one of ring a and ring B by a single bond or a linking group. become,

R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ may be bonded to at least one of ring a and ring E by a single bond or a linking group. become,

The C ring and D ring, the G ring and the B ring, and the F ring and the E ring may each independently be bonded by a single bond or a linking group,

However, in the formula (1A), the CD bond of ring C and ring D, and R of >NR as X ¹ (wherein R is optionally substituted aryl, optionally substituted heteroaryl, or substituted X 1 B bond of ring B) and X ¹ B bond of ring B, and R of >NR as X ² (wherein R is optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted cycloalkyl) (limited to) and among the three bonds of X ² E bond of the E ring, any one or two bonds exist,

In the formula (1B), any one or two bonds are present among the three bonds: the CD bond of the C and D rings, the GB bond of the G and B rings, and the FE bond of the F and E rings. are doing,

At least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B) is at least one cyclo may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;

At least one hydrogen in the compound represented by the formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen.

Section 2.

In the above formula (1A) or (1B),

R ^a is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted di Rylboryl (two aryls may be bonded by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;

"-C(-R ^a )=" in ring a may be substituted with "-N=",

Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is optionally substituted aryl, and optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (two aryls are bonded through a single bond or a linking group) may be substituted), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;

Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R of Ge(-R)- is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl;

X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, and at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ is a single bond, -CH=CH-, -CR =CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently , hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent R may form a ring and may form cycloalkylene, arylene, or heteroarylene,

R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, at least of ring a and ring B may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring E, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ -R each independently represents hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, even if at least one hydrogen in R is substituted with alkyl or cycloalkyl and two adjacent R's may form a ring, and may form cycloalkylene, arylene, and heteroarylene;

C ring and D ring, G ring and B ring, and F ring and E ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl , or cycloalkyl, at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring, cycloalkylene, arylene, and hetero Arylene may be formed,

However, in the formula (1A), the CD bond of the C rings and the D rings, and R of >NR as X ¹ , wherein R is the aryl, the heteroaryl, or the above optionally substituted with the above alkyl or cycloalkyl. Limited to cycloalkyl) and the X ¹ B bond of the B ring, and R of >NR as X ² (wherein R is limited to the aryl, heteroaryl, or cycloalkyl optionally substituted with the above alkyl or cycloalkyl) ) and among the three bonds of the X ² E bond of the E ring, any one or two bonds exist,

In the formula (1B), any one or two bonds are present among the three bonds: the CD bond of the C and D rings, the GB bond of the G and B rings, and the FE bond of the F and E rings. are doing,

At least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B) is at least one cyclo may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;

At least one hydrogen in the compound represented by the formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen;

The polycyclic aromatic compound according to claim 1.

Section 3.

The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2A) or the following general formula (2B).

[Formula 9]

In the above formula (2A) or (2B),

R ^a is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in R ^a is aryl, heteroaryl, alkyl , or may be substituted with cycloalkyl,

"-C(-R ^a )=" in ring a may be substituted with "-N=",

R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 aryl may be bound by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g adjacent to each other are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring or a hetero An aryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are a single bond or a linking group) may be substituted with), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, At least one hydrogen in the substituent may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl;

In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”, and any “-C(-R)=C(-R)-” (where R is R ^b , R ^c , R ^{d )} , ^{Re , R f ,} or R ^g ) is “-N(-R)-”, “-O-”, “-S-”, “-C(-R) ₂ -”, “-Si (-R) ₂ -" or "-Se-" may be substituted, and R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si R in (-R) ₂ -" is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and the above "-C At least one of the two Rs of (-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" is a single bond, -CH=CH-, -CR=CR-, -C ≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring; , cycloalkylene, arylene, or heteroarylene may be formed,

Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R of Ge(-R)- is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl;

X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, and at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ is a single bond, -CH=CH-, -CR =CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently , hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent R each may form a ring and may form cycloalkylene, arylene, or heteroarylene;

R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- by at least an a ring and a b ring may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring e, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ -R each independently represents hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, even if at least one hydrogen in R is substituted with alkyl or cycloalkyl and two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene,

c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl , or cycloalkyl, at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring, cycloalkylene, arylene, and hetero Arylene may be formed,

However, in the formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R is the aryl, the heteroaryl, or the above optionally substituted with the above-mentioned alkyl or cycloalkyl. limited to cycloalkyl) and the X ¹ b bond of the b ring, and R of >NR as X ² (wherein R is limited to the above aryl, heteroaryl, or cycloalkyl which may be substituted with the above alkyl or cycloalkyl) ) and among the three bonds of the X ² e bond of the e ring, any one or two bonds exist,

In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,

In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. , C1-C24 alkyl, or C3-C24 cycloalkyl may be substituted, and at least one -CH ₂ - in this cycloalkane may be substituted with -O-,

At least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen.

Section 4.

In the above formula (2A) or (2B),

R ^a is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl has 6 to 12 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in R ^a has 6 carbon atoms It may be substituted with aryl of to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms;

"-C(-R ^a )=" in ring a may be substituted with "-N=",

R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl has carbon atoms 6-12 aryl), diarylboryl (provided that aryl is C6-C12 aryl, and the two aryls may be bonded by a single bond or a linking group), C1-C24 alkyl, or C3-C12 aryl 24 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or heteroaryl having 2 to 15 carbon atoms. may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are bonded to each other Together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one Hydrogen is an aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 12 carbon atoms, The two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms may be substituted, and at least one hydrogen in these substituents has 6 carbon atoms It may be substituted with aryl of to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms;

In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”, and any “-C(-R)=C(-R)-” (where R is R ^b , R ^c , R ^{d )} , ^{Re , R f ,} or R ^g ) is “-N(-R)-”, “-O-”, “-S-”, “-C(-R) ₂ -”, “-Si (-R) ₂ -" or "-Se-" may be substituted, and R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si R in (-R) ₂ -" is hydrogen, aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons, or cycloalkyl having 3 to 14 carbons, At least one hydrogen may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and the two Rs in “-C(-R) ₂ -” and “-Si(-R) At least one of the two Rs in " _2- " is a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, It may be bonded by -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and R of -CR=CR-, R of -N(-R)-, -C R of (-R) ₂ - and R of -Si(-R) ₂ - are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms; alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. may be substituted with alkyl, and two adjacent Rs form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms; may be,

Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R in Ge(-R)- is each independently an aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen of may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,

X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or 3 carbon atoms. to 14 cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms;

R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- by at least an a ring and a b ring may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) 2 is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring e, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ - R is each independently hydrogen, aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons, alkenyl having 1 to 6 carbons, alkynyl having 1 to 6 carbons , or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring and form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms;

c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, C6-C12 aryl, C2-C15 heteroaryl, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R is It may be substituted with 6-alkyl or C3-C14 cycloalkyl, and two adjacent R's form a ring, and C3-C14 cycloalkylene, C6-C12 arylene, or C6-C12 2 to 15 heteroarylene may be formed,

However, in the formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. , the above-mentioned aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms) and the X ¹ b bond of ring b, and R of >NR as X ² (wherein R is , limited to the aforementioned aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, which may be substituted with the alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. ) and among the three bonds of the X ² e bond of the e ring, any one or two bonds exist,

In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,

In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms or heteroaryl having 2 to 15 carbon atoms. , may be substituted with alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,

At least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen;

The polycyclic aromatic compound according to item 3.

Section 5.

In the above formula (2A) or (2B),

R ^a is hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 to 10 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ^a has 6 carbon atoms It may be substituted with -10 aryl, C2-C10 heteroaryl, C1-C5 alkyl, or C5-C10 cycloalkyl,

"-C(-R ^a )=" in ring a may be substituted with "-N=",

R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl has carbon atoms 6 to 10 aryl), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or 3 to carbon atoms 16 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , Re ^e , R ^f , and R ^g is aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, heteroaryl having 2 to 10 carbons may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are bonded to each other Together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one Hydrogen is an aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, The two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in these substituents has 6 carbon atoms It may be substituted with -10 aryl, C2-C10 heteroaryl, C1-C5 alkyl, or C5-C10 cycloalkyl,

In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”,

Y ¹ , Y ² , and Y ³ are each independently >B-, >P-, >P(=O)-, or >P(=S)-;

X ¹ and X ² are each independently >NR, >O, >S, or >C(-R) ₂ , wherein R of >NR and R of >C(-R) ₂ are each independently , hydrogen, aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, alkyl having 1 to 5 carbons, or cycloalkyl having 5 to 10 carbons, at least one hydrogen in R is from 1 to 5 carbons may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms,

R of >NR as X ¹ or R of >C(-R) ₂ is by a single bond, -N(-R)-, -O-, -S-, or -C(-R) ₂ - , may be bonded to ring b, and as X ² , R of >NR or R of >C(-R) ² is a single bond, -N(-R)-, -O-, -S-, or -C (-R) ₂ - may be bonded to the e-ring, and R of -N(-R)- and R of -C(-R) ₂ - are each independently hydrogen and having 6 to 10 carbon atoms. aryl, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, wherein at least one hydrogen in R is alkyl having 1 to 5 carbon atoms or alkyl having 5 to 10 carbon atoms. may be substituted with cycloalkyl,

c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -N(-R)-, -O-, -S-, or -C(-R) ₂ It may be bonded by -, and R in -N(-R)- and R in -C(-R) ₂ - are each independently hydrogen, aryl having 6 to 10 carbons, hetero having 2 to 10 carbons. aryl, C1-5 alkyl, or C5-10 cycloalkyl, wherein at least one hydrogen in R may be substituted with C1-5 alkyl or C5-10 cycloalkyl;

However, in the above formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. , limited to aryl having 6 to 10 carbon atoms) and X ¹ b bond of ring b, and R of >NR as X ² (wherein R is substituted with alkyl having 1 to 5 carbons or cycloalkyl having 5 to 10 carbons, Any one or two bonds among the three bonds of the X ² e bond of the e-ring and the aryl having 6 to 10 carbon atoms that may be present are present;

In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,

In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms. , may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,

At least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen;

The polycyclic aromatic compound according to item 3.

Section 6.

In the above formula (2A) or (2B),

R ^a is hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 to 10 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ^a is It may be substituted with -5 alkyl or C5-C10 cycloalkyl,

R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl has carbon atoms 6 to 10 aryl), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or 3 to carbon atoms 16 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. may be substituted,

Y ¹ , Y ² , and Y ³ are >B-;

X ¹ and X ² are >NR, and R in >NR is hydrogen, aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, alkyl having 1 to 5 carbons, or cycloalkyl having 5 to 10 carbons. and at least one hydrogen in R may be substituted with alkyl having 1 to 5 carbon atoms,

R of >NR as X ¹ may be bonded to the b ring by a single bond, and R in >NR as X ² may be bonded to the e ring by a single bond,

The c ring and d ring, the g ring and the b ring, and the f ring and the e ring may each independently be bonded by a single bond,

However, in the formula (2A), the cd bond of the c and d rings and R of >NR as X ¹ (wherein R is limited to aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms) ) and X ¹ b bond of ring b, and R of >NR as X ² (this R is limited to aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms) and X ² e bond of ring e Among the three bonds, any one or two bonds are present,

In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,

In the compound represented by the formula (2A) or (2B), among the ring b, the c ring, the d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl At least one may be condensed with at least one cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 5 carbon atoms;

At least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen;

The polycyclic aromatic compound according to item 3.

Section 7.

The polycyclic aromatic compound according to claim 3, which is represented by any one of the following structural formulas.

[Formula 10]

during each expression,

R is each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 carbon atoms) to 10 aryl, two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R is may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;

o is each independently an integer of 1 to 3,

p is each independently an integer of 1 to 4,

q is each independently an integer of 1 to 5,

At least one hydrogen in the compound represented by the above formulas may be substituted with deuterium, cyano, or halogen.

Section 8.

The polycyclic aromatic compound according to claim 1, which is represented by any one of the following structural formulas.

[Formula 11]

[Formula 12]

[Formula 13]

Section 9.

A reactive compound in which a reactive substituent is substituted for the polycyclic aromatic compound according to any one of Items 1 to 8.

Section 10.

A polymer compound obtained by polymerizing the reactive compound according to item 9 as a monomer, or a cross-linked polymer obtained by further crosslinking the polymer compound.

Section 11.

A pendant polymer compound in which a main chain polymer is substituted with the reactive compound described in Item 9, or a crosslinked pendant polymer in which the pendant polymer compound is further crosslinked.

Section 12.

A material for an organic device comprising the polycyclic aromatic compound according to any one of claims 1 to 8.

Section 13.

A material for an organic device comprising the reactive compound according to claim 9.

Section 14.

A material for an organic device comprising the polymer compound or polymer crosslinked product according to item 10.

Section 15.

A material for an organic device comprising the pendant polymer compound according to Item 11 or a pendant polymer crosslinked product.

Section 16.

The material for an organic device according to any one of items 12 to 15, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter.

Section 17.

The material for an organic device according to item 16, wherein the material for an organic electroluminescent element is a material for a light emitting layer.

Section 18.

An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent.

Section 19.

An ink composition comprising the reactive compound according to claim 9 and an organic solvent.

Section 20.

An ink composition comprising a main chain polymer, the reactive compound according to item 9, and an organic solvent.

Section 21.

An ink composition comprising the polymer compound or polymer crosslinked product according to Item 10 and an organic solvent.

Article 22.

An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to item 11 and an organic solvent.

Section 23.

A pair of electrodes comprising an anode and a cathode, and disposed between the pair of electrodes, the polycyclic aromatic compound according to any one of Items 1 to 8, the reactive compound according to Item 9, the polymer compound according to Item 10, or polymer crosslinking An organic electroluminescent device comprising a sieve or an organic layer containing the pendant polymer compound or pendant polymer crosslinked product according to item 11.

Section 24.

The organic electroluminescent device according to item 23, wherein the organic layer is a light emitting layer.

Article 25.

The organic electroluminescent device according to item 24, wherein the light emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or crosslinked pendant polymer as a dopant.

Article 26.

The light emitting layer includes a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), and a structure represented by the following general formula (H4) The organic electroluminescent device according to item 25, further comprising at least one selected from the group consisting of a compound, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material.

[Formula 14]

In the general formula (H1), L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms,

In the general formula (H2), L ² and L ³ are each independently an aryl having 6 to 30 carbon atoms or heteroaryl having 2 to 30 carbon atoms;

In the general formula (H3), MU is each independently a divalent group represented by excluding any two hydrogen atoms from an aromatic compound, EC is each independently represented by excluding any one hydrogen atom from an aromatic compound It is a monovalent group, two hydrogens in MU are substituted with EC or MU, and k is an integer of 2-50000,

In the general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- is substituted with a substituent or a structure represented by another formula (H4). may be,

In the general formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹¹ Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;

Adjacent groups among R ¹ to R ¹¹ may combine with each other to form an aryl ring or a heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, It may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be,

In ring a, ring b, and ring c, arbitrary "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) may be substituted with "-N=",

In the general formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹⁶ Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;

Adjacent groups among R ¹ to R ¹⁶ may combine with each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen in the formed ring is aryl; Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl may be substituted, and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be further substituted with, and

At least one hydrogen in the compound or structure represented by the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

Article 27.

at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, or a BO derivative , anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives The organic electroluminescent device according to any one of items 23 to 26, containing at least one selected from the group consisting of silol derivatives and azoline derivatives.

Section 28.

At least one of the electron transport layer and the electron injection layer is an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, a rare earth metal The organic electroluminescent device according to item 27, further comprising at least one selected from the group consisting of 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.

Section 29.

At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a high molecular compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or the high molecular compound further crosslinked Item 23, which includes a crosslinked polymer, a pendant polymer compound in which a low molecular weight compound capable of forming each layer is reacted with a main chain polymer, or a crosslinked pendant polymer in which the pendant polymer compound is further crosslinked The organic electroluminescent device in any one of -28.

Section 30.

A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 23 to 29.

Section 31.

A wavelength conversion filter comprising the material for a wavelength conversion filter according to item 16.

According to a preferred aspect of the present invention, by producing an organic EL device using a novel polycyclic aromatic compound as a dopant material, for example, an organic EL device having a narrow half-width of emission spectrum and excellent color purity, and furthermore, an organic EL device having excellent quantum efficiency and device lifetime An EL element can be provided. In addition, the novel polycyclic aromatic compound of the present invention has a sharper emission spectrum, a narrower half-width of the emission spectrum, and many compounds that emit light with high color purity also in that it has a rigid structure.

Specifically, the present inventors found that a polycyclic aromatic compound in which an aromatic ring is connected with a hetero element such as boron, phosphorus, oxygen, nitrogen, or sulfur has a large HOMO-LUMO gap (bandgap Eg in a thin film) and found to have high triplet energies. This is because the 6-membered ring containing the hetero element has low aromaticity, so the reduction of the HOMO-LUMO gap due to the extension of the conjugated system is suppressed. Localization is thought to be the cause.

Further, in the polycyclic aromatic compound containing a hetero element according to the present invention, the exchange interaction between both orbitals becomes small due to localization of SOMO1 and SOMO2 in the triplet excited state, so that the triplet excited state and the singlet Since the energy difference between excited states is small and thermally activated delayed fluorescence is exhibited, it is useful also as a fluorescent material for organic EL devices. A material having a high triplet energy is also useful as an electron transporting layer or a hole transporting layer of a phosphorescent organic EL device or an organic EL device using thermally activated delayed fluorescence. Furthermore, since these polycyclic aromatic compounds can freely move the energies of HOMO and LUMO by introduction of a substituent, it is possible to optimize the ionization potential or electron affinity according to the surrounding material.

BRIEF DESCRIPTION OF THE DRAWINGS It is a schematic sectional drawing which shows the organic electroluminescent element which concerns on this embodiment.

1. Polycyclic aromatic compound of the present invention

<Description of the overall structure of the compound>

The present invention is a polycyclic aromatic compound represented by the following general formula (1A) or (1B), preferably a polycyclic aromatic compound represented by the following general formula (2A) or (2B). In addition, in the above formulas, "B" to "G" in a circle is a symbol indicating a ring structure represented by a circle, and "a" to "g" in a 6-membered aromatic ring is a benzene ring, but in some cases, it is a benzene ring. It is a ring (a 6-membered or 5-membered heteroaromatic ring, etc.), and the other symbols are the same as the above-mentioned definition. Furthermore, the definition of the code|symbol in all structural formulas shown after this paragraph is the same as that of the above-mentioned definition.

[Formula 15]

[Formula 16]

The compound of the present invention is characterized by having one or two carbazole-like structures in the molecule. As will be described below, in each formula, the carbazole-like structure may be formed at three locations, and the carbazole-like structure is formed at one or two of the three locations.

The details of this carbazole-like structure will be described later, but in Formula (1A), for example, a C ring and a D ring are formed including "N", and in addition, X ¹ or X ² is >NR It is formed when R in the case of is bonded to the B ring or the E ring, respectively. In the formula (2A), for example, it is formed including "N" by the bond between the c-ring and the d-ring (the bond between Rc and Rd), and in addition, R when X ¹ or X ² is >NR It is formed when each of these is bonded to a b-ring or an e-ring (a bond between R and Rb or Re). Similarly in the formula (1B), it is formed including "N" by the bond between the C ring and the D ring, and is formed including "N" by the bond between the G ring and the B ring, and furthermore, the F ring and the E ring It is formed including "N" by the bond of a ring. In the formula (2B), similarly, for example, "N" is formed by the bond between the c-ring and the d-ring (the bond between Rc and Rd), and, in addition, the bond between the g-ring and the b-ring (Rg and Rb). is formed including "N" by the bonding of), and is formed including "N" by the bonding of the f-ring and the e-ring (the bonding between Rf and Re).

<Description of ring structure and its substituents>

R ^a is hydrogen or a substituent. Examples of the substituent include optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, and optionally substituted diarylboryl. (two aryls may be bonded by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl is preferable. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the details of the substituents enumerated here will be collectively described later.

Ring B, ring C, ring D, ring E, ring F, and ring g are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. Examples of the substituent include optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, and optionally substituted diarylboryl. (two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl is preferable. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the details of the rings and substituents enumerated here will be collectively described later.

R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 aryl may be bound by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the details of the substituents enumerated here will be collectively described later.

The aryl ring or heteroaryl ring (ie, ring B to ring G) in formulas (1A) and (1B) has a 5-membered ring or 6-membered ring that shares a bond with the condensed bicyclic structure contained in each formula it is preferable

Here, the "condensed bicyclic structure" in Formula (1A) is a structure in which two saturated hydrocarbon rings comprising Y ¹ , X ¹ , and N are condensed (the first condensed bicyclic structure on the left in the formula) and , Y ² , X ² , and means a structure in which two saturated hydrocarbon rings including N are condensed (the second condensed bicyclic structure on the right in the formula). Similarly, in Formula (1B), a structure in which two saturated hydrocarbon rings comprising Y ¹ and two Ns are condensed (the first condensed bicyclic structure on the left in the formula), Y ² and two N ^A structure in which two saturated hydrocarbon rings constituted including 3rd condensed bicyclic structure). In addition, although not shown in Formula (2A) and Formula (2B), a condensed bicyclic structure exists in the same position.

In addition, "a 6-membered ring which shares a bond with a condensed bicyclic structure" is, for example, a b-ring (benzene ring (6-membered ring) condensed with a condensed bicyclic structure as shown in Formula (2A) or Formula (2B). ) means In addition, "(B ring) aryl ring or heteroaryl ring has this 6-membered ring" means that a B ring is formed only with this 6-membered ring, or other rings etc. are further condensed to this 6-membered ring to include this 6-membered ring. It means that the B ring is formed. In other words, the "aryl ring or heteroaryl ring having a 6-membered ring (which is a B ring)" as used herein means that the 6-membered rings constituting all or part of the B ring are condensed in a condensed bicyclic structure. The same explanation is given for "C ring (c ring)", "D ring (d ring)", "E ring (e ring)", "F ring (f ring)", and "G ring (g ring)" This applies, and the same explanation is also applied to the "five-membered ring".

Ring B, ring C, ring D, and ring E in formula (1A) are, respectively, ring b and its substituent R ^b in formula (2A), c ring and its substituent R ^c , d ring and its substituent R ^d , and e ring and its substituent R ^e . That is, formula (2A) corresponds to the structure in which "ring B to E ring having 6-membered ring" is selected as ring B to E ring in formula (1A). As will be described later, "having" a 6-membered ring means, for example, with respect to a 6-membered ring b, adjacent groups among the four substituents Rb are bonded to each other to form a ring, and to the 6-membered ring b ring. This is because, in some cases, the other ring further condensed corresponds to the B ring. In this sense, each ring in the formula (2A) is represented by a lowercase letter b to e, while each ring in the formula (1A) is represented by uppercase letters B to E.

Ring B, ring C, ring D, ring E, ring F, and ring g in formula (1B) are, respectively, ring b and its substituent R ^b , c ring and its substituent R ^c , d in formula (2B) It corresponds to the ring and its substituent R ^d , the e ring and its substituent R ^e , the f ring and its substituent R ^f , and the g ring and its substituent R ^g . That is, Formula (2B) corresponds to the structure in which "B ring to G ring having 6-membered ring" is selected as ring B to G ring of Formula (1B). As will be described later, "having" a 6-membered ring means, for example, with respect to a 6-membered ring b, adjacent groups among the four substituents R ^b are bonded to form a ring, for example, a 6-membered ring b ring This is because there are cases where the fact that another ring is further condensed corresponds to the B ring. In this sense, each ring in the formula (2B) is represented by a lowercase letter b to g, while each ring in the formula (1B) is represented by uppercase letters B to G.

<Explanation of change in ring structure due to bonding of substituents>

In each of the substituents R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g of the b ring, c ring, d ring, e ring, f ring, and ring g ring, adjacent groups are bonded to each other, and each b Together with the ring, c-ring, d-ring, e-ring, f-ring, and g-ring, an aryl ring or a heteroaryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino , diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tri It may be substituted with cycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. In addition, the details of the rings and substituents enumerated here will be collectively described later.

Therefore, the polycyclic aromatic compound of formula (2A) or formula (2B), depending on the mutual bonding form of the substituents in ring b to ring g, is, for example, the following formulas (2A-fr) and (2B-fr) ), the ring structure constituting the compound changes. Ring B' and ring C' in the following formula correspond to ring B and ring C in formulas (1A) and (1B), respectively. In addition, ring d to ring g may be changed similarly.

[Formula 17]

When the B' ring and the C' ring in the formulas (2A-fr) and (2B-fr) are described with the formulas (2A) and (2B), adjacent groups among the plurality of substituents R ^b and R ^c are and represents an aryl ring or heteroaryl ring formed together with ring b and ring c, respectively (it may also be referred to as a condensed ring formed by condensation of other ring structures on ring b or c). Moreover, as can be seen from the above formula, for example, R b of ring ^b and R c of ring ^c , that is, substituents in different rings do not correspond to "adjacent groups", and are basically not bonded thereto. That is, "adjacent group" means group adjacent to the same ring.

In the above formulas (2A-fr) and (2B-fr), for the benzene ring that is ring b or ring c, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring It has a B' ring or C' ring formed by condensing, and the formed condensed ring B' or condensed ring C' is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, respectively. .

More specific examples of the formulas (2A-fr) and (2B-fr) are shown below.

[Formula 18]

The formulas (2A-fr-ex) and (2B-fr-ex) are specific examples of the formulas (2A-fr) and (2B-fr), respectively, and b in the formulas (2A) and (2B) Two adjacent R ^b in the ring are bonded, together with the b ring (benzene ring), an aryl ring (naphthalene ring) represented by B' is formed, and two adjacent R ^c in the c ring are bonded Thus, it is an example in which the aryl ring (dibenzofuran ring) represented by C' was formed together with the c ring (benzene ring). The formed aryl ring has a 6-membered ring (benzene ring b or c) that shares a bond with the above-described condensed bicyclic structure. Optional substituents in the aryl rings B' and C' (B rings and C rings in formulas (1A) and (1B)) are also represented by n Rs in addition to R ^b and R ^c , and the upper limit of n is substitutable is the maximum In addition, these descriptions are similarly applicable to all forms other than the above-mentioned specific example, for example, to the case where d ring - g ring is changed, or another aryl ring or heteroaryl ring is formed.

<Explanation of central elements Y ¹ to Y ³ in the compound>

Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > Each R of Ge(-R)- is independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. As Y ¹ , Y ² , and Y 3 , >B-, >P-, >P(=O)-, or >P(=S)- is preferable, and >B- is more preferable. In addition, the details of the substituents enumerated here will be collectively described later.

<Explanation of the change in the ring structure due to the bond between the rings>

Rings C and D in formulas (1A) and (1B) may be bonded by a single bond or a linking group (these are collectively referred to as a bonding group). Further, the G ring and the B ring in the formula (1B), and the F ring and the E ring may also be each independently bonded by a single bond or a coupling group (these are collectively referred to as a bonding group). The bond between the C and D rings is called a CD bond, the bond between the G and B rings is called a GB bond, and the bond between the F and E rings is also called an FE bond.

As a linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)- , -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-. In addition, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is alkyl or It may be substituted with cycloalkyl. Moreover, two adjacent R's may form a ring, and may form cycloalkylene, arylene, and hetero arylene. In addition, the details of the substituents enumerated here will be collectively described later.

As a linking group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a linking group Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond and a linking group are more preferable, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are still more preferable, and a single bond is most preferable.

The position where two rings are bonded by a bonding group is not particularly limited as long as it is a bonding position, but bonding is preferably at the most adjacent position, for example, the bonding position of "N" in each ring (1st position) It is preferable to bond with each other at the positions of Ortho (2nd position) as a reference (refer to the structural formulas of formulas (1A) and (1B)).

The c-rings and d-rings in the formulas (2A) and (2B) of the lower formulas may also be bonded by a single bond or a linking group (these are collectively referred to as a linking group) as in the upper formula. In addition, the g ring and the b ring, and the f ring and the e ring in the formula (2B) of the sub-formula may also be independently bonded by a single bond or a linking group (these are collectively referred to as a bonding group), as in the upper formula. . The bond between rings c and d is called a cd bond, the bond between rings g and b is called a gb bond, and the bond between rings f and e is called a fe bond. The description of the above formula can be cited for the type of linking group or the bonding position.

<Description of a carbazole-like structure (1)>

In the compound of the present invention, as described above, C and D rings (c and d rings), G and B rings (g and b rings), and F and E rings (f and e rings) can bind, the first carbazole-like structure in formulas (1A) and (2A) and the first, second and third carbazole-like structures in formulas (1B) and (2B) are formed. can be A dotted line in the following structural formula means a linking group (single bond and linking group). However, the compound of the present invention is characterized in that one or two of the three carbazole-like structures that can be formed in the molecule are formed.

[Formula 19]

[Formula 20]

The reason why it is called a "carbazole-like structure" is, for example, described by the formula (2A), the c-ring and the d-ring are the position of Ortho (2nd position) with reference to the bonding position of "N" (1st position) This is because a carbazole structure as the most basic structure is formed in the molecule when they are bonded to each other by a single bond. Further, as described above, the bonding group includes other than a single bond, and the bonding position between the rings is not limited, and as described elsewhere, each ring such as c ring is a ring by bonding between adjacent substituents. Since the structure is changed, structures other than carbazole are also formed. For this reason, it is called "carbazole-like structure" in the meaning that a structure similar to carbazole is also formed.

When a carbazole-like structure is formed, a single bond as a linking group, -CH ₂ -CH ₂ - as a linking group, -CHR-CHR-, -CR ₂ -CR ₂ -, -CR=CR-, -N(-R )-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred, single bond, -CR=CR-, -N as a linking group (-R)-, -O-, -S-, and -C(-R) ₂ - are more preferable, and -CR=CR-, -N(-R)-, -O- as a single bond and a linking group , and -S- are even more preferred, and a single bond is most preferred.

When a carbazole-like structure is formed, the position where two rings are bonded by a bonding group is not particularly limited as long as it is a bonding position, but bonding is preferably at the most adjacent position, for example, "N" in each ring Based on the binding position (1st position) of ", it is preferable to combine the positions of Ortho (2nd position) (Formula (1A), Formula (1B), Formula (2A), and Formula (2B) See structural formula).

When a carbazole-like structure is formed, it is preferable that both rings to be bonded are benzene rings.

<Description of the linking elements X ¹ and X ² in the compound>

X ¹ and X ² in formulas (1A) and (2A) are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or > Se, wherein R of >NR, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl; It is optionally substituted alkyl, or optionally substituted cycloalkyl. In addition, the details of the substituents enumerated here will be collectively described later.

As X ¹ and X ² , >NR, >O, >S, or >C(-R) ₂ is preferable, >NR or >O is more preferable, and >NR is even more preferable. From the viewpoint of good TADF properties, >NR, >O and >S are preferable, and more specifically, >NR is preferable from the viewpoint of orbital localization due to the multiple resonance effect, and >S is preferable from the viewpoint of the heavy atom effect. Do. Further, from the viewpoint of the emission wavelength, >O is preferable for emission of a short wavelength, and >NR or >S is preferable for emission of a long wavelength.

At least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ may be bonded by a single bond or a linking group (these are collectively referred to as a bonding group). As this linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- are mentioned, For example, the following structures are mentioned. In addition, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is alkyl or It may be substituted with cycloalkyl. Moreover, two adjacent R's may form a ring, and may form cycloalkylene, arylene, and hetero arylene. In addition, the details of the substituents enumerated here will be collectively described later.

[Formula 21]

As a linking group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a linking group Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond and a linking group are more preferable, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are still more preferable, and a single bond is most preferable.

The position where two R bonds by a bonding group is not particularly limited as long as it is a bondable position, but bonding is preferably at the most adjacent position, for example, when two R are phenyl groups, "C" in the phenyl group It is preferable to combine the positions of Ortho (2nd position) with the bonding position (1st position) of "Si" as a reference (refer to the structural formula above).

<Explanation of the change in the ring structure due to the bond between X ¹ or X ² and the ring>

R of >NR as X ¹ in formulas (1A) and (2A), R of >C(-R) ² , or R of >Si(-R) ₂ is a single bond or a linking group (collectively, these are It may be bonded to at least one of ring a and ring B (ring b) by a bonding group).

R of >NR as X ² in formulas (1A) and (2A), R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond or a linking group (collectively these It may be bonded to at least one of ring a and ring E (ring e) by a bonding group).

As a linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)- , -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se-. In addition, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is alkyl or It may be substituted with cycloalkyl. Moreover, two adjacent R's may form a ring, and may form cycloalkylene, arylene, and hetero arylene. In addition, the details of the substituents enumerated here will be collectively described later.

As X ¹ or X ² involved in bonding, >NR and >C(-R) ₂ are preferable, and >NR is more preferable.

As a linking group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a linking group Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond and a linking group are more preferable, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are still more preferable, and a single bond is most preferable.

As the ring to be bonded, a B ring (ring b) is preferable for X ¹ , and a ring E (ring e) is preferable for X ² .

In Formula (1A) of the upper formula, "R of >NR, R of >C(-R) ₂ , or R of >Si(-R) ₂ is a ring and B by a single bond or a linking group The regulation that it is bonded to at least one of the rings (or E rings)” is defined as “R of >NR, R of >C(-R) ₂ , or >Si(-R) in the formula (2A) of the subformulae. ) ₂ R is a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- is bonded to at least one of an a-ring and a b-ring (or an e-ring)".

This regulation can be expressed by the following structural formula, for example. On the other hand, although substituents R ^a , R ^b , R ^c , R ^d , and ^Re in the structural formula are not indicated, they are actually present.

[Formula 22]

In the structural formula on the left, R in the X ¹ and X ² options (>NR, >C(-R) ₂ , and >Si(-R) ₂ ) is an example in which R is bonded to ring b and ring e, respectively, and ring b A compound having a B' ring and an E' ring formed by condensing other rings to accept X ¹ or X ² with respect to (benzene ring) and e ring (benzene ring) is shown. The formed condensed ring B' and condensed ring E' are, for example, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring.

The structural formula in the center shows a more specific example of the structural formula on the left, wherein R (phenyl group) of >NR, which is X ¹ and X ² , is a ring b (benzene ring) and an e ring (benzene ring) by a single bond, respectively This is an example in which carbazole rings B' and E' surrounded by broken lines are formed by bonding.

The structural formula on the right shows a more specific example of the structural formula on the left, wherein R (phenyl group) of >NR which is X ¹ and X ² is bonded to the b ring (benzene ring) by -O- as a linking group, respectively, and a broken line This is an example in which a phenoxazine ring B' surrounded by a is formed, and the phenothiazine ring E' surrounded by a broken line is formed by bonding to an e ring (benzene ring) by -S-, a linking group.

R in the options of X ¹ and X ² (>NR, >C(-R) ₂ , and >Si(-R) ₂ ) is a ring (B ring, E ring, b ring and e ring) by a bonding group The bonding position is not particularly limited as long as it is a bonding position, but bonding is preferably at the most adjacent position, for example, when R is a phenyl group, “X ¹ ” or “ It is preferable to bond with each other at positions of Ortho (2nd position) based on the bonding position (1st position) of X ² ' (refer to the structural formula above).

In addition, the description of the above-mentioned specific examples can be applied similarly to all forms other than these specific examples, for example, when either one of X ¹ and X ² is bonded to a ring, bonded to a ring, bonded to another linking group, etc. .

<Description of a carbazole-like structure (2)>

In the compound of the present invention, as described above, R in X ¹ and X ² in formulas (1A) and (2A) can be bonded to an adjacent ring, but among these bonding forms, “>NR” as X ¹ of R" (wherein R is limited to the optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted cycloalkyl) and a bond formed by "B ring" or "b ring" (X ¹ By B bond or X ¹ b bond), the second carbazole-like structure is further formed as ">NR R" as X ² (wherein R is optionally substituted aryl, optionally substituted hetero A third carbazole-like structure exists by the bond (limited to aryl or the above optionally substituted cycloalkyl) and a bond formed by “E ring” or “e ring” (also referred to as X ² E bond or X ² e bond). can

[Formula 23]

As R of >N-R capable of forming a carbazole-like structure, optionally substituted aryl is preferable.

Moreover, as a bonding group of R and a ring, a single bond is preferable.

<Description of the number of carbazole-like structures>

As described above, in formulas (1A) and (2A), the first carbazole-like structure is formed from a CD bond or a cd bond, and the second structure is formed from an X ¹ B bond or an X ¹ b bond. It is formed from the origin, and the third structure is formed from the X ² E bond or the X ² e bond. In addition, in formulas (1B) and (2B), the first carbazole-like structure is formed from a CD bond or a cd bond, the second structure is formed from a GB bond or a gb bond, and the third The structure is formed from FE bonds or fe bonds. The compounds of the present invention are characterized in that one or two of these three carbazole-like structures that can be formed within the molecule are formed.

In formulas (1A) and (2A), when only the first carbazole-like structure exists (1Cz body), when only the second carbazole-like structure exists (2Cz body), the first and second carbazole-like structures When a basole-like structure exists (12Cz body), there are cases where second and third carbazole-like structures exist (23Cz body), but 1Cz body, 12Cz body, and 23Cz body are preferable, 1Cz body and 12Cz body are more preferable, , 1Cz body is more preferable.

In the formulas (1B) and (2B), when only the first carbazole-like structure exists (1Cz body), there are cases where the first and second carbazole-like structures exist (12Cz body), but the 1Cz body is preferable Do.

<Explanation of structural change of ring a and ring b to g>

In the description so far, ring a, ring b, ring c, ring d, ring e, ring f, and ring g are illustrated and explained as benzene rings, but below, ring a, ring b to ring g is not a benzene ring, 5 An example in which the structure is changed to an aryl ring or heteroaryl ring of a membered ring or 6 membered ring will be described. In addition, the description so far will be understood similarly also about the case where these rings made the following structural change.

<Structural change of ring a>

In the formulas (1A) and (2A), "-C(-R ^a )=" in the a-ring may be substituted with "-N=" to form a pyridine ring. In addition, the following structural diagram is a figure which extracted only a part of a ring and its surrounding structure.

[Formula 24]

<Structural change of ring b to g>

Any "-C(-R)=" in the b ring, c ring, d ring, e ring, f ring, and g ring in formulas (2A) and (2B) (where R is R ^b , R ^c , R ^d , ^Re , R ^f , or R ^g ) may be substituted with “-N=”.

[Formula 25]

As shown above, for example, the position of "-C(-R ^d )=" in ring d may be substituted with "-N=", and in this way, d represented as a benzene ring in each formula The ring may change to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or another nitrogen-containing heteroaryl ring. In addition, when adjacent groups exist on ring d (in the formula, the remaining two adjacent R ^d ), they combine to form a heteroaryl ring (quinoline ring in the formula) together with ring d, and the formed ring is further Those which may be substituted (represented by n Rs) are as described above.

In addition, there are also the following modified examples.

[Formula 26]

It is preferable that "-C(-R ^d )=" at the ortho or para site is substituted with "-N=" with respect to the carbon to which X ¹ , X ² , or >N- is bonded.

The same applies to the case where other positions are substituted with "-N=" or when the b ring, c ring, e ring, f ring, and g ring other than the d ring are changed.

Any "-C(-R)=C(-R)-" in the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring in formulas (2A) and (2B) (wherein R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) is "-N(-R)-", "-O-", "-S-", "-C (-R) ₂ -", "-Si(-R) ₂ -", or "-Se-" may be substituted, and R in the above "-N(-R)-", "-C(-R R in "2-" and R in "-Si(-R) ₂ -" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R is alkyl or cyclo It may be substituted with alkyl. In addition, the details of the substituents enumerated here will be collectively described later.

[Formula 27]

As shown above, for example, the position of "-C(-R ^d )=C(-R ^d )-" in ring d is "-N(-R)-", "-O-", It may be substituted with "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -", or "-Se-", and in this way, it is expressed as a benzene ring in each formula Ring d may be changed to R-substituted pyrrole ring, furan ring, thiophene ring, and other nitrogen-oxygen-sulfur heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). In addition, when adjacent groups exist on ring d (in the above formula, the remaining two adjacent R ^d ), they combine to form a heteroaryl ring together with ring d (in the above formula, R-substituted indole ring, benzofuran ring, or a ring such as a benzothiophene ring) or an aryl ring, and the formed ring may be further substituted (represented by n R) is as described above.

In addition, there are also the following modified examples.

[Formula 28]

Other positions are "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -", or "-Se-" or when the b ring, c ring, e ring, f ring, and g ring other than the d ring are changed.

At least one of the two Rs of "-C(-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" is a single bond or a linking group (collectively referred to as a bonding group) may be connected by As this linking group, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- are mentioned, For example, the following structures are mentioned. In addition, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is alkyl or It may be substituted with cycloalkyl. In addition, two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene. In addition, the details of the substituents enumerated here will be collectively described later.

[Formula 29]

As a linking group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a linking group Se- is preferable, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a single bond and a linking group are more preferable, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are still more preferable, and a single bond is most preferable.

The position where two R bonds by a bonding group is not particularly limited as long as it is a bondable position, but bonding is preferably at the most adjacent position, for example, when two R are phenyl groups, "C" in the phenyl group It is preferable to combine the positions of Ortho (2nd position) with the bonding position (1st position) of "Si" as a reference (refer to the structural formula above).

<Specific description of the ring or substituent>

Next, the details of the rings and substituents (including the second substituent further substituted for the first substituent) listed in the description so far will be summarized and described.

"Aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 6 carbon atoms. and an aryl ring of 10.

In the formulas (1A) and (1B), the “aryl ring” as the B to G rings refers to “R ^b , R ^c , R ^d , R ^e ” defined in the formulas (2A) and (2B). , R ^f , and R ^g adjacent groups are bonded to each other to correspond to an aryl ring formed together with the b ring, c ring, d ring, e ring, f ring, and g ring, respectively, and this "formed aryl ring" Regarding , since ring b to ring g is already constituted by a benzene ring having 6 carbon atoms, the total number of carbon atoms in the condensed ring in which the minimum 5-membered ring is condensed to the benzene ring is 9 as the lower limit.

However, since the rings b to g, which are the benzene rings, may change to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing sulfur heteroaryl ring (5-membered ring) as described above, in this case, Accordingly, the carbon number of the lower limit changes.

A specific "aryl ring" is, for example, a monocyclic benzene ring, a condensed bicyclic naphthalene ring, a condensed tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, or a phenanthrene ring, an anthracene ring, a condensed 4 ring. a ring system, a triphenylene ring, a pyrene ring, or a naphthacene ring, or a perylene ring or a pentacene ring which is a condensed 5-ring system.

"Heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, or a heteroaryl ring having 2 to 15 carbon atoms. , or a heteroaryl ring having 2 to 10 carbon atoms. The "heteroaryl ring" is, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

In addition, the "heteroaryl ring" as the B ring to the G ring in the formulas (1A) and (1B) means "R ^b , R ^c , R ^d , R" defined in the formulas (2A) and (2B). Adjacent groups among ^e , R ^f , and R ^g are bonded to each other to correspond to a heteroaryl ring formed together with the b ring, c ring, d ring, e ring, f ring, and g ring, respectively, and this "formed hetero aryl ring", since ring b to ring g is already constituted by a benzene ring having 6 carbon atoms, the total number of carbon atoms in the condensed ring in which the minimum 5-membered ring is condensed to this benzene ring is the lower limit.

However, since the rings b to g, which are the benzene rings, may change to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-containing sulfur heteroaryl ring (5-membered ring) as described above, in this case, Accordingly, the carbon number of the lower limit changes.

Specific "heteroaryl ring" includes, for example, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring , isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxatiin ring Noxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring , isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, benzophospholoxide ring, dibenzophospholoxide ring, furazane ring, thianthrene ring, indole a locarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, or an oxazoline ring.

"Aryl" is, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 10 carbon atoms. .

Specific "aryl" is, for example, monocyclic phenyl, bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), condensed bicyclic naphthyl (1- naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl -3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4 -yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p -terphenyl-4-yl), condensed tricyclic, acenaphthylene-(1-, 3-, 4-, or 5-)yl, fluorene-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl, quaternary phenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl -4-yl, or m-quaterphenyl), condensed tetracyclic, triphenylen-(1- or 2-)yl, pyren-(1-, 2-, or 4-)yl, or naphthacene-( 1-, 2-, or 5-)yl, or a condensed pentacyclic, perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-) days, etc.

In addition, in aryl as a second substituent, that is, aryl as a substituent (second substituent) further substituted with a substituent (first substituent), at least one hydrogen in the aryl is aryl such as phenyl (specific examples are the above-mentioned Group), a structure substituted with alkyl such as methyl (specific examples are groups described later), or cycloalkyls such as cyclohexyl or adamantyl (specific examples are groups described later) are also included in aryl as the second substituent.

As an example, when the second substituent is a fluorenyl group, at least one hydrogen in the 9th position is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl a fluorenyl group and the like, and such groups are also included in aryl as the second substituent.

"Arylene" is, for example, arylene having 6 to 30 carbon atoms, preferably arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or arylene having 6 to carbon atoms. arylene of 10 and the like.

Specific "arylene" includes, for example, a structure in which one hydrogen is removed from the above-mentioned "aryl" (monovalent group) and used as a divalent group.

"Heteroaryl" is, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, heteroaryl having 2 to 20 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or heteroaryl having 2 to 15 carbon atoms. 10 heteroaryl; In addition, "heteroaryl" is, for example, a monovalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

As a specific "heteroaryl", for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyrazolyl Dinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl , isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, Phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, Isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl , indolocarbazolyl, benzoindolocarbazolyl, benzobenzoindolocarbazolyl, imidazolinyl, or oxazolinyl.

In addition, in heteroaryl as a second substituent, that is, heteroaryl as a substituent (second substituent) further substituted with a substituent (first substituent), at least one hydrogen in the heteroaryl is an aryl such as phenyl (specific example is the above-mentioned group), alkyl such as methyl (specific examples are groups to be described later), or cycloalkyl such as cyclohexyl or adamantyl (specific examples are groups to be described later) substituted structure diagram, heteroaryl as a second substituent included in

As an example, when the second substituent is a carbazolyl group, at least one hydrogen in the 9th position is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl carbazolyl group and the like, and such groups are also included in heteroaryl as the second substituent.

"Heteroarylene" is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, heteroarylene having 2 to 15 carbon atoms. , or heteroarylene having 2 to 10 carbon atoms. In addition, "heteroarylene" is, for example, a divalent group such as a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific "heteroarylene" includes, for example, a structure in which a bivalent group is obtained by removing one hydrogen from the above-mentioned "heteroaryl" (monovalent group).

"Diarylamino" is an amino group in which two aryls are substituted, and the description of "aryl" described above can be cited for the details of this aryl.

"Diheteroarylamino" is an amino group in which two heteroaryls are substituted, and for the details of this heteroaryl, the description of "heteroaryl" described above can be cited.

"Arylheteroarylamino" is an amino group substituted with aryl and heteroaryl, and the description of "aryl" and "heteroaryl" described above can be cited for details of the aryl and heteroaryl.

"Diarylboryl" is a boyl group substituted with two aryls, and the description of "aryl" described above can be cited for the details of this aryl. In addition, these two aryls are a single bond or a linking group (for example, -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se) may be bonded. wherein R of -CR=CR-, R of >NR, R of >C(-R) ₂ , and R of >Si(-R) ₂ are aryl, heteroaryl, diarylamino, alkyl, al It is kenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least 1 hydrogen in this R may be further substituted by aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Moreover, two adjacent R's may form a ring, and may form cycloalkylene, arylene, and hetero arylene. For details of the substituents listed here, the description of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" described above, and "alkyl" and " The description of "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" can be cited.

"Alkyl" may be either linear or branched, for example, linear alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, preferably alkyl having 1 to 18 carbon atoms ( 18 branched chain alkyl), C1-12 alkyl (C3-12 branched chain alkyl), C1-6 alkyl (C3-6 branched chain alkyl), C1-5 alkyl (C3 branched chain alkyl having ∼5), alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms), and the like.

Specific "alkyl" is, for example, methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1 ,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3 ,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethyl Butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl -1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1 -Methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-Dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyl octyl, n-nonyl, n-decyl, 1-methyldecyl , n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl.

For "alkenyl", reference can be made to the description of "alkyl" described above, and it is a group in which a C-C single bond in the structure of "alkyl" is substituted with a C=C double bond, and not only one but two or more single bonds Also included are groups substituted with this double bond (also called alkadien-yl or alkanetrien-yl).

For "alkynyl", reference can be made to the description of "alkyl" described above, and it is a group in which a C-C single bond in the structure of "alkyl" is substituted with a C≡C triple bond, and not only one but two or more groups Also included are groups in which the bond is substituted with a triple bond (also called alkadiyn-yl or alkanetriin-yl).

"Cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, or cycloalkyl having 3 to 12 carbon atoms. of cycloalkyl, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or cycloalkyl having 5 carbon atoms.

Specific "cycloalkyl" is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or these alkyl having 1 to 5 or 1 to 4 carbon atoms (especially methyl)substituent, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0 ]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, dimantyl, decahydronaphthalenyl, or decahydroazulenyl.

"Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms. , cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, or cycloalkylene having 5 carbon atoms.

Specific "cycloalkylene" includes, for example, a structure in which one hydrogen is removed from the above-mentioned "cycloalkyl" (monovalent group) to be a divalent group.

"Alkoxy" may be either straight chain or branched chain, for example, straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms, preferably alkoxy having 1 to 18 carbon atoms ( Branched chain alkoxy having 18 carbon atoms), alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms), alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms), alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms) branched chain alkoxy having ∼5), alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms), and the like.

Specific "alkoxy" is, for example, methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2- Trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2 -ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyl Oxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1, 4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1, 5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy , 2,6-dimethyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n -decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecylox cy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy; and the like.

"Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)", and the description of "aryl" described above can be cited for the details of this aryl.

"Substituted silyl" is, for example, silyl substituted with at least one of aryl, alkyl, and cycloalkyl, preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl dicycloalkylsilyl.

"Triarylsilyl" is a silyl group substituted with three aryls, and for the details of this aryl, the description of "aryl" above can be cited.

Specific "triarylsilyl" is, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl.

"Trialkylsilyl" is a silyl group substituted with three alkyls, and the description of "alkyl" described above can be cited for the details of this alkyl.

Specific "trialkylsilyl" is, for example, trimethylsilyl, triethylsilyl, trin-propylsilyl, triisopropylsilyl, trin-butylsilyl, triisobutylsilyl, tris-butylsilyl, trit- Butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldi Ethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldin-propylsilyl, ethyldin-propylsilyl, n-butyldin- Propylsilyl, s-butyldin-propylsilyl, t-butyldin-propylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t -Butyldiisopropylsilyl and the like.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyls, and the description of "cycloalkyl" described above can be cited for the details of this cycloalkyl.

Specific "tricycloalkylsilyl" is, for example, tricyclopentylsilyl or tricyclohexylsilyl.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyl and one cycloalkyl, and for details of these alkyl and cycloalkyl, the description of "alkyl" and "cycloalkyl" described above can be cited. there is.

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyls, and for the details of these alkyl and cycloalkyl, the description of "alkyl" and "cycloalkyl" described above can be cited. there is.

Specifically, the emission wavelength can be adjusted by the structural steric hindrance, electron donating and electron withdrawing properties of the first or second substituent, preferably a group represented by the following structural formula, more preferably methyl; t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-Mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6- di-t-butylcarbazolyl and phenoxy, even more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6- xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3 ,6-di-t-butylcarbazolyl. From the viewpoint of easiness of synthesis, the one with larger steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4 -xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6 -Dimethyl carbazolyl and 3,6-di-t-butyl carbazolyl are preferred.

In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents a bonding position.

[Formula 30]

[Formula 31]

[Formula 32]

[Formula 33]

[Formula 34]

[Formula 35]

[Formula 36]

[Formula 37]

[Formula 38]

[Formula 39]

[Formula 40]

[Formula 41]

[Formula 42]

[Formula 43]

[Formula 44]

[Formula 45]

[Formula 46]

[Formula 47]

<Description of cycloalkane condensation>

In addition, at least one of an aromatic ring and a heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

For example, in the compound represented by formula (1A) or formula (1B), B ring, C ring, D ring, E ring, F ring, G ring, aryl, and heteroaryl, formula (2A) or In the compound represented by formula (2B), at least one of the b-ring, c-ring, d-ring, e-ring, f-ring, g-ring, the "formed ring", aryl, and heteroaryl is at least one cyclo You may condense with an alkane.

Examples of "cycloalkane" include cycloalkane having 3 to 24 carbon atoms, cycloalkane having 3 to 20 carbon atoms, cycloalkane having 3 to 16 carbon atoms, cycloalkane having 3 to 14 carbon atoms, cycloalkane having 5 to 10 carbon atoms, and cycloalkane having 5 to 8 carbon atoms. cycloalkane, cycloalkane having 5 to 6 carbon atoms, cycloalkane having 5 carbon atoms, and the like.

Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, Bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, dia and mantane, decahydronaphthalene and decahydroazrene, and alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents and deuterium substituents thereof.

Among these, for example, as shown in the following structural formula, at least one in the α-position carbon of the cycloalkane (the carbon in the position adjacent to the carbon of the condensation site in the cycloalkyl condensed to an aromatic ring or a heteroaromatic ring) A structure in which hydrogen is substituted is preferable, a structure in which two hydrogens at the carbons at the α-position are substituted is more preferable, and a structure in which a total of four hydrogens at the carbons at the two α-positions is substituted is even more preferable. . Examples of the substituent include an alkyl (especially methyl) substituent having 1 to 5 carbon atoms, a halogen (especially fluorine) substituent, and a deuterium substituent.

[Formula 48]

1-3 pieces are preferable, as for the number of the cycloalkanes condensed to one aromatic ring or a heteroaromatic ring, 1 piece or 2 pieces are more preferable, and 1 piece is still more preferable. For example, the example in which one or several cycloalkane was condensed to one benzene ring (phenyl group) is shown below. * in each structural formula means that it is a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and in the case of a phenyl group, it means the bond substituted by the skeleton structure of a compound. Cycloalkanes condensed as shown in formulas (Cy-1-4) and (Cy-2-4) may be condensed. Even when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), even when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

[Formula 49]

At least one -CH ₂ - in the cycloalkane may be substituted with -O-. However, when a plurality of -CH ₂ - is substituted with -O-, adjacent -CH ₂ - is not substituted with -O-. For example, an example in which one or more -CH ₂ - in the cycloalkane condensed to one benzene ring (phenyl group) is substituted with -O- is shown below. * in each structural formula means that it is a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and in the case of a phenyl group, it means the bond substituted by the skeleton structure of a compound. Even when the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), even when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

[Formula 50]

At least one hydrogen in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano or halogen, and for these details, the description of the first substituent described above is cited can do. Among these substituents, alkyl (eg, alkyl having 1 to 6 carbon atoms), cycloalkyl (eg cycloalkyl having 3 to 14 carbon atoms), halogen (eg, fluorine), deuterium, and the like are preferable. In addition, when cycloalkyl is substituted, it may be a substituted form which forms a spiro structure, For example, the example in which the spiro structure was formed in the cycloalkane condensed to one benzene ring (phenyl group) is shown below. * in each structural formula means that it is a benzene ring contained in the skeleton structure of a compound in the case of a benzene ring, and in the case of a phenyl group, it means the bond substituted by the skeleton structure of a compound.

[Formula 51]

As another form of cycloalkane condensation, the polycyclic aromatic compound of the present invention is, for example, a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety), and a carbazolyl group condensed with a cycloalkane (this benzene ring Condensed to a moiety) or a benzocarbazolyl group condensed with a cycloalkane (condensed to this benzene ring moiety) may be substituted. Regarding the "diarylamino group", the above description can be cited.

Further, as a more specific example, R ^a in the polycyclic aromatic compound represented by Formula (1A) or Formula (2A) is a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety) or a cycloalkane An example of a carbazolyl group (condensed to this benzene ring moiety) is given.

<Explanation of Substitution with Deuterium, Cyano, or Halogen>

At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, and fluorine, chlorine, or bromine is preferable, and fluorine or chlorine is more preferable.

<Description of specific examples of the polycyclic aromatic compound of the present invention>

For example, a compound represented by any one of the following structural formulas is preferable.

[Formula 52]

[Formula 53]

[Formula 54]

[Formula 55]

during each expression,

R is each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 carbon atoms) to 10 aryl, two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R is may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;

o is each independently an integer of 1 to 3,

p is each independently an integer of 1 to 4,

q is each independently an integer of 1 to 5,

At least one hydrogen in the compound represented by the above formulas may be substituted with deuterium, cyano, or halogen.

For a more specific description of R, the description of aryl and the like described above can be cited. Moreover, as o, p, and q, 1 or 2 is preferable, 1 is more preferable, and 0 is still more preferable.

<Use as heat activated delayed fluorescence (TADF) material>

The compound of the present invention can also be used as a TADF material. In particular, the compound represented by the formulas (1A) and (2A) is preferable to the compound represented by the formulas (1B) and (2B), and in the B ring to G ring or the b ring to the g ring, It is preferable that the ring sharing a bond with the condensed bicyclic structure of is a 6-membered ring, and it is more preferable that it is a 6-membered aryl ring including a ring.

In addition, as a bonding group for forming a carbazole-like structure, a single bond is preferable (as an example, the following structural formula), and when only the first carbazole-like structure exists (1Cz form), it is preferable (1A-111, 1A- 112, structural formulas other than 1A-214), among carbazole-like structures, a phenyl group, etc. It is preferable that the aryl ring of is substituted (structural formulas other than 1A-214, 1A-331, and 1A-702), and based on the bonding position of X ¹ and X ² , the meta site (especially the meta position in the b ring or e ring) position) is preferably substituted with a nitrogen-containing group such as a diarylamino group or a carbazolyl group (structural formulas of 1A-31, 1A-32, 1A-38, and 1A-407).

[Formula 56]

[Formula 57]

<Description of specific examples of the polycyclic aromatic compound of the present invention>

As a more specific example of a polycyclic aromatic compound, the compound represented by the following structural formula is mentioned. In addition, in the following structural formula, "Me" represents a methyl group, "tBu" represents a t-butyl group, and "D" represents deuterium.

[Formula 58]

[Formula 59]

[Formula 60]

[Formula 61]

[Formula 62]

[Formula 63]

[Formula 64]

[Formula 65]

[Formula 66]

[Formula 67]

[Formula 68]

[Formula 69]

[Formula 70]

[Formula 71]

[Formula 72]

[Formula 73]

[Formula 74]

[Formula 75]

[Formula 76]

[Formula 77]

[Formula 78]

[Formula 79]

[Formula 80]

[Formula 81]

[Formula 82]

[Formula 83]

[Formula 84]

[Formula 85]

[Formula 86]

[Formula 87]

[Formula 88]

[Formula 89]

[Formula 90]

[Formula 91]

[Formula 92]

[Formula 93]

[Formula 94]

[Formula 95]

[Formula 96]

The polycyclic aromatic compound according to the present invention is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent thereto as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or the polymer compound further A crosslinked polymer crosslinked product (the polymer compound for obtaining the crosslinked polymer compound has a crosslinkable substituent), or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound (for obtaining this crosslinked polymer compound) The reactive compound has a reactive substituent) or a pendant polymer crosslinked product further crosslinked with the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked product has a crosslinkable substituent), organic It can be used for a material for devices, for example, a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a wavelength conversion filter.

As the above-mentioned reactive substituents (including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant polymer, hereinafter also simply referred to as “reactive substituent”), the polycyclic aromatic compound can be made high in molecular weight Although it will not specifically limit as long as it is a substituent which exists, if it is a substituent which can further bridge|crosslink the polymer compound obtained in this way, and can pendant react with a main-chain polymer|macromolecule, The substituent of the following structure is preferable. * in each structural formula represents a bonding position.

[Formula 97]

L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and 1 carbon atom -12 polyoxyalkylene. Among the above substituents, a group represented by a formula (XLS-1), a formula (XLS-2), a formula (XLS-3), a formula (XLS-9), a formula (XLS-10), or a formula (XLS-17) is preferable. and the group represented by a formula (XLS-1), a formula (XLS-3), or a formula (XLS-17) is more preferable.

Such polymer compounds, crosslinked polymers, pendant polymer compounds, and crosslinked pendant polymers include, in addition to the repeating unit of the polycyclic aromatic compound according to the present invention, substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, , substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, At least one member selected from the group consisting of substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran may be included as a repeating unit.

As a substituent in these repeating units, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group) ), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. For the "aryl" of triarylamine and details of these substituents, the description of the polycyclic aromatic compound according to the present invention can be cited.

The details of the uses of such polymer compounds, cross-linked polymers, pendant-type polymers, and cross-linked pendant polymers (hereinafter, simply referred to as "polymer compounds and cross-linked polymers") will be described later.

2. Method for preparing polycyclic aromatic compound according to the present invention

The polycyclic aromatic compound of the present invention is basically an intermediate by first bonding ring a and ring B to ring G or ring b to ring g with a bonding group (a group containing “N” or X ¹ or X ² ). After preparation (first reaction), a final product can be prepared by bonding ring a and ring B to ring G or ring b to ring g with a bonding group (group containing Y ¹ to Y ³ ). 2 reaction). The manufacturing method described in International Publication No. 2015/102118 can be referred to.

In the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullman reaction may be used, and if it is an amination reaction, a general reaction such as a Birchwald-Hartwick reaction may be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic sphere substitution reaction, the same hereinafter) can be used.

The second reaction is a reaction in which ring a and Y ¹ to Y ³ bonding ring B to ring G or ring b to ring g is introduced, as shown in the following schemes (1) and (2). First, a hydrogen atom between "N" and X ¹ and X ² or a hydrogen atom between "N" is orthometalized with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Then, a halide of Y ¹ to Y ³ such as boron trichloride or boron tribromide is added to perform lithium-boron metal exchange, and then a Bronsted base such as N,N-diisopropylethylamine is further added. By doing so, a tandem bora Friedel Crafts reaction can be carried out to obtain the target product. In the second reaction, in order to accelerate the reaction, a Lewis acid such as aluminum trichloride may be added. In addition, the definition of the code|symbol in each structural formula in following scheme (1) and (2) further in the following scheme is the same as the definition mentioned above.

[Formula 98]

[Formula 99]

In the above scheme, lithium was introduced at a desired position by orthometalation, but as in the following scheme (3), a bromine atom or the like is introduced at a position where lithium is to be introduced, and lithium is also at a desired position by halogen-metal exchange. can be introduced. According to this method, even in a case in which ortho-metalization cannot be performed due to the influence of a substituent, the target product can be manufactured and is useful.

[Formula 100]

The above schemes (1) to (3) are typical manufacturing methods in which Y ¹ to Y ³ are boron (B) or the like.

Next, as an example, the following schemes (4) and (5) show the case where Y1 to Y3 are phosphorus sulfide, phosphorous oxide or phosphorus atom. As before, first, a hydrogen atom between "N" and X ¹ and X ² and a hydrogen atom between "N" are orthometalized with n-butyllithium or the like. Then, phosphorus trichloride and sulfur are added in this order, and finally, a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to cause a tandem phosphor Friedel-Crafts reaction, and Y The compound whose ¹ -Y< ³ > is phosphorus can be obtained. Further, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), a compound in which Y ¹ to Y ³ is a phosphoroxide can be obtained, and by treating with triethylphosphine, Y ¹ to Y ³ is a phosphorus atom A phosphorus compound can be obtained.

[Formula 101]

[Formula 102]

^In the said scheme, although Y1 ^- Y3 mainly described examples, such as B, P, P=O, or P=S, another compound can also be manufactured by changing a raw material suitably.

In the above scheme, before adding a halide of Y ¹ to Y ³ such as boron trichloride or boron tribromide, a hydrogen atom (or halogen atom) between “N” and X ¹ and X ² or between “N” An example in which a tandem hetero Friedel Crafts reaction was performed by ortho-metalizing an intervening hydrogen atom (or a halogen atom) with butyllithium or the like was presented, but without ortho-metalization using butyllithium or the like, boron trichloride, boron tribromide, etc. It is also possible to advance the reaction by adding a halide of Y ¹ to Y ³ .

Examples of the solvent used in the above scheme include t-butylbenzene and xylene.

Examples of the ortho metallization reagent used in the above scheme include alkyl lithium such as methyl lithium, n-butyl lithium, sec-butyl lithium and t-butyl lithium, lithium diisopropylamide, lithium tetramethyl piperidide, and lithium hexamethyl di Dispersion alkali metals, such as organic alkali compounds, such as silazide and potassium hexamethyldisilazide, and organic solvent dispersion|distribution Na, are mentioned.

Examples of the metal-(Y ¹ to Y ³ ) metal exchange reagent used in the above scheme include the trifluoride of Y ¹ to Y ³ , the trichloride of Y ¹ to Y ³ , the tribromide of Y ¹ to Y ³ , and Y ¹ Y 1 to Y ³ halides such as triiodide of to Y ^{3 , amination halide of Y 1 to Y 3 such as CIPN} (NEt ₂ ) ₂ , alkoxide of Y ¹ to Y ³ , Y ¹ to Y The aryloxide of ³ , etc. are mentioned.

As the Bronsted base used in the above scheme, N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-penta Methylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Si (on the other hand, Ar is aryl such as phenyl) and the like.

As the Lewis acid used in the above scheme, AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ ·OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In(OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaOTf, KOTf, Me ₃ SiOTf, Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , CoBr ₃ and the like.

In the above scheme, a Bronsted base or a Lewis acid may be used to promote the tandem hetero Friedel Crafts reaction. However, halides of Y ¹ to Y ³ such as trifluoride of Y ¹ to Y ³ , trichloride of Y ¹ to Y ³ , tribromide of Y ¹ to Y ³ , and triiodide of Y ¹ to Y ³ When used, an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated along with the progress of the aromatic sphere substitution reaction, so the use of a Bronsted base that captures an acid is effective. ^On the other hand, when the amination halide of Y1 ^- Y3 ^and the alkoxide of Y1 ^- Y3 are used, since an amine and alcohol are produced|generated with advancing of an aromatic sphere substitution reaction, in many cases, Broens' Although it is not necessary to use a Ted base, since the detachment ability of an amino group or an alkoxy group is low, use of the Lewis acid which accelerates|stimulates the detachment is effective.

In addition, the polycyclic aromatic compound of the present invention includes a compound in which at least a part of hydrogen is substituted with deuterium, cyano, or halogen. In such compounds, the desired position is deuterated, cyanoized, fluorinated or chlorinated. By using a halogenated raw material, it can manufacture similarly to the above.

3. Organic Devices

In the chemical structural formulas illustrated below, "Me" represents a methyl group, and "tBu" represents a t-butyl group.

The polycyclic aromatic compound according to the present invention can be used as a material for an organic device. As an organic device, an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, etc. are mentioned, for example.

3-1. organic electroluminescent device

Hereinafter, an organic EL device according to the present embodiment will be described in detail with reference to the drawings. 1 is a schematic cross-sectional view showing an organic EL device according to the present embodiment.

<Structure of organic electroluminescent device>

The organic EL device 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 injection layer ( 103) provided on the hole transport layer 104, the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and electron injection provided on the electron transport layer 106 It has a layer 107 and a cathode 108 provided on the electron injection layer 107 .

In the organic EL device 100 , for example, the substrate 101 , the cathode 108 provided on the substrate 101 , and the electron injection layer ( 107 , an electron transport layer 106 provided on the electron injection layer 107 , a light emitting layer 105 provided on the electron transport layer 106 , a hole transport layer 104 provided on the light emitting layer 105 , and a hole transport layer It is good also as a structure which has the positive hole injection layer 103 provided on 104, and the anode 102 provided on the positive hole injection layer 103. As shown in FIG.

All of the above layers are not indispensable, and the minimum structural unit is a configuration comprising the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, and the electron transport layer 106 ), the electron injection layer 107 is an arbitrarily provided layer. In addition, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

As an aspect of the layer constituting the organic EL element, in addition to the configuration aspect of "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode" described above, "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 / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light emitting layer /electron injection layer/cathode”, “substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode”, “substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode”, “substrate/anode/hole injection layer” /light-emitting layer/electron transporting layer/cathode", "substrate/anode/light-emitting layer/electron transporting layer/cathode", and "substrate/anode/light-emitting layer/electron injection layer/cathode" may be a structural aspect.

<Substrate in organic electroluminescent element>

The board|substrate 101 is a support body of the organic electroluminescent element 100, Quartz, glass, metal, plastic, etc. are used normally. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, metal foil, a plastic film, a plastic sheet, or the like is used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate and polysulfone are preferable. In the case of a glass substrate, soda-lime glass, an alkali-free glass, etc. are used, and since thickness also just needs to have sufficient thickness in order to maintain mechanical strength, what is necessary is just to be 0.2 mm or more, for example. As an upper limit of thickness, it is 2 mm or less, for example, Preferably it is 1 mm or less. About the material of glass, since it is good that there are few ions eluted from glass, although alkali-free glass is preferable, since soda _- lime glass which gave barrier coating, such as SiO2, is also marketed, it can be used. In addition, in order to improve gas barrier properties, a gas barrier film such as a dense silicon oxide film may be formed on at least one surface of the substrate 101, and a synthetic resin plate, film or sheet having particularly low gas barrier properties is applied to the substrate ( 101), it is preferable to form a gas barrier film.

<Anode in organic electroluminescent element>

The anode 102 serves to inject holes into the light emitting layer 105 . In addition, 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 the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO)) etc.), a metal halide (copper iodide etc.), copper sulfide, carbon black, ITO glass, Nessa glass, etc. are mentioned. Examples of the organic compound include polythiophene such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can select and use suitably from the material used as an anode of organic electroluminescent 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 is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω/square or less functions as an element electrode, but now it is possible to supply a substrate of about 10 Ω/square, for example, 100 to 5 Ω/square, preferably 50 to 5 Ω/ It is particularly desirable to use a low-resistance product of □. Although the thickness of ITO can be arbitrarily selected according to a resistance value, Usually, it is used between 50-300 nm in many cases.

<Hole injection layer and hole transport layer in organic electroluminescent element>

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104 . The hole transport layer 104 serves to efficiently transport 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 . Each of the hole injection layer 103 and the hole transport layer 104 is formed by laminating one or two or more types of hole injection/transport materials, respectively, or a mixture of the hole injection/transport material and a polymer binder. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

As the hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes to which an electric field is applied, and it is preferable to have high hole injection efficiency and to efficiently transport the injected holes. For this purpose, it is preferable that the ionization potential is small, the hole mobility is large, and furthermore, the material is excellent in stability, and the impurity that becomes a trap is difficult to generate during manufacture and use. In the present invention, as a material for the hole injection layer and the hole transport layer, the polycyclic aromatic compound represented by the general formula (1A) or (1B) can be used.

As a material for forming the hole injection layer 103 and the hole transport layer 104, a compound conventionally used as a charge transport material for holes in a photoconductive material, a p-type semiconductor, a hole injection layer and a hole of an organic EL device Any compound can be selected and used from the well-known compounds used for a transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine Derivatives (polymers having aromatic tertiary amino in the main chain or side chains, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3) -Methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N ,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl -1,1'-diamine, N4,N4'-diphenyl-N4, N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4 '-diamine, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4, Triphenylamine derivatives such as 4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, 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 having the above monomers in the side chain, polyvinylcarbazole, polysilane, etc. Although it is preferable, if it is a compound which can form the thin film required for manufacture of a light emitting element, can inject a hole from an anode, and can also transport a hole, it will not specifically limit.

Moreover, it is also known that the electroconductivity of an organic semiconductor is strongly influenced by the doping. Such an organic semiconductor matrix material is composed of a compound having a good electron donating property or a good electron accepting compound. For doping of the electron donor material, a strong electron acceptor such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) is used. known (eg, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998) and J. Blochwitz , M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). They generate so-called holes by an electron transfer process in an electron-donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material changes significantly. As a matrix material having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (especially zinc phthalocyanine ZnPc, etc.) are known (Japanese Patent Laid-Open No. 2005-167175). No. Gazette).

The material for the hole injection layer and the material for the hole transport layer described above is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a cross-linked polymer thereof, or a main chain polymer and the reactive compound. It can also be used for a hole layer material as a pendant polymer compound or a crosslinked pendant polymer compound. As the reactive substituent in this case, the description in the polycyclic aromatic compound represented by the general formula (1A) or (1B) can be cited.

Details of the use of such a high molecular compound and a polymer crosslinked product will be described later.

<Light emitting layer in organic electroluminescent element>

The light emitting layer 105 is a layer that emits light by recombination of the holes injected from the anode 102 and the electrons injected from the cathode 108 between the electrodes to which an electric field is applied. The material for forming the light emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light emitting compound). It is preferable that it is a compound which represents In the present invention, as a material for the light emitting layer, a host material and, for example, a polycyclic aromatic compound represented by the general formula (1A) or (1B) as a dopant material can be used.

A single layer may be sufficient as a single layer, and it may consist of multiple layers, and is respectively formed of the material for light-emitting layers (host material, dopant material). The number of each of a host material and a dopant material may be one, and a several combination may be sufficient as it. The dopant material may be contained in the whole host material, and may be contained partially. As a doping method, although it can form by the method of co-evaporation with a host material, you may vapor-deposit simultaneously after pre-mixing with a host material, or you may form into a film by the wet film-forming method after pre-mixing with a host material together with an organic solvent.

The usage-amount of a host material changes with the kind of host material, and what is necessary is just to set it according to the characteristic of the host material. The standard of the usage-amount of a host material becomes like this. Preferably it is 50 to 99.9 weight% of the whole material for light emitting layer, More preferably, it is 80 to 99.95 weight%, More preferably, it is 90 to 99.9 weight%.

The usage-amount of a dopant material changes with the kind of dopant material, and what is necessary is just to set it according to the characteristic of the dopant material. The reference amount of the dopant material used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight of the total weight of the light emitting layer material. If it is in the above range, for example, it is preferable from the point of being able to prevent a density|concentration quenching phenomenon. Moreover, it is also preferable that a part or all of hydrogen atoms of a dopant material are deuterated from a viewpoint of durability.

On the other hand, in an organic electroluminescent device using a thermally activated delayed fluorescent dopant material, a low concentration of the dopant material is preferable in terms of preventing the concentration quenching phenomenon. It is preferable from the viewpoint of the efficiency of the delayed fluorescence apparatus. In addition, in an organic electroluminescent device using a thermally activated delayed fluorescence assisting dopant material, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant material, it is preferable that the amount of the dopant material is lower than that of the assist dopant material. .

When the assist dopant material is used, the standards for the amount of the host material, the assist dopant material and the dopant material used are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight of the total material for the light emitting layer, respectively. , Preferably, they are 60 to 99.99 weight%, 39 to 5 weight%, and 10 to 0.01 weight%, respectively, More preferably, they are 70 to 99.95 weight%, 29 to 10 weight%, and 5 to 0.05 weight%. The compound represented by the said general formula (1A) or general formula (1B) and its high molecular compound can also be used as an assist dopant material.

Examples of the host material include condensed cyclic derivatives such as anthracene and pyrene, which have been previously known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, A benzofluorene derivative etc. are mentioned.

The triplet energy of the host material is preferably higher than the triplet energy of the dopant or assist dopant having the highest triplet energy in the light emitting layer, from the viewpoint of promoting the generation of TADF in the light emitting layer without inhibiting it, specifically As for the triplet energy of the host material, 0.01 eV or more is preferable, 0.03 eV or more is more preferable, and 0.1 eV or more is still more preferable. Moreover, you may use the compound which is TADF active for a host material.

As the host material, for example, a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound represented by the following general formula (H4) The compound containing a structure, the compound represented by the following general formula (H5), the compound represented by the following general formula (H6), and TADF material are mentioned. Preferably, it is a compound represented by general formula (H1).

[Formula 103]

<The compound represented by the general formula (H1)>

[Formula 104]

In the formula (H1), L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms, preferably arylene having 6 to 24 carbon atoms, more preferably arylene having 6 to 16 carbon atoms, , more preferably arylene having 6 to 12 carbon atoms, particularly preferably arylene having 6 to 10 carbon atoms, more preferably heteroarylene having 2 to 25 carbon atoms, more preferably heteroarylene having 2 to 20 carbon atoms Preferably, heteroarylene having 2 to 15 carbon atoms is more preferable, and heteroarylene having 2 to 10 carbon atoms is particularly preferable. Specifically as arylene, a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and Bivalent groups, such as a pentacene ring, are mentioned. Moreover, specifically as heteroarylene, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring , pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, iso Quinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring , phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazane ring, thiant Bivalent groups, such as a renyl ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring, are mentioned.

At least one hydrogen in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

<The compound represented by the general formula (H2)>

[Formula 105]

In the formula (H2), L ² and L ³ each independently represent aryl having 6 to 30 carbon atoms or heteroaryl having 2 to 30 carbon atoms. As aryl, C6-C24 aryl is preferable, C6-C16 aryl is more preferable, C6-C12 aryl is still more preferable, C6-C10 aryl is especially preferable, Specifically, , benzene ring, biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perylene ring and pentacene ring can be lifted As heteroaryl, C2-C25 heteroaryl is preferable, C2-C20 heteroaryl is more preferable, C2-C15 heteroaryl is still more preferable, C2-C10 heteroaryl is especially preferable. and specifically, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring , pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, new Noline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, Phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazane ring, thiantrene ring, indolo Monovalent groups, such as a carbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring, are mentioned.

At least one hydrogen in the compound represented by the formula (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

<The compound represented by the general formula (H3) (an example of a polymer host material)>

[Formula 106]

In formula (H3),

MU is each independently a divalent group represented by excluding any two hydrogen atoms in an aromatic compound, EC is each independently a monovalent group represented by excluding any one hydrogen atom in an aromatic compound, and 2 in MU n hydrogens are substituted with EC or MU, and k is an integer from 2 to 50000.

More specifically,

MU is, each independently, arylene, heteroarylene, diarylene arylamino, diarylene arylboryl, oxaborine-diyl, azaborine-diyl,

EC is, each independently, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy;

At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;

k is an integer from 2 to 50000;

It is preferable that it is an integer of 20-50000, and, as for k, it is more preferable that it is an integer of 100-50000.

At least one hydrogen in MU and EC in formula (H3) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen or deuterium, and any -CH ₂ - may be substituted with -O- or -Si(CH ₃ ) ₂ -, and any -CH ₂ - other than -CH ₂ - directly connected to EC in formula (H3) in the above alkyl may be substituted with arylene having 6 to 24 carbon atoms, and arbitrary hydrogen in the alkyl may be substituted with fluorine.

Examples of MU include a divalent group represented by excluding any two hydrogen atoms in any one of the following compounds.

[Formula 107]

More specifically, the divalent group represented by the structure in any one of the following is mentioned. In these, a MU binds to another MU or EC at *.

[Formula 108]

[Formula 109]

[Formula 110]

[Formula 111]

[Formula 112]

[Formula 113]

[Formula 114]

[Formula 115]

[Formula 116]

Moreover, as EC, the monovalent group represented by any one of the structures below is mentioned, for example. In these, EC binds to MU at *.

[Formula 117]

[Formula 118]

In the compound represented by formula (H3), from the viewpoint of solubility and coating film forming properties, it is preferable that 10 to 100% of the total number of MUs in the molecule (k) have an alkyl having 1 to 24 carbon atoms, and the total number of MUs in the molecule ( It is more preferable that 30 to 100% of the MUs in k) have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and 50 to 100% of the MUs in the total number of MUs in the molecule (k) have 1 to 18 carbon atoms. It is even more preferred to have -12 alkyl (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total MU number (k) in the molecule has an alkyl of 7 to 24 carbon atoms, and 30 to 100% of the total MU number (k) in the molecule It is more preferable that MU of has an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

<Compound containing the structure represented by the general formula (H4)>

The compound is a compound containing a structure represented by the following formula (H4), and has a plurality of structures, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 2 , Most preferably, one is included, and when a plurality of structures are included, the structures are directly bonded to each other by a single bond, or bonded to a specific linking group.

[Formula 119]

In the general formula (H4), each G is independently “=C(-H)-” or “=N-”, and H in the “=C(-H)-” is a substituent or another formula (H4) You may be substituted by the structure represented by

For the compound containing the structure represented by the general formula (H4), for example, the compounds described in International Publication Nos. 2012/153780 and International Publication Nos. 2013/038650 and the like can be used, and manufactured according to the method described in the above documents can do.

Examples of the substituent when H in "=C(-H)-" which is G is substituted, for example, is as follows, but is not limited thereto.

Specific examples of the "aryl group" as a substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, benzoanthryl, triphenylenyl , fluorenyl, 9,9-dimethyl fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc., preferably phenyl , biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of the aryl group having a substituent include tolyl, xylyl and 9,9-dimethylfluorenyl. As shown in the specific example, the aryl group includes both a condensed aryl group and a non-condensed aryl group.

Specific examples of the "heteroaryl group" as a substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, Indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, aza Dibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothia Zinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl, etc. are mentioned, Preferably, di benzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl and azadibenzothienyl; and the like. Even more preferred are dibenzofuranyl, dibenzothienyl, azadibenzofuranyl or azadibenzothienyl.

The "substituted silyl group" as a substituent is also preferably a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group.

Specific examples of the substituted or unsubstituted trialkylsilyl group include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl group include diphenylmethylsilyl, ditolylmethylsilyl and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl and tritolylsilyl.

It is also preferable that the "substituted phosphine oxide group" which is a substituent is a substituted or unsubstituted diaryl phosphine oxide group. Specific examples of the substituted or unsubstituted diaryl phosphine oxide group include diphenyl phosphine oxide and ditolyl phosphine oxide.

As a "substituted carboxy group" which is a substituent, benzoyloxy etc. are mentioned, for example.

Examples of the linking group for bonding a plurality of structures represented by formula (H4) include divalent, divalent, divalent, or divalent derivatives of aryl and heteroaryl described above.

The specific example of the compound containing the structure represented by general formula (H4) is shown below.

[Formula 120]

[Formula 121]

<The compound represented by the general formula (H5)>

[Formula 122]

In the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substituent), and R ¹ to R At least one hydrogen in ¹¹ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, second substituent);

Adjacent groups among R ¹ to R ¹¹ may combine with each other to form an aryl ring or a heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, It may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substituent), and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, may be further substituted with alkyl or cycloalkyl (above, the second substituent);

In ring a, ring b, and ring c, arbitrary "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) may be substituted with "-N=",

At least one hydrogen in the compound represented by the formula (H5) may be independently substituted with halogen or deuterium.

Any "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) in ring a, ring b, and ring c in formula (H5) is substituted with "-N=", and pyridine You may change to a ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, and another nitrogen-containing heteroaryl ring. For the detailed content of this description, the description in the said General formula (2A) and Formula (2B) can be referred.

Preferably, in the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ¹ to R ¹¹ is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl has 6 to 12 carbon atoms) aryl), may be further substituted with alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms;

Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the ring a, ring b, or ring c, and at least in the formed ring One hydrogen is aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, diarylamino (however, aryl is aryl having 6 to 12 carbons), alkyl having 1 to 12 carbons, or cycloalkyl having 3 to 16 carbons may be substituted, and at least one hydrogen in these substituents is aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, diarylamino (provided that aryl is aryl having 6 to 12 carbons), and 1 to carbon atoms. It may further be substituted with 12 alkyl or C3-C16 cycloalkyl.

More preferably, in the formula (H5),

R ¹ to R ¹¹ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in R ¹ to R ¹¹ is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl has 6 to carbon atoms) 10 aryl), may be further substituted with C 1 to C 6 alkyl or C 3 to C 14 cycloalkyl;

Adjacent groups of R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the ring a, ring b, or ring c, and at least in the formed ring One hydrogen is aryl having 6 to 16 carbons, heteroaryl having 2 to 15 carbons, diarylamino (however, aryl is aryl having 6 to 10 carbons), alkyl having 1 to 6 carbons, or cycloalkyl having 3 to 14 carbons may be substituted with, and at least one hydrogen in these substituents is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), and 1 to carbon atoms. It may further be substituted with 6-alkyl or C3-C14 cycloalkyl.

In the first and second substituents described above, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following examples.

Specific "aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, more preferably aryl having 6 to 16 carbon atoms. More preferably, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, terphenylyl which is tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl , p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-ter Phenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, ace Naphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl , (1-,2-,3-,4-,9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-ter Phenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1- ,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1- ,2-,5-,6-) days and the like.

Specific "heteroaryl" includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, and heteroaryl having 2 to 15 carbon atoms. of heteroaryl is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyri Dazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, syn Nolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothiazinyl, phenazinyl, Phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar and bazolyl and benzobenzoindolocarbazolyl.

In the first and second substituents, the "alkyl" may be either straight-chain or branched, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, , alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable. 3 to 6 branched chain alkyl) is more preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) or alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable. and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n -Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-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, n-octadecyl, n -Eicosil, etc. are mentioned. Also, 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-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

In the above first and second substituents, "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. and cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents having 1 to 4 carbon atoms and bicyclo[1.1.0] Butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[ 2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

When the first substituent is aryl, the substitution position is preferably R ¹ , R ³ , R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ , for example, substitution with R ¹ and R ³ , R ⁵ and R Substitution with ¹⁰ and substitution with R ⁴ and R ¹¹ are more preferable, and aryl is preferably a phenyl group.

When the first substituent is heteroaryl, the substitution position is preferably R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ and R ¹¹ , for example, substitution with R ¹ , more preferably substitution with R ² , substitution with R ³ , substitution with R ¹ and R ³ , substitution with R ⁴ and R ¹¹ , substitution with R ⁵ and R ¹⁰ , substitution with R ⁶ and R ⁹ , Heteroaryl is preferably a carbazolyl group. This heteroaryl (eg, carbazolyl) may be substituted at the above position via a phenylene group.

Specific examples of the compound represented by the formula (H5) include compounds represented by the following structural formula. In addition, "Me" in a formula is a methyl group.

[Formula 123]

[Formula 124]

For the compound represented by the formula (H5), an intermediate is prepared by first bonding the a to c rings with a bonding group (-O-) (first reaction), and then, by bonding the a to c rings with B (boron) The final product can be prepared (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or a Ullman reaction can be used. In the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic ball electron substitution reaction) can be used. For details of the first and second reactions, the description described in International Publication No. 2015/102118 may be referred to.

<The compound represented by the general formula (H6)>

[Formula 125]

In the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substituent), and R ¹ to R At least one hydrogen in ¹⁶ may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (above, a second substituent);

Adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring, or the d ring, and at least one hydrogen in the formed ring is aryl , heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl (above, the first substituent) may be substituted, and at least one hydrogen in these substituents is aryl, heteroaryl, It may be further substituted with diarylamino, alkyl or cycloalkyl (above, the second substituent);

At least one hydrogen in the compound represented by the formula (H6) may be independently substituted with halogen or deuterium.

Preferably, in the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ¹ to R ¹⁶ is aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl has 6 to carbon atoms) 12 aryl), may be further substituted with C1-C12 alkyl or C3-C16 cycloalkyl;

Adjacent groups of R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, b ring, c ring, or d ring, and the ring formed At least one hydrogen in is an aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 12 carbon atoms, or 3 to carbon atoms It may be substituted with cycloalkyl of 16, and at least one hydrogen in these substituents is aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, diarylamino (however, aryl is aryl having 6 to 12 carbons) , may be further substituted with alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms.

More preferably, in the formula (H6),

R ¹ to R ¹⁶ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in R ¹ to R ¹⁶ is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl has 6 to carbon atoms) 10 aryl), may be further substituted with C 1 to C 6 alkyl or C 3 to C 14 cycloalkyl;

Adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with the a ring, b ring, c ring, or d ring, and the ring formed At least one hydrogen in is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or 3 to carbon atoms It may be substituted with cycloalkyl of 14, and at least one hydrogen in these substituents is aryl having 6 to 16 carbons, heteroaryl having 2 to 15 carbons, diarylamino (however, aryl is aryl having 6 to 10 carbons) , may be further substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms.

In the first and second substituents described above, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following examples.

Specific "aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, more preferably aryl having 6 to 16 carbon atoms. More preferably, aryl having 6 to 12 carbon atoms is particularly preferable, and aryl having 6 to 10 carbon atoms is most preferable. For example, phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, terphenylyl which is tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl , p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-ter Phenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, ace Naphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl , (1-,2-,3-,4-,9-) phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-ter Phenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1- ,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1- ,2-,5-,6-) days and the like.

Specific "heteroaryl" includes, for example, heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, and heteroaryl having 2 to 15 carbon atoms. of heteroaryl is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyri Dazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, syn Nolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothiazinyl, phenazinyl, Phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar and bazolyl and benzobenzoindolocarbazolyl.

In the first and second substituents, the "alkyl" may be either straight-chain or branched, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, , alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable. 3 to 6 branched chain alkyl) is more preferable, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) or alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferable. and methyl is most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n -Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-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, n-octadecyl, n -Eicosil, etc. are mentioned. Also, 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-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

In the above first and second substituents, "cycloalkyl" includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, and cycloalkyl having 3 to 14 carbon atoms. and cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents having 1 to 4 carbon atoms and bicyclo[1.1.0] Butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[ 2.2.2] octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

The compound represented by Formula (H6) can be manufactured with reference to the description described in International Publication No. 2014/042197.

<TADF material>

By reducing the energy difference between the excited singlet state and the excited triplet state, the reverse energy transfer from the excited triplet state to the excited singlet state, which normally has a low transition probability, is produced with high efficiency, and light emission from the singlet (thermal activation delayed fluorescence, TADF). In normal fluorescence, 75% of triplet excitons generated by current excitation pass through a thermal deactivation path, and therefore cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL device is realized.

As a TADF material which can be used for such a purpose, the compound represented by the following general formula (H7), or the compound which has the following general formula (H7) as a partial structure is mentioned, for example.

[Formula 126]

In formula (H7), ED is an electron-donating group, Ln is a bonding group, EA is an electron-accepting group, singlet energy (S ¹ ) and triplet energy (T ¹ ) of the compound represented by formula (H7) The energy difference (ΔS ¹ T ¹ ) is 0.2 eV or less (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS ¹ T ¹ ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and still more preferably 0.08 eV or less.

TADF materials are designed to localize HOMO and LUMO in molecules using electron-donating substituents called donors and electron-accepting substituents called acceptors, so that efficient reverse intersystem crossing occurs. - It is preferable that it is an acceptor type TADF compound (D-A type TADF compound).

Here, in the present specification, "electron-donating substituent" (donor) means a substituent and partial structure in which the LUMO orbital is localized in a TADF compound molecule, and "electron-accepting substituent" (acceptor) is a TADF compound molecule Among them, the HOMO orbital shall mean a localized substituent and partial structure.

In general, a TADF compound using a donor or acceptor has a large spin orbit coupling (SOC) due to its structure, a small exchange interaction between HOMO and LUMO, and a small ΔE(ST). A fast crossover speed is obtained. On the other hand, a TADF compound using a donor or acceptor has a large structural relaxation in the excited state (for some molecules, the ground state and the excited state have different stable structures, so conversion from the ground state to the excited state by an external stimulus) When this occurs, the structure changes to a stable structure in an excited state after that), and since it gives a broad emission spectrum, when used as a light emitting material, there is a possibility that the color purity may be reduced.

When the color purity is lowered by the TADF material, as another component, a fluorescent compound may be added to the light emitting layer or a layer adjacent to the light emitting layer. The TADF material functions as an assisting dopant and the other component as an emitting dopant. As another component, what is necessary is just a compound whose absorption spectrum of this compound overlaps with the emission peak of an assisting dopant at least in part.

As a structure of the donor property and acceptor property used for a TADF material, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used, for example. Examples of ED include a functional group containing sp ³ nitrogen, and more specifically, carbazole, dimethylcarbazole, di-tbutylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluoro Locarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydro Phenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, (bis(tbutyl)phenyl)amine, ((diphenyl amino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetra and groups derived from methyl-dihydro-indenoacridine and diphenyl-dihydrodibenzoazacilline. Examples of EA include sp ² nitrogen-containing aromatic rings, CN-substituted aromatic rings, ketone-containing rings and cyano groups, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), Benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxa) sol), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fluorenedicarbonitrile, pyrazine Dicarbonitrile, pyridinedicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, and groups derived from thianthrene tetraoxide and tris(dimethylphenyl)borane. As Ln, a single bond and arylene are mentioned, for example, More specifically, phenylene, biphenylene, naphthylene, etc. are mentioned. In addition, in any structure, hydrogen may be substituted by alkyl, cycloalkyl, and aryl. In particular, as partial structures, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, It is preferably a compound having at least one selected from thiadiazole and benzophenone.

More specifically, the compound represented by the general formula (H7) is a compound represented by any one of the following general formulas (H7-1), (H7-2) and (H7-3).

[Formula 127]

In the above general formula (H7-1), formula (H7-2) and formula (H7-3),

M is, each independently, a single bond, -O-, >N-Ar or >C(-Ar) ₂ , and the depth of the HOMO of the forming partial structure and the height of the singlet excitation energy level and the triplet excitation energy level From the point of view, preferably, a single bond, -O- or >N-Ar,

J is a spacer structure dividing the partial structure of the donor property and the partial structure of the acceptor property, each independently an arylene having 6 to 18 carbon atoms, from the viewpoint of the size of the conjugate obtained from the donor partial structure and the acceptor partial structure, the number of carbon atoms Arylene of 6 to 12 is preferable, and more specifically, phenylene, methylphenylene and dimethylphenylene are mentioned,

Q is, each independently, =C(-H)- or =N-, and in view of the shallowness of the LUMO of the forming partial structure and the height of the singlet excitation energy level and the triplet excitation energy level, preferably, = is N-;

Ar is each independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 18 carbon atoms, the depth and excitation of the HOMO of the partial structure to be formed From the viewpoint of the height of the singlet energy level and the excitation triplet energy level, preferably hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 6 to 10 carbon atoms and more preferably, hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-t-butylcarbazolyl, benzo imidazole or phenylbenzoimidazole, even more preferably hydrogen, phenyl or carbazolyl;

m is 1 or 2,

n is an integer of 2 to (6-m), and preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance.

Further, at least one hydrogen in the compound represented by the above formulas may be substituted with halogen or deuterium.

As a compound represented by Formula (H7), the compound represented by the following structure is mentioned, for example. In addition, * in the structural formula represents a bonding position, "Me" represents a methyl group, and "tBu" represents a t-butyl group.

[Formula 128]

[Formula 129]

[Formula 130]

[Formula 131]

[Formula 132]

[Formula 133]

[Formula 134]

[Formula 135]

[Formula 136]

As a compound represented by general formula (H7), especially among the said specific compounds, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA- Preference is given to TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz.

In addition, as a dopant material, other than the polycyclic aromatic compound represented by the said general formula (1A) or general formula (1B), a known compound can be used, and it can select from various materials according to the desired luminescent color. Specifically, for example, condensed cyclic derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene and chrysene, benzoxazole derivatives, and benzothiazole Derivatives, benzoimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, Bisstyryl derivatives such as tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Laid-Open No. Hei 1-245087), bisstyryl arylene derivatives (Japanese Patent Laid-Open No. Hei 2) -247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimethylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl) Isobenzofuran derivatives such as isobenzofuran and phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives; Coumarin derivatives such as 7-acetoxycoumarin derivative, 3-benzothiazolyl coumarin derivative, 3-benzoimidazolyl coumarin derivative, 3-benzooxazolyl coumarin derivative, dicyanomethylenepyran derivative, dicyanomethylenethiopyran derivative, polyethylene Methine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacry Don derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, biolantorone derivatives , phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

When exemplified by color emitting light, examples of the blue to cyan dopant material include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof, furan, pyrrole, and thiene. Offene, silol, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthy Aromatic heterocyclic compounds such as ridine, quinoxaline, pyrrolopyridine, and thioxanthene, and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazole, thiazole, thia Azole derivatives, such as diazole, carbazole, oxazole, oxadiazole, and triazole, and their metal complexes, and N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-di and aromatic amine derivatives typified by phenyl-1,1'-diamine.

In addition, as the green to yellow dopant material, coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, rubrene, etc. naphthacene derivative of can be heard as

Furthermore, as the light to red dopant material, a ligand (ligand) such as a naphthalimide derivative such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, a perinone derivative, acetylacetone, benzoylacetone, and phenanthroline, etc. Rare earth complexes such as Eu complex, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran or its analogs, and metal phthalocyanines such as magnesium phthalocyanine and aluminum chlorophthalocyanine Derivatives, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, biolanthrone derivatives, phenazine derivatives , phenoxazone derivatives and thiadiazolopyrene derivatives, and the like. In addition, to the compounds exemplified as the above blue to cyan and green to yellow dopant materials, aryl, heteroaryl, arylvinyl, amino, cyano, etc. are subjected to longer wavelengths. A compound having a substituent introduced thereto is also exemplified as a preferable example.

In addition, as a dopant, it can select suitably from the compound etc. which were described in the chemical industry June 2004 issue, page 13, and the references|references published therein, etc. and can be used.

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

The amine having a stilbene structure is represented by the following formula, for example.

[Formula 137]

In the formula, Ar ¹ is an m-valent group derived from aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are each independently aryl having 6 to 30 carbon atoms, and at least one of Ar ¹ to Ar ³ is stilbene has a structure, and Ar ¹ to Ar ³ may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and m is an integer from 1 to 4.

The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula.

[Formula 138]

In the formula, Ar ² and Ar ³ are each independently aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (in aryl, alkyl and cycloalkyl) It may be substituted with at least one tri-substituted silyl) or cyano.

Specific examples of aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphtha cenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, distyrylfluorenyl, and the like.

Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'- tetra(1-naphthyl)-4,4'-diaminostilbene, N,N, N', N'-tetra(2-naphthyl)-4, 4'-diaminostilbene, N,N' -di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diphenyl-4, 4'-diaminostilbene, 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]- Benzene, 2,7-bis [4'-bis (diphenylamino) styryl] -9, 9-dimethylfluorene, 4,4'-bis (9-ethyl-3-carbazovinylene) -biphenyl , 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like.

Moreover, you may use the amine which has a stilbene structure described in Unexamined-Japanese-Patent No. 2003-347056, Unexamined-Japanese-Patent No. 2001-307884, etc.

Examples of the perylene derivative include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, and 3,10-diphenylphenyl. Lylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)- 8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, 3,3'-bis(8,11-di(t) -butyl) perylenyl) etc. are mentioned.

In addition, Japanese Patent Application Laid-Open No. 11-97178, Japanese Patent Application Laid-Open No. 2000-133457, Japanese Patent Application Laid-Open No. 2000-26324, Japanese Patent Application Laid-Open No. 2001-267079, Japanese Patent Application Laid-Open No. 2001-267078, Japanese Patents You may use the perylene derivatives described in Unexamined-Japanese-Patent No. 2001-267076, Unexamined-Japanese-Patent No. 2000-34234, Unexamined-Japanese-Patent No. 2001-267075, and Unexamined-Japanese-Patent No. 2001-217077, etc.

Examples of the borane derivative include 1,8-diphenyl-10-(dimethylboryl)anthracene, 9-phenyl-10-(dimethylboryl)anthracene, and 4-(9'-anthryl)dimethyl Tylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimethylborylnaphthalene, 9-(dimethylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimethyl tylboryl)anthracene, 9-(4'-(N-carbazolyl)phenyl)-10-(dimethylboryl)anthracene, etc. are mentioned.

Moreover, you may use the borane derivative described in the international publication 2000/40586 pamphlet etc.

The aromatic amine derivative is represented by the following formula, for example.

[Formula 139]

In the formula, Ar ⁴ is an n-valent group derived from aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ are aryl, heteroaryl, It may be substituted with alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is an integer of 1 to 4.

In particular, Ar ⁴ is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene, Ar ⁵ and Ar ⁶ are each independently aryl having 6 to 30 carbon atoms, and Ar ⁴ to Ar ⁶ are, More preferred is an aromatic amine derivative which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl trisubstituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 2 .

Specific examples of aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl , perylenyl, pentacenyl, and the like.

As the aromatic amine derivative, the chrysene-based derivatives include, for example, N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl) Chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-iso Propylphenyl) chrysene-6,12-diamine, N,N,N',N'-tetra (naphthalen-2-yl)chrysene-6,12-diamine, N,N'-diphenyl-N,N '-di(p-tolyl)chrysene-6,12-diamine, N,N '-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N' -diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene -6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine, etc. are mentioned.

In addition, as a pyrene type, for example, N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1, 6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1 ,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p- Tolyl) pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N' -bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N '-Bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl) -3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N, N'-diphenylpyrene-1,8-diamine, N ¹ ,N ⁶ -diphenyl-N ¹ ,N ⁶ -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6- Diamine etc. are mentioned.

Moreover, as anthracene type, N,N,N,N- tetraphenylanthracene-9,10- diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10- Diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene -9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis( 4-Isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis (4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p -tolyl) anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine; 2,6-di-t-Butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl -N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4 -Isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis( 4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di- p-Tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6-diphenylamino-2 -naphthyl) anthracene etc. are mentioned.

In addition, [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine , 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[ 4-diphenylaminonaphthalen-1-yl]-p-terphenyl, 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl, etc. are mentioned.

Moreover, you may use the aromatic amine derivative described in Unexamined-Japanese-Patent No. 2006-156888 etc.

Examples of the coumarin derivative include coumarin-6 and coumarin-334.

Moreover, you may use the coumarin derivative described in Unexamined-Japanese-Patent No. 2004-43646, Unexamined-Japanese-Patent No. 2001-76876, and Unexamined-Japanese-Patent No. 6-298758, etc.

The following DCM, DCJTB, etc. are mentioned as a pyran derivative.

[Formula 140]

In addition, Japanese Patent Laid-Open No. 2005-126399, Japanese Patent Application Laid-Open No. 2005-097283, Japanese Patent Application Laid-Open No. 2002-234892, Japanese Patent Application Laid-Open No. 2001-220577, Japanese Patent Application Laid-Open No. 2001-081090, and Japanese Patents You may use the pyran derivative described in Unexamined-Japanese-Patent No. 2001-052869, etc.

The material for the light emitting layer (host material and dopant material) described above is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a cross-linked polymer thereof, or a main chain polymer and the reactive compound. The reacted pendant polymer compound or the pendant polymer crosslinked product can also be used as a material for a light emitting layer. As the reactive substituent in this case, the description in the polycyclic aromatic compound represented by the general formula (1A) or (1B) can be cited.

Details of the use of such a high molecular compound and a polymer crosslinked product will be described later.

<Electron injection layer and electron transport layer in organic electroluminescent element>

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106 . The electron transport layer 106 serves to efficiently transport 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 each formed by laminating and mixing one or two or more of the electron transporting/injecting material, or a mixture of the electron transporting/injecting material and the polymer binder.

The electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting electrons, and it is preferable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is preferable that the material has high electron affinity, high electron mobility, excellent stability, and is difficult to generate trap impurities during manufacture and use. However, when the hole and electron transport balance is considered, the effect of improving the luminous efficiency is not so high even if the electron transport ability is not very high, when the main role is to effectively block the flow of the holes from the anode to the cathode side without recombination. It has the same as materials with high electron transport ability. Accordingly, the electron injection/transport layer in the present embodiment may also include a function of a layer capable of effectively blocking the movement of holes.

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 device It can be arbitrarily selected from among the known compounds used and can be used. In the present invention, as the electron transport material, a polycyclic aromatic compound represented by the general formula (1A) or (1B) can be used.

Examples of the material used for the electron transport layer or the electron injection layer include compounds comprising an aromatic ring or heteroaromatic ring composed of at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives and condensed ring derivatives thereof; It is preferable to contain at least 1 sort(s) selected from the metal complex which has electron-accepting nitrogen. Specifically, condensed ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives , quinone derivatives such as anthraquinone and diphenoquinone, phosphate derivatives, carbazole derivatives, and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex, and benzoquinoline metal complex. These materials may be used alone, but may be used in combination with other materials.

In addition, as specific examples of other electron transport compounds, pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinones Derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N- naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazoles Compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9' -spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives , oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6',2"-terpyridin-4'-yl)benzene, etc.), naphthyridine derivatives ( Bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc. can be heard

A metal complex having electron-accepting nitrogen may also be used, for example, a quinolinol-based metal complex or a hydroxyazole complex such as a hydroxyphenyloxazole complex, an azomethine complex, a tropolone metal complex, or a flavonol metal complex. and a benzoquinoline metal complex.

The above-mentioned materials may be used alone, but may be used in combination with other materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, Phenanthroline derivatives and quinolinol-based metal complexes are preferred.

<Borane derivatives>

The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and details are disclosed in Japanese Patent Application Laid-Open No. 2007-27587.

[Formula 141]

In the formula (ETM-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano at least one of, R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, X is optionally substituted arylene, Y is, It is optionally substituted C16 or less aryl, substituted boril, or optionally substituted carbazolyl, and n is each independently an integer of 0 to 3. Moreover, as a substituent in the case of "which may be substituted" or "it is substituted," aryl, heteroaryl, alkyl, cycloalkyl, etc. are mentioned.

Among the compounds represented by the general formula (ETM-1), the compounds represented by the following general formula (ETM-1-1) and the compounds represented by the following general formula (ETM-1-2) are preferable.

[Formula 142]

In formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cya. and R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, R ²¹ and R ²² are each independently hydrogen; At least one of alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X ¹ is optionally substituted arylene having 20 or less carbon atoms, n are each independently an integer from 0 to 3, and m is each independently an integer from 0 to 4. Moreover, as a substituent in the case of "which may be substituted" or "it is substituted," aryl, heteroaryl, alkyl, cycloalkyl, etc. are mentioned.

[Formula 143]

In formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cya. and R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and X ¹ is optionally substituted aryl having 20 or less carbon atoms. Ren, and n is each independently an integer of 0 to 3. Moreover, as a substituent in the case of "which may be substituted" or "it is substituted," aryl, heteroaryl, alkyl, cycloalkyl, etc. are mentioned.

Specific examples of X ¹ include a divalent group represented by any one of the following formulas (X-1) to (X-9). * in each structural formula represents a bonding position.

[Formula 144]

(In each formula, R ^a is each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

Specific examples of the borane derivative include the following compounds.

[Formula 145]

This borane derivative can be produced using a known raw material and a known synthesis method.

<Pyridine derivatives>

The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or (ETM-2-2).

[Formula 146]

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

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

In the formula (ETM-2-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cyclo) alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms), and R ¹¹ and R ¹² may be bonded to each other 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 are each independently an alkyl having 1 to 4 carbon atoms or an alkyl having 5 to 10 carbon atoms. It may be substituted with cycloalkyl. In addition, the pyridine-type substituent may couple|bond with (phi), an anthracene ring, or a fluorene ring in each formula via a phenylene group or a naphthylene group. * in each structural formula represents a bonding position.

[Formula 147]

The pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15), and among these, any one of the following formulas (Py-21) to (Py-44) is preferable. * in each structural formula represents a bonding position.

[Formula 148]

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

The "alkyl" for R ¹¹ to R ¹⁸ may be either straight chain or branched chain, and examples thereof include straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is C1-C18 alkyl (C3-C18 branched alkyl). A more preferable "alkyl" is C1-C12 alkyl (C3-C12 branched chain alkyl). Even more preferable "alkyl" is C1-C6 alkyl (C3-C6 branched alkyl). A particularly preferable "alkyl" is C1-C4 alkyl (C3-C4 branched chain alkyl).

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, and t-pentyl (t-amyl). , n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-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, n-octadecyl, n-eicosyl, etc. are mentioned.

Also, for example, 1-ethyl-1-methyl propyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethyl pentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methyl butyl, 1,1-dimethylhexyl etc. can also be mentioned.

As the alkyl having 1 to 4 carbon atoms substituted by the pyridine-based substituent, the description of the above alkyl can be cited.

Examples of the “cycloalkyl” for R ¹¹ to R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferably, "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl.

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

As "aryl" for R ¹¹ to R ¹⁸ , preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, even more preferably aryl having 6 to 14 carbon atoms, especially Preferably, it is C6-C12 aryl.

Specific examples of "C6-C30 aryl" include phenyl which is monocyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, and acenaphthylene-(1-,3-,4 which is condensed tricyclic aryl). -,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-, 4-,9-)phenanthryl, condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2- , 5-)yl, perylene-(1-,2-,3-)yl which is condensed pentacyclic aryl, pentacene-(1-,2-,5-,6-)yl, etc. are mentioned.

Preferred "C6-C30 aryl" includes phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, and still more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl. and particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

R ¹¹ and R ¹² in the formula (ETM-2-2) may be bonded to form a ring, and as a result, the 5-membered ring of the fluorene skeleton includes cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, Cyclohexane, fluorene, indene, etc. may couple|bond with spiro.

Specific examples of the pyridine derivative include the following compounds.

[Formula 149]

This pyridine derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Fluoranthene derivative>

The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and details are disclosed in International Publication No. 2010/134352.

[Formula 150]

In the formula (ETM-3), X ¹² to X ²¹ are hydrogen, halogen, straight chain, branched or cyclic alkyl, straight chain, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl indicates Here, examples of the substituent in the case of substitution include aryl, heteroaryl, alkyl or cycloalkyl.

Specific examples of the fluoranthene derivative include the following compounds.

[Formula 151]

<BO derivatives>

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

[Formula 152]

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded through a single bond or a linking group) ), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, and at least one hydrogen in R ¹ to R ¹¹ may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

In addition, adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring is aryl or heteroaryl , diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl may be present, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Moreover, at least 1 hydrogen in the compound or structure represented by Formula (ETM-4) may be substituted by halogen or deuterium.

The description of a multimer formed by combining a plurality of substituents and ring-forming forms in the formula (ETM-4) and a plurality of structures of the formula (ETM-4) is represented by the general formula (1A) or (1B), may cite the description of polycyclic aromatic compounds.

Specific examples of the BO-based derivative include the following compounds.

[Formula 153]

This BO-based derivative can be produced using a known raw material and a known synthesis method.

<Anthracene Derivatives>

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

[Formula 154]

Ar is each independently divalent benzene or naphthalene, and R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

Ar each independently can be appropriately selected from divalent benzene or naphthalene, and the two Ars may be different or the same, but preferably the same from the viewpoint of easiness of synthesizing the anthracene derivative. Ar binds to pyridine to form "a moiety consisting of Ar and pyridine", which is a group represented by, for example, any one of the following formulas (Py-1) to (Py-12) and binds to anthracene are doing * in each structural formula represents a bonding position.

[Formula 155]

Among these groups, a group represented by any one of the formulas (Py-1) to (Py-9) is preferable, and a group represented by any one of the formulas (Py-1) to (Py-6) is more preferable. . The two "sites consisting of Ar and pyridine" bonding to anthracene may have the same or different structures, but preferably have the same structure from the viewpoint of easiness in synthesizing the anthracene derivative. However, from the viewpoint of device characteristics, it is preferable even if the structures of the two "sites consisting of Ar and pyridine" are the same or different.

The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either linear or branched. That is, straight-chain alkyl having 1 to 6 carbon atoms or branched chain alkyl having 3 to 6 carbon atoms. More preferably, it is C1-C4 alkyl (C3-C4 branched alkyl). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, and the like, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl , s-butyl, or t-butyl is preferable, and methyl, ethyl, or t-butyl is more preferable.

Specific examples of the cycloalkyl having 3 to 6 carbon atoms in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl. can

About C6-C20 aryl in R1 ^{- R4} , C6-C16 aryl is preferable, C6-C12 aryl is more preferable, C6-C10 aryl is especially preferable.

Specific examples of "aryl having 6 to 20 carbon atoms" include phenyl which is a monocyclic aryl, (o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6- ,3,4-,3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-,m-,p-)cumenyl, bicyclic aryl (2-,3- ,4-)biphenylyl, condensed bicyclic aryl (1-,2-)naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl) , m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl- 2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, anthracen-(1-,2-,9-)yl, acenaphthylene-(1- ,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2 -,3-,4-,9-)phenanthryl, condensed tetracyclic aryl triphenylen-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracene-( 1-,2-,5-)yl and perylene-(1-,2-,3-)yl which is a condensed 5-ring system aryl, etc. are mentioned.

Preferred "C6-C20 aryl" is phenyl, biphenylyl, terphenylyl or naphthyl, More preferably, phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl -5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

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

[Formula 156]

Ar ¹ is each independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar ² is each independently aryl having 6 to 20 carbons, and the same description as “aryl having 6 to 20 carbons” in the formula (ETM-5-1) can be cited. C6-C16 aryl is preferable, C6-C12 aryl is more preferable, C6-C10 aryl is especially preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc. can

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the description in the above formula (ETM-5-1) is can be quoted

Specific examples of the anthracene derivative include the following compounds.

[Formula 157]

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

<benzofluorene derivative>

A benzofluorene derivative is a compound represented, for example by a following formula (ETM-6).

[Formula 158]

Ar ¹ is each independently aryl having 6 to 20 carbons, and the same explanation as “aryl having 6 to 20 carbons” in the formula (ETM-5-1) can be cited. C6-C16 aryl is preferable, C6-C12 aryl is more preferable, C6-C10 aryl is especially preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc. can

Ar ² is each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl) and two Ar ² may be bonded to form a ring.

The "alkyl" in Ar ² may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is C1-C18 alkyl (C3-C18 branched alkyl). A more preferable "alkyl" is C1-C12 alkyl (C3-C12 branched chain alkyl). Even more preferable "alkyl" is C1-C6 alkyl (C3-C6 branched alkyl). A particularly preferable "alkyl" is C1-C4 alkyl (C3-C4 branched chain alkyl). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, and t-pentyl (t-amyl). , n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

Examples of "cycloalkyl" for Ar ² include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferable "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferable "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl.

As "aryl" for Ar ² , preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferably aryl having 6 to 14 carbon atoms, particularly preferably It is an aryl having 6 to 12 carbon atoms.

Specific examples of “aryl having 6 to 30 carbon atoms” include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, and the like. can

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

Specific examples of the benzofluorene derivative include the following compounds.

[Formula 159]

This benzofluorene derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Phosphine oxide derivative>

A phosphine oxide derivative is a compound represented, for example by a following formula (ETM-7-1). Details are also described in International Publication No. 2013/079217.

[Formula 160]

R ⁵ is substituted or unsubstituted alkyl having 1 to 20 carbons, cycloalkyl having 3 to 20 carbons, aryl having 6 to 20 carbons, or heteroaryl having 5 to 20 carbons;

R ⁶ is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms or aryloxy having 6 to 20 carbon atoms;

R ⁷ and R ⁸ are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms;

R ⁹ is oxygen or sulfur,

j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.

Here, examples of the substituent in the case of substitution include aryl, heteroaryl, alkyl or cycloalkyl.

The compound represented by a following formula (ETM-7-2) may be sufficient as a phosphine oxide derivative, for example.

[Formula 161]

R ¹ to R ³ may be the same or different, and hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an arylether group, an arylthioether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, amino group, nitro group, silyl group, and a condensed ring formed between adjacent substituents.

Ar ¹ may be the same or different, and is an arylene group or a heteroarylene group. Ar ² may be the same or different, and is an aryl group or a heteroaryl group. However, at least one of Ar ¹ and Ar ² has a substituent or forms a condensed ring between adjacent substituents. n is an integer of 0 to 3, and when n is 0, the unsaturated structural moiety does not exist, and when n is 3, R ¹ does not exist.

Among these substituents, an alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. There is no restriction|limiting in particular in the substituent in the case of being substituted, For example, an alkyl group, an aryl group, a heterocyclic group, etc. are mentioned, These points are common also to the following description. In addition, carbon number of an alkyl group is although it does not specifically limit, From the point of availability and cost, it is the range of 1-20 normally.

In addition, a cycloalkyl group represents, for example, saturated alicyclic hydrocarbon groups, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and it does not matter whether it is unsubstituted or substituted. Although carbon number of an alkyl group part is not specifically limited, Usually, it is the range of 3-20.

In addition, an aralkyl group represents, for example, the aromatic hydrocarbon group via aliphatic hydrocarbons, such as a benzyl group and a phenylethyl group, Even if both the aliphatic hydrocarbon and the aromatic hydrocarbon are unsubstituted, they may be substituted. Although carbon number of an aliphatic part is not specifically limited, Usually, it is the range of 1-20.

In addition, an alkenyl group shows, for example, the unsaturated aliphatic hydrocarbon group containing double bonds, such as a vinyl group, an allyl group, a butadienyl group, Even if this is unsubstituted, it may be substituted. Although carbon number of an alkenyl group is not specifically limited, Usually, it is the range of 2-20.

In addition, a cycloalkenyl group represents, for example, the unsaturated alicyclic hydrocarbon group containing double bonds, such as a cyclopentenyl group, a cyclopentadienyl group, a cyclohexene group, It does not matter whether it is unsubstituted or substituted.

In addition, an alkynyl group shows, for example, the unsaturated aliphatic hydrocarbon group containing triple bonds, such as an acetylenyl group, and even if this is unsubstituted, it is not cared about substituted. Although carbon number of an alkynyl group is not specifically limited, Usually, it is the range of 2-20.

In addition, an alkoxy group represents, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an alkoxy group is not specifically limited, Usually, it is the range of 1-20.

In addition, the alkylthio group is the group by which the oxygen atom of the ether bond of the alkoxy group was substituted with the sulfur atom.

In addition, the cycloalkylthio group is the group by which the oxygen atom of the ether bond of the cycloalkoxy group was substituted with the sulfur atom.

In addition, the aryl ether group represents, for example, an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. Although carbon number of an aryl ether group is not specifically limited, Usually, it is the range of 6-40.

In addition, an arylthioether group is the group by which the oxygen atom of the ether bond of the arylether group was substituted by the sulfur atom.

In addition, an aryl group represents aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenylyl group, and a pyrenyl group, for example. Even if the aryl group is unsubstituted, even if it is substituted, it is not cared about. Although carbon number of an aryl group is not specifically limited, Usually, it is the range of 6-40.

In addition, the heterocyclic group represents, for example, a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group, which is substituted even if unsubstituted it doesn't matter if Although carbon number of a heterocyclic group is not specifically limited, Usually, it is the range of 2-30.

Halogen represents fluorine, chlorine, bromine, and iodine.

The aldehyde group, the carbonyl group, and the amino group may include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, or the like.

In addition, an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, and a heterocyclic ring may be unsubstituted or may be substituted.

A silyl group shows, for example, silicon compound groups, such as a trimethylsilyl group, even if this is unsubstituted, it does not matter even if it is substituted. Although carbon number of a silyl group is not specifically limited, Usually, it is the range of 3-20. In addition, the number of silicon is 1-6 normally.

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 Ar It is a conjugated or non-conjugated condensed ring formed between ² and the like. Here, when n is 1, two R< ¹ > may form a conjugated or non-conjugated condensed ring. These condensed rings may contain nitrogen, oxygen, and sulfur atoms in the ring structure, or may be further condensed with other rings.

As a specific example of this phosphine oxide derivative, the following compounds are mentioned, for example.

[Formula 162]

This phosphine oxide derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Pyrimidine derivatives>

The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Detailed information is also described in International Publication No. 2011/021689.

[Formula 163]

Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1-4, Preferably it is an integer of 1-3, More preferably, it is 2 or 3.

Examples of "aryl" in "aryl which may be substituted" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, more More preferably, it is C6-C12 aryl.

Specific examples of “aryl” include phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, and ter which is tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2- )yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyrene-( 1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days and the like.

Examples of "heteroaryl" of "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, heteroaryl having 2 to 15 carbon atoms is still more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar and bazolyl and benzobenzoindolocarbazolyl.

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

Specific examples of this pyrimidine derivative include the following compounds.

[Formula 164]

This pyrimidine derivative can be produced using a known raw material and a known synthesis method.

<Carbazole derivatives>

The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which multiple bonds are formed by a single bond or the like. Details are described in US Publication No. 2014/0197386.

[Formula 165]

Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is each independently an integer of 0-4, Preferably it is an integer of 0-3, More preferably, it is 0 or 1.

Examples of "aryl" in "aryl which may be substituted" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, more More preferably, it is C6-C12 aryl.

Specific examples of “aryl” include phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, and ter which is tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2- )yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-( 1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days and the like.

Examples of "heteroaryl" in "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, heteroaryl having 2 to 15 carbon atoms is still more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar and bazolyl and benzobenzoindolocarbazolyl.

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

The carbazole derivative may be a multimer in which the compound represented by the above formula (ETM-9) is bonded to a plurality of them by a single bond or the like. In this case, other than a single bond, it may be bonded by an aryl ring (preferably a polyvalent benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or a triphenylene ring).

As a specific example of this carbazole derivative, the following compounds are mentioned, for example.

[Formula 166]

This carbazole derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Triazine derivatives>

The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/0156013.

[Formula 167]

Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer of 1-3, Preferably it is 2 or 3.

Examples of "aryl" in "aryl which may be substituted" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, more More preferably, it is C6-C12 aryl.

Specific examples of “aryl” include phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, and ter which is tricyclic aryl. Phenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4' -yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o -terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl , acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2- )yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m -terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-( 1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-( 1-, 2-, 5-, 6-) days and the like.

Examples of "heteroaryl" in "heteroaryl which may be substituted" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. More preferably, heteroaryl having 2 to 15 carbon atoms is even more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, iso Quinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothia Zinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naph Tobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of benzophosphoroxide ring, monovalent group of dibenzophosphoroxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocar and bazolyl and benzobenzoindolocarbazolyl.

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

Specific examples of the triazine derivative include the following compounds.

[Formula 168]

This triazine derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<benzoimidazole derivatives>

The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

[Formula 169]

φ is an n-valent aryl ring (preferably an n-valent benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or a triphenylene ring), and n is 1 to 4 It is an integer, and the "benzoimidazole-based substituent" means that the pyridyl group in the "pyridine-based substituent" in the formulas (ETM-2), (ETM-2-1) and (ETM-2-2) is benzo It is a substituent substituted with an imidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium. * in the following structural formula represents a bonding position.

[Formula 170]

R ¹¹ in the benzimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and formulas (ETM-2-1) and (ETM) The description of R ¹¹ in -2-2) can be cited.

phi is further preferably an anthracene ring or a fluorene ring, and for the structure in this case, the description in the above formula (ETM-2-1) or (ETM-2-2) can be cited, and in each formula For R ¹¹ to R ¹⁸ , the description in the above formula (ETM-2-1) or (ETM-2-2) may be cited. In addition, in the above formula (ETM-2-1) or (ETM-2-2), two pyridine-based substituents are described in a combined form. When substituted with a benzimidazole-based substituent, both pyridine-based substituents may be substituted with a benzimidazole-based substituent (ie, n=2), one pyridine-based substituent may be substituted with a benzimidazole-based substituent, and the other pyridine-based substituent may be substituted with R ¹¹ to R ¹⁸ . (i.e. n=1). Further, 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 this benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10) -(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl) )phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imi Dazole, 1- (4- (10- (naphthalen-2-yl) anthracen-9-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 2- (4- (9,10-di (naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracene-2 -yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H- Benzo[d]imidazole, etc. are mentioned.

[Formula 171]

This benzimidazole derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Phenanthroline derivatives>

A phenanthroline derivative is a compound represented, for example by a following formula (ETM-12) or a formula (ETM-12-1). Details are described in International Publication No. 2006/021982.

[Formula 172]

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

R ¹¹ to R ¹⁸ in each formula are each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl), or aryl (preferably C1-C24 alkyl) 6 to 30 aryl). In addition, in the 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 phenanthroline derivative may be substituted with deuterium.

As the alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ , the description of R ¹¹ to R ¹⁸ in the above formula (ETM-2) can be cited. In addition, the following structural formulas are mentioned for phi other than the above-mentioned example, for example. In addition, R in the following structural formula is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. In addition, * in each structural formula represents a bonding position.

[Formula 173]

Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9, 10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10- Phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), vasocuproin, 1,3-bis(2-phenyl-1 , 10-phenanthroline-9-yl) benzene, a compound represented by the following structural formula, and the like.

[Formula 174]

This phenanthroline derivative can be manufactured using a known raw material and a known synthesis method.

<quinolinol-based metal complex>

The quinolinol-based metal complex is, for example, a compound represented by the following general formula (ETM-13).

[Formula 175]

wherein R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al, Ga, Be or Zn; n is an integer of 1 to 3.

Specific examples of the quinolinol-based metal complex include 8-quinolinollithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, and tris(5-methyl-8- Quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8 -quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenollatto)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenollatto)aluminum, bis (2-methyl-8-quinolinolato)(3-methylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(4-methylphenollatto)aluminum, bis(2-methyl-8 -quinolinolato)(2-phenylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(3-phenylphenollatto)aluminum, bis(2-methyl-8-quinolinolato) (4-phenylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(2,3-dimethylphenollatto)aluminum, bis(2-methyl-8-quinolinolato)(2,6 -Dimethylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(3,4-dimethylphenollatto)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethyl Phenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6 -diphenylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenollatto)aluminum, bis(2-methyl-8-quinolinolato)(2 ,4,6-trimethylphenollato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,5,6-tetramethylphenollato)aluminum, bis(2-methyl-8-quinolinolato) Norato)(1-naphthorato)aluminum, bis(2-methyl-8-quinolinolato)(2-naphthorato)aluminum, bis(2,4-dimethyl-8-quinolinolato)( 2-phenylphenollato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3-phenylphenollatto)aluminum, bis(2,4-dimethyl-8-quinolinolato)(4- Phenylphenollato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(3,5-dimethylphenollatto)aluminum,bis(2,4-dimethyl-8-quinolinolato)(3, 5-di-t-butylphenolato)aluminum, bis( 2-methyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-8-quinolinolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)aluminum-μ -oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-4-ethyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4 -Ethyl-8-quinolinolato)aluminum, bis(2-methyl-4-methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-qui Nolinolato)aluminum, bis(2-methyl-5-cyano-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolato)aluminum; Bis(2-methyl-5-trifluoromethyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolato)aluminum, bis( 10-hydroxybenzo [h] quinoline) beryllium etc. are mentioned.

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

<thiazole derivatives and benzothiazole derivatives>

The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

[Formula 176]

A benzothiazole derivative is a compound represented, for example by a following formula (ETM-14-2).

[Formula 177]

phi in each formula is an n-valent aryl ring (preferably an n-valent benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or a triphenylene ring), and n is 1 It is an integer of -4, and "thiazole-type substituent" and "benzothiazole-type substituent" are "pyridine-based substituents" in the formulas (ETM-2), (ETM-2-1) and (ETM-2-2). The pyridyl group in "system substituent" is a substituent substituted with the following thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with deuterium. * in the following structural formula represents a bonding position.

[Formula 178]

phi is further preferably an anthracene ring or a fluorene ring, and for the structure in this case, the description in the above formula (ETM-2-1) or (ETM-2-2) can be cited, and in each formula For R ¹¹ to R ¹⁸ , the description in the above formula (ETM-2-1) or (ETM-2-2) may be cited. In addition, in the above formula (ETM-2-1) or (ETM-2-2), two pyridine-based substituents are described in a combined form, but when they are substituted with a thiazole-based substituent (or a benzothiazole-based substituent), Both pyridine-based substituents may be substituted with thiazole-based substituents (or benzothiazole-based substituents) (that is, n=2), one pyridine-based substituent is substituted with thiazole-based substituents (or benzothiazole-based substituents), and the other The other pyridine-based substituent may be substituted with R ¹¹ to R ¹⁸ (ie, n=1). Further, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) is substituted with a thiazole-based substituent (or benzothiazole-based substituent) and the “pyridine-based substituent” is replaced with R ¹¹ to R ¹⁸ may be replaced with

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

<Silol derivatives>

A silol derivative is a compound represented, for example by a following formula (ETM-15). Details are described in Japanese Patent Laid-Open No. 9-194487.

[Formula 179]

X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, and these may be substituted. For the details of these groups, the descriptions in the formulas (1A) and (1B), and furthermore, the description in the formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl part in alkoxy was substituted with alkenyl or alkynyl, respectively, For details of these alkenyl and alkynyl, the said formula (ETM-7-2) The explanation in the can be cited.

In addition, X and Y may combine to form a cycloalkyl ring (and a ring whose part is unsaturated), The details of this cycloalkyl ring are cycloalkyl in the said general formula (1A) and general formula (1B). Reference may be made to the description of alkyl.

R ¹ to R ⁴ are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy , arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso , formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and adjacent substituents You may form a condensed ring between

For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in R ¹ to R ⁴ , the above general formulas (1A) and (1B) ) can be cited.

alkyl in R ¹ to R ⁴ in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy; The description in the said General formula (1A) and General formula (1B) can be cited also about the detailed content of aryl and alkoxy.

Examples of the silyl include a silyl group and a group in which at least one of three hydrogens of the silyl group is each independently substituted with aryl, alkyl or cycloalkyl, preferably tri-substituted silyl, triarylsilyl or trialkyl silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl and alkyldicycloalkylsilyl; and the like. In these, the description in the said General formula (1A) and General formula (1B) can be quoted about the detailed content of aryl, alkyl, and cycloalkyl.

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, oxygen, and sulfur atoms in the ring structure, and further may be condensed with another ring.

However, preferably, when R ¹ and R ⁴ are a phenyl group, X and Y are not alkyl or phenyl. Also, preferably, when R ¹ and R ⁴ are thienyl groups, X and Y are alkyl, R ² and R ³ are alkyl, aryl, alkenyl, or R ² and R ³ are bonded to form a ring It is a structure that does not simultaneously satisfy cycloalkyl. Preferably, when R ¹ and R ⁴ are silyl groups, R ² , R ³ , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. Preferably, in the case of a structure in which a benzene ring is condensed in R ¹ and R ² , X and Y are not alkyl or phenyl.

This silol derivative can be manufactured using a well-known raw material and a well-known synthesis method.

<Azoline derivatives>

The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in International Publication No. 2017/014226.

[Formula 180]

In the formula (ETM-16),

φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen in φ is an alkyl having 1 to 6 carbon atoms, 3 to 14 carbon atoms may be substituted with cycloalkyl, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms,

Y is each independently -O-, -S- or >N-Ar, Ar is aryl having 6 to 12 carbons or heteroaryl having 2 to 12 carbons, and at least one hydrogen of Ar is 1 to 4 carbons may be substituted with alkyl of 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and R ¹ to R ⁵ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or carbon atoms. 5 to 10 cycloalkyl, with the proviso that any one of Ar in >N-Ar and R ¹ to R ⁵ is a site bonded to L,

L is each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

[Formula 181]

In formula (L-1), X ¹ to X ⁶ are each independently =CR ⁶ - or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, and 2 out of X ¹ to X ⁶ R ⁶ in =CR ⁶ - is a site bonding to φ or an azoline ring, and R ⁶ in other =CR ⁶ - is hydrogen,

In formula (L-2), X ⁷ to X ¹⁴ each independently represents =CR ⁶ - or =N-, at least two of X ⁷ to X ¹⁴ are =CR ⁶ -, and 2 out of X ⁷ to X ¹⁴ R ⁶ in =CR ⁶ - is a site bonding to φ or an azoline ring, and R ⁶ in other =CR ⁶ - is hydrogen,

At least one hydrogen in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms,

m is an integer of 1 to 4, and when m is 2 to 4, the group formed by the azoline 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 substituted with deuterium.

A specific azoline derivative is a compound represented by the following general formula (ETM-16-1) or general formula (ETM-16-2).

[Formula 182]

In formula (ETM-16-1) and formula (ETM-16-2),

φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen in φ is an alkyl having 1 to 6 carbon atoms, 3 to 14 carbon atoms may be substituted with cycloalkyl, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms,

In the formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, Ar at least one hydrogen may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms,

In the formula (ETM-16-1), R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same,

In the formula (ETM-16-2), R ¹ to R ⁵ are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, and R ³ and R ⁴ are the same,

In formula (ETM-16-1) and formula (ETM-16-2),

L is each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

[Formula 183]

In formula (L-1), X ¹ to X ⁶ are each independently =CR ⁶ - or =N-, at least two of X ¹ to X ⁶ are =CR ⁶ -, and 2 out of X ¹ to X ⁶ R ⁶ in =CR ⁶ - is a site bonding to φ or an azoline ring, and R ⁶ in other =CR ⁶ - is hydrogen,

In formula (L-2), X ⁷ to X ¹⁴ are each independently =CR ⁶ - or =N-, at least two of X ⁷ to X ¹⁴ are =CR ⁶ -, and 2 out of X ⁷ to X ¹⁴ R ⁶ in =CR ⁶ - is a site bonding to φ or an azoline ring, and R ⁶ in other =CR ⁶ - is hydrogen,

At least one hydrogen in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms,

m is an integer of 1 to 4, and when m is 2 to 4, the group formed by the azoline ring and L may be the same or different, and

At least one hydrogen in the compound represented by the formula (ETM-16-1) or (ETM-16-2) may be substituted with deuterium.

Preferably, phi is a monovalent group represented by the following formulas (φ1-1) to (φ1-18), a divalent group represented by the following formulas (φ2-1) to (φ2-34), It is selected from the group consisting of a trivalent group represented by a formula (φ3-1) to a formula (φ3-3), and a tetravalent group represented by the following formulas (φ4-1) to a formula (φ4-2), and at least among φ One hydrogen may be substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, aryl having 6 to 18 carbons, or heteroaryl having 2 to 18 carbons. * in the following structural formula represents a bonding position.

[Formula 184]

[Formula 185]

[Formula 186]

In the above formula, Z is >CR2, >N-Ar, >NL, -O- or -S-, and R in >CR2 is each independently an alkyl having ₁ to 4 carbon atoms, 5 to 10 carbon atoms. of cycloalkyl, aryl having 6 to 12 carbons, or heteroaryl having 2 to 12 carbons, R may be bonded to each other to form a ring, and Ar in >N-Ar is aryl having 6 to 12 carbons or aryl having 2 to 12 carbons. It is a heteroaryl of -12, and L in >NL is L in the said general formula (ETM-16), a formula (ETM-16-1), or a general formula (ETM-16-2).

Preferably, L is benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine It is a divalent group of a ring selected from the group consisting of, wherein at least one hydrogen in L is substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms there may be

Preferably, Ar for >N-Ar as Y or Z is phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthy selected from the group consisting of ridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y has 1 to 4 carbon atoms may be substituted with alkyl, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

Preferably, R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R ¹ and R ² are the same, R ³ and R ⁴ are the same, , and not all of R ¹ to R ⁴ simultaneously become hydrogen, and m is 1 or 2, and when m is 2, the group formed by the azoline ring and L is the same.

Specific examples of the azoline derivative include the following compounds. In addition, "Me" in a structural formula represents a methyl group.

[Formula 187]

[Formula 188]

More preferably, ? is a divalent group represented by the following formulas (?2-1), (?2-31), (?2-32), (?2-33), and (?2-34) selected from the group, at least one hydrogen in φ may be substituted with aryl having 6 to 18 carbon atoms, * in each structural formula represents a bonding position,

[Formula 189]

L is a divalent group to a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen in L is an alkyl having 1 to 4 carbon atoms, 5 to 10 carbon atoms may be substituted with cycloalkyl, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms;

Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen in Ar has 1 to 4 carbon atoms may be substituted with alkyl, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms,

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R ¹ and R ² are the same, R ³ and R ⁴ are the same, and R Not all of ¹ to R ⁴ become hydrogen at the same time, and

m is 2, and the group formed by the azoline ring and L is the same.

As another specific example of an azoline derivative, the following compounds are mentioned, for example. In addition, "Me" in a structural formula represents a methyl group.

[Formula 190]

For details of alkyl, cycloalkyl, aryl or heteroaryl in each of the formulas that define this azoline derivative, the explanations in the formulas (1A) and (1B) can be cited.

This azoline derivative can be manufactured using a well-known raw material and a well-known synthesis method.

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. Various substances are used as the reducing substance as long as it has a certain reducing property, for example, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, At least one selected from the group consisting of 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 can be preferably used. .

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV copper), Rb ( 2.16 eV copper) or Cs (1.95 eV copper), Ca (2.9 eV copper), Sr (2.0 copper) to 2.5 eV) or an alkaline earth metal such as Ba (2.52 eV copper), and a material having a work function of 2.9 eV or less is particularly preferable. Among these, a more preferable reducing substance is an alkali metal of K, Rb, or Cs, More preferably, it is Rb or Cs, Most preferably, it is Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to a material for forming the electron transport layer or the electron injection layer, the luminance of light emission in the organic EL device and the lifespan of the organic EL device are improved. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and A combination of Na and K is preferred. By containing Cs, the reducing ability can be exhibited efficiently, and the improvement of the light emission luminance in an organic electroluminescent element and lengthening of lifetime are attained by addition to the material which forms an electron carrying layer or an electron injection layer.

The material for the electron injection layer and the material for the electron transport layer described above is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a cross-linked polymer thereof, or a main chain polymer and the reactive compound. It can also be used as a material for an electronic layer as the pendant polymer compound or its pendant polymer crosslinked product. As the reactive substituent in this case, the description in the polycyclic aromatic compound represented by the general formula (1A) or (1B) can be cited.

Details of the use of such a high molecular compound and a polymer crosslinked product will be described later.

<Cathode in organic electroluminescent element>

The cathode 108 serves to inject electrons into the emission layer 105 through 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 is a material capable of efficiently injecting electrons into the organic layer, but the same material as the material 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 thereof (magnesium-silver alloy, magnesium -Indium alloy, aluminum-lithium alloy, such as lithium fluoride/aluminum, etc.) etc. are preferable. In order to increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, these low work function metals are generally unstable in the atmosphere in many cases. In order to improve this point, for example, a method of using an electrode with high stability by doping a trace amount of lithium, cesium, or magnesium into an organic layer is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

In addition, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon A preferred example of laminating a high molecular weight compound or the like is exemplified. The manufacturing method of these electrodes is also not restrict|limited in particular as long as conduction|electrical_connection, such as resistance heating, electron beam vapor deposition, sputtering, ion plating, and coating, can be taken.

<Binder that can be used in each layer>

The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer independently, but as a polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcar Bazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS Solvent-soluble resins such as resins and polyurethane resins, phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. It is also possible

<Method for manufacturing organic electroluminescent device>

Each layer constituting the organic EL element is formed by depositing the material constituting each layer into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method, or casting method, or coating method. It can be formed by There is no limitation in particular about the film thickness of each layer formed in this way, Although it can set suitably according to the property of a material, Usually, it is the range of 2 nm - 5000 nm. The film thickness can be usually measured with a crystal oscillation type film thickness measuring device or the like. In the case of thin film formation using the vapor deposition method, the deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. Vapor deposition conditions are generally: boat heating temperature +50 to +400 °C, vacuum degree 10 ^-6 to 10 ^-3 Pa, deposition rate 0.01 to 50 nm/sec, substrate temperature -150 to +300 °C, film thickness of 2 nm to 5 µm. It is preferable to set it appropriately in the range.

When a DC voltage is applied to the organic EL device obtained in this way, the anode may be applied with the positive polarity of + and the cathode with negative polarity. and both) can observe luminescence. In addition, this organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the alternating current to be applied may be arbitrary.

Next, as an example of a method of manufacturing an organic EL device, an organic EL device comprising an anode/hole injection layer/hole transport layer/a light emitting layer/electron transport layer/electron injection layer/cathode made of a host material and a dopant material. Explain.

<Deposition method>

On a suitable substrate, a thin film of an anode material is formed by vapor deposition or the like to prepare an anode, and then thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for a cathode is formed by a vapor deposition method or the like to form a cathode. An organic EL device is obtained. In the production of the organic EL device described above, it is also possible to produce 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 in the order by reversing the production order.

<Wet film forming method>

The wet film-forming method is performed by preparing the low molecular compound which can form each organic layer of an organic electroluminescent element as a liquid composition for organic layer formation, and using this. When there is no suitable organic solvent for dissolving the low-molecular compound, the low-molecular compound is a reactive compound in which a reactive substituent is substituted, and a composition for forming an organic layer is made from other monomers having a solubility function or a polymer compound polymerized with a main chain polymer. may be prepared.

Generally, the wet film-forming method forms a coating film by passing through the application process of apply|coating the composition for organic layer formation to a board|substrate, and the drying process of removing a solvent from the apply|coated composition for organic layer formation. When the polymer compound has a crosslinkable substituent (this is also referred to as a crosslinkable polymer compound), it is further crosslinked by this drying step to form a crosslinked polymer compound. Depending on the difference in the application process, the method using a spin coater is the spin coat method, the method using a slit coater is the slit coat method, and the method using a plate is gravure, offset, reverse offset, flexographic printing, and inkjet printer. The method used is called the inkjet method, and the method of spraying in the form of a mist is called the spray method. The drying process includes methods such as air drying, heating, and reduced pressure drying. A drying process may be performed only once, and may be performed multiple times using another method and conditions. Moreover, you may use another method together like baking under reduced pressure, for example.

The wet film-forming method is a film-forming method using a solution, and is, for example, a partial printing method (inkjet method), a spin coating method or a casting method, a coating method, and the like. Unlike the vacuum deposition method, the wet film formation method does not require the use of an expensive vacuum deposition apparatus, and can form a film under atmospheric pressure. In addition, the wet film-forming method enables a large area and continuous production, leading to a reduction in manufacturing cost.

On the other hand, when compared to the vacuum deposition method, the wet film forming method may be difficult to laminate. In the case of producing a laminated film using the wet film forming method, it is necessary to prevent dissolution of the lower layer by the composition of the upper layer. this is spoken However, even when these techniques are used, it is sometimes difficult to use the wet film forming method for application of all films.

Accordingly, in general, a method of manufacturing an organic EL device using a wet film forming method for only a few layers and vacuum evaporation for the rest is adopted.

For example, a procedure for manufacturing an organic EL device by partially applying a wet film forming method is shown below.

(Procedure 1) Film formation by vacuum deposition of an anode

(Procedure 2) Film-forming by wet film-forming method of the composition for hole injection layer formation containing the hole injection layer material

(Procedure 3) Film-forming by wet film-forming method of the composition for hole-transporting layer formation containing the material for hole-transporting layer

(Procedure 4) Film-forming by wet film-forming method of the composition for light emitting layer formation containing a host material and a dopant material

(Procedure 5) Formation of electron transport layer by vacuum evaporation method

(Procedure 6) Formation of electron injection layer by vacuum evaporation method

(Procedure 7) Film formation by vacuum deposition of cathode

By going through this procedure, an organic EL device composed of an anode/hole injection layer/hole transport layer/a light emitting layer/electron transport layer/electron injection layer/cathode composed of a host material and a dopant material is obtained.

Of course, there is a means for preventing the dissolution of the light emitting layer of the lower layer, or by using a means for forming a film from the cathode side opposite to the above procedure, prepared as a composition for forming a layer containing the material for the electron transport layer or the material for the electron injection layer, , these can be formed by a wet film-forming method.

<Other methods of film formation>

A laser heating drawing method (LITI) can be used for film-forming of the composition for organic layer formation. LITI is a method of heating and depositing a compound attached to a substrate with a laser, and a composition for forming an organic layer may be used in a material applied to the substrate.

<Arbitrary process>

You may put an appropriate processing process, a washing|cleaning process, and a drying process suitably before and behind each process of film-forming. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, washing treatment using an appropriate solvent, and heat treatment. In addition, a series of steps for manufacturing the bank may also be included.

A photolithography technique can be used for the manufacture of a bank. As a bank material usable by photolithography, a positive resist material and a negative resist material can be used. Moreover, patternable printing methods, such as an inkjet method, gravure offset printing, reverse offset printing, and screen printing, can also be used. In this case, a permanent resist material may be used.

Materials used for the bank include polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, and polyethers. Mid, polysulfide, polysulfone, polyphenylene, polyphenylether, polyurethane, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (ABS) ), silicone resin, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene, etc. Although an olefin-hydrocarbon olefin copolymer and a fluorocarbon polymer are mentioned, it is not limited only to them.

<Composition for forming organic layer used in wet film forming method>

The composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL device or a high molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or a high molecular compound thereof) as at least one dopant material as a first component, at least one host material as a second component, and at least one as a third component. Contains organic solvents of the species. The first component functions as a dopant component of the light emitting layer obtained from the composition, and the second component functions as a host component of the light emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition and upon application imparts a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

<Organic solvent>

The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film formability, the presence or absence of defects in the coating film, surface roughness, and smoothness. In addition, at the time of film formation using the inkjet method, the ejection property can be controlled and improved by controlling the meniscus stability in the pinhole of the inkjet head. Furthermore, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescent properties, efficiency, and lifespan of an organic EL device having an organic layer obtained from the composition for forming an organic layer.

(1) Physical properties of organic solvents

The boiling point of at least 1 sort(s) of organic solvent is 130 degreeC - 300 degreeC, 140 degreeC - 270 degreeC are more preferable, 150 degreeC - 250 degreeC are still more preferable. When a boiling point is higher than 130 degreeC, it is preferable from a viewpoint of the ejection property of an inkjet. In addition, when the boiling point is lower than 300° C., it is preferable from the viewpoint of defects of the coating film, surface roughness, residual solvent and smoothness. The organic solvent has a more preferable configuration containing two or more organic solvents from the viewpoints of good inkjet ejection properties, film formability, smoothness, and low residual solvent. In addition, depending on the case, the composition made into the solid state by removing a solvent from the composition for organic layer formation in consideration of transportability etc. may be sufficient.

Further, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP _GS ) of the good solvent (GS) is the boiling point (BP _PS ) of the poor solvent (PS) A lower configuration is particularly preferred.

By adding the poor solvent of high boiling point, the good solvent of low boiling point volatilizes first at the time of film-forming, and the density|concentration of the content in a composition and the density|concentration of a poor solvent increase, and rapid film-forming is accelerated|stimulated. Thereby, a coating film with few defects, small surface roughness, and high smoothness is obtained.

The difference in solubility (S _GS -S _PS ) is preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. The difference in boiling points (BP _PS -BP _GS ) is preferably 10°C or higher, more preferably 30°C or higher, and still more preferably 50°C or higher.

The organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating after film formation. When heating, it is preferable to carry out at least 1 sort(s) of glass transition temperature (Tg) of a solute +30 degreeC or less from a viewpoint of coating film-forming property improvement. In addition, from the viewpoint of reducing the residual solvent, it is preferable to heat at least one glass transition point (Tg) of at least one of the solutes to -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, since the film is thin, the organic solvent is sufficiently removed. Moreover, you may dry several times at different temperatures, and may use several drying method together.

(2) Specific examples of organic solvents

Examples of the organic solvent used in the composition for forming an organic layer include an alkylbenzene-based solvent, a phenylether-based solvent, an alkylether-based solvent, a cyclic ketone-based solvent, an aliphatic ketone-based solvent, a monocyclic ketone-based solvent, a solvent having a diester skeleton, and and a fluorine-based solvent, and specific examples thereof include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptane-2- Ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, ter Pineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol Monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, Triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine , 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene , 2-methylanisole, phenetol, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3- Trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene) , neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene , veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene , 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4- (propoxymethyl ) benzene, 1-methyl-4- (butyloxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) benzene, 1-methyl-4- (heptyl) oxymethyl) benzene, benzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyl octyl ether, and the like, but are not limited thereto. In addition, a solvent may be used individually and may be mixed.

<Optional ingredients>

The composition for organic layer formation may contain the arbitrary component in the range which does not impair the property. As an optional component, a binder, surfactant, etc. are mentioned.

(1) binder

The composition for organic layer formation may contain the binder. A binder forms a film|membrane at the time of film-forming, and joins the obtained film|membrane with a board|substrate. In addition, it serves to dissolve, disperse, and bind other components in the composition for forming the organic layer.

Examples of the binder used in the composition for forming the organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, Ionomer, chlorinated polyether, diarylphthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers, but are not limited thereto does not

One type may be sufficient as the binder used for the composition for organic layer formation, and multiple types may be mixed and used for it.

(2) Surfactant

The composition for organic layer formation may contain surfactant for control of the film surface uniformity of the composition for organic layer formation, the solvent-philicity of a film surface, and liquid repellency, for example. Surfactants are classified into ionic and nonionic according to the structure of the hydrophilic group, and further classified into alkyl, silicone, and fluorine based on the structure of the hydrophobic group. Further, according to the molecular structure, it is classified into a monomolecular system having a relatively small molecular weight and a simple structure and a high molecular weight system having a side chain or branching having a large molecular weight. In addition, according to the composition, it is classified into a single system and a mixed system in which two or more types of surfactants and a substrate are mixed. As the surfactant that can be used in the composition for forming the organic layer, all kinds of surfactants can be used.

As surfactant, Polyflow No.45, Polyflow KL-245, Polyflow No.75, Polyflow No.90, Polyflow No.95 (trade name, Kyoeisha Chemical Industry Co., Ltd. product) are, for example, polyflow No.45, for example. , Disperbake 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK300 , BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (brand name, made by Big Chemie Japan), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (Brand name, manufactured by Shin-Etsu Chemical Co., Ltd.), Suffreon SC-101, Suffreon KH-40 (brand name, manufactured by Seimi Chemical Co., Ltd.), Ftagent 222F, Ftagent 251, FTX-218 (trade name, ( Neos Co.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi Materials), Megapack F-470, Megapack F -471, Megapack F-475, Megapack R-08, Megapack F-477, Megapack F-479, Megapack F-553, Megapack F-554 (trade name, manufactured by DIC Corporation), Fluoro Alkylbenzenesulfonate, fluoroalkylcarbonate, fluoroalkylpolyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerin tetrakis(fluoroalkylpolyoxyethylene) ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxy Ethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitanolate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate Tate, polyoxyethylene sorbitan stearay salt, polyoxyethylene sorbitanolate, polyoxyethylene naphthyl ether, alkylbenzenesulfonate, and alkyldiphenyletherdisulfonate.

In addition, surfactant may be used by 1 type and may use 2 or more types together.

<Composition and physical properties of the composition for forming an organic layer>

The content of each component in the composition for forming an organic layer is determined by using each component in the composition for forming an organic layer has good solubility, storage stability and film formability, and the film quality of a coating film obtained from the composition for forming an organic layer is of good quality, and the inkjet method is used. It is determined in consideration of the favorable discharge property in the case of the above-mentioned composition, the favorable electrical characteristics of the organic electroluminescent element which has an organic layer produced using the said composition, the light emitting characteristic, efficiency, and a viewpoint of lifetime. For example, in the case of the composition for forming a light emitting layer, the first component is 0.0001 wt % to 2.0 wt % based on the total weight of the composition for forming the light emitting layer, and the second component is 0.0999 wt % with respect to the total weight of the composition for forming the light emitting layer. % - 8.0 weight%, it is preferable that the 3rd component is 90.0 weight% - 99.9 weight% with respect to the total weight of the composition for light emitting layer formation.

More preferably, the first component is 0.005% by weight to 1.0% by weight based on the total weight of the composition for forming the light emitting layer, the second component is 0.095% by weight to 4.0% by weight based on the total weight of the composition for forming the light emitting layer, the second component 3 components are 95.0 weight% - 99.9 weight% with respect to the total weight of the composition for light emitting layer formation. Even more preferably, the first component is 0.05 wt% to 0.5 wt%, based on the total weight of the composition for forming the light emitting layer, the second component is 0.25 wt% to 2.5 wt%, based on the total weight of the composition for forming the light emitting layer, The third component is 97.0 wt% to 99.7 wt% with respect to the total weight of the composition for forming a light emitting layer.

The composition for organic layer formation can be manufactured by selecting suitably stirring, mixing, heating, cooling, dissolution, dispersion, etc. for the above-mentioned component by a well-known method, and performing it. After preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas replacement/encapsulation treatment, and the like may be appropriately selected and performed.

As a viscosity of the composition for organic layer formation, the favorable discharge property at the time of using the favorable film-forming property and the inkjet method that the one with high viscosity is acquired. On the other hand, the one with a low viscosity is easy to make a thin film|membrane. From this point, it is preferable that the viscosity in 25 degreeC is 0.3-3 mPa*s, and, as for the viscosity of this composition for organic layer formation, it is more preferable that it is 1-3 mPa*s. In the present invention, the viscosity is a value measured using a conical plate rotational viscometer (corn plate type).

As the surface tension of the composition for forming an organic layer, a coating film having good film formability and no defects can be obtained with a lower one. On the other hand, the higher one can obtain favorable inkjet ejection property. From this point, it is preferable that the surface tension in 25 degreeC is 20-40 mN/m, and, as for the viscosity of this composition for organic layer formation, it is more preferable that it is 20-30 mN/m. In the present invention, the surface tension is a value measured using the drop method.

<Crosslinkable high molecular compound: compound represented by general formula (XLP-1)>

Next, a case in which the above-described polymer compound has a crosslinkable substituent will be described. Such a crosslinkable high molecular compound is, for example, a compound represented by the following general formula (XLP-1).

[Formula 191]

In the formula (XLP-1),

MUx, ECx and k have the same definitions as MU, EC, and k in the formula (H3), provided that the compound represented by the formula (XLP-1) has at least one crosslinkable substituent (XLS), preferably Preferably, the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80 wt% in the molecule.

0.5 to 50 weight% is preferable and, as for content of the monovalent|monohydric or bivalent aromatic compound which has a crosslinkable substituent, 1 to 20 weight% is more preferable.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the above-described polymer compound, but a substituent having the following structure is preferable. * in each structural formula represents a bonding position.

[Formula 192]

L is each independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and 1 carbon atom -12 polyoxyalkylene. Among the above substituents, a group represented by a formula (XLS-1), a formula (XLS-2), a formula (XLS-3), a formula (XLS-9), a formula (XLS-10), or a formula (XLS-17) is preferable. and the group represented by a formula (XLS-1), a formula (XLS-3), or a formula (XLS-17) is more preferable.

As a divalent aromatic compound which has a crosslinkable substituent, the compound which has the following partial structure is mentioned, for example. * in the following structural formula represents a bonding position.

[Formula 193]

[Formula 194]

[Formula 195]

[Formula 196]

<Method for producing polymer compound and cross-linkable polymer compound>

The high molecular compound and the manufacturing method of a crosslinkable high molecular compound are demonstrated taking as an example the compound represented by the above-mentioned formula (H3) and the compound represented by a formula (XLP-1). These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include an aromatic solvent, a saturated/unsaturated hydrocarbon solvent, an alcohol solvent, and an ether-based solvent. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2- (2-ethoxyethoxy)ethane etc. are mentioned.

In addition, you may perform reaction in a two-phase system. When making it react in a two-phase system, you may add phase transfer catalysts, such as a quaternary ammonium salt, as needed.

When manufacturing the compound of Formula (H3) and the compound of Formula (XLP-1), you may manufacture in one step, and you may manufacture through multiple steps. In addition, it may be carried out by a batch polymerization method in which the reaction starts after all the raw materials are put into the reaction vessel, or it may be carried out by a dropping polymerization method in which the raw materials are added dropwise into the reaction vessel, or precipitation in which the product precipitates as the reaction proceeds. You may carry out by the polymerization method, and these can be combined suitably and can be synthesize|combined. For example, when synthesizing the compound represented by formula (H3) in one step, the target product is obtained by reacting in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. Further, when synthesizing the compound represented by the general formula (H3) in multiple steps, the monomer unit (MU) is polymerized to a desired molecular weight, and then the end cap unit (EC) is added and reacted to obtain the target product. When the reaction is performed by adding different types of monomer units (MU) in multiple steps, a polymer having a concentration gradient with respect to the structure of the monomer units can be prepared. Further, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (Scheme 1 of Synthesis Scheme), a polymer having a regular primary structure (Scheme 2 and 3 of Synthesis Scheme), etc. and can be used in an appropriate combination according to the target object. In addition, if a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[Formula 197]

As a monomer unit usable in the present invention, Japanese Patent Application Laid-Open No. 2010-189630, International Publication No. 2012/086671, International Publication No. 2013/191088, International Publication No. 2002/045184, International Publication No. 2011/049241 , International Publication No. 2013/146806, International Publication No. 2005/049546, International Publication No. 2015/145871, Japanese Patent Publication No. 2008-106241, Japanese Patent Publication No. 2010-215886, International Publication No. 2016/031639 , can be synthesized according to the method described in Japanese Patent Application Laid-Open No. 2011-174062.

In addition, for specific polymer synthesis procedures, Japanese Patent Application Laid-Open No. 2012-036388, International Publication No. 2015/008851, Japanese Patent Application Laid-Open No. 2012-36381, Japanese Patent Application Laid-Open No. 2012-144722, International Publication No. 2015/194448 No., International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2011/049241 Can be synthesized according to the method described in .

<Application example of organic electroluminescent device>

Moreover, this invention can be applied also to the display apparatus provided with organic electroluminescent element, the lighting apparatus provided with organic electroluminescent element, etc.

A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment to a known driving device, and known such as direct current driving, pulse driving, alternating current driving, etc. It can be driven by appropriately using the driving method of

As a display apparatus, flexible displays, such as panel displays, such as a color flat panel display, and a flexible color organic electroluminescence (EL) display, etc. are mentioned, for example (For example, Unexamined-Japanese-Patent No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Application Laid-Open No. 2004-281086, etc.). Moreover, as a display system of a display, a matrix, a segment system, etc. are mentioned, for example. In addition, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally, such as in a grid shape or a mosaic shape, and a character or an image is displayed by a set of pixels. The shape or size of a pixel is determined according to its use. For example, a square pixel of 300 µm or less on one side is usually used to display images and characters on computers, monitors, and televisions, and in the case of a large display such as a display panel, pixels on the order of mm are used on one side. will do In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are arranged and displayed. In this case, there are typically a delta type and a stripe type. Incidentally, as a method of driving this matrix, either a linear driving method or an active matrix may be used. Although line-sequential driving has an advantage in that it has a simple structure, the active matrix method is sometimes excellent when the operating characteristics are taken into consideration.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is made to emit light. For example, time and temperature display by a digital watch or thermometer, operation state display of an audio device, an electronic cooker, etc., and a panel display of an automobile, etc. are mentioned.

Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, and the like (for example, Japanese Patent Laid-Open Nos. 2003-257621, 2003-277741, and Japanese Patents See Publication No. 2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used in a liquid crystal display device, a watch, an audio device, an automobile panel, a display panel, a cover, and the like. In particular, considering that it is difficult to reduce the thickness of a liquid crystal display device, in particular, as a backlight for computer use in which thickness reduction is a problem because the conventional method consists of a fluorescent lamp or a light guide plate, the backlight using the light emitting element according to the present embodiment is thin. and is characterized by being lightweight.

3-2. other organic devices

The polycyclic aromatic compound according to the present invention can be used for production of an organic field effect transistor, an organic thin film solar cell, or a wavelength conversion filter in addition to the organic electroluminescent device described above.

An organic field effect transistor is a transistor that controls a current by an electric field generated by voltage input, and a gate electrode is provided in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated and the current can be controlled by blocking the flow of electrons (or holes) flowing between the source electrode and the drain electrode. BACKGROUND ART Field effect transistors can be easily downsized compared to simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

In the structure of an organic field effect transistor, a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and further, an insulating layer (dielectric layer) in contact with the organic semiconductor active layer is interposed and the gate electrode is installed. As the element structure, the following structures are mentioned, for example.

(1) substrate/gate electrode/insulator layer/source electrode/drain electrode/organic semiconductor active layer

(2) substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode/drain electrode

(3) substrate/organic semiconductor active layer/source electrode/drain electrode/insulator layer/gate electrode

(4) substrate/source electrode/drain electrode/organic semiconductor active layer/insulator layer/gate electrode

The organic field effect transistor constituted in this way can be applied as an active matrix driving type liquid crystal monitor, a pixel driving switching element of an organic light emitting element display, or the like.

The organic thin film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transporting layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transporting layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. In addition to the above, the organic thin film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin film solar cell can be used in combination by appropriately selecting a known material used for the organic thin film solar cell.

A quantum dot with a narrow emission half maximum width is used as a phosphor of a wavelength conversion filter for the purpose of making a display light gamut. On the other hand, there are problems such as instability to oxidation, high cohesiveness due to nano-sized fine particles, and regulated metals used as contaminants. The polycyclic aromatic compound according to the present invention can be used as a phosphor of a wavelength conversion filter. As the matrix in which the polycyclic aromatic compound is dispersed, a polymer material having high transparency, low water vapor permeability, low oxygen permeability and high thermal stability is preferable, for example, (meth)acrylic polymer such as polymethyl (meth)acrylate and Cycloolefin polymers, such as Zeonex, etc. are mentioned.

[Example]

Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these. First, the synthesis example of a polycyclic aromatic compound is demonstrated below.

Synthesis Example (1): Synthesis of compound (1A-18)

In a flask containing compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) and o-dichlorobenzene (400 ml) at room temperature under nitrogen atmosphere, boron tribromide (1.13 ml, 12 mmol, 4 eq.) was added. After completion|finish of dripping, it heated up to 180 degreeC, and stirred for 20 hours. After that, it was cooled to room temperature again, N,N-diisopropylethylamine (7.70 ml, 45 mmol, 15 eq.) was added, and the mixture was stirred until the exotherm subsided. Thereafter, the reaction solution was distilled off under reduced pressure at 60°C to obtain a crude product. The obtained crude product was washed in this order with acetonitrile, methanol, and toluene, purified by a silica gel column (eluent: toluene), and the crude product was recrystallized twice from o-dichlorobenzene to obtain compound (1A-18) ( 0.84 g).

[Formula 198]

¹ H-NMR((CDCl ₂ ) ₂ , 500 MHz): δ=2.51 (m, 12H), 5.21 (s, 1H), 6.73 (d, 2H), 6.89 (d, 4H), 7.23-7.28 (m, 6H), 7.50(t, 2H), 7.62(t, 4H), 7.92(d, 4H), 8.59(s, 2H), 8.74(s, 2H), 9.13(s, 2H).

The target compound (1A-18) was identified at m/z=801.35 by MALDI-MS.

Synthesis Example (2): Synthesis of compound (1A-32)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-32) (3.36 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-32) was obtained (0.38 g).

[Formula 199]

¹ H-NMR (CDCl ₃ , 500 MHz): δ = 9.16 (s, 2H), 8.96 (d, 2H), 8.68 (s, 2H), 7.91 (d, 4H), 7.57 (t, 4H), 7.43 ( t, 2H), 7.21(t, 8H), 7.11(d, 8H), 7.02(t, 6H), 6.82(s, 2H), 6.61(s, 4H), 6.37(d, 2H), 5.31(s) , 1H), 2.17 (s, 12H).

The target compound (1A-32) was identified at m/z=1135.50 by MALDI-MS.

Synthesis Example (3): Synthesis of compound (1A-111)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-111) (2.64 g, 3.0 mmol, 1eq.) in the same procedure as in Synthesis Example 1 (1A-111) was obtained (0.21 g).

[Formula 200]

The target compound (1A-111) was identified at m/z=895.33 by MALDI-MS.

Synthesis Example (4): Synthesis of compound (1A-214)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-214) (3.64 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-214) was obtained (0.30 g).

[Formula 201]

The target compound (1A-214) was identified at m/z=1229.48 by MALDI-MS.

Synthesis Example (5): Synthesis of compound (1A-303)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-303) (4.11 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-303) was obtained (0.60 g).

[Formula 202]

¹ H-NMR (CDCl ₃ , 500 MHz): δ = 1.50 (s, 36H), 1.88 (s, 12H), 2.49 (s, 6H), 5.49 (s, 1H), 7.04 (s, 4H), 7.08 ( d, 2H), 7.33 (t, 2H), 7.42 (t, 4H), 7.50 (dd, 4H), 7.65 (d, 4H), 7.72 (dd, 2H), 7.81 (d, 4H), 8.21 (s) , 4H), 8.77(s, 2H), 9.20(s, 2H), 9.47(s, 2H).

The target compound (1A-303) was identified at m/z=1383.75 by MALDI-MS.

Synthesis Example (6): Synthesis of compound (1A-407)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-407) (3.35 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-407) was obtained (0.56 g).

[Formula 203]

¹ H-NMR((CDCl ₂ ) ₂ , 500 MHz): δ=1.63(s, 12H), 2.03(s, 6H), 5.20(s, 1H), 6.31(s, 2H), 6.53(s, 4H) , 7.04-7.10(m, 4H), 7.15(d, 4H), 7.22-7.27(m, 6H), 7.38-7.45(m, 6H), 7.48(s, 2H), 7.57-7.60(m, 6H) , 7.66(d, 2H), 7.76(d, 2H), 7.95(d, 4H), 8.75(s, 2H), 9.00(d, 2H), 9.21(s, 2H).

The target compound (1A-407) was identified at m/z=1263.56 by MALDI-MS.

Synthesis Example (7): Synthesis of (1A-702)

The compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-702) (1.62 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-702) was obtained (0.42 g).

[Formula 204]

The target compound (1A-702) was confirmed at m/z=555.25 by MALDI-MS.

Synthesis Example (8): Synthesis of compound (1A-331)

Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int-1A-331) (2.05 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-331) was obtained (0.10 g).

[Formula 205]

¹ H-NMR((CDCl ₂ ) ₂ , 500 MHz): δ=5.01(s, 1H), 6.74(d, 2H), 7.00-7.01(m, 4H), 7.27-7.29(m, 2H), 7.42 7.44(m, 8H), 7.49(t, 1H), 7.54(t, 1H), 7.62(t, 1H), 7.91(d, 1H), 8.15(d, 1H), 8.30(d, 1H), 8.81 (d, 1H), 8.91-8.95 (m, 2H), 9.33 (s, 1H).

The target compound (1A-331) was identified at m/z=699.21 by MALDI-MS.

Synthesis Example (9): Synthesis of compound (1A-902)

Compound (Int-1A-18) (2.36 g, 3.0 mmol, 1eq.) was replaced with compound (Int-1A-902) (2.32 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1A-902) was obtained (0.50 g).

[Formula 206]

The target compound (1A-902) was identified at m/z=789.26 by MALDI-MS.

Synthesis Example (10): Synthesis of compound (1A-214) (Other Method 1)

In a flask containing compound (Int1-1A-214) (2.36 g, 3.0 mmol, 1eq.) and t-butylbenzene (400 ml), while ice-cooling under a nitrogen atmosphere, a 1.6 mol/L tBuLi-heptane solution (9.3 ml, 15 mmol) , 5 eq.) was added. After completion of the dropwise addition, the mixture was stirred at room temperature for 4 hours. Then, boron tribromide (2.25 g, 9.0 mmol, 3eq.) was slowly added while cooling on ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 24 hours. Then, 1,2,2,6,6-pentamethylpiperidine (1.86 g, 12 mmol, 4 eq.) was added while cooling on ice. Then, the mixture was stirred at 170° C. for 24 hours. Return to room temperature, and water was added until the exotherm subsided. After that, extraction was performed with toluene, the organic solvents were collected and concentrated under reduced pressure to obtain a crude product. The obtained crude product was washed in this order with acetonitrile, methanol and toluene, purified by a silica gel column (eluent: toluene), and the crude product was recrystallized twice from o-dichlorobenzene to obtain compound (1A-214) (1.10). g).

[Formula 207]

The target compound (1A-214) was identified at m/z=1229.4801 by MALDI-MS.

Synthesis Example (11): Synthesis of compound (1A-702) (Other Method 1)

The compound (Int1-1A-214) (2.36 g, 3.0 mmol, 1eq.) was replaced with the compound (Int1-1A-702) (1.62 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 10. (1A-702) was obtained (0.97 g).

[Formula 208]

The target compound (1A-702) was confirmed at m/z=555.2522 by MALDI-MS.

Other polycyclic aromatic compounds of the present invention can be synthesized by a method similar to the above-mentioned synthesis examples by appropriately changing the raw material compounds.

Next, evaluation of basic physical properties of the compound of the present invention and fabrication and evaluation of an organic EL device using the compound of the present invention will be described. However, the application of the compound of the present invention is not limited to the examples shown below, and the film thickness and constituent material of each layer can be appropriately changed according to the basic physical properties of the compound of the present invention.

<Evaluation of basic properties>

Compound (1A-18), compound (1A-32), compound (1A-111), compound (1A-214), compound (1A-303), compound (1A-331), compound (1A-407) of the present invention ), compound (1A-702), and comparative compounds RGD-1, RGD-2, RGD-3, and RBD-1, each dissolved in toluene with PMMA (polymethyl methacrylate) to 1 wt% Then, a thin film was formed on a transparent support substrate (10 mmХ10 mm) made of quartz by spin coating to prepare a PMMA dispersion film.

Photoluminescence was measured by excitation at a wavelength of 280 nm at room temperature. Further, the fluorescence lifetime was measured at 300 K using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, a light emission component with a fast fluorescence lifetime and a light emission component with a slow fluorescence lifetime were observed at the maximum emission wavelength measured at an excitation wavelength of 280 nm. In the measurement of the fluorescence lifetime at room temperature of general organic EL materials that emit fluorescence, a slow emission component involving a triplet component derived from phosphorescence is rarely observed due to thermal deactivation of the triplet component. When a slow luminescence component is observed in the compound to be evaluated, triplet energy with a long excitation lifetime is transferred to singlet energy due to thermal activation, indicating that it is observed as delayed fluorescence. A result is shown in Table 1.

[Table 1]

Chemical structures of RGD-1, RGD-2, RGD-3, and RBD-1 in Table 1 are shown below.

[Formula 209]

<Evaluation of vapor deposition organic EL device>

Organic EL devices according to Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-4 were fabricated, and at a luminance of 500 cd/m ² , emission wavelength, full width at half maximum, driving voltage, and external quantum Efficiency and LT50 (time until reaching 250 cd/m ² when continuously driven with a current density at an initial luminance of 500 cd/m ² ) were measured.

[Table 2]

In Table 2, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, and "TcTa" is 4,4',4"-tris (N-carbazolyl)triphenylamine, "mCP" is 1,3-bis(N-carbazolyl)benzene, "Ir(ppy)3" is tris(2-phenylpyridinato)iridium (III), "2CzBN" is 3,4-dicarbazolylbenzonitrile, "BPy-TP2" is 2,7-di([2,2'-bipyridin]-5-yl)triphenylene Together with "GH-1", the chemical structure is shown below.

[Formula 210]

<Example 1-1>

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm in which ITO formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and NPD, TcTa, mCP, GH-1, compound (1A-18), 2CzBN, and BPy-TP2 were each applied thereto. A molybdenum vapor deposition boat and a tungsten vapor deposition boat containing LiF and aluminum respectively were mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, NPD was heated and vapor-deposited so that it might become a film thickness of 40 nm, and the hole injection layer was formed. Next, TcTa was heated to vapor-deposit to a film thickness of 15 nm, and further, mCP was heated and vapor-deposited to a film thickness of 15 nm to form a two-layer hole transport layer. Next, GH-1 and compound (1A-18) were simultaneously heated and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of GH-1 and compound (1A-18) was about 99 to 1. Next, 2CzBN was heated to vapor-deposit to a film thickness of 10 nm, and further, BPy-TP2 was heated and vapor-deposited to a film thickness of 20 nm to form an electron transporting layer comprising two layers. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Examples 1-2 to Examples 1-4>

Each device was manufactured by changing the compound (1A-18), which is the dopant of Example 1, to each dopant shown in Table 2.

<Comparative Example 1-1 to Comparative Example 1-4>

Each device was manufactured by changing the compound (1A-18), which is the dopant of Example 1, to each dopant shown in Table 2.

Table 3 shows the evaluation results of each element.

[Table 3]

In Examples 1-1 to 1-4, compared with Comparative Examples 1-1 to 1-4, green (500 to 550 nm) light emission was obtained, and the half maximum width of the emission spectrum, color purity, external quantum efficiency, and Balanced results were obtained at high levels of device lifetime.

Organic EL devices according to Examples 1-5 to 1-8, Comparative Example 1-5, Examples 1-9 to 1-12 and Comparative Example 1-6 were fabricated, and the luminance was 500 cd/m ² . , emission wavelength, full width at half maximum, driving voltage, external quantum efficiency, and LT50 (time until 250 cd/m ² when continuously driven with a current density at an initial luminance of 500 cd/m ² ) were measured.

[Table 4]

In Table 4, the chemical structures of "HATCN", "TBB", "CBP", "GH-2" and "TPBi" are shown below.

[Formula 211]

<Example 1-5>

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm in which ITO formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HATCN, TBB, TcTa, CBP, compound (1A-32) and TPBi are put in a molybdenum vapor deposition boat; A tungsten deposition boat containing LiF and aluminum, respectively, was mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, HATCN was heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer. Next, TBB was heated to vapor-deposit to a film thickness of 65 nm, and further, TcTa was heated and vapor-deposited to a film thickness of 10 nm to form a two-layer hole transporting layer. Next, CBP and compound (1A-32) were simultaneously heated and vapor-deposited to a film thickness of 30 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of CBP and compound (1A-32) was about 99 to 1. Next, TPBi was heated and vapor-deposited to a film thickness of 50 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to obtain a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Example 1-6 to Example 1-8, Comparative Example 1-5, Example 1-9 to Example 1-12 and Comparative Example 1-6>

Each device was manufactured by changing the host CBP, dopant compound (1A-32), and mixing ratio of Example 1-5 to each host, dopant, and mixing ratio shown in Table 4.

Table 5 shows the evaluation results of each element.

[Table 5]

In Example 1-5 to Example 1-8 and Example 1-9 to Example 1-12, compared with Comparative Example 1-5 and Comparative Example 1-6, the half width of the emission spectrum was narrow, high efficiency and long The device lifetime was obtained.

Organic EL devices according to Example 1-13, Comparative Example 1-7, Example 1-14, Example 1-15, Example 1-16, and Comparative Example 1-8 were fabricated, and at a luminance of 500 cd/m ² , emission wavelength, full width at half maximum, driving voltage, external quantum efficiency, and LT50 (time until 250 cd/m ² when continuously driven at an initial luminance of 500 cd/m ² at current density) were measured.

[Table 6]

In Table 6, the chemical structures of "4CzIPN", "BCC-TPTA", "T2T", and "Liq" are shown below.

[Formula 212]

<Example 1-13>

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm in which ITO formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum containing HATCN, TBB, TcTa, 4CzIPN, compound (1A-32), T2T, TPBi and Liq respectively. A vapor deposition boat and a tungsten vapor deposition boat in which LiF and aluminum were respectively placed were mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, HATCN was heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer. Next, TBB was heated to vapor-deposit to a film thickness of 65 nm, and further, TcTa was heated and vapor-deposited to a film thickness of 10 nm to form a two-layer hole transporting layer. Next, TcTa, 4CzIPN, and compound (1A-32) were simultaneously heated and evaporated to a thickness of 30 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of TcTa, 4CzIPN, and compound (1A-32) was about 85 to 14 to 1. Next, T2T was heated to vapor-deposit to a film thickness of 10 nm, and then, TPBi and Liq were heated and vapor-deposited to a film thickness of 40 nm to form an electron transporting layer composed of two layers. The deposition rate was adjusted so that the weight ratio of TPBi and Liq was about 70 to 30. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to obtain a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Comparative Example 1-7, Example 1-14, Example 1-15, Example 1-16 and Comparative Example 1-8>

A device was manufactured by changing the host TcTa of Example 1-13, the assisting dopant 4CzIPN, and the dopant compound (1A-32) and the mixing ratio to each assisting dopant and each dopant and each mixing ratio described in Table 6.

Table 7 shows the evaluation results of each element.

[Table 7]

In Example 1-13, compared with Comparative Example 1-7, the half width of the emission spectrum was narrow, and high efficiency and long device lifetime were obtained.

In addition, by changing the dopant of Example 1-13, a blue light-emitting device like Example 1-14 can be realized.

Similarly, by changing the device configuration of Examples 1-13, a device using an exciplex and an assisting dopant as in Examples 1-15 can be realized.

Compared with Comparative Examples 1-8, Examples 1-16 exhibited blue light emission, the emission spectrum had a narrow half maximum width, and high efficiency and long device lifetime were obtained.

<Evaluation of coating type organic EL element>

Next, an organic EL device obtained by coating an organic layer will be described.

<Polymer host compound: Synthesis of SPH-101>

According to the method described in International Publication No. 2015/008851, SPH-101 was synthesized. A copolymer to which M2 or M3 is bonded is obtained next to M1, and it is estimated that each unit is 50:26:24 (molar ratio) from the input ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is a connection position of each unit.

[Formula 213]

<Polymer hole transport compound: Synthesis of XLP-101>

According to the method described in Japanese Patent Laid-Open No. 2018-61028, XLP-101 was synthesized. A copolymer to which M5 or M6 is bonded is obtained next to M4, and it is estimated that each unit is 40:10:50 (molar ratio) from the input ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is a connection position of each unit.

[Formula 214]

<Example 2-1 to Example 2-9>

A coating-type organic EL device is produced by preparing a solution for application of the material forming each layer.

<Production of organic EL devices of Examples 2-1 to 2-3>

Table 8 shows the material configuration of each layer in the organic EL device.

[Table 8]

In Table 8, the structure of "ET1" is shown below.

[Formula 215]

<Preparation of the composition (1) for forming a light emitting layer>

The composition (1) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution. By spin-coating the prepared composition for light emitting layer formation on a glass substrate, and drying by heat under reduced pressure, there is no film|membrane defect and the coating film excellent in smoothness is obtained.

Compound (A) 0.04% by weight

SPH-101 1.96 wt%

69.00% by weight of xylene

Decalin 29.00 wt%

In addition, the compound (A) is a polycyclic aromatic compound represented by the general formula (1A) or (1B) (eg, compound (1A-32)), and the polycyclic aromatic compound is a monomer (that is, the monomer is reactive It is a high molecular compound polymerized with a substituent (having a substituent), or a polymer crosslinked product obtained by further crosslinking the high molecular compound. A polymer compound for obtaining a crosslinked polymer has a crosslinkable substituent.

<PEDOT:PSS solution>

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

[Formula 216]

<Preparation of OTPD solution>

OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (photocationic polymerization initiator, manufactured by San Apro Corporation) are dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight .

[Formula 217]

<Preparation of XLP-101 solution>

XLP-101 is dissolved in xylene at a concentration of 0.6 wt% to prepare a 0.6 wt% XLP-101 solution.

<Preparation of PCz solution>

PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7 wt% PCz solution.

[Formula 218]

<Example 2-1>

On a glass substrate on which ITO was deposited to a thickness of 150 nm, a PEDOT:PSS solution was spin-coated and baked on a hot plate at 200°C for 1 hour to form a PEDOT:PSS film with a film thickness of 40 nm (hole injection layer). Then, the OTPD solution was spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, exposed with an exposure machine at an exposure intensity of 100 mJ/cm ² , and baked on a hot plate at 100 ° C. for 1 hour, whereby a film insoluble in solution An OTPD film with a thickness of 30 nm is formed (hole transport layer). Next, the composition (1) for forming a light-emitting layer is spin-coated and baked on a hot plate at 120°C for 1 hour to form a light-emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boat containing ET1, molybdenum vapor deposition boat containing LiF, tungsten vapor deposition boat containing aluminum to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, ET1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Thereafter, LiF is heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness is 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 2-2>

An organic EL device was obtained in the same manner as in Example 2-1. The hole transport layer is formed by spin-coating the XLP-101 solution and baking it on a hot plate at 200°C for 1 hour to form a film having a thickness of 30 nm.

<Example 2-3>

An organic EL device was obtained in the same manner as in Example 2-1. Further, the hole transport layer is formed by spin-coating a PCz solution and baking it on a hot plate at 120°C for 1 hour to form a film having a thickness of 30 nm.

<Evaluation of the organic EL device of Examples 2-1 to 2-3>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency, like the deposition-type organic EL device.

<Production of organic EL devices of Examples 2-4 to 2-6>

Table 9 shows the material configuration of each layer in the organic EL device.

[Table 9]

<Preparation of compositions (2) to (4) for light emitting layer formation>

The composition (2) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

mCBP 1.98 wt%

98.00% by weight of toluene

The composition (3) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

SPH-101 1.98 wt%

98.00% by weight of xylene

The composition (4) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

DOBNA 1.98 wt%

98.00% by weight of toluene

In Table 9, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "DOBNA" is 3,11-di-o-tolyl-5,9- It is dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structure is shown below.

[Formula 219]

<Example 2-4>

After spin-coating ND-3202 (manufactured by Nissan Chemical Industry Co., Ltd.) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, heated at 50 ° C. for 3 minutes in an atmospheric atmosphere, and then heated again at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Then, the XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes under a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the composition (2) for forming a light-emitting layer is spin-coated and heated at 130°C for 10 minutes in a nitrogen gas atmosphere to form a light-emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and TSPO1 is put in a molybdenum vapor deposition boat, LiF is put in a molybdenum vapor deposition boat, and aluminum is put in a tungsten vapor deposition boat. to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Thereafter, LiF is heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness is 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-5 and Examples 2-6>

An organic EL device is obtained in the same manner as in Example 2-4 using the composition (3) or (4) for forming a light emitting layer.

<Evaluation of the organic EL device of Examples 2-4 to 2-6>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency like the deposition-type organic EL device.

<Production of organic EL devices of Examples 2-7 to 2-9>

Table 10 shows the material configuration of each layer in the organic EL device.

[Table 10]

<Preparation of compositions (5) to (7) for light emitting layer formation>

The composition (5) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

mCBP 1.80 wt%

98.00% by weight of toluene

The composition (6) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

SPH-101 1.80 wt%

98.00% by weight of xylene

The composition (7) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

DOBNA 1.80 wt%

98.00% by weight of toluene

In Table 10, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene))bis (10H-phenoxazine). The chemical structure is shown below.

[Formula 220]

<Example 2-7>

After spin-coating ND-3202 (manufactured by Nissan Chemical Industry Co., Ltd.) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, heated at 50 ° C. for 3 minutes in an atmospheric atmosphere, and then heated again at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Then, the XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes under a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Then, the composition 5 for forming a light-emitting layer is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light-emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and TSPO1 is put in a molybdenum vapor deposition boat, LiF is put in a molybdenum vapor deposition boat, and aluminum is put in a tungsten vapor deposition boat. to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, TSPO1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Thereafter, LiF is heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec so that the film thickness is 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-8 and Examples 2-9>

An organic EL device was obtained in the same manner as in Example 2-7 using the composition (6) or (7) for forming a light emitting layer.

<Evaluation of the organic EL device of Examples 2-7 to 2-9>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency, like the deposition-type organic EL device.

As described above, some of the compounds according to the present invention were evaluated as materials for organic EL devices and were shown to be excellent materials. Since it is a compound having a compound, it can be understood by those skilled in the art that it is an excellent material for an organic EL device as well.

According to a preferred aspect of the present invention, by producing an organic EL device using a novel polycyclic aromatic compound as a dopant material, for example, an organic EL device having a narrow half-width of emission spectrum and excellent color purity, and furthermore, an organic EL device having excellent quantum efficiency and device lifetime An EL element can be provided. In addition, the novel polycyclic aromatic compound of the present invention has a sharper emission spectrum, a narrower half-width of the emission spectrum, and many compounds exhibiting high color purity light emission from the viewpoint of having a rigid structure.

100 organic electroluminescent device
101 board
102 anode
103 hole injection layer
104 hole transport layer
105 light emitting layer
106 electron transport layer
107 electron injection layer
108 cathode

Claims (31)

A polycyclic aromatic compound represented by the following general formula (1A) or (1B).
[Formula 1]

In the above formula (1A) or (1B),
R ^a is hydrogen or a substituent, and "-C(-R ^a )=" in ring a may be substituted with "-N=",
Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted;
Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > Each R of Ge(-R)- is independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl;
X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cyclo alkyl, wherein at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ may be bonded by a single bond or a linking group;
R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ may be bonded to at least one of ring a and ring B by a single bond or a linking group. become,
R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ may be bonded to at least one of ring a and ring E by a single bond or a linking group. become,
The C ring and D ring, the G ring and the B ring, and the F ring and the E ring may each independently be bonded by a single bond or a linking group,
However, in the formula (1A), the CD bond of ring C and ring D, and R of >NR as X ¹ (wherein R is optionally substituted aryl, optionally substituted heteroaryl, or substituted X 1 B bond of ring B) and X ¹ B bond of ring B, and R of >NR as X ² (wherein R is optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted cycloalkyl) (limited to) and among the three bonds of X ² E bond of the E ring, any one or two bonds exist,
In the formula (1B), any one or two bonds are present among the three bonds: the CD bond of the C and D rings, the GB bond of the G and B rings, and the FE bond of the F and E rings. are doing,
At least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B) is at least one cyclo may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;
At least one hydrogen in the compound represented by the formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen. The method of claim 1,
In the above formula (1A) or (1B),
R ^a is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted di Rylboryl (two aryls may be bonded by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;
"-C(-R ^a )=" in ring a may be substituted with "-N=",
Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (two aryls are bonded through a single bond or a linking group) may be substituted), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl;
Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R of Ge(-R)- is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl;
X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, and at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ is a single bond, -CH=CH-, -CR =CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently , hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent R may form a ring and may form cycloalkylene, arylene, or heteroarylene,
R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, at least of ring a and ring B may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring E, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ -R each independently represents hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, even if at least one hydrogen in R is substituted with alkyl or cycloalkyl and two adjacent R's may form a ring, and may form cycloalkylene, arylene, and heteroarylene;
C ring and D ring, G ring and B ring, and F ring and E ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl , or cycloalkyl, at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring, cycloalkylene, arylene, and hetero Arylene may be formed,
However, in the formula (1A), the CD bond of the C rings and the D rings, and R of >NR as X ¹ , wherein R is the aryl, the heteroaryl, or the above optionally substituted with the above alkyl or cycloalkyl. Limited to cycloalkyl) and the X ¹ B bond of the B ring, and R of >NR as X ² (wherein R is limited to the aryl, heteroaryl, or cycloalkyl optionally substituted with the above alkyl or cycloalkyl) ) and among the three bonds of the X ² E bond of the E ring, any one or two bonds exist,
In the formula (1B), any one or two bonds are present among the three bonds: the CD bond of the C and D rings, the GB bond of the G and B rings, and the FE bond of the F and E rings. are doing,
At least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B) is at least one cyclo may be condensed with an alkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen. The method of claim 1,
A polycyclic aromatic compound represented by the following general formula (2A) or the following general formula (2B).
[Formula 2]

In the above formula (2A) or (2B),
R ^a is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in R ^a is aryl, heteroaryl, alkyl , or may be substituted with cycloalkyl,
"-C(-R ^a )=" in ring a may be substituted with "-N=",
R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 aryl may be bound by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g adjacent to each other are bonded to each other, and together with the b ring, c ring, d ring, e ring, f ring, and g ring, an aryl ring or a hetero An aryl ring may be formed, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are a single bond or a linking group) may be substituted with), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, At least one hydrogen in the substituent may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl;
In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”, and any “-C(-R)=C(-R)-” (where R is R ^b , R ^c , R ^{d )} , ^{Re , R f ,} or R ^g ) is “-N(-R)-”, “-O-”, “-S-”, “-C(-R) ₂ -”, “-Si (-R) ₂ -" or "-Se-" may be substituted, and R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si R in (-R) ₂ -" is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and the above "-C At least one of the two Rs of (-R) ₂ -" and the two Rs of "-Si(-R) ₂ -" is a single bond, -CH=CH-, -CR=CR-, -C ≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring; , cycloalkylene, arylene, or heteroarylene may be formed,
Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R of Ge(-R)- is each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl;
X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R is alkyl or It may be substituted with cycloalkyl, and at least one of the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ is a single bond, -CH=CH-, -CR =CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded, and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently , hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent R each may form a ring and may form cycloalkylene, arylene, or heteroarylene;
R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- by at least an a ring and a b ring may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring e, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ -R each independently represents hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, even if at least one hydrogen in R is substituted with alkyl or cycloalkyl and two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene,
c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl , or cycloalkyl, at least one hydrogen in R may be substituted with alkyl or cycloalkyl, and two adjacent Rs form a ring, cycloalkylene, arylene, and hetero Arylene may be formed,
However, in the formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R is the aryl, the heteroaryl, or the above optionally substituted with the above-mentioned alkyl or cycloalkyl. limited to cycloalkyl) and the X ¹ b bond of the b ring, and R of >NR as X ² (wherein R is limited to the above aryl, heteroaryl, or cycloalkyl which may be substituted with the above alkyl or cycloalkyl) ) and among the three bonds of the X ² e bond of the e ring, any one or two bonds exist,
In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,
In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. , C1-C24 alkyl, or C3-C24 cycloalkyl may be substituted, and at least one -CH ₂ - in this cycloalkane may be substituted with -O-,
At least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen. 4. The method of claim 3,
In the above formula (2A) or (2B),
R ^a is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl has 6 to 12 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in R ^a has 6 carbon atoms It may be substituted with aryl of to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms;
"-C(-R ^a )=" in ring a may be substituted with "-N=",
R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl has carbon atoms 6-12 aryl), diarylboryl (provided that aryl is C6-C12 aryl, and the two aryls may be bonded by a single bond or a linking group), C1-C24 alkyl, or C3-C12 aryl 24 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or heteroaryl having 2 to 15 carbon atoms. may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are bonded to each other Together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one Hydrogen is an aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 12 carbon atoms, The two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms may be substituted, and at least one hydrogen in these substituents has 6 carbon atoms It may be substituted with aryl of to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms;
In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”, and any “-C(-R)=C(-R)-” (where R is R ^b , R ^c , R ^{d )} , ^{Re , R f ,} or R ^g ) is “-N(-R)-”, “-O-”, “-S-”, “-C(-R) ₂ -”, “-Si (-R) ₂ -" or "-Se-" may be substituted, and R of "-N(-R)-", R of "-C(-R) ₂ -", and "-Si R in (-R) ₂ -" is hydrogen, aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons, or cycloalkyl having 3 to 14 carbons, At least one hydrogen may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and the two Rs in “-C(-R) ₂ -” and “-Si(-R) At least one of the two Rs in " _2- " is a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, It may be bonded by -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and R of -CR=CR-, R of -N(-R)-, -C R of (-R) ₂ - and R of -Si(-R) ₂ - are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms; alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. may be substituted with alkyl, and two adjacent Rs form a ring to form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms; may be,
Y ¹ , Y ² , and Y ³ are, each independently, >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As- , >C(-R)-, >Si(-R)-, or >Ge(-R)-, wherein R of >C(-R)-, R of >Si(-R)-, and > R in Ge(-R)- is each independently an aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen of may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
X ¹ and X ² are each independently >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, wherein R of >NR, >C( R of -R) ₂ and R of >Si(-R) ₂ are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or 3 carbon atoms. to 14 cycloalkyl, wherein at least one hydrogen in R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms;
R of >NR as X ¹ , R of >C(-R) ₂ , or R of >Si(-R) ₂ is a single bond, -CH=CH-, -CR=CR-, -C≡C -, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- by at least an a ring and a b ring may be bonded to one, and R of >NR as X ² , R of >C(-R) ₂ , or R of >Si(-R) 2 is a single bond, -CH=CH-, -CR= by CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, may be bonded to at least one of ring a and ring e, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R ) ₂ - R is each independently hydrogen, aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons, alkenyl having 1 to 6 carbons, alkynyl having 1 to 6 carbons , or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent R may form a ring and form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms;
c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R) -, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- may be bonded to each other, and R, -N in -CR=CR- R of (-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, C6-C12 aryl, C2-C15 heteroaryl, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, wherein at least one hydrogen in R is It may be substituted with 6-alkyl or C3-C14 cycloalkyl, and two adjacent R's form a ring, and C3-C14 cycloalkylene, C6-C12 arylene, or C6-C12 2 to 15 heteroarylene may be formed,
However, in the formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. , the above-mentioned aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms) and the X ¹ b bond of ring b, and R of >NR as X ² (wherein R is , limited to the aforementioned aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, which may be substituted with the alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. ) and among the three bonds of the X ² e bond of the e ring, any one or two bonds exist,
In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,
In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 16 carbon atoms or heteroaryl having 2 to 15 carbon atoms. , may be substituted with alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen. 4. The method of claim 3,
In the above formula (2A) or (2B),
R ^a is hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 to 10 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ^a has 6 carbon atoms It may be substituted with -10 aryl, C2-C10 heteroaryl, C1-C5 alkyl, or C5-C10 cycloalkyl,
"-C(-R ^a )=" in ring a may be substituted with "-N=",
R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl has carbon atoms 6 to 10 aryl), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or 3 to carbon atoms 16 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , Re ^e , R ^f , and R ^g is aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, heteroaryl having 2 to 10 carbons may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are bonded to each other Together with the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms may be formed, and at least one Hydrogen is an aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, The two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in these substituents has 6 carbon atoms It may be substituted with -10 aryl, C2-C10 heteroaryl, C1-C5 alkyl, or C5-C10 cycloalkyl,
In ring b, ring c, ring d, ring e, ring f, and ring g, any "-C(-R)=" (where R is R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g ) may be substituted with “-N=”,
Y ¹ , Y ² , and Y ³ are each independently >B-, >P-, >P(=O)-, or >P(=S)-;
X ¹ and X ² are each independently >NR, >O, >S, or >C(-R) ₂ , wherein R of >NR and R of >C(-R) ₂ are each independently , hydrogen, aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, alkyl having 1 to 5 carbons, or cycloalkyl having 5 to 10 carbons, at least one hydrogen in R is from 1 to 5 carbons may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms,
R of >NR as X ¹ or R of >C(-R) ₂ is by a single bond, -N(-R)-, -O-, -S-, or -C(-R) ₂ - , may be bonded to ring b, and as X ² , R of >NR or R of >C(-R) ² is a single bond, -N(-R)-, -O-, -S-, or -C (-R) ₂ - may be bonded to the e-ring, and R of -N(-R)- and R of -C(-R) ₂ - are each independently hydrogen and having 6 to 10 carbon atoms. aryl, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, wherein at least one hydrogen in R is alkyl having 1 to 5 carbon atoms or alkyl having 5 to 10 carbon atoms. may be substituted with cycloalkyl,
c-ring and d-ring, g-ring and b-ring, and f-ring and e-ring are each independently a single bond, -N(-R)-, -O-, -S-, or -C(-R) ₂ It may be bonded by -, and R in -N(-R)- and R in -C(-R) ₂ - are each independently hydrogen, aryl having 6 to 10 carbons, hetero having 2 to 10 carbons. aryl, C1-5 alkyl, or C5-10 cycloalkyl, wherein at least one hydrogen in R may be substituted with C1-5 alkyl or C5-10 cycloalkyl;
However, in the above formula (2A), the cd bond of the c-ring and the d-ring, and R of >NR as X ¹ , wherein R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. , limited to aryl having 6 to 10 carbon atoms) and X ¹ b bond of ring b, and R of >NR as X ² (wherein R is substituted with alkyl having 1 to 5 carbons or cycloalkyl having 5 to 10 carbons, Any one or two bonds among the three bonds of the X ² e bond of the e-ring and the aryl having 6 to 10 carbon atoms that may be present are present;
In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,
In the compound represented by the formula (2A) or (2B), the b ring, the c ring, the d ring, the e ring, the f ring, the g ring, the formed ring, the aryl, and At least one of the heteroaryls may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane is an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms. , may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen. 4. The method of claim 3,
In the above formula (2A) or (2B),
R ^a is hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 to 10 carbon atoms) aryl, and two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R ^a is It may be substituted with -5 alkyl or C5-C10 cycloalkyl,
R ^b , R ^c , R ^d , ^Re , R ^f , and R ^g are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl has carbon atoms 6 to 10 aryl), diarylboryl (provided that aryl is aryl having 6 to 10 carbon atoms, and the two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or 3 to carbon atoms 16 cycloalkyl, and at least one hydrogen in R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g is alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. may be substituted,
Y ¹ , Y ² , and Y ³ are >B-;
X ¹ and X ² are >NR, and R in >NR is hydrogen, aryl having 6 to 10 carbons, heteroaryl having 2 to 10 carbons, alkyl having 1 to 5 carbons, or cycloalkyl having 5 to 10 carbons. and at least one hydrogen in R may be substituted with alkyl having 1 to 5 carbon atoms,
R of >NR as X ¹ may be bonded to the b ring by a single bond, and R in >NR as X ² may be bonded to the e ring by a single bond,
The c ring and d ring, the g ring and the b ring, and the f ring and the e ring may each independently be bonded by a single bond,
However, in the formula (2A), the cd bond of the c and d rings and R of >NR as X ¹ (wherein R is limited to aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms) ) and X ¹ b bond of ring b, and R of >NR as X ² (this R is limited to aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 5 carbon atoms) and X ² e bond of ring e Among the three bonds, any one or two bonds are present,
In the formula (2B), any one or two bonds are present among the three bonds: the cd bond of the c and d rings, the gb bond of the g and b rings, and the fe bond of the f and e rings. are doing,
In the compound represented by the formula (2A) or (2B), among the ring b, the c ring, the d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl At least one may be condensed with at least one cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with alkyl having 1 to 5 carbon atoms;
A polycyclic aromatic compound wherein at least one hydrogen in the compound represented by the formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen. 4. The method of claim 3,
A polycyclic aromatic compound represented by any one of the following structural formulas.
[Formula 3]

during each expression,
R is each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), diarylboryl (provided that aryl has 6 carbon atoms) to 10 aryl, two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in R is may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms;
o is each independently an integer of 1 to 3,
p is each independently an integer of 1 to 4,
q is each independently an integer of 1 to 5,
At least one hydrogen in the compound represented by the above formulas may be substituted with deuterium, cyano, or halogen. The method of claim 1,
A polycyclic aromatic compound represented by any one of the following structural formulas.
[Formula 4]

[Formula 5]

[Formula 6]

A reactive compound in which a reactive substituent is substituted for the polycyclic aromatic compound according to any one of claims 1 to 8. A polymer compound obtained by polymerizing the reactive compound according to claim 9 as a monomer, or a cross-linked polymer obtained by further crosslinking the polymer compound. A pendant polymer compound in which a main chain polymer is substituted with the reactive compound according to claim 9, or a crosslinked pendant polymer in which the pendant polymer compound is further crosslinked. The material for organic devices containing the polycyclic aromatic compound in any one of Claims 1-8. The material for organic devices containing the reactive compound of Claim 9. A material for an organic device comprising the polymer compound according to claim 10 or a polymer crosslinked product. A material for an organic device comprising the pendant polymer compound according to claim 11 or a pendant polymer crosslinked product. 16. The method according to any one of claims 12 to 15,
The material for an organic device, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter. 17. The method of claim 16,
The material for an organic device, wherein the material for an organic electroluminescent element is a material for a light emitting layer. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent. An ink composition comprising the reactive compound according to claim 9 and an organic solvent. An ink composition comprising a main chain polymer, the reactive compound according to claim 9, and an organic solvent. An ink composition comprising the polymer compound or polymer crosslinked product according to claim 10 and an organic solvent. An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to claim 11 and an organic solvent. A pair of electrodes comprising an anode and a cathode, and disposed between the pair of electrodes, the polycyclic aromatic compound according to any one of claims 1 to 8, the reactive compound according to claim 9, and the reactive compound according to claim 10 An organic electroluminescent device comprising a polymer compound or a crosslinked polymer, or an organic layer containing the pendant polymer compound or crosslinked pendant polymer according to claim 11. 24. The method of claim 23,
The organic layer is a light emitting layer, an organic electroluminescent device. 25. The method of claim 24,
The organic electroluminescent device, wherein the light emitting layer includes a host and the polycyclic aromatic compound, a reactive compound, a polymer compound, a crosslinked polymer, a pendant polymer compound, or a crosslinked pendant polymer as a dopant. 26. The method of claim 25,
The light emitting layer includes a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), and a structure represented by the following general formula (H4) An organic electroluminescent device further comprising at least one selected from the group consisting of a compound, a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material.
[Formula 7]

In the general formula (H1), L ¹ is arylene having 6 to 30 carbon atoms or heteroarylene having 2 to 30 carbon atoms,
In the general formula (H2), L ² and L ³ are each independently an aryl having 6 to 30 carbon atoms or heteroaryl having 2 to 30 carbon atoms;
In the general formula (H3), MU is each independently a divalent group represented by excluding any two hydrogen atoms from an aromatic compound, EC is each independently represented by excluding any one hydrogen atom from an aromatic compound It is a monovalent group, two hydrogens in MU are substituted with EC or MU, and k is an integer of 2-50000,
In the general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- is substituted with a substituent or a structure represented by another formula (H4). may be,
In the general formula (H5),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹¹ Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;
Adjacent groups among R ¹ to R ¹¹ may combine with each other to form an aryl ring or a heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring is aryl, heteroaryl, It may be substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents is further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be,
In ring a, ring b, and ring c, arbitrary "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) may be substituted with "-N=",
In the general formula (H6),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one of R ¹ to R ¹⁶ Hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl;
Adjacent groups among R ¹ to R ¹⁶ may combine with each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen in the formed ring is aryl; Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl may be substituted, and at least one hydrogen in these substituents is aryl, heteroaryl, diarylamino, alkyl or cycloalkyl may be further substituted with, and
At least one hydrogen in the compound or structure represented by the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium. 27. The method according to any one of claims 23 to 26,
at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, or a BO derivative , anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzoimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives , An organic electroluminescent device containing at least one selected from the group consisting of silol derivatives and azoline derivatives. 28. The method of claim 27,
At least one of the electron transport layer and the electron injection layer is an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, a rare earth metal An organic electroluminescent device further comprising at least one selected from the group consisting of 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. 29. The method according to any one of claims 23 to 28,
At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer is a high molecular compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or the high molecular compound further crosslinked An organic electric field comprising a cross-linked polymer or a cross-linked pendant polymer in which a low-molecular compound capable of forming each layer is reacted with a main chain polymer, or a cross-linked pendant polymer in which the pendant polymer compound is further cross-linked light emitting element. The display device or lighting device provided with the organic electroluminescent element in any one of Claims 23-29. The wavelength conversion filter containing the material for wavelength conversion filters of Claim 16.

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