Polycyclic aromatic compound, Organic device material, Organic electroluminescent element, Display device, and Lighting device

Abstract

This invention provides a polycyclic aromatic compound, a material for organic devices, an organic electroluminescent element, a display device, and a lighting device. The polycyclic aromatic compound has a structure comprising one or more structural units represented by formula (1); typically, at least one of ring A, ring B, and ring C is a ring represented by formula (Het), and the others are substituted aryl rings, Y... 1 For B, X 1 and X 2 For >N-R, X 3 and X 4 For >O, >N-R, or >C(-Me) 2 R is a substituted or unsubstituted aryl group, and any two or three consecutive Zs are related to Y. 1 and X 1 and / or X 2 Directly bonded carbon atoms, with other Z atoms being N or C-R. Z R Z The aryl ring or heteroaryl ring in the structure may be condensed from at least one cycloalkane, and may be hydrogen or a substituent.

Description

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

[0001] This invention relates to a polycyclic aromatic compound. More particularly, it relates to a polycyclic aromatic compound comprising nitrogen and boron. Furthermore, it relates to an organic device material comprising the said polycyclic aromatic compound, an organic electroluminescent element, and a display device and lighting device. Background Technology

[0002] Previously, display devices using electroluminescent elements were extensively researched due to their ability to achieve power savings or thinner designs. Furthermore, organic electroluminescent elements incorporating organic materials have been actively researched due to their ease of lightweighting or scaling. In particular, the development of organic materials exhibiting luminescent properties such as blue (one of the three primary colors of light), and the development of organic materials with charge transport capabilities including holes and electrons (possibly leading to semiconductor or superconductor properties), have been actively studied to date, with both high-molecular-weight and low-molecular-weight compounds being actively researched.

[0003] Organic electroluminescent devices have a structure comprising: a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound. The layers containing the organic compound may include a light-emitting layer, or a charge transport / injection layer for transporting or injecting charges such as holes or electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent Documents 1 and 2 disclose materials in which boron-containing polycyclic aromatic compounds are effectively used as organic electroluminescent elements. Reports indicate that organic electroluminescent elements containing these polycyclic aromatic compounds exhibit good external quantum efficiency.

[0005] [Existing technical documents]

[0006] [Patent Literature]

[0007] [Patent Document 1] Chinese Patent Application Publication No. 106467554

[0008] [Patent Document 2] International Publication No. 2015 / 102118 Summary of the Invention

[0009] [The problem the invention aims to solve]

[0010] As mentioned above, various materials have been developed for use in organic electroluminescence (EL) devices, but in order to increase the selection of materials for organic EL devices, it is desirable to develop a material containing compounds that are different from those used before.

[0011] The problem of the present invention is to provide a novel compound that can be effectively used as a material for organic devices such as organic EL elements.

[0012] [Technical means to solve the problem]

[0013] To solve the aforementioned problems, the inventors have conducted diligent research and successfully manufactured a novel polycyclic aromatic compound with superior luminescent properties among polycyclic aromatic compounds having a structure similar to that described in Patent Document 1. Furthermore, it was discovered that by configuring a layer containing the aforementioned polycyclic aromatic compound between a pair of electrodes to construct an organic EL (electroluminescence) device, an excellent organic EL device can be obtained, thus completing the present invention. In other words, the present invention provides the following polycyclic aromatic compound, and materials for organic devices containing the following polycyclic aromatic compound, etc.

[0014] <1> A polycyclic aromatic compound having a structure comprising one or more structural units represented by the following formula (1);

[0015] [Chemistry 1]

[0016]

[0017] In equation (1),

[0018] Rings A, B, and C are each independently a substituted aryl ring or a substituted heteroaryl ring, wherein at least one ring selected from the group consisting of rings A, B, and C is the ring represented by formula (Het).

[0019] Y 1 The components are B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein the R in Si-R and Ge-R is a substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0020] X 1 and X 2Each of the following is independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. The R in >NR is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The R in >C(-R)2 and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded to each other to form a ring. Furthermore, the R in >NR and / or the R in >C(-R)2 can be bonded to ring A and / or ring B, or ring A and / or ring C, via a linking group or a single bond.

[0021] In the formula (Het), X 3 and X 4 The R in >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se are independently represented by >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se. The R in >NR is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The R in >C(-R)2 and >Si(-R)2 are independently represented by hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs can be bonded to each other to form a ring. Furthermore, the R in >NR and / or the R in >C(-R)2 can be bonded to one or two Z bonds via a linker group or a single bond.

[0022] Any two or three consecutive Z's are respectively related to Y's 1 and X 1 and / or X 2 Directly bonded carbon atoms, with other Z atoms being N or CR respectively. Z The CR Z R Z For hydrogen or substituents, two adjacent CRs Z R Z They can bond with each other to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0023] Z = Z can be independently >O, >NR, >C(-R)2, >Si(-R)2, >S, >CO, >SO, >SO2, or >Se. The R in >NR, >C(-R)2, and >Si(-R)2 can be independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded together to form a ring.

[0024] At least one of the aryl ring or heteroaryl ring in the structure may be condensed from at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- atom in the cycloalkane may be substituted with -O-.

[0025] At least one hydrogen atom in the structure may be substituted by a cyano group, a halogen, or a deuterium.

[0026] <2> according to <1> The polycyclic aromatic compounds are represented by the following formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f);

[0027] [Chemistry 2]

[0028]

[0029] In equations (1-a), (1-b), (1-c), (1-d), and (1-e),

[0030] Z can be N or CR independently. Z The CR Z R Z Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboroyl (the two aryl groups may be linked by a single bond or a linker group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group.

[0031] Two adjacent CRs Z R Z They can bond together to form a ring, which can be substituted by hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups can be bonded by a single bond or a linker group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen can be substituted by an alkyl, cycloalkyl, or substituted silyl group.

[0032] X 1 and X 2Each of the following is independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. The R in >NR is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The R in >C(-R)2 and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded to each other to form a ring. Furthermore, the R in >NR and / or the R in >C(-R)2 can be linked by a linking group or a single bond to form a CR. Z R in Z Z One or two bonds,

[0033] X 3 X 4 X 5 and X 6 Each of the following can be independently represented as >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se, wherein the R in >NR is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the R in >C(-R)2 can be independently represented as hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and the two Rs can be bonded to each other to form a ring.

[0034] Z = Z can be independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. The R in >NR, >C(-R)2, and >Si(-R)2 can be independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded together to form a ring.

[0035] At least one of the aryl or heteroaryl rings in the compounds represented by formulas (1-a), (1-b), (1-c), (1-d), or (1-e) may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- atom in the cycloalkane may be substituted with -O-.

[0036] At least one hydrogen atom in the compound represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d) or formula (1-e) may be substituted by a cyano group, a halogen or a deuterium.

[0037] <3> according to <2> The polycyclic aromatic compounds are represented by formula (1-b).

[0038] <4> according to <3> The polycyclic aromatic compounds mentioned above, wherein Z is all CR Z .

[0039] <5> according to <1> to <4> The polycyclic aromatic compound in any one of the following statements, wherein X 3 For >NR, as X 3 The R in >NR is a substituted or unsubstituted aryl group.

[0040] <6> according to <5> The polycyclic aromatic compound, wherein X is... 3 The R in >NR is a phenyl group substituted with a tertiary alkyl group.

[0041] <7> according to <1> to <6> The polycyclic aromatic compound in any one of the following statements, wherein X 4 For >C(-R)2, as X 4 In the case of >C(-R)2, all R are methyl groups.

[0042] <8> according to <1> to <7> The polycyclic aromatic compound described in any one of the following statements, wherein Y 1 The answer is B.

[0043] <9> according to <1> to <8> The polycyclic aromatic compound in any one of the following statements, wherein X 1 and X 2 All are >NR.

[0044] <10> according to <4> The polycyclic aromatic compounds are represented by formula (1-bZ);

[0045] [Chemistry 3]

[0046]

[0047] In equation (1-bZ),

[0048] R X1 and R X2 R is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. X1 It can be linked to R via a base or a single bond. X1 Any loop bond of the N direct bond, R X2 It can be linked to R via a base or a single bond. X1 and R X2Any loop bond of the N direct bond,

[0049] X 13 Each of the following can be independently >O, >NR, or >C(-R)2, wherein the R in >NR is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and the R in >C(-R)2 can be independently an unsubstituted alkyl group. The two Rs can be bonded to each other to form a cycloalkane ring.

[0050] R X4 Each is an unsubstituted alkyl group, and the two Rs are independent. X4 They can bond with each other to form cycloalkane rings.

[0051] R Z1 It is an unsubstituted alkyl group.

[0052] R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2.

[0053] R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2.

[0054] In the structure represented by formula (1-bZ), at least one of the aryl ring or heteroaryl ring can be a structure formed by bonding a portion of the structure represented by formula (B) with adjacent carbon atoms.

[0055] [Chemistry 4]

[0056]

[0057] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0058] At least one hydrogen atom in the structure represented by formula (1-bZ) may be substituted by a cyano group, a halogen, or a deuterium.

[0059] <11> according to <10> The polycyclic aromatic compounds are represented by any of the following formulas;

[0060] [Chemistry 5]

[0061]

[0062] In the formula, Me represents methyl and tBu represents tert-butyl.

[0063] <12> according to <3> The polycyclic aromatic compounds are represented by formula (1-bT);

[0064] [Chemistry 6]

[0065]

[0066] In equation (1-bT),

[0067] R X1 and R X2 R is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. X1 It can be linked to R via a base or a single bond. X1 Any loop bond of the N direct bond, R X2 It can be linked to R via a base or a single bond. X1 and R X2 Any loop bond of the N direct bond,

[0068] X 13 Each of the following can be independently >O, >NR, or >C(-R)2, wherein the R in >NR is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and the R in >C(-R)2 can be independently an unsubstituted alkyl group. The two Rs can be bonded to each other to form a cycloalkane ring.

[0069] R X4 Each is an unsubstituted alkyl group, and the two Rs are independent. X4 They can bond with each other to form cycloalkane rings.

[0070] R Z1 It is an unsubstituted alkyl group.

[0071] R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2.

[0072] R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2.

[0073] In the structure represented by formula (1-bT), at least one of the aryl ring or heteroaryl ring can be a structure formed by bonding a partial structure represented by formula (B) to an adjacent carbon atom.

[0074] [Chemistry 7]

[0075]

[0076] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0077] At least one hydrogen atom in the structure represented by formula (1-bT) may be substituted by a cyano group, a halogen, or a deuterium.

[0078] <13> according to <12> The polycyclic aromatic compounds are represented by any of the following formulas.

[0079] [Chemistry 8]

[0080]

[0081] In the formula, Me represents methyl and tBu represents tert-butyl.

[0082] <14> A material for organic devices, containing according to <1> to <13> The polycyclic aromatic compound mentioned in any one of the following.

[0083] <15> An organic electroluminescent device includes: a pair of electrodes, comprising an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, wherein...

[0084] The light-emitting layer contains according to <1> to <13> The polycyclic aromatic compound mentioned in any one of the following.

[0085] <16> according to <15> The organic electroluminescent element, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

[0086] <17> according to <16> The organic electroluminescent element, wherein the host is an anthracene compound, a fluorene compound, or a dibenzo[a]benzene compound. System of compounds.

[0087] <18> A display device or lighting device, comprising according to <15> to <17> The organic electroluminescent element as described in any one of the following.

[0088] [The effects of the invention]

[0089] According to the present invention, a novel polycyclic aromatic compound is provided that is effectively used as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used to manufacture organic devices such as organic electroluminescent elements. Attached Figure Description

[0090] Figure 1 is a schematic cross-sectional view showing an example of an organic electroluminescent device.

[0091] Figure 2 is an energy level diagram showing the energy relationships between the body, auxiliary dopant, and emission dopant of a TAF element using common fluorescent dopants.

[0092] Figure 3 is an energy level diagram illustrating an example of the energy relationship between the host, auxiliary dopant, and emitting dopant in an organic electroluminescent element according to an embodiment of the present invention.

[0093] [Explanation of Symbols]

[0094] 100: Organic electroluminescent element

[0095] 101: Substrate

[0096] 102: Anode

[0097] 103: Hole Injection Layer

[0098] 104: Hole Transport Layer

[0099] 105: Emissive layer

[0100] 106: Electron Transport Layer

[0101] 107: Electron Injection Layer

[0102] 108: Cathode. Detailed Implementation

[0103] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, in this specification, the numerical range indicated by “~” refers to the range including the values ​​described before and after “~” as both the lower and upper limits. Additionally, in this specification, “hydrogen” in the description of the structural formula refers to “hydrogen atom (H)”.

[0104] In this specification, organic electroluminescent elements are sometimes referred to as organic EL elements.

[0105] In this specification, the number of carbon atoms is sometimes used to represent chemical structures or substituents. However, when a substituent is substituted in a chemical structure, or when a substituent is further substituted on a substituent, the number of carbon atoms refers to the individual carbon atom of the chemical structure or substituent, and not the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituents. For example, "substituent B with carbon atom number X replaced by substituent A with carbon atom number X" means that "substituent A with carbon atom number X" is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Similarly, "substituent B with carbon atom number Y replaced by substituent A" means that "substituent A (without a specified number of carbon atoms) is substituted on "substituent B with carbon atom number Y". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0106] This specification describes the structural formulas of several aromatic compounds. Aromatic compounds are described by combining double and single bonds; however, due to π-electron resonance, multiple equivalent resonance structures, such as alternating double and single bonds, exist for a single substance. In this specification, only one resonance structural formula is described for each substance, but unless otherwise specified, other resonance structural formulas that are equivalent in organic chemistry are also included. This is referred to in the descriptions such as "Z=Z" described later. That is, when referred to as "Z=Z" in this specification, it includes not only the case where the described structure is represented as "Z=Z," but also the case where the resonance structure is represented as "ZZ." For example, regarding "Z=Z" in formula (1-b) described later, an example is given below. However, this is not a limitation; it applies not only to the single described resonance structural formula but also to other equivalent resonance structural formulas.

[0107] [Chemistry 9]

[0108]

[0109] In this specification, "adjacent" means that atoms on the same ring are directly bonded to each other unless otherwise specified. "Adjacent base" refers to a base that is directly bonded to atoms that are directly bonded to each other on the same ring.

[0110] 1. Polycyclic aromatic compounds

[0111] The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having one or more structural units comprising the structural unit represented by formula (1). The polycyclic aromatic compounds of the present invention have at least one ring represented by formula (Het) as ring A, ring B, or ring C in formula (1). The polycyclic aromatic compounds of the present invention exhibit high photoluminescence quantum yield (PLQY), narrow half-width at half-maximum (WWHM), and excellent color purity.

[0112] [Chemistry 10]

[0113]

[0114] The ring represented by equation (Het) is selected from one or more structures containing the structural unit represented by equation (1) and at least one ring selected from the group consisting of ring A, ring B and ring C.

[0115] In a structure comprising a structural unit represented by equation (1), it is preferable to select one or two rings from the group consisting of rings A, B, and C as the ring represented by equation (Het). When one ring is the ring represented by equation (Het), the ring is not particularly limited, but ring B or ring C is preferred. When two rings are the rings represented by equation (Het), these rings are not particularly limited, but rings B and C are preferred. In a structure comprising a structural unit represented by equation (1), it is more preferable to have one ring represented by equation (Het).

[0116] In two or more structures that include the structural unit represented by equation (1), each structural unit represented by equation (1) may include at least one ring represented by equation (Het), or may not include any. That is, when at least one of rings A, B and C is two or more, it is sufficient that at least one ring in one or more structures that include the structural unit represented by equation (1) is the ring represented by equation (Het).

[0117] In the formula (Het), X 3 and X 4 Each of these can be independently represented as >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se. As X 3 or X 4 The R in >NR is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. As X 3 or X 4 In the >C(-R)2 and >Si(-R)2, the R can be hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, respectively. The two R can bond to each other to form a ring.

[0118] In the formula (Het), X 3 and X 4 Preferably, they are independently >O, >NR, >C(-R)2, >S, >Si(-R)2 or >Se, and more preferably they are independently >O, >C(-R)2 or >NR. X 3 and X 4 They can be the same or different. X is particularly preferred. 3 For >NR, >C(-R)2, or >O, and X 4 It is >C(-R)2.

[0119] As X 3 or X 4In the >NR, R is preferably a substituted aryl group, more preferably an aryl group substituted with an unsubstituted aryl or alkyl group, and even more preferably a phenyl group substituted with a phenyl or tertiary alkyl group. As X 3 or X 4 In the >C(-R)2 and >Si(-R)2, R is preferably a substituted alkyl group, more preferably an unsubstituted alkyl group, and even more preferably an unsubstituted methyl group.

[0120] In formula (Het), any two or three consecutive groups in Z are respectively related to Y. 1 and X 1 and / or X 2 Directly bonded C (carbon atom). That is, when the B ring is the ring represented by formula (Het), any two consecutive atoms in any group are respectively bonded to Y. 1 and X 1 In a direct bonded C, when the C ring is the ring represented by equation (Het), any two consecutive bonds in any group are respectively connected to Y. 1 and X 2 In a direct bond C, when loop A is the loop represented by equation (Het), any three consecutive bonds in a group are respectively bonded to Y. 1 X 1 and X 2 The C in the direct bond is the N, and the other Zs are independently N or CR. Z The CR Z R Z It is hydrogen or a substituent. Preferred substituents at this time are substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted diheteroarylamino groups, substituted or unsubstituted arylheteroarylamino groups (amino groups having aryl and heteroaryl groups), substituted or unsubstituted diarylboroyl groups (the two aryl groups may be bonded via a single bond or a linker), substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, or substituted silyl groups. Two adjacent CR Z R in Z They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted. The substituents are preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (an amino group having aryl and heteroaryl groups), substituted or unsubstituted diarylboroyl (the two aryl groups can be bonded by a single bond or a linker), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl.

[0121] For details regarding these substituents, please refer to the descriptions of the first and second substituents described later.

[0122] Furthermore, in formula (Het), Z = Z can be independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. Among these, >O, >NR, >C(-R)2, or >S are preferred. The R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded to each other to form a ring. For a single ring (monocyclic ring) in formula (Het), the following examples show a Z = Z of >NR, >O, >S with the remaining Z being CH, and an example of a Z = Z of >NR, >O, >S with the remaining Z adjacent to and all being CR. Z And these CRs Z Examples of benzene rings formed by mutual bonding.

[0123] [Chemistry 11]

[0124]

[0125] In the formula (Het), X is included. 3 and X 4 Of the two rings other than the ring in question, at least one is preferably a six-membered ring. Additionally, with Y... 1 and X 1 and / or X 2 The preferred ring for the bonding is a six-membered ring.

[0126] In formula (Het), the number of rings (single rings) containing Z as N is 0 to 2, more preferably 0 to 1. In formula (Het), it is also preferable to have a ring with Y... 1 and X 1 and / or X 2 All Z atoms except Z in the C (carbon atom) bond are CR. Z .

[0127] In formula (Het), in the ring (monocyclic ring) containing Z as N, it is preferred that one or two of the plurality of Zs is N, and when two are N, it is preferred that the two Ns are not adjacent to each other. When the six-membered ring is a ring containing Z as N, it is preferably a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, more preferably a pyridine ring or a pyrimidine ring.

[0128] Examples of rings containing Z as N in a group of five-membered rings where Z = Z is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se include thiazole rings and oxazole rings.

[0129] In the formula (Het), X 3 or X 4 When R and / or X are greater than NR, the value of R and / or X is greater than NR. 3 or X 4 When the value is >C(-R)2, the R in >C(-R)2 can be bonded to one or two Z bonds via a linker base or a single bond. The Z bonded is preferably with X. 3 or X 4 The Z atom adjacent to the bonding atom. Furthermore, the Z atom involved in the bonding only needs to be a carbon atom with a bonding bond. As this type of linker, X can be referred to later. 1 X 2 Examples of linker bases with B-ring and C-ring bonds. As X 3 or X 4 Examples of structures in which R forms a bond as described above can be listed by the following formulas.

[0130] [Chemistry 12]

[0131]

[0132] In the formula, Me is a methyl group, and X is present at the positions of the two *. 3 or X 4 One of the two loops of the bond is bonded to the other loop at the ** position.

[0133] Examples of this structure include the structures of compounds represented by any of the formulas (1-182) to (1-204) and (1-319) to (1-333) described below.

[0134] In one or more structures containing the structural unit represented by formula (1), the rings other than the rings that are A ring, B ring and C ring and that are the rings represented by formula (Het) are independently substituted aryl rings or substituted heteroaryl rings.

[0135] The aryl ring or heteroaryl ring in rings A, B, and C is preferably a five-membered or six-membered ring with Y. 1 and X 1 and / or X 2 Bonding. The so-called "bonding with a pentagonal or hexacyclic ring and Y..." 1 and X 1 and / or X 2"Binding" refers to a ring formed solely by the aforementioned pentagonal or hexacyclic rings, or a ring formed by condensing other rings in a manner that includes the aforementioned pentagonal or hexacyclic rings. In other words, it refers to a ring consisting entirely or partially of pentagonal or hexacyclic rings and Y-shaped rings. 1 and X 1 and / or X 2 Bonding. In aryl or heteroaryl rings within rings A, B, and C, as long as two or three consecutive ring-constituting atoms (carbon atoms) are bonded to Y... 1 and X 1 and / or X 2 Direct bonding is sufficient. That is, in the aryl or heteroaryl rings within the B ring, any group of consecutive ring-forming atoms (carbon atoms) bond to two atoms with Y. 1 and X 1 Direct bonding, in the aryl or heteroaryl rings of the C ring, any group of consecutive ring constituent atoms (carbon atoms) are bonded to two Y atoms. 1 and X 2 Direct bonding occurs when any group of consecutive rings (carbon atoms) in the aryl or heteroaryl rings of ring A are bonded to Y. 1 X 1 and X 2 Direct bonding.

[0136] As the "aryl ring" in rings A, B and C of formula (1), for example, aryl rings with 6 to 30 carbons can be listed, preferably aryl rings with 6 to 16 carbons, more preferably aryl rings with 6 to 12 carbons, and particularly preferably aryl rings with 6 to 10 carbons.

[0137] Specific examples of "aryl rings" include: benzene rings (monocyclic), biphenyl rings (bicyclic), naphthalene rings, 5,6,7,8-tetrahydronaphthalene rings, and indene rings (condensed bicyclic), terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl) (tricyclic), acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, and anthracene rings (condensed tricyclic), and triphenylene rings, pyrene rings, and tetraphenylene rings (condensed tetracyclic). The rings include perylene rings and pentane rings, which are condensed pentacyclic rings. Additionally, fluorene rings, benzo[a]fluorene rings, and indene rings also include structures with fluorene rings, benzo[a]fluorene rings, and cyclopentane rings linked by spiral bonds. Furthermore, in tetrahydronaphthalene rings, fluorene rings, benzo[a]fluorene rings, and indene rings, two of the two hydrogens of the methylene group are replaced with alkyl groups such as methyl groups (described later as first substituents) to form rings such as 1,1,4,4-tetrahydronaphthalene rings, dimethylfluorene rings, dimethylbenzo[a]fluorene rings, and dimethyl indene rings.

[0138] The "heteroaryl ring" of rings A, B, and C in formula (1) can be exemplified by heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, and even more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Furthermore, the "heteroaryl ring" can be exemplified by heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms.

[0139] Specific examples of "heteroaryl rings" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetraazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cyclophosphine ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring. Carbazole ring, acridine ring, phenthiazine ring, phenazine ring, phenazasiline ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazine ring, thiathracene ring, indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthonium ring, thioxanthonium ring, dibenzodioxin ring, etc. Furthermore, the dihydroacridine ring, xanthonium ring, and thioxanthonium ring are preferably formed by substituting two of the two hydrogens of the methylene group with alkyl groups such as methyl groups (described later as first substituents) to form a dimethyldihydroacridine ring, a dimethylxanthonium ring, a dimethylthioxanthonium ring, etc. In addition, bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, which are bicyclic systems, and terpyridyl rings, bispyridylphenyl rings, and pyridylbiphenyl rings, which are tricyclic systems, can also be listed as "heteroaryl rings". Furthermore, pyran rings are also included in the category of "heteroaryl rings".

[0140] Alternatively, rings represented by the following formula (BO) can also be listed as heteroaryl rings.

[0141] [Chemistry 13]

[0142]

[0143] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be a substituted or unsubstituted "aryl" as a first substituent, a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (the two aryl groups may be linked by a single bond or a linking group)", or a substituted or unsubstituted "alkyl". The substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy" or substituted "silyl" as the first substituent, "aryl" or "heteroaryl", "aryl of "diarylamino", "heteroaryl of "diheteroarylamino", "aryl and heteroaryl of "arylheteroarylamino", "aryl of "diarylboryl", and "aryloxy" can be listed as monovalent groups of the "aryl ring" or "heteroaryl ring".

[0144] Specifically, as "aryl", examples include aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 24 carbon atoms, more preferably aryl groups with 6 to 20 carbon atoms, even more preferably aryl groups with 6 to 16 carbon atoms, particularly preferably aryl groups with 6 to 12 carbon atoms, and most preferably aryl groups with 6 to 10 carbon atoms.

[0145] Specific examples of aryl groups include: phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a condensed dicyclic aryl group; (1-, 2-)5,6,7,8-tetrahydronaphthyl; (2-, 3-, 4-, 5-, 6-, 7-)indenyl as a dicyclic aryl group; and terphenyl as a tricyclic aryl group (meta-terphenyl-2′-yl, meta-terphenyl-...). 4′-yl, m-triphenyl-5′-yl, o-triphenyl-3′-yl, o-triphenyl-4′-yl, p-triphenyl-2′-yl, m-triphenyl-2-yl, m-triphenyl-3-yl, m-triphenyl-4-yl, o-triphenyl-2-yl, o-triphenyl-3-yl, o-triphenyl-4-yl, p-triphenyl-2-yl, p-triphenyl-3-yl, p-triphenyl-4-yl) Anthracene-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-)yl, acenaphthene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenatenyl-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthrene-, as condensed tricyclic aryl groups; and tetraphenyl-(5′-phenyl-m-terphenyl-) 2-yl, 5′-phenyl-m-terphenyl-3-yl, 5′-phenyl-m-terphenyl-4-yl, m-tetraphenyl), as condensed tetracyclic aryl groups, triphenyl-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and benzotetraphenyl-(1-, 2-, 5-)yl, as condensed pentacyclic aryl groups, perylene-(1-, 2-, 3-)yl, and benzopentaphenyl-(1-, 2-, 5-, 6-)yl, etc.

[0146] Furthermore, examples of "heteroaryl" include heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Additionally, examples of heteroaryl groups include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, excluding carbon atoms.

[0147] Specific heteroaryl groups include, for example: furanyl, thiophene, pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, pyrazolyl, oxadiazolyl, furazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thiophene, dibenzothiophene, indolyl, isoindolyl, 1H-indazoleyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazoyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, thiazothiazyl, thiazothiazyl, indazinyl, etc.

[0148] Furthermore, the "alkyl" as the first substituent can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), further preferably an alkyl with 1 to 8 carbon atoms (branched alkyl with 3 to 8 carbon atoms), particularly preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and most preferably an alkyl with 1 to 5 carbon atoms (branched alkyl with 3 to 5 carbon atoms).

[0149] Specific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-pentyl)(t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0150] In addition, examples include: 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc.

[0151] As the substituent containing "alkyl", the tertiary alkyl group represented by the following formula (tR) is one of the particularly preferred substituents when at least one hydrogen atom in the aryl ring or heteroaryl ring is replaced by a substituent. This is because the intermolecular distance increases with such a large substituent, thus increasing the luminescence quantum yield (PLQY). Furthermore, it is also preferred that the tertiary alkyl group represented by formula (tR) is used as a second substituent to replace other substituents. Specifically, examples include diarylamino groups substituted with the tertiary alkyl group represented by (tR), carbazolyl groups (preferably N-carbazolyl) substituted with the tertiary alkyl group represented by (tR), or benzocarbazolyl groups (preferably N-benzocarbazolyl) substituted with the tertiary alkyl group represented by (tR). Regarding "diarylamino groups", groups described below as "first substituents" can be listed. As for the substitution forms of the group of formula (tR) for diarylamino, carbazolyl and benzocarbazolyl, examples can be given of the substitution of some or all of the hydrogens of the aryl ring or benzene ring in these groups by the group of formula (tR).

[0152] [Chemistry 14]

[0153]

[0154] In equation (tR), R a R b and R c Each is an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is substituted at * with at least one hydrogen atom in the compound or structure represented by formula (1).

[0155] R a R b and R c The term "alkyl group having 1 to 24 carbon atoms" can be either straight-chain or branched. Examples include: straight-chain alkyl groups having 1 to 24 carbon atoms or branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0156] In equation (1), R in equation (tR) a R b and R c The total number of carbons is preferably 3 to 20, and more preferably 3 to 10.

[0157] As R a R b and R cSpecific alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0158] Examples of groups represented by formula (tR) include: tert-butyl, tert-pentyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 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. Among these, tert-butyl and tert-pentyl are preferred.

[0159] In addition, examples of "cycloalkyl" as the first substituent include cycloalkyl with 3 to 24 carbons, cycloalkyl with 3 to 20 carbons, cycloalkyl with 3 to 16 carbons, cycloalkyl with 3 to 14 carbons, cycloalkyl with 5 to 10 carbons, cycloalkyl with 5 to 8 carbons, cycloalkyl with 5 to 6 carbons, and cycloalkyl with 5 carbons.

[0160] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl and their alkyl (especially methyl) substituted derivatives having 1 to 5 carbon atoms, or 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 (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0161] Furthermore, examples of "alkoxy groups" as the first substituent include straight-chain alkoxy groups having 1 to 24 carbon atoms or branched-chain alkoxy groups having 3 to 24 carbon atoms. Preferably, it is an alkoxy group having 1 to 18 carbon atoms (branched-chain alkoxy groups having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched-chain alkoxy groups having 3 to 12 carbon atoms), and even more preferably an alkoxy group having 1 to 6 carbon atoms (branched-chain alkoxy groups having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 5 carbon atoms (branched-chain alkoxy groups having 3 to 5 carbon atoms).

[0162] Specific alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-pentoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0163] Furthermore, "substituted silyl" as the first substituent can be exemplified by silyl groups substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl groups. Examples include: trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0164] As "trialkylsilyl", a group in which each of the three hydrogens in a silyl group is independently replaced by an alkyl group can be listed, and the alkyl group can be referred to as "alkyl" in the first substituent. For substitution, the preferred alkyl group is an alkyl group having 1 to 5 carbon atoms, and specifically, examples include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc.

[0165] Specific examples of trialkylsilyl groups include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, tritert-pentylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, tert-pentyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl dimethylsilyl, methyl diethylsilyl, propyl diethyl ... Ethyl silane, butyl diethyl silane, sec-butyl diethyl silane, tert-butyl diethyl silane, tert-pentyl diethyl silane, methyl dipropyl silane, ethyl dipropyl silane, butyl dipropyl silane, sec-butyl dipropyl silane, tert-butyl dipropyl silane, tert-pentyl dipropyl silane, methyl diisopropyl silane, ethyl diisopropyl silane, butyl diisopropyl silane, sec-butyl diisopropyl silane, tert-butyl diisopropyl silane, tert-pentyl diisopropyl silane, etc.

[0166] As "tricycloalkylsilyl", a group in which the three hydrogens of the silyl group are each independently replaced by a cycloalkyl group can be listed, and the cycloalkyl group can be referred to as "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are cycloalkyl groups with 5 to 10 carbon atoms, specifically including: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, decahydronaphthyl, decahydroazyl, etc.

[0167] Specific examples of tricycloalkylsilyl groups include tricyclopentylsilyl and tricyclohexylsilyl.

[0168] As specific examples of substituted dialkylcycloalkylsilyl groups with two alkyl groups and one cycloalkyl group, and substituted alkyldicycloalkylsilyl groups with one alkyl group and two cycloalkyl groups, examples include silyl groups substituted with groups selected from the specific alkyl and cycloalkyl groups.

[0169] Specific examples of dialkylarylsilyl substituted with two alkyl groups and one aryl group, alkyldiarylsilyl substituted with one alkyl group and two aryl groups, and triarylsilyl substituted with three aryl groups include silyl substituted with groups selected from the specific alkyl and aryl groups. Specifically, triphenylsilyl substituted is a specific example of a triarylsilyl substituted alkyl group.

[0170] Additionally, the "aryl" in "diarylboryl" of the first substituent can be referenced from the description of the aryl group. Furthermore, the two aryl groups can be linked via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above are the first substituents), which may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are the second substituents). Specific examples of these groups can be referenced from the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[0171] As a first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboroyl (the two aryl groups may be linked by a single bond or a linker group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silylalkyl", as described as substituted or unsubstituted, at least one hydrogen atom in any of them may be substituted by a second substituent. Examples of the second substituent include, for example, aryl, heteroaryl, alkyl, or cycloalkyl, with specific examples referring to the description of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as the first substituent. Furthermore, in the aryl or heteroaryl groups that are the second substituents, structures in which at least one hydrogen atom is replaced by an aryl group such as phenyl (specifically, the groups described above), an alkyl group such as methyl, tert-butyl (specifically, the groups described above), or a cycloalkyl group such as cyclohexyl (specifically, the groups described above) are also included in the aryl or heteroaryl groups that are the second substituents. As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group that is the second substituent.

[0172] The description of the second substituent also applies to substituents referred to as "substituted or unsubstituted" that are not separately described in this specification.

[0173] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the first substituent. Preferably, the radicals are those represented by the following structural formulas, more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and phenoxy, and even more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-trimethylylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole. From the viewpoint of ease of synthesis, sterically hindered groups are preferred for selective synthesis. Specifically, tert-butyl, tert-pentyl, tert-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole are preferred.

[0174] In the following structural formula, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, "tOct" represents tert-octyl, and * represents the bond position.

[0175] [Chemistry 15]

[0176]

[0177] [Chemistry 16]

[0178]

[0179] [Chemistry 17]

[0180]

[0181] [Chemistry 18]

[0182]

[0183] [Chemistry 19]

[0184]

[0185] [Chemistry 20]

[0186]

[0187] [Chemistry 21]

[0188]

[0189] [Chemistry 22]

[0190]

[0191] [Chemistry 23]

[0192]

[0193] [Chemistry 24]

[0194]

[0195] [Chemistry 25]

[0196]

[0197] [Chemistry 26]

[0198]

[0199] [Chemistry 27]

[0200]

[0201] [Chemistry 28]

[0202]

[0203] [Chemistry 29]

[0204]

[0205] Polycyclic aromatic compounds having a structure containing one or more structural units represented by formula (1) are preferably structures containing at least one tertiary alkyl (tert-butyl or tert-pentyl, etc.), neopentyl, or adamantyl group represented by formula (tR), and more preferably tertiary alkyl (tert-butyl or tert-pentyl, etc.) represented by formula (tR). This is because the intermolecular distance increases with such a large substituent, thus improving the luminescent quantum yield (PLQY). Furthermore, diarylamino groups are also preferred as substituents.

[0206] In equation (1), Y 1 Each of the following can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein the R in Si-R and Ge-R is a substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Examples of the aryl, alkyl, or cycloalkyl groups described above are listed. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). 1 Preferably, it is B, P, P=O, P=S, or Si-R, with B being particularly preferred. Regarding Y in equation (1) 1 The explanation also applies to Y in equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) described later. 1 .

[0207] X in equation (1) 1 and X 2 Each can be independently represented as >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se. X in equation (1) 1 and X 2 Preferably, at least one of them is >NR, more preferably both are >NR; or one is >NR and the other is >C(-R)2 or >O, and even more preferably both are >NR. In addition, when it is stated as "both are >NR", the R of the two >NR may be the same or different.

[0208] As X 1 or X 2 In the case of >NR, R is hydrogen, a substituted aryl group (wherein, as a substituent, excluding amino), a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group. As X 1 or X 2 In the case of >Si(-R)2, R is independently hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group. As X 1 or X 2 In the >C(-R)2, the Rs are independently hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group, and the two Rs are preferably the same and can be bonded to form a ring. Regarding X 1 or X 2 The aryl, heteroaryl, alkyl, and cycloalkyl groups in R of >NR, >Si(-R)2, or >C(-R)2 can be referred to the description of these as the first substituent.

[0209] As X 1 or X 2 The R in >NR is preferably a substituted aryl, a substituted heteroaryl, or a substituted cycloalkyl, more preferably a substituted aryl or a substituted heteroaryl. Examples of cycloalkyl groups are given later. Here, as an aryl group, phenyl, biphenyl (especially 2-biphenyl), and terphenyl (especially terphenyl-2′-yl) are preferred; as a heteroaryl group, benzothiophene (2-benzothiophene, 6-benzothiophene, etc.), benzofuran (2-benzofuran, 3-benzofuran, 5-benzofuran, etc.), dibenzofuran (4-dibenzofuran, etc.), dimethylxanthonyl (2-dimethylxanthonyl, etc.), dibenzodioxane-hexenyl, etc. are preferred. As a substituent, tertiary alkyl (especially tert-butyl) or cycloalkyl (especially adamantyl) represented by the formula (tR) are preferred. The number of substituents in the aryl and heteroaryl groups is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the aryl group is condensed from a substituted cycloalkanes, as described later. For specific cycloalkanes, refer to the cycloalkanes described later.

[0210] As X 1 or X 2 Particularly preferred examples of R in the form of >NR include substituted phenyl groups, substituted 2-biphenyl groups, substituted terphenyl-2′-yl groups, substituted terphenyl-4′-yl groups, and aryl groups condensed from cycloalkane (substitutable). As substituted phenyl groups, substituted 2-biphenyl groups, substituted terphenyl-2′-yl groups, and substituted terphenyl-4′-yl groups, the form substituted with 1 to 3 tert-butyl groups is preferred. As aryl groups condensed from cycloalkane, the forms described below are particularly preferred.

[0211] [Chemistry 30]

[0212]

[0213] (In the formula, Me represents methyl, tBu represents tert-butyl, and * indicates the bond position.)

[0214] As X 1 or X 2 The R in at least one of >NR, >Si(-R)2, and >C(-R)2 can be bonded to the A ring and / or B ring, or the A ring and / or C ring, via a linker group or a single bond. That is, as X 1 In >NR, >Si(-R)2, or >C(-R)2, R can be bonded to A ring and / or B ring via linker groups or single bonds, serving as X. 2The R in >NR, >Si(-R)2, or >C(-R)2 can be bonded to the A ring and / or C ring via a linker or a single bond. Preferably, the linker is -O-, -S-, or -C(-R)2-. Furthermore, the R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This specification can be represented by compounds of formula (1-3-1) and having X. 1 or X 2 The ring structure introduced into fused rings B′ and C′. That is, for example, a ring structure with other rings to introduce X. 1 (or X) 2 Compounds that form a B′ ring (or C′ ring) by condensation of the B ring (or C ring) which is a benzene ring. The resulting fused ring B′ (or fused ring C′) can be, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0215] Alternatively, the specification can also be represented by a compound, which is represented by formula (1-3-2) or formula (1-3-3) and has X. 1 and / or X 2 The ring structure introduced into the fused ring A′. That is, for example, a ring structure with other rings to introduce X. 1 (and / or X) 2 Compounds that form an A′ ring by condensation of the A ring, which is a benzene ring, in a manner that allows for the formation of an A′ ring. The resulting fused A′ ring can be, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0216] [Chemistry 31]

[0217]

[0218] As an example, it is also preferable that the R in >NR is a substituted cycloalkyl group, and is bonded to the A, B, or C rings via a single bond. As a cycloalkyl group, a substituted cyclopentyl or a substituted cyclohexyl group is preferred.

[0219] As a particularly preferred example, the structure represented by enumeration (A11) can be used.

[0220] [Chemistry 32]

[0221]

[0222] In formula (A11), Me is a methyl group, and it is adjacent to X at the positions of the two *. 1 or X 2 One of the two loops of the bond is bonded to the other loop at the ** position.

[0223] Examples of this structure include the structures of compounds represented by any of the formulas (1-7), (1-30), (1-53), (1-96), (1-112), (1-144), (1-174), (1-179) to (1-181), (1-202) to (1-204), (1-211), and (1-223) described below.

[0224] By using >NR, where R is within the preferred range, as X 1 or X 2 The compounds of the present invention, when used as luminescent materials, can further improve luminous efficiency or device lifespan.

[0225] X as in equation (1) 1 or X 2 In the case of >Si(-R)2, R can be a substituted aryl group, a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group. Here, the second substituent described above can be listed as a substituent when substituted. The groups described as first substituents can be listed as the aryl, heteroaryl, alkyl, or cycloalkyl groups. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0226] X as in equation (1) 1 or X 2 In the case of >C(-R)2, R is hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group. Here, the second substituent described above can be listed as a substituent when substituted. The aryl, heteroaryl, alkyl, or cycloalkyl groups described above can be listed as first substituents. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0227] As X in equation (1) 1 X 2 The linking group that bonds with at least one of the rings A, B, and C can be, for example, -O-, -S-, -C(-R)2-, or a single bond, where R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. Examples of the alkyl or cycloalkyl groups that serve as the first substituent include groups described above. Particularly preferred are alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0228] Regarding X in equation (1) above 1 X 2 The explanation also applies to X in equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) described later. 1 X 2 .

[0229] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure comprising one or more structural units represented by formula (1). Examples of polycyclic aromatic compounds having a structure comprising one of the structural units described above include polycyclic aromatic compounds whose structural units are represented by the formula described above. Examples of polycyclic aromatic compounds having a structure comprising two or more structural units represented by formula (1) include compounds equivalent to polymers of polycyclic aromatic compounds whose structural units are represented by the formula described above. The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer can be any form having multiple structural units in one compound, and can be a form in which multiple structural units are bonded together by sharing any ring (A ring, B ring, or C ring) contained in the structural unit. Furthermore, it can be a form in which any ring (A ring, B ring, or C ring) contained in the structural unit is condensed together with each other. Alternatively, the unit structure may be configured with multiple linkages such as single bonds, alkylene groups with 1 to 3 carbon atoms, phenylene groups, or naphthylene groups. Among these, the configuration of bonding in the form of a common ring is preferred.

[0230] Polycyclic aromatic compounds having a structure comprising one or more structural units represented by formula (1) may be condensed from at least one cycloalkane by a group consisting of aryl rings and heteroaryl rings. The same applies to polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f) described below, and the following description also applies to polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f).

[0231] As a cycloalkane, it is acceptable to have a cycloalkane with 3 to 24 carbon atoms. At least one hydrogen atom in the cycloalkane may be substituted by an aryl group with 6 to 30 carbon atoms, a heteroaryl group with 2 to 30 carbon atoms, an alkyl group with 1 to 24 carbon atoms, or a cycloalkyl group with 3 to 24 carbon atoms, and at least one -CH2- atom in the cycloalkane may be substituted by -O- atom.

[0232] In the case where at least one of the structural units represented by formula (1) is selected from the group consisting of aryl rings and heteroaryl rings and is condensed by at least one cycloalkane, the at least one cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, and is a cycloalkane in which at least one hydrogen atom can be replaced by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0233] As for "cycloalkanes", cycloalkanes with 3 to 24 carbon atoms are preferred, and further preferred examples include: cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, and cycloalkanes with 5 to 6 carbon atoms.

[0234] Specific examples of cycloalkanes include: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, 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 (norbornene), bicyclo[2.2.2]octane, adamantane, diadamantane, decahydronaphthalene and decahydroazine, as well as their alkyl (especially methyl) substituted derivatives, halogen (especially fluorine) substituted derivatives, and deuterium substituted derivatives, etc., having carbon numbers of 1 to 5.

[0235] Among these, a preferred structure is one in which at least one hydrogen atom on the α-carbon of the cycloalkane (the carbon atom in the cycloalkyl group condensed in the aryl ring or heteroaryl ring that is directly bonded to the carbon at the condensation site) is substituted, as shown in the following structural formula. More preferably, a structure in which two hydrogen atoms on the α-carbon are substituted, and even more preferably, a structure in which a total of four hydrogen atoms on the two α-carbons are substituted. Examples of substituents include alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents. A particularly preferred structure is one in which a portion of the structure represented by formula (B) is bonded to adjacent carbon atoms in the aryl ring or heteroaryl ring.

[0236] [Chemistry 33]

[0237]

[0238] In formula (B), Me represents a methyl group, and * represents the bond position.

[0239] Examples of this structure include equations (1-10), (1-33), (1-56), (1-99), (1-115), (1-147), (1-188) to (1-190), (1-196) to (1-198), (1-226), (1-356), (1-357), (1-361), (1-365) to (1-376), and (1-38). The structure of a compound represented by any one of the following formulas: (1-385), (1-404), (1-406), (1-408), (1-420), (1-422), (1-424), (1-435), (1-436), (1-438), (1-439), (1-444), (1-450), (1-451), (1-456), and (1-457).

[0240] The number of cycloalkanes condensed in an aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples are shown below of one or more cycloalkanes condensed in a benzene ring (phenyl). * indicates the bonding position, which can be any carbon atom constituting the benzene ring and not constituting a cycloalkane. Cycloalkanes condensed as in formulas (Cy-1-4) and (Cy-2-4) can also condense with each other. This is the same whether the condensed ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or whether the condensed cycloalkanes are cycloalkanes other than cyclopentane or cyclohexane.

[0241] [Chemistry 34]

[0242]

[0243] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows examples of one or more -CH2- in a cycloalkane condensed on a benzene ring (phenyl) being substituted with -O-. This is the same whether the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or whether the cycloalkane undergoing condensation is a cycloalkane other than cyclopentane or cyclohexane.

[0244] [Chemistry 35]

[0245]

[0246] At least one hydrogen atom in the cycloalkane may be substituted as a substituent, such as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups may be linked by a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, details of which can be found in the description of the first substituent. Among these substituents, alkyl (e.g., alkyl with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl with 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, it may be in a spirocyclic form, as illustrated in the examples below.

[0247] [Chemistry 36]

[0248]

[0249] As a form of cycloalkane condensation, examples can be given of polycyclic aromatic compounds having one or more of the aryl or heteroaryl rings of rings A, B, and C in formula (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) that are condensed with cycloalkane, specifically aryl or heteroaryl rings of rings a, b, c, a11, b11, c11, a13, b13, and c13. Examples of fused rings in this form include tetrahydronaphthiophene rings or tetrahydronaphthothiophene rings.

[0250] Other forms of cycloalkane condensation include polycyclic aromatic compounds having one or more structural units represented by formula (1), or polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f) having an aryl group condensed from a cycloalkane or a heteroaryl group condensed from a cycloalkane as a substituent, or as part of a substituent. For example, examples include X... 1 ~X 4In any of the >NR, R is in the form of an aryl group condensed from a cycloalkane or a heteroaryl group condensed from a cycloalkane. Other examples include diarylamino groups condensed from cycloalkane (condensed to their aryl moiety), arylheteroarylamino groups condensed from cycloalkane (condensed to their aryl and / or heteroaryl moiety), diarylamino groups condensed from cycloalkane (condensed to their heteroaryl moiety), carbazolyl groups condensed from cycloalkane (condensed to their benzene ring moiety), or benzo[a]carbazolyl groups condensed from cycloalkane (condensed to their benzene ring moiety), and other substituents such as aryl groups condensed from cycloalkane, or heteroaryl groups condensed from cycloalkane, or partial structures of substituents (e.g., the aryl portion of an aryloxy group, etc.) having aryl groups condensed from cycloalkane, or heteroaryl groups condensed from cycloalkane. Regarding "diarylamino," examples of groups described as the "first substituent" can be listed.

[0251] Furthermore, as more specific examples, the polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) can be listed, in which the α ring is located on the Y ring. 1 The opposite R Z Examples include diarylamino groups condensed from cycloalkanes (condensed to their aryl moiety) or carbazole groups condensed from cycloalkanes (condensed to their benzene ring moiety).

[0252] All or part of the hydrogen in one or more of the structural units represented by formula (1) may be deuterium, cyano, or halogen. The same applies to the polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f) described below, and the following description also applies to the polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f).

[0253] For example, in a structure containing one or more structural units represented by formula (1), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents targeting rings A to C, and Y 1 When R is Si-R or Ge-R (R is alkyl, cycloalkyl, or aryl), and X 1 and X 2When the hydrogen in R (where R is an alkyl, cycloalkyl, or aryl group) is >NR, >C(=R)2, or >Si(-R)2, it can be replaced by deuterium, cyano, or halogen. Examples of such substitutions include those in which all or part of the hydrogen in the aryl or heteroaryl group is replaced by deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. Furthermore, from the viewpoint of durability, it is also preferable that all or part of the hydrogen in one or more structures containing the structural unit represented by formula (1) is deuterated, more preferably in the form where all hydrogen directly bonded to the aromatic ring is deuterated, or in the form where all hydrogen is deuterated, and most preferably in the form where all hydrogen directly bonded to the aromatic ring is deuterated.

[0254] Preferred examples of polycyclic aromatic compounds having one or more structural units comprising the structural unit represented by formula (1) include polycyclic aromatic compounds represented by any of the following formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f). Furthermore, regarding the structure and preferred range of substituents or contained rings in formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), refer to the descriptions of the corresponding formulas (1).

[0255] [Chemistry 37]

[0256]

[0257] In equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), Y 1 X 1 and X 2 respectively with Y in equation (1) 1 X 1 and X 2 For the same meaning, the preferred range is also the same. Furthermore, X in equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) 3 and X 4 respectively with X in equation (Het) 3 and X 4 For the same meaning, the preferred range is also the same. Furthermore, X in equations (1-d) and (1-e) 5 and X 6 respectively with X in equation (Het) 4 and X 3 The meanings are the same, and the preferred ranges are also the same.

[0258] Here, regarding X in equation (1) 1and X 2 The provision that "R in at least one of >NR, >Si(-R)2 and >C(=R)2 is bonded to ring A and / or ring B, or ring A and / or ring C by a linker or single bond" corresponds to the provision in equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) that "R in at least one of >NR, >Si(-R)2 and >C(=R)2 is bonded to ring C by a linker or single bond." Z R in Z Z The specification states that "one or two bonds" are involved. Specifically, R can be the one spatially closest to the ring shown below as CR. Z Z-bonds.

[0259] Equation (1-a): X 1 R in the equation represents the a-ring, and X represents the x-ring. 2 R in the equation represents the a-ring and / or c-ring.

[0260] Equation (1-b): X 1 In this context, R represents the a-ring and / or b11-ring, and X... 2 R in the equation represents the a-ring and / or c-ring.

[0261] Equation (1-c): X 1 In this context, R represents the a-ring and / or b11-ring, and X... 2 R in the equation represents the a-ring and / or c-ring.

[0262] Equation (1-d): X 1 In this context, R represents the a-ring and / or b11-ring, and X... 2 R in the equation represents the a ring and / or the c11 ring.

[0263] Equation (1-e): X 1 In this context, R represents the a-ring, and X... 2 R in the equation represents the a-ring.

[0264] Equation (1-f): X 1 R in the equation represents the a11 ring and / or the b ring, and X represents the x ring. 2 R in the equation represents a c-ring.

[0265] In equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), Z is independently N or CR, respectively. Z As the CR Z R Z R can be referred to in the formula (Het). Z Explanation. Z is preferably CR. Z The form of R. Multiple R in each formula. Z They can be the same or different.

[0266] Furthermore, Z=Z can be independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. Among these, >O, >NR, >C(-R)2, or >S are preferred. The R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. The two Rs in >C(-R)2 and >Si(-R)2 can be bonded to each other to form a ring. For example, when a Z=Z is >NR, >O, or >S, a pyrrole ring, furan ring, or thiophene ring is formed in the same way as described with respect to one ring (monocyclic ring) in formula (Het). The remaining Zs are adjacent to and are all CR. Z In these cases, these medium R Z When bonded together to form a benzene ring, it forms an indole ring, benzofuran ring, or benzothiophene ring in the same way as described with respect to one ring (monocyclic ring) in formula (Het).

[0267] In each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), the number of rings (single rings) containing Z as N is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1. In each of formulas (1-a), (1-b), (1-c), (1-d), and (1-e), Z is also preferably entirely composed of CR. Z .

[0268] In formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), in the ring (monocyclic ring) containing Z as N, it is preferable that one or two of the plurality of Zs is N; when two are N, it is preferable that the two Ns are not adjacent to each other. When the six-membered ring is a ring containing Z as N, it is preferably a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, more preferably a pyridine ring or a pyrimidine ring. When the five-membered ring is a ring containing Z as N, it is preferably a thiazole ring or an oxazole ring.

[0269] In formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), formulas (1-a), (1-b), (1-c), or (1-d) are preferred, formulas (1-a), (1-b), or (1-c) are more preferred, and formula (1-b) is the most preferred.

[0270] In equations (1-a), (1-b), (1-c), (1-d), and (1-e), the preferred Z-value for each of the a11 ring, a13 ring, b ring, b11 ring, b13 ring, c11 ring, and c13 ring is CR. Z Furthermore, in the c-ring, it is preferable that Z is always CR. Z Alternatively, one Z = Z is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se (for its morphology and preferred examples, please refer to the specification), and the remaining Z is CR. Z R Z They are bonded together to form aryl rings (preferably benzene rings) or heteroaryl rings, more preferably the c ring is a benzene ring, or a benzothiophene ring, a benzofuran ring, an indole ring, or an indene ring, most preferably a benzene ring or a benzothiophene ring.

[0271] As a polycyclic aromatic compound represented by formula (1-b), it is particularly preferred to be a polycyclic aromatic compound represented by formula (1-bZ) or formula (1-bT).

[0272] [Chemistry 38]

[0273]

[0274] In equations (1-bZ) and (1-bT),

[0275] R X1 and R X2 R is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. X1 It can be linked to R via a base or a single bond. X1 Any loop bond of the N direct bond, R X2 It can be linked to R via a base or a single bond. X1 and R X2 Any loop bond of the N direct bond, X 13 Each of the following can be independently represented as >O, >NR, or >C(-R)2, where the R in >NR is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, and the R in >C(-R)2 can be independently an unsubstituted alkyl group. The two Rs can be bonded together to form a cycloalkane ring.

[0276] R X4 Each is an unsubstituted alkyl group, and the two Rs are independent. X4 They can bond with each other to form cycloalkane rings.

[0277] R Z1 Each is an unsubstituted alkyl group,

[0278] R Z2 Each is an unsubstituted alkyl group, m is an integer from 0 to 2, and R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2. In the structure represented by formula (1-bZ) or formula (1-bT), at least one of the aryl ring or heteroaryl ring can be a structure formed by bonding a partial structure represented by formula (B) to an adjacent carbon atom.

[0279] [Chemistry 39]

[0280]

[0281] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0282] At least one hydrogen atom in the structure represented by formula (1-bZ) or formula (1-bT) may be substituted by a cyano group, a halogen, or a deuterium.

[0283] In equations (1-bZ) and (1-bT), R X1 and R X2 Preferably, all are substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or as NR. X1 or NR X2 The structure represented by formula (A11). Regarding R X1 and R X2 The preferred range can be referred to as X in the above formula (1). 1 or X 2 The preferred range of R in >NR is recorded.

[0284] As X 13 The R in >NR is preferably an aryl group that can be substituted with an alkyl or aryl group, or a heteroaryl group that can be substituted with an alkyl or aryl group, more preferably a phenyl group that can be substituted with an alkyl group having 1 to 6 carbon atoms (preferably tert-butyl).

[0285] As X 13 The R in >C(-R)2 is preferably all methyl.

[0286] R X4 Preferably, all of them are methyl.

[0287] R Z1 Preferably, each is an alkyl group having 1 to 6 carbon atoms, more preferably methyl or tert-butyl. Z2 Preferably, each alkyl group has 1 to 6 carbon atoms, more preferably methyl or tert-butyl. m is preferably 0 or 1. R Z3 Preferably, each is an alkyl group having 1 to 6 carbon atoms, more preferably methyl or tert-butyl. n is preferably 0 or 1. When n is 1, RZ3 Preferably relative to X 13 And it is in the opposite position.

[0288] Furthermore, in the structures represented by formulas (1-bZ) and (1-bT), 0 to 2 of the aryl rings or heteroaryl rings are preferably structures formed by bonding a portion of the structure represented by formula (B) to adjacent carbon atoms in the ring. When the structures represented by formulas (1-bZ) and (1-bT) each include a portion of the structure represented by formula (B), the ring bonded by the portion of the structure represented by formula (B) is preferably R. Z2 The bonded benzene ring or R X1 Or R X2 Any one of the aryl rings.

[0289] As a more specific example of the polycyclic aromatic compound represented by formula (1) of the present invention, the following compounds can be listed. In the following structural formulas, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, and "D" represents deuterium. In addition, the following structure is an example.

[0290] [Chemistry 40]

[0291]

[0292] [Chemistry 41]

[0293]

[0294] [Chemistry 42]

[0295]

[0296] [Chemistry 43]

[0297]

[0298] [Chemistry 44]

[0299]

[0300] [Chemistry 45]

[0301]

[0302] [Chemistry 46]

[0303]

[0304] [Chemistry 47]

[0305]

[0306] [Chemistry 48]

[0307]

[0308] [Chemistry 49]

[0309]

[0310] [Transformation 50]

[0311]

[0312] [Chemistry 51]

[0313]

[0314] [Chemistry 52]

[0315]

[0316] [Chemistry 53]

[0317]

[0318] [Chemistry 54]

[0319]

[0320] [Chemistry 55]

[0321]

[0322] [Chemistry 56]

[0323]

[0324] [Chemistry 57]

[0325]

[0326] [Chem.58]

[0327]

[0328] [Chemistry 59]

[0329]

[0330] [Transformation 60]

[0331]

[0332] [Chemistry 61]

[0333]

[0334] [Chemistry 62]

[0335]

[0336] [Chemistry 63]

[0337]

[0338] [Chemistry 64]

[0339]

[0340] [Chemistry 65]

[0341]

[0342] [Chemistry 66]

[0343]

[0344] [Chemistry 67]

[0345]

[0346] [Chemistry 68]

[0347]

[0348] [Chemistry 69]

[0349]

[0350] The polycyclic aromatic compounds of the present invention may exist as enantiomers or diastereomers depending on the type of substituents, but regardless of the described structural formula, any pure form of any stereoisomer, any mixture of stereoisomers, racemates, etc. are included within the scope of the present invention.

[0351] Polycyclic aromatic compounds having one or more structural units represented by formula (1) can also be used as polymers (the monomer used to obtain the polymer has polymeric substituents) or polymer crosslinkers (the polymer used to obtain the polymer crosslinker has crosslinking substituents), or suspended polymers (the reactive compound used to obtain the suspended polymer has reactive substituents) or suspended polymer crosslinkers (the suspended polymer used to obtain the suspended polymer crosslinker has crosslinking substituents) in materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field-effective transistors, or materials for organic thin-film solar cells. The polymer is obtained by polymerizing a reactive compound, which is obtained by replacing the reactive substituents in the polycyclic aromatic compound represented by formula (1), as a monomer. The polymer crosslinker is obtained by further crosslinking the polymer. The suspended polymer is obtained by reacting a main-chain polymer with the reactive compound. The suspended polymer crosslinker is obtained by further crosslinking the suspended polymer.

[0352] As the reactive substituent (including the polymerizable substituent, the crosslinking substituent, and the reactive substituent for obtaining a suspended polymer, hereinafter also simply referred to as "reactive substituent"), there are no particular limitations as long as it is a substituent that can increase the molecular weight of the polycyclic aromatic compound, a substituent that can further crosslink the polymer obtained in this manner, or a substituent that can carry out a suspension reaction in a main-chain polymer. Examples include alkenyl, alkynyl, unsaturated forms of cycloalkyl (e.g., cyclobutenyl), at least one -CH2- substituted by -O- in cycloalkyl (e.g., epoxy group), unsaturated forms of condensed cycloalkanes (e.g., condensed cyclobutene), etc., preferably substituents with the following structures. * in each structural formula indicates a bond position.

[0353] [Chemistry 70]

[0354]

[0355] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group with 1 to 12 carbon atoms, oxoalkylene group with 1 to 12 carbon atoms, or polyoxoalkylene group with 1 to 12 carbon atoms. The substituents are preferably those represented by formulas (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17), and more preferably those represented by formulas (XLS-1), (XLS-3), or (XLS-17).

[0356] Details regarding the uses of such polymers, polymer crosslinkers, suspended polymers and suspended polymer crosslinkers (hereinafter also referred to as "polymers and polymer crosslinkers") will be described later.

[0357] Methods for manufacturing polycyclic aromatic compounds

[0358] Polycyclic aromatic compounds having one or more structural units represented by formula (1) or polycyclic aromatic compounds represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f) generally utilize bonding groups (containing X) 1 or X 2 The group (containing Y) bonds ring A (a ring) to ring B (b ring) and ring C (c ring), thereby creating an intermediate (first reaction). Then, using the bonding group (containing Y) 1 The group ( ) bonds the A ring (a ring), B ring (b ring), and C ring (c ring) together, thereby producing the final product (second reaction). In the first reaction, for example, if it is an etherification reaction, a conventional reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used; if it is an amination reaction, a conventional reaction such as a Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem Hetero-Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, the same below) can be used. By using a starting material with a desired fused ring at some point in the reaction process or by adding a step to condense the ring, compounds selected from the group consisting of the A ring, B ring, and C ring, whose at least one ring is the ring represented by formula (Het) can be produced.

[0359] Manufacturing method via intermediate-1

[0360] The polycyclic aromatic compounds of the present invention can be manufactured by a manufacturing method comprising the following steps. Reference can be made to International Publication No. 2015 / 102118 for details of each of these steps.

[0361] The manufacturing method includes the following reaction steps: using an organic base compound to react X in intermediate-1 below. 1 With X 2 Metallization of halogen atoms (Hal) between them; using Y... 1 halides, Y 1 Aminated halides, Y 1 alkoxylated compounds and Y 1 The reagents in the group consisting of aryloxyides react the metal with Y 1 Exchange; and utilize the Y by means of a series of aromatic electrophilic substitution reactions using Brønsted bases. 1 This allows the B ring to bond with the C ring.

[0362] [Chemistry 71]

[0363]

[0364] Manufacturing method via intermediate-2

[0365] The polycyclic aromatic compounds of the present invention are preferably manufactured by a manufacturing method including a reaction step of reacting an acid with the intermediate-2 described below. For details, please refer to the description in Japanese Patent Application Publication No. 2018-76281, etc.

[0366] [Chemistry 72]

[0367]

[0368] (In intermediate-2, Z is -B(OH)2, which can be esterified.)

[0369] In intermediate-2, Z is esterifiable -B(OH)2. Preferred Y... 1 It is an esterified group of -B(OH)2.

[0370] The group that is esterified from -B(OH)2 (-B(OR)2) is not particularly limited, and examples include groups obtained by reacting an alcohol containing a diol or a carboxylic acid with boric acid. The R group in -B(OR)2 can be any substituted alkyl group having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms), where the R groups can bond to each other to form a ring, or the formed ring may contain an aromatic ring such as benzene. Specifically, groups with the following structures can be listed. In the following structures, "Me" represents methyl, "Et" represents ethyl, "iPr" represents isopropyl, and * indicates the bonding position.

[0371] [Chemistry 73]

[0372]

[0373] For details regarding the manufacturing method of boric acid or borate esters such as intermediate-2, please refer to Japanese Patent Application Publication No. 2018-76281.

[0374] 2. Organic devices

[0375] The polycyclic aromatic compounds of this invention can be used as materials for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effective transistors, and organic thin-film solar cells.

[0376] 2-1. Organic electroluminescent element

[0377] 2-1-1. Structure of Organic Electroluminescent Element

[0378] Figure 1 is a schematic cross-sectional view showing an example of an organic EL element.

[0379] The organic EL element 100 shown in Figure 1 includes: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

[0380] Furthermore, the organic EL element 100 can also be fabricated in reverse order to form a structure such as the following, which includes: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0381] Not all of the layers are indispensable. The smallest structural unit is set to include an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are arbitrarily arranged layers. In addition, each layer may consist of a single layer or multiple layers.

[0382] In addition to the aforementioned structure of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", the morphology of the layers constituting an organic EL device can also be "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting ...". The structural forms are: “substrate / anode / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / electron transport layer / cathode”, “substrate / anode / electron transport layer / cathode”, “substrate / anode / electron transport layer / cathode”.

[0383] 2-1-2. The light-emitting layer in organic electroluminescent devices

[0384] The polycyclic aromatic compounds of the present invention are preferably used as materials for forming any one or more organic layers in an organic electroluminescent element, and more preferably as materials for forming a light-emitting layer.

[0385] The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 with electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material for forming the light-emitting layer 105, any compound that emits light upon excitation by the recombination of holes and electrons (a luminescent compound) is acceptable, and preferably a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state.

[0386] The polycyclic aromatic compounds of the present invention can be used as materials for light-emitting layers, as dopant materials, or as host materials.

[0387] The polycyclic aromatic compound of the present invention is preferably a material for the light-emitting layer, and more preferably a dopant material.

[0388] Furthermore, there are examples of using auxiliary dopants and emitting dopants together as dopants, but in this specification, when simply referred to as "dopant," it refers to an emitting dopant used alone.

[0389] The light-emitting layer can be a single layer or multiple layers, either of which is acceptable, and is formed from light-emitting layer materials (host material and dopant material). The host material and dopant material can each be one type or a combination of multiple types, either of which is acceptable. The dopant material can be contained entirely within the host material or partially within the host material, either of which is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or it can be pre-mixed with the host material and then simultaneously evaporated. Furthermore, it is preferable to pre-mix multiple host materials and co-evaporate them with the dopant material. Specific examples of dopant combinations with the compounds of the present invention are shown below when the dopant is set to multiple combinations. In the following structural formulas, "Me" represents methyl, "tBu" represents tert-butyl, and "D" represents deuterium.

[0390] [Chemistry 74]

[0391]

[0392] [Chemistry 75]

[0393]

[0394] [Chemistry 76]

[0395]

[0396] [Chemistry 77]

[0397]

[0398] [Chemistry 78]

[0399]

[0400] The amount of main material used varies depending on the type of main material, and can be determined by considering the characteristics of the main material. The preferred basis for the amount of main material used is 50% to 99.999% of the total mass of the material used in the light-emitting layer, more preferably 80% to 99.95% of the total mass, and even more preferably 90% to 99.9% of the total mass.

[0401] The amount of dopant material used varies depending on the type of dopant material, and can be determined in accordance with the characteristics of the dopant material. The preferred amount of dopant is 0.001% to 50% of the total mass of the material used in the luminescent layer, more preferably 0.05% to 20% by mass, and even more preferably 0.1% to 10% by mass. If it falls within this range, it is preferred, for example, in terms of preventing concentration quenching.

[0402] Main materials

[0403] As the main material, anthracene, pyrene, and dibenzoxane can be listed as previously known luminescent materials. Fluorene and other fused-ring derivatives, bis(styrene) anthracene derivatives or styrene benzene derivatives, bis(styrene) derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, dibenzo[a]fluorene derivatives, etc. Compounds, etc.

[0404] Alternatively, as the main material, a compound represented by any of the following formulas (H1), (H2), and (H3) can be used, for example.

[0405] [Chemistry 79]

[0406]

[0407] In equations (H1), (H2), and (H3), L 1 It is an arylene with 6 to 24 carbons, a heteroarylene with 2 to 24 carbons, a heteroarylene with 6 to 24 carbons, or a heteroarylene with 6 to 24 carbons, preferably an arylene with 6 to 16 carbons, more preferably an arylene with 6 to 12 carbons, and particularly preferably an arylene with 6 to 10 carbons. Specifically, divalent groups such as benzene rings, biphenyl rings, terphenyl rings, and fluorene rings can be listed. As a heteroaryl group, a heteroaryl group having 2 to 24 carbon atoms is preferred, a heteroaryl group having 2 to 20 carbon atoms is more preferred, a heteroaryl group having 2 to 15 carbon atoms is even more preferred, and a heteroaryl group having 2 to 10 carbon atoms is particularly preferred. Specifically, examples include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetraazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H - Divalent groups of indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cyclophosphine ring, quinazolin ring, quinoxaline ring, phthalazine ring, naphthidine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxthia ring, phenoxazine ring, phenthiazine ring, phenazine ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazine ring, oxadiazole ring, and thiathrone ring, etc.

[0408] At least one hydrogen atom in the compounds represented by the formulas may be substituted by an alkyl group, a cyano group, a halogen, or a deuterium having 1 to 6 carbon atoms.

[0409] As preferred specific examples, compounds represented by any of the structural formulas listed below can be cited. Furthermore, in the structural formulas listed below, at least one hydrogen atom may be substituted by a halogen, a cyano group, an alkyl group having 1 to 4 carbon atoms (e.g., methyl or tert-butyl), a phenyl group, or a naphthyl group.

[0410] [Chemistry 80]

[0411]

[0412] [Chemistry 81]

[0413]

[0414] [Chemistry 82]

[0415]

[0416] [Chemistry 83]

[0417]

[0418] <Anthracene compounds>

[0419] Anthracene compounds, such as those represented by formula (3-H) and formula (3-H2), can be listed as examples.

[0420] [Chemistry 84]

[0421]

[0422] In equation (3-H),

[0423] X and Ar 4 Each of the following is independently hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted diarylamino group, a substituted diheteroarylamino group, a substituted arylheteroarylamino group, a substituted alkyl group, a substituted cycloalkyl group, a substituted alkenyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, or a substituted silyl group, X and Ar 4 Not all of them will become hydrogen at the same time.

[0424] At least one hydrogen atom in the compound represented by formula (3-H) may be substituted by a halogen, cyano, deuterium or a substituted heteroaryl group.

[0425] Alternatively, the structure represented by formula (3-H) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples can be given of unit structures represented by formula (3-H) that are linked to each other via X bonds. As X, examples can include single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.), and heteroarylene groups (pyridine rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, benzocarbazole rings, and phenyl-substituted carbazole rings, etc., groups having divalent bonding valences).

[0426] Details of each group in the compound represented by formula (3-H) can be found in the description in formula (1), and further described in the preferred form section below.

[0427] The preferred forms of the anthracene compounds are described below. The definitions of the symbols in the following structures are the same as those described above.

[0428] [Chemistry 85]

[0429]

[0430] In formula (3-H), X is independently a base represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the base represented by formula (3-X1), formula (3-X2), or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at the * position. Preferably, the two X's do not simultaneously become the base represented by formula (3-X3). More preferably, the two X's do not simultaneously become the base represented by formula (3-X2).

[0431] Alternatively, the structure represented by formula (3-H) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples can be given of unit structures represented by formula (3-H) that are linked to each other via X bonds. As X, examples can include single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.), and heteroarylene groups (pyridine rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, benzocarbazole rings, and phenyl-substituted carbazole rings, etc., groups having divalent bonding valences).

[0432] The naphthyl group in formulas (3-X1) and (3-X2) can be formed by the condensation of a benzene ring. The structure formed by the condensation in this manner is shown below.

[0433] [Chemistry 86]

[0434]

[0435] Ar 1 and Ar 2 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The group consisting of hydroxyl, triphenylene, pyrene, or the group represented by formula (A) described below (including carbazole, benzocarbazole, and phenyl-substituted carbazole). Furthermore, in Ar... 1 Or Ar 2 In the case of the base represented by formula (A) described later, the base represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the * position.

[0436] Ar 3 It is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The group consisting of hydroxyl, triphenylene, pyrene, or any group represented by formula (A) (including carbazole, benzocarbazole, and phenyl-substituted carbazole). Furthermore, in Ar... 3 In the case of the base represented by formula (A), the base represented by formula (A) is bonded at the * position to the single bond represented by the straight line in formula (3-X3). That is, the anthracene ring of formula (3-H) is directly bonded to the base represented by formula (A).

[0437] Additionally, Ar 3 It can have substituents, Ar 3 At least one hydrogen atom in the form can be derived from an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorene group, or a phenyl group. Substitution with alkyl, triphenylene, pyrene, or alkyl groups represented by formula (A) (including carbazole and phenyl-substituted carbazole groups). Furthermore, in Ar... 3 When the substituent is the one represented by formula (A), the one represented by formula (A) at the * position is the same as Ar in formula (3-X3). 3 Bond.

[0438] Ar 4 Each is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and / or a cycloalkyl group having 5 to 10 carbon atoms.

[0439] Examples of alkyl groups with 1 to 4 carbon atoms that can be substituted in silanes include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, and cyclobutyl, etc., in which the three hydrogens in the silane are independently substituted by these alkyl groups.

[0440] Specific examples of "silyl groups substituted with alkyl groups having 1 to 4 carbon atoms" include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl diisopropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0441] Examples of cycloalkyl groups with 5 to 10 carbon atoms that can be substituted in silanes include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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 (norbornyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazyl, etc., in which the three hydrogens in the silane are independently substituted by their respective cycloalkyl groups.

[0442] Specific examples of "silyl groups substituted by cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilane and tricyclohexylsilane.

[0443] As substituted silyl groups, there are also dialkylcycloalkylsilyl groups substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl groups substituted with one alkyl group and two cycloalkyl groups. As specific examples of substituted alkyl and cycloalkyl groups, the groups described above can be listed.

[0444] Furthermore, the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) can also be substituted by the group represented by formula (A). In the case of substitution by the group represented by formula (A), the group represented by formula (A) is substituted at the * position with at least one hydrogen in the compound represented by formula (3-H).

[0445] The group represented by formula (A) is one of the substituents that anthracene compounds represented by formula (3-H) and anthracene compounds represented by formula (3-H2) described later may have.

[0446] [Chemistry 87]

[0447]

[0448] In equation (A), Y is -O-, -S-, or >NR. 29 R 21 ~R 28 Each of the following is independently hydrogen, a substituted alkyl group, a substituted cycloalkyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkoxy group, a substituted aryloxy group, a substituted arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkyldicycloalkylsilyl group, a substituted amino group, a halogen, a hydroxyl group, or a cyano group, R. 21 ~R 28 The adjacent groups in R can bond with each other to form hydrocarbon rings, aryl rings, or heteroaryl rings. 29 It is hydrogen or a substituted aryl group.

[0449] In formula (A), Y is preferably -O-.

[0450] As R 21 ~R 28 The "alkyl" in "substitutable alkyl" can be either straight-chain or branched, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), even more preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0451] Specific examples of "alkyl groups" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0452] As R 21 ~R 28 The "cycloalkyl" in "substitutable cycloalkyl" can be exemplified by: cycloalkyl with 3 to 24 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cycloalkyl with 3 to 16 carbon atoms, cycloalkyl with 3 to 14 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, cycloalkyl with 5 to 8 carbon atoms, cycloalkyl with 5 to 6 carbon atoms, cycloalkyl with 5 carbon atoms, etc.

[0453] Specific examples of "cycloalkyl" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, or 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 (norbornyl), bicyclo[2.2.2]octyl, adamantyl, adamantyl, decahydronaphthyl, decahydroazyl, etc.

[0454] As R 21 ~R 28 The "aryl" in "substitutable aryl" can be exemplified by aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 16 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms.

[0455] Specific examples of "aryl" groups include: phenyl as a monocyclic compound, biphenyl as a bicyclic compound, naphthyl as a condensed bicyclic compound, terphenyl as a tricyclic compound (m-terphenyl, o-terphenyl, p-terphenyl), acenaphthene, fluorenyl, phenatenyl, and phenanthrene as condensed tricyclic compounds, triphenylene, pyrene, and tetraphenyl as condensed tetracyclic compounds, and perylene and pentaphenyl as condensed pentacyclic compounds.

[0456] As R 21 ~R 28 The term "heteroaryl" in "substitutable heteroaryl" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, and even more preferably heteroaryl groups with 2 to 15 carbon atoms, particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, examples of heteroaryl groups include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms.

[0457] Specific examples of "heteroaryl" groups include: pyrrole, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isoindole, 1H-indazole, benzimidazole, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, and isoquinolinyl. , ...

[0458] As R 21 ~R 28 The "alkoxy group" in "substitutable alkoxy group" can include, for example, straight-chain alkoxy groups with 1 to 24 carbon atoms or branched-chain alkoxy groups with 3 to 24 carbon atoms. Preferably, it is an alkoxy group with 1 to 18 carbon atoms (branched-chain alkoxy groups with 3 to 18 carbon atoms), more preferably an alkoxy group with 1 to 12 carbon atoms (branched-chain alkoxy groups with 3 to 12 carbon atoms), and even more preferably an alkoxy group with 1 to 6 carbon atoms (branched-chain alkoxy groups with 3 to 6 carbon atoms), and particularly preferably an alkoxy group with 1 to 4 carbon atoms (branched-chain alkoxy groups with 3 to 4 carbon atoms).

[0459] Specific examples of "alkoxy groups" include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0460] R 21 ~R 28 In the phrase "substitutable aryloxy group", the "aryloxy group" is a group in which the hydrogen of the -OH group is replaced by an aryl group, and the aryl group can be referenced as the R group. 21 ~R 28 The "aryl" in the text refers to the base.

[0461] R 21 ~R 28 The "arylthio" in "substitutable arylthio" refers to a group in which the hydrogen of the -SH group is replaced by an aryl group, and the aryl group can be referenced as the R. 21 ~R 28 The "aryl" in the text refers to the base.

[0462] As R 21 ~R 28 The term "trialkylsilyl" can be an example of a silyl group in which each of the three hydrogens is independently replaced by an alkyl group, and the alkyl group can be referenced as R. 21 ~R 28 The "alkyl" in the text refers to the group. For substitution, the preferred alkyl group is an alkyl group having 1 to 4 carbon atoms, specifically including: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclobutyl, etc.

[0463] Specific examples of "trialkylsilyl" include: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl diisopropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0464] As R 21 ~R 28 The term "tricycloalkylsilyl" can be an example of a silyl group in which each of the three hydrogens is independently replaced by a cycloalkyl group, and the cycloalkyl group can be referenced as R. 21 ~R 28 The term "cycloalkyl" refers to the group used for substitution. Preferred cycloalkyl groups for substitution are those with 5 to 10 carbon atoms, specifically including: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, decahydronaphthyl, decahydroazyl, etc.

[0465] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

[0466] As specific examples of substituted dialkylcycloalkylsilyl groups with two alkyl groups and one cycloalkyl group, and substituted alkyldicycloalkylsilyl groups with one alkyl group and two cycloalkyl groups, examples include silyl groups substituted with groups selected from the specific alkyl and cycloalkyl groups.

[0467] As R 21 ~R 28 The term "substituted amino group" in the phrase "substituteable amino group" can include, for example, amino groups in which two hydrogen atoms are substituted by an aryl or heteroaryl group. An amino group in which two hydrogen atoms are substituted by an aryl group is a diaryl-substituted amino group, an amino group in which two hydrogen atoms are substituted by a heteroaryl group is a dihexanel-substituted amino group, and an amino group in which both hydrogen atoms are substituted by an aryl and a heteroaryl group is an arylhexanel-substituted amino group. The aryl or heteroaryl group can be referenced as R. 21 ~R 28 The group is described by the "aryl" or "heteroaryl" in the text.

[0468] Specific examples of "substituted amino groups" include: diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

[0469] As R 21 ~R 28 The "halogens" mentioned include: fluorine, chlorine, bromine, and iodine.

[0470] As R 21 ~R 28 Among the groups described, several groups can also be substituted in the manner described above. Examples of substituents in this case include alkyl, cycloalkyl, aryl, or heteroaryl groups. The alkyl, cycloalkyl, aryl, or heteroaryl groups can be referenced as R. 21 ~R 28 The group is indicated by "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0471] As Y > NR 29 R in " 29 The aryl group is hydrogen or a substituted aryl group, which can be referenced as R. 21 ~R 28 The "aryl" in the text refers to the group, and furthermore, as the substituent, it can be cited as a group targeting R. 21 ~R 28 The base is explained by the substituent.

[0472] R 21 ~R 28 The adjacent groups in the formula can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. The group that does not form a ring is represented by the group in formula (A-1) below; for example, the groups represented by formulas (A-2) to (A-14) below can be listed as ring-forming groups. Furthermore, at least one hydrogen atom in any of the groups represented by formulas (A-1) to (A-14) can be substituted by an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano group.

[0473] [Chemistry 88]

[0474]

[0475] A ring formed by the mutual bonding of adjacent groups can be a hydrocarbon ring, such as the cyclohexane ring; or an aryl or heteroaryl ring, such as the R group. 21 ~R 28The ring structure described in “aryl” or “heteroaryl” is formed by condensation with one or both benzene rings of formula (A-1).

[0476] The base represented by formula (A) is obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. That is, the base represented by formula (A) can use any position as a bonding site. For example, it can be any carbon atom on either of the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 The atoms on any ring formed by the mutual bonding of adjacent bases in the structure, or the ">NR" of Y in the structure of formula (A) 29 "R" 29 Any position in or ">NR 29 "N(R) 29 The basis is directly bonded (for the bonded bond). The same applies to the basis represented by any of the equations (A-1) to (A-14).

[0477] As a basis represented by formula (A), for example, any of the formulas (A-1) to (A-14) can be listed as a basis, preferably any of the formulas (A-1) to (A-5) and (A-12) to (A-14) as a basis, more preferably any of the formulas (A-1) to (A-4) as a basis, and even more preferably any of the formulas (A-1), (A-3) and (A-4) as a basis, and particularly preferably the basis represented by formula (A-1).

[0478] As a basis represented by equation (A), the following bases can be listed for example. The definitions of Y and * in the equation are the same as those above.

[0479] [Chemistry 89]

[0480]

[0481] [Chemistry 90]

[0482]

[0483] In the compound represented by formula (3-H), the group represented by formula (A) is preferably related to the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and / or the Ar group in formula (3-X3). 3 The shape of the bond.

[0484] In addition, all or part of the hydrogen in the chemical structure of the anthracene compounds represented by formula (3-H) can be deuterium.

[0485] The main anthracene compounds can be, for example, compounds represented by the following formula (3-H2).

[0486] [Chemistry 91]

[0487]

[0488] In equation (3-H2), Ar c R is a substituted aryl group or a substituted heteroaryl group. c Ar is hydrogen, alkyl, or cycloalkyl. 11 Ar 12 Ar 13 Ar 14 Ar 15 A 16 Ar 17 and Ar 18 The hydrogen atom in the compound represented by formula (3-H-2) may be substituted by a halogen, a cyano group, or a deuterium, and may be independently hydrogen, substituted aryl, substituted heteroaryl, substituted diarylamino, substituted diheteroarylamino, substituted arylheteroarylamino, substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted alkoxy, substituted aryloxy, substituted arylthio, or substituted silyl, respectively.

[0489] The definitions of “substituted aryl”, “substituted heteroaryl”, “substituted diarylamino”, “substituted diheteroarylamino”, “substituted arylheteroarylamino”, “substituted alkyl”, “substituted cycloalkyl”, “substituted alkenyl”, “substituted alkoxy”, “substituted aryloxy”, “substituted arylthio” or “substituted silyl” in formula (3-H2) are the same as those shown in formula (3-H) and can be referenced in the description of formula (1).

[0490] As a "substitutable aryl group", it is also preferred to be a group represented by any of the following formulas (3-H2-X1) to (3-H2-X7).

[0491] [Chemistry 92]

[0492]

[0493] In equations (3-H2-X1) to (3-H2-X7), * indicates the location of the bond.

[0494] In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 and Ar23 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The radical, triphenylene, pyrene, anthracene, or any radical represented by formula (A). Furthermore, in the description of formula (3-H2), the radical represented by formula (A) is the same as the radical described in the anthracene compounds represented by formula (3-H).

[0495] In equations (3-H2-X4) to (3-H2-X7), Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, and fluorene. The radical, triphenylene, pyrene, or the radical represented by formula (A) described later.

[0496] In addition, any one or more hydrogen atoms in each of the groups represented by formulas (3-H2-X1) to (3-H2-X7) may be replaced by alkyl groups having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

[0497] Furthermore, as preferred examples of "substituted aryl groups", those selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, etc., can be listed. Triphenyl groups substituted with one or more of the groups represented by the radical, triphenylene, pyrene, and the radical represented by formula (A) (especially meta-triphenyl-5′-yl).

[0498] As a “substitutable heteroaryl group”, the group represented by formula (A) can also be listed.

[0499] In addition, specific examples of "substitutable aryl" and "substitutable heteroaryl" include dibenzofuranyl, naphthobenzofuranyl, and phenyl-substituted dibenzofuranyl.

[0500] At least one hydrogen atom in the compound represented by formula (3-H) may be substituted with a halogen, a cyano group, or deuterium. Examples of "halogen" in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms are substituted with deuterium are particularly preferred.

[0501] In equation (3-H2), R c It is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or tert-butyl, and more preferably hydrogen.

[0502] In formula (3-H2), Ar is preferred. 11 ~Ar 18At least two of them are substituted aryl groups or substituted heteroaryl groups. That is, the anthracene compound represented by formula (3-H2) is preferably a structure having at least three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl groups and substituted heteroaryl groups.

[0503] Among the anthracene compounds represented by formula (3-H2), Ar is more preferred. 11 ~Ar 18 Two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, substituted alkyl, substituted cycloalkyl, substituted alkenyl or substituted alkoxy groups. That is, the anthracene compound represented by formula (3-H2) is more preferably a structure having three substituents bonded to the anthracene ring, selected from the group consisting of substituted aryl and substituted heteroaryl groups.

[0504] Among the anthracene compounds represented by formula (3-H2), Ar is more preferred. 11 ~Ar 18 Any two of them are substituted aryl or substituted heteroaryl, and the other six are hydrogen, methyl or tert-butyl.

[0505] Therefore, in equation (3-H2), R is preferred. c It is hydrogen, and Ar 11 ~Ar 18 Any six of them are hydrogen.

[0506] The anthracene compounds represented by formula (3-H2) are preferably those represented by formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E).

[0507] [Chemistry 93]

[0508]

[0509] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Ar c′ Ar 11′ Ar 12′ Ar 13′ Ar 14′ Ar 15′ Ar 17′ and Ar 18′ Each of the following is independently a phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The group may be phenyl, triphenyl, pyrene, or a group represented by formula (A), wherein at least one hydrogen atom in these groups may be derived from phenyl, biphenyl, triphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, or phenyl[b]fluorenyl. Substitution with phenyl, triphenylene, pyrene, or the alkyl group represented by formula (A). Here, when the hydrogens of the methylene groups in both the fluorenyl and benzo[a]fluorenyl groups are substituted with phenyl groups, these phenyl groups can be bonded to each other by single bonds. Unbonded Ar c′ Ar 11′ Ar 12′ Ar 13′ Ar 14′ Ar 15′ Ar 17′ and Ar 18′ The carbon atom of the anthracene ring can be bonded with a methyl or tert-butyl group instead of a hydrogen atom.

[0510] When Ar c′ Ar 11′ Ar 12′ Ar 13′ Ar 14′ Ar 15′ Ar 17′ and Ar 18′ When the radical is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, it is preferably a radical represented by any one of the formulas (3-H2-X1) to (3-H2-X7).

[0511] Ar c′ Ar 11′ Ar 12′ Ar 13′ Ar 14′ Ar 15′ Ar 17′ and Ar 18′ More preferably, the group is independently represented by phenyl, biphenyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenyl (especially meta-terphenyl-5′-yl), naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4), in which case at least one hydrogen atom of these groups may be substituted by a group represented by phenyl, biphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

[0512] In addition, at least one hydrogen atom in the compounds represented by formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E) may be substituted with a halogen, a cyano group or a deuterium.

[0513] As particularly preferred anthracene compounds represented by formula (3-H2), examples include anthracene compounds represented by formula (3-H2-Aa).

[0514] [Chemistry 94]

[0515]

[0516] In formula (3-H2-Aa), Ar c′ Ar 14′ and Ar 15′ Each of the following is independently phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, fluorenyl, benzo[a]fluorenyl, The group may be represented by a phenyl group, a triphenylene group, a pyrene group, or a group of any of the formulas (A-1) to (A-11), wherein at least one hydrogen atom in these groups may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorene group, a benzo[a]fluorene group, or a group of other phenyl groups. Substitution of the methyl group, triphenylene, pyrene, or any of the methyl groups represented by formulas (A-1) to (A-11). Here, when the hydrogens of the methylene groups in both the fluorene and benzo[a]fluorene groups are substituted with phenyl groups, these phenyl groups can be bonded to each other by single bonds. Additionally, unbonded Ar... c′ Ar 14′ and Ar 15′ The carbon atom of the anthracene ring may be substituted with a methyl or tert-butyl group instead of a hydrogen atom. At least one hydrogen atom in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or cyano group, and at least one hydrogen atom in the compound represented by formula (3-H2-Aa) may be substituted with a deuterium group.

[0517] In formula (3-H2-Aa), Ar c′ Ar 14′ and Ar 15′ Preferably, the group is independently represented by phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4), wherein at least one hydrogen atom of these groups may be substituted by a group represented by phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups (A-1) to (A-4).

[0518] In compounds represented by formula (3-H2-Aa), the preferred element is at least the carbon at position 10 of the anthracene ring (with Ar... c′ The hydrogen at the 9-position (where the carbon atom is set to 9) is replaced with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably the compound represented by formula (3-H2-Ab). Furthermore, in formula (3-H2-Ab), D is deuterium, and Ar... c′ Ar 14′ and Ar 15′ Same as the definition in formula (3-H2-Aa). In formula (3-H2-Ab), D indicates that at least the position is deuterium, and any one or more of the other hydrogens in formula (3-H2-Aa) can be deuterium at the same time, and preferably all hydrogens in formula (3-H2-Aa) are deuterium.

[0519] [Chem. 95]

[0520]

[0521] Specific examples of anthracene compounds include the following compounds. Furthermore, in the following structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents tert-butyl.

[0522] [Chemistry 96]

[0523]

[0524] [Chemistry 97]

[0525]

[0526] [Chem. 98]

[0527]

[0528] [Chemistry 99]

[0529]

[0530] [Chemistry 100]

[0531]

[0532] [Chemistry 101]

[0533]

[0534] [Chemistry 102]

[0535]

[0536] [Chemistry 103]

[0537]

[0538] In addition, other specific examples of anthracene compounds include compounds represented by formulas (3-131-Y) to (3-179-Y), compounds represented by formulas (3-180-Y) to (3-182-Y), compounds represented by formulas (3-183-N), (3-184-Y) to (3-254-Y), (3-254-Y) to (3-269-Y), and compounds represented by formulas (3-500) to (3-557). In the compounds represented by formulas (3-131-Y) to (3-179-Y), the compounds represented by formulas (3-180-Y) to (3-182-Y), the compounds represented by formulas (3-183-N), (3-184-Y) to (3-254-Y), (3-254-Y) to (3-269-Y), and (3-500) to (3-557), the hydrogen atom may be partially or completely substituted with deuterium. Y in the formula may be -O-, -S-, or >NR. 29 (R 29 (The definition is the same as described above) or >C(-R 30 )2(R 30 R is any of the aryl or alkyl groups that can be linked. 29 For example, phenyl, R 30 For example, methyl. Regarding formula numbering, for example, when Y is O, formula (3-131-Y) is set as formula (3-131-O), and when Y is -S- or >NR... 29 In the case of , they are respectively set as equation (3-131-S) or equation (3-131-N).

[0539] [Chemistry 104]

[0540]

[0541] [Chemistry 105]

[0542]

[0543] [Chemistry 106]

[0544]

[0545] [Chemistry 107]

[0546]

[0547] [Chemistry 108]

[0548]

[0549] [Chemistry 109]

[0550]

[0551] [Chemical 110]

[0552]

[0553] [Chemistry 111]

[0554]

[0555] [Chemistry 112]

[0556]

[0557] [Chemistry 113]

[0558]

[0559] [Chemistry 114]

[0560]

[0561] [Chemistry 115]

[0562]

[0563] [Chemistry 116]

[0564]

[0565] [Chemistry 117]

[0566]

[0567] [Chemistry 118]

[0568]

[0569] [Chemistry 119]

[0570]

[0571] [Chemistry 120]

[0572]

[0573] [Chemistry 121]

[0574]

[0575] [Chemistry 122]

[0576]

[0577] The preferred compounds are those of formulas (3-131-Y) to (3-134-Y), (3-138-Y), (3-140-Y) to (3-143-Y), (3-150-Y), (3-153-Y) to (3-156-Y), (3-166-Y), (3-168-Y), (3-173-Y), (3-177-Y), (3-180-Y) to (3-183-N), (3-185-Y), and (3-134-Y). Compounds represented by formulas (3-190-Y), (3-223-Y), (3-241-Y), (3-250-Y), (3-252-Y) to (3-254-Y), (3-501), (3-507), (3-508), (3-509), (3-513), (3-514), (3-519), (3-521), (3-538) to (3-547), or (3-600) to (3-620). Furthermore, Y is preferably -O-.

[0578] The anthracene compounds represented by formula (3-H) can be compounds with reactive groups at desired positions on the anthracene skeleton, as well as compounds with reactive groups at X, Ar, and other positions. 4 The compound having a reactive group in part of its structure, such as that of formula (A), is used as a starting material and manufactured by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in the said reactive compound include halogens or boric acids. For a specific manufacturing method, see, for example, the synthesis method described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725.

[0579] <fluorene compounds>

[0580] The compound represented by formula (4-H) essentially functions as the main component.

[0581] [Chemistry 123]

[0582]

[0583] In equation (4-H),

[0584] R 1 To R 10 Each of these groups is independently hydrogen, aryl, heteroaryl (the heteroaryl group may be bonded to the fluorene skeleton of formula (4-H) via a linker), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0585] Additionally, R 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 R 7 With R 8 Or R 9 With R 10 They can be independently bonded to form fused rings or spiro rings, and at least one hydrogen in the formed ring can be replaced by an aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a linker), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, and at least one hydrogen in these groups can be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl group, and moreover,

[0586] At least one hydrogen atom in the compound represented by formula (4-H) may be substituted by a halogen, a cyano group or a deuterium.

[0587] For details of the groups in the definition of formula (4-H), please refer to the description of polycyclic aromatic compounds of formula (1) above.

[0588] As R 1 To R 10 The alkenyl group in the text can be, for example, an alkenyl group with 2 to 30 carbon atoms, preferably an alkenyl group with 2 to 20 carbon atoms, more preferably an alkenyl group with 2 to 10 carbon atoms, and even more preferably an alkenyl group with 2 to 6 carbon atoms, particularly preferably an alkenyl group with 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0589] Furthermore, as specific examples of heteroaryl groups, monovalent groups can also be represented by removing any one hydrogen atom from compounds of the following formulas (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0590] [Chemistry 124]

[0591]

[0592] In equations (4-Arl) to (4-Ar5), Y 1 Each can be independently O, S, or NR, where R is phenyl, biphenyl, naphthyl, anthracene, or hydrogen.

[0593] At least one hydrogen atom in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl or butyl.

[0594] These heteroaryl groups can be bonded to the fluorene skeleton in formula (4-H) via a linker group. That is, the fluorene skeleton in formula (4-H) can be directly bonded to the heteroaryl group, or they can be bonded to each other via a linker group. Examples of such linker groups include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0595] Additionally, R in equation (4-H) 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 Or R 7 With R 8 They can be independently bonded and form fused rings, R 9 With R 10 They can bond and form helical rings. (From R) 1 To R 8 The formed fused ring is a ring formed by condensation on the benzene ring in formula (4-H), and is either an aliphatic ring or an aromatic ring. An aromatic ring is preferred; examples of structures containing the benzene ring in formula (4-H) include naphthalene rings or phenanthrene rings. (From R...) 9 With R 10 The resulting helical ring is a ring formed by a helical bond on a five-membered ring in formula (4-H), and is either an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples include fluorene rings.

[0596] The compound represented by formula (4-H) is preferably a compound represented by formula (4-H-1), formula (4-H-2), or formula (4-H-3), wherein R in formula (4-H) is a specific compound. 1 With R 2Compounds formed by the condensation of benzene rings through bonding, and R in formula (4-H) 3 With R 4 Compounds formed by the condensation of benzene rings through bonding, where R in formula (4-H) 1 To R 8 Compounds in which neither of the elements is bonded.

[0597] [Chemistry 125]

[0598]

[0599] R in equations (4-H-1), (4-H-2), and (4-H-3) 1 To R 10 The definition of R in equation (4-H) 1 To R 10 Similarly, R in equations (4-H-1) and (4-H-2) 11 To R 14 The definition is also the same as R in equation (4). 1 To R 10 same.

[0600] The compound represented by formula (4-H) is further preferably a compound represented by formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A), wherein R is a molecule in formula (4-H-1), formula (4-H-2), or formula (4-H-3), respectively. 9 With R 10 Compounds that form spirofluorene rings through bonding.

[0601] [Chemistry 126]

[0602]

[0603] R in equations (4-1A), (4-2A) and (4-3A) 2 To R 7 The definition of R corresponding to equations (4-1), (4-2), and (4-3) 2 To R 7 The same, and R in equations (4-1A) and (4-2A) 11 To R 14 The definition is also the same as R in equations (4-1) and (4-2). 11 To R 14 same.

[0604] In addition, all or part of the hydrogen in the compound represented by formula (4-H) may be replaced by halogen, cyano or deuterium.

[0605] More specific examples of fluorene compounds as the main body can be listed by the compounds represented by the following structural formulas. Furthermore, Me represents methyl.

[0606] [Chemistry 127]

[0607]

[0608] Dibenzo-p-ethyl System compounds>

[0609] dibenzo[a] as the main component The compounds are, for example, those represented by the following formula (5-H).

[0610] [Chemistry 128]

[0611]

[0612] In equation (5-H),

[0613] R 1 To R 16 Each of the following is independently hydrogen, aryl, or heteroaryl (the heteroaryl group can be linked to the dibenzo[5-H] in formula (5-H) via a linker). (Skeletal bond), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0614] Additionally, R 1 To R 16 The adjacent groups in the ring can bond to each other to form a fused ring, and at least one hydrogen in the formed ring can be replaced by an aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a linker), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, and at least one hydrogen in these groups can be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl group, and moreover,

[0615] At least one hydrogen atom in the compound represented by formula (5-H) may be substituted by a halogen, a cyano group or a deuterium.

[0616] For details of the groups in the definition of formula (5-H), please refer to the description of polycyclic aromatic compounds of formula (1) above.

[0617] As an alkenyl group in the definition of formula (5-H), examples include alkenyl groups with 2 to 30 carbon atoms, preferably alkenyl groups with 2 to 20 carbon atoms, more preferably alkenyl groups with 2 to 10 carbon atoms, and even more preferably alkenyl groups with 2 to 6 carbon atoms, particularly preferably alkenyl groups with 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0618] Furthermore, as specific examples of heteroaryl groups, monovalent groups can also be represented by removing any one hydrogen atom from compounds of the following formulas (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0619] [Chemistry 129]

[0620]

[0621] In equations (5-Ar1) to (5-Ar5), Y 1 Each can be independently O, S, or NR, where R is phenyl, biphenyl, naphthyl, anthracene, or hydrogen.

[0622] At least one hydrogen atom in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted by phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl or butyl.

[0623] These heteroaryl groups can bind to dibenzo[5-H] via a linker group. Skeletal bonding. That is, the dibenzo[5-H] in formula (5-H) The skeleton and the heteroaryl group can be directly bonded, or they can be bonded together via a linker group. Examples of such linker groups include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0624] The compound represented by formula (5-H) is preferably R. 1 R 4 R 5 R 8 R 9 R 12 R 13 and R 16 It is hydrogen. In this case, R in formula (5-H) 2 R 3 R 6 R 7 R 10R 11 R 14 and R 15 Preferably, it is a monovalent group that is independently hydrogen, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, or has a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5). (The monovalent group having said structure can be associated with dibenzo-p-phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O- via dibenzo-p-phenylene in formula (5-H).) (Skeleton bonds), methyl, ethyl, propyl, or butyl.

[0625] The compound represented by formula (5-H) is more preferably R. 1 R 2 R 4 R 5 R 7 R 8 R 9 R 10 R 12 R 13 R 15 and R 16 It is hydrogen. In this case, R in formula (5-H) 3 R 6 R 11 R 14 At least one (preferably one or two, more preferably one) is a monovalent group having a structure of formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5) having a mesostatic single bond, phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0626] The least one other (i.e., the position other than that replaced by the monovalent group having the structure) is hydrogen, phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl or butyl, wherein at least one of the hydrogens may be substituted by phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl or butyl.

[0627] Additionally, R in equation (5-H) 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15When selecting a monovalent group having a structure represented by formulas (5-Arl) to (5-Ar5), at least one hydrogen in the structure can react with R in formula (5-H). 1 To R 16 A single bond is formed by bonding any one of the bonds.

[0628] dibenzo[a] as the main component More specific examples of compounds can be listed by the following structural formulas. Furthermore, "tBu" represents tert-butyl.

[0629] [Chemistry 130]

[0630]

[0631] [Chemistry 131]

[0632]

[0633] The light-emitting layer material (both the host material and the dopant material) may also be used in the light-emitting layer material as a polymeric compound or a polymeric crosslink thereof, or as a suspended polymeric compound or a suspended polymeric crosslink thereof. The polymeric compound is obtained by polymerizing a reactive compound, which is a monomer formed by replacing reactive substituents in the light-emitting layer material (both the host material and the dopant material). The suspended polymeric compound is obtained by reacting a main-chain polymer with the reactive compound. The description of the reactive substituent in the above cases can be found in the polycyclic aromatic compounds represented by formula (1).

[0634] Details regarding the applications of this polymer compound and its crosslinked polymers will be described later.

[0635] <An Example of a Polymer Host Material>

[0636] [Chemistry 132]

[0637]

[0638] In formula (SPH-1),

[0639] MU is independently a divalent aromatic group, EC is independently a monovalent aromatic group, the two hydrogens in MU are replaced by EC or MU, and k is an integer from 2 to 50000.

[0640] More specifically,

[0641] MU can be independently arylene, heteroarylene, diarylenearylamino, diarylenearylboryl, oxaborane-diyl, or azaborane-diyl.

[0642] EC can be independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, respectively.

[0643] At least one hydrogen atom in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl groups.

[0644] k is an integer from 2 to 50000.

[0645] k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0646] At least one hydrogen in MU and EC in formula (SPH-1) may be substituted by an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the alkyl group may be substituted by -O- or -Si(CH3)2-. Any -CH2- in the alkyl group other than the -CH2- that is directly bonded to EC in formula (SPH-1) may be substituted by an aryl group having 6 to 24 carbon atoms. Any hydrogen in the alkyl group may be substituted by fluorine.

[0647] Examples of divalent derivatives of the following structures can be cited as MU (e.g., divalent groups represented by removing any two hydrogen atoms from any compound of the following structures, divalent groups consisting of two or more combinations of divalent groups represented by removing any two hydrogen atoms from any compound of the following structures, divalent groups obtained by substituting at least one hydrogen atom in these groups with an alkyl group, etc.).

[0648] [Chemistry 133]

[0649]

[0650] More specifically, examples of divalent bases represented by any of the following structures can be listed. In these, MU is bonded to other MU or EC at the * position.

[0651] [Chemistry 134]

[0652]

[0653] [Chemistry 135]

[0654]

[0655] [Chemistry 136]

[0656]

[0657] [Chemistry 137]

[0658]

[0659] [Chemistry 138]

[0660]

[0661] [Chemistry 139]

[0662]

[0663] [Chemistry 140]

[0664]

[0665] [Chemistry 141]

[0666]

[0667] [Chemistry 142]

[0668]

[0669] Furthermore, as an EC, one can exemplify any of the following structures representing a monovalent base. In these, the EC is bonded to MU at *.

[0670] [Chemistry 143]

[0671]

[0672] [Chemistry 144]

[0673]

[0674] From the viewpoint of solubility and coating film-forming properties, the compound represented by formula (SPH-1) preferably has 10% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 24 carbons, more preferably 30% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 18 carbons (branched alkyl groups with 3 to 18 carbons), and even more preferably 50% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 1 to 12 carbons (branched alkyl groups with 3 to 12 carbons). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10% to 100% of the total number of MUs (k) in the molecule has alkyl groups with 7 to 24 carbons, more preferably 30% to 100% of the total number of MUs (k) in the molecule having alkyl groups with 7 to 24 carbons (branched alkyl groups with 7 to 24 carbons).

[0675] A light-emitting layer containing auxiliary dopants and emission dopants

[0676] The light-emitting layer in an organic electroluminescent device may include a host compound as a first component, an auxiliary dopant (compound) as a second component, and an emitting dopant (compound) as a third component.

[0677] The polycyclic aromatic compounds of the present invention are also preferably used as emission dopants.

[0678] Thermally active delayed phosphors can be used as auxiliary dopants (compounds).

[0679] In the following description, organic electroluminescent elements that use thermally activated delayed fluorescence as an auxiliary dopant are sometimes referred to as "TAF elements" (Thermally Activated Delayed Fluorescence (TADF) Assisting Fluorescence elements).

[0680] In TAF elements, the “host compound” refers to a compound whose excited singlet energy level, determined by the shoulder peak on the short wavelength side of the fluorescence spectrum peak, is higher than that of the excited singlet energy level of the thermally active delayed phosphor (as the second component) and the emission dopant (as the third component).

[0681] The term "thermally active delayed fluorescence" refers to a compound that absorbs thermal energy, undergoes a reverse intersystem transition from a self-excited triplet state to an excited singlet state, and is radioactively deactivated from the excited singlet state, thereby emitting delayed fluorescence. "Thermally active delayed fluorescence" also includes cases where a higher-order triplet state is involved during the excitation process from the self-excited triplet state to the excited singlet state. Examples include papers by Monkman et al. from Durham University (Nature Communications, 7:13680, Digital Object Identifier (DOI): 10.1038 / ncomms13680), Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (AIST) (Science Advances, Sci. Adv. 2017; 3:e1603282), and Sato et al. from Kyoto University (Scientific Reports). Reports), 7:4820, DOI: 10.1038 / s41598-017-05007-7, and a conference presentation by Sato et al. of Kyoto University (98th Spring Meeting of the Chemical Society of Japan, Presentation No.: 2I4-15, Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using Diazaboranaphthoanthracene (DABNA) as the Luminescent Molecule, Graduate School of Engineering, Kyoto University), etc. In this invention, regarding samples containing the target compound, the target compound is determined to be a "thermally active delayed phosphor" based on the observation of a slow fluorescence component when the fluorescence lifetime is measured at 300K. Here, the slow fluorescence component refers to a component with a fluorescence lifetime of 0.1 μsec or more. The fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring device (Hamamatsu Photonics, C11367-01).

[0682] The polycyclic aromatic compounds of the present invention can function as emission dopants, and the "thermally active delayed phosphor" can function as auxiliary dopants to assist the luminescence of the polycyclic aromatic compounds of the present invention.

[0683] Figure 2 shows the energy level diagram of the emitting layer of a TAF device using a common fluorescent dopant as the emitting dopant (ED). In the figure, the ground state energy level of the host (H) is set as E(1, G), the excited singlet state energy level of the host derived from the shoulder peak of the short-wavelength side of the fluorescence spectrum is set as E(1, S, Sh), the excited triplet state energy level of the host derived from the shoulder peak of the short-wavelength side of the phosphorescence spectrum is set as E(1, T, Sh), the ground state energy level of the auxiliary dopant (AD) as the second component is set as E(2, G), and the excited singlet state energy level of the auxiliary dopant as the second component derived from the shoulder peak of the short-wavelength side of the fluorescence spectrum is set as E(2, S, Sh). The excited triplet energy level of the auxiliary dopant (as the second component), derived from the shoulder peak on the short wavelength side of the phosphorescence spectrum, is denoted as E(2, T, Sh). The ground state energy level of the emission dopant (as the third component) is denoted as E(3, G). The excited singlet energy level of the emission dopant (as the third component), derived from the shoulder peak on the short wavelength side of the fluorescence spectrum, is denoted as E(3, S, Sh). The excited triplet energy level of the emission dopant (as the third component), derived from the shoulder peak on the short wavelength side of the phosphorescence spectrum, is denoted as E(3, T, Sh). + The symbol represents a hole, e- represents an electron, and FRET represents fluorescence resonance energy transfer. In TAF devices, when using a common fluorescent dopant as the emitter (ED), the energy from the upconversion of the auxiliary dopant is transferred to the excited singlet level E(3, s, sh) of the emitter dopant, resulting in luminescence. However, a portion of the excited triplet level E(2, t, sh) on the auxiliary dopant moves to the excited triplet level E(3, t, sh) of the emitter dopant, or an intersystem crossing occurs on the emitter dopant from the self-excited singlet level E(3, s, sh) to the excited triplet level E(3, t, sh), followed by thermal deactivation to the ground state E(3, g). Due to this pathway, a portion of the energy is not used for luminescence, resulting in energy waste.

[0684] In contrast, the organic electroluminescent element of this embodiment can efficiently utilize the energy transferred from the auxiliary dopant to the emitting dopant for luminescence, thereby achieving high luminescence efficiency. This is presumed to be due to the following luminescence mechanism.

[0685] The preferred energy relationships in the organic electroluminescent element of this embodiment are shown in Figure 3. In the organic electroluminescent element of this embodiment, the compound containing boron atoms, which serves as the emission dopant, has a high excited triplet energy level E(3, T, Sh). Therefore, when the excited singlet energy upconverted by the auxiliary dopant is transferred to the excited triplet energy level E(3, T, Sh) via the emission dopant, it is also upconverted at the emission dopant or recovered to the excited triplet energy level E(2, T, Sh) at the auxiliary dopant (thermally active delayed phosphor). Therefore, the generated excitation energy can be used for luminescence without waste. In addition, it is contemplated that by distributing the upconversion and luminescence functions to the two molecules with prominent functions, the high-energy residence time is reduced, and the burden on the compound is reduced.

[0686] In this embodiment, known compounds can be used as the main compound, such as compounds having at least one of a carbazole ring and a furan ring. Preferably, compounds formed by bonding at least one of a furanyl group and a carbazole group with at least one of an aryl group and a heteroaryl group are used. Specific examples include mCP or mCBP.

[0687] From the viewpoint of promoting rather than hindering the generation of thermally activated delayed fluorescence (TADF) within the emissive layer, the excited triplet energy level E(1, T, Sh) of the host compound, derived from the shoulder peak on the short wavelength side of the phosphorescence spectrum peak, is preferably higher than the excited triplet energy levels E(2, T, Sh) and E(3, T, Sh) of the emitting dopant or auxiliary dopant that have the highest excited triplet energy level within the emissive layer. Specifically, compared to E(2, T, Sh) and E(3, T, Sh), the excited triplet energy level E(1, T, Sh) of the host compound is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Furthermore, a TADF-active compound may also be used in the host compound.

[0688] The host compound may be, for example, a compound represented by any of the formulas (H1), (H2) and (H3).

[0689] <Thermoactive Delayed Phosphors (Auxiliary Dopant)>

[0690] The thermally active delayed fluorescent (TADF) compounds used in TAF elements are preferably donor-acceptor type thermally active delayed fluorescent (DA-type TADF) compounds: they are designed to use electron-donating substituents called donors and electron-accepting substituents called acceptors to locally exist the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) in the molecule, so as to produce efficient reverse intersystem crossing.

[0691] In this specification, "electron-donating substituent" (donor) refers to the substituent and part of the structure that is locally present in the HOMO orbital of a thermally active delayed fluorophore molecule, and "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure that is locally present in the LUMO orbital of a thermally active delayed fluorophore molecule.

[0692] Generally, thermally active delayed-action fluorescent transluminometers using donors or acceptors exhibit high spin-orbit coupling (SOC) and low exchange interaction between HOMO and LUMO due to their structure, resulting in low ΔE. ST The small size allows for very fast reverse intersystem crossing speeds. On the other hand, thermally active delayed phosphors using donors or acceptors exhibit greater structural relaxation in the excited state (in a molecule, the stable structures in the ground and excited states differ; therefore, if a transition from the ground state to the excited state occurs through external stimulation, the subsequent structural change is to the stable structure in the excited state), thus providing a broad emission spectrum. However, this may reduce color purity when used as a luminescent material.

[0693] As a thermally active delayed phosphor in a TAF element, a compound in which the donor and acceptor are directly or via a spacer can be used, for example. The electron-donating group (donor-like structure) and electron-accepting group (acceptor-like structure) used in the thermally active delayed phosphor of the present invention can, for example, use the structures described in Chemistry of Materials, 2017, 29, 1946-1963. Examples of donor structures include: carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothiophenecarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazole, tetraphenylcarbazole diamine, phenoxazine, dihydrophenazine, phenthiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butyl)phenylamine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylphenyl-1,4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indoacridine, and diphenyl-dihydrodibenzodiazeline, etc. Examples of receptor-like structures include: sulfonyl diphenyl, benzophenone, phenylene bis(phenyl ketone), benzonitrile, isoniconitrile, o-phthalonitrile, isophthalonitrile, terephthalonitrile, benzotricarbonyl, triazole, oxazole, thiadiazole, benzothiazolium, benzobis(thiazolium), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoline, heptaazafinaene, thioxanone dioxide, dimethylanthrone, anthrone, 5H-cyclohepta[1,2-b:5,4-b′]bipyridine, fluorenedicarboxylon, triphenyltriazine, pyrazinedicarboxylon, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarboxylon, dibenzoquinoxalinedicarboxylon, bis(phenylsulfonyl)benzene, dimethylthioxanone dioxide, thiathronetetraoxide, and tri(dimethylphenyl)borane. In particular, the compound with thermally active delayed fluorescence in the TAF element is preferably a compound having at least one of the following as a partial structure: carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanol, benzonitrile, o-phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole and benzophenone.

[0694] The compound used as the second component of the emitting layer in a TAF element is a thermally active delayed phosphor, and preferably a compound whose emission spectrum at least partially overlaps with the absorption peak of the emission dopant. Hereinafter, compounds that can be used as the second component (thermally active delayed phosphor) of the emitting layer in a TAF element are illustrated. However, the compounds that can be used as thermally active delayed phosphors in a TAF element are not limited to the illustrated compounds below. In the following formulas, Me represents methyl, tBu represents tert-butyl, Ph represents phenyl, and the wavy line indicates the bond position.

[0695] [Chemistry 145]

[0696]

[0697] [Chemistry 146]

[0698]

[0699] [Chemistry 147]

[0700]

[0701] [Chemistry 148]

[0702]

[0703] [Chemistry 149]

[0704]

[0705] [Chemistry 150]

[0706]

[0707] [Chemistry 151]

[0708]

[0709] [Chemistry 152]

[0710]

[0711] [Chemistry 153]

[0712]

[0713] [Chemistry 154]

[0714]

[0715] [Chemistry 155]

[0716]

[0717] [Chemistry 156]

[0718]

[0719] [Chemistry 157]

[0720]

[0721] [Chemistry 158]

[0722]

[0723] [Chemistry 159]

[0724]

[0725] [Chemistry 160]

[0726]

[0727] [Chemistry 161]

[0728]

[0729] [Chemistry 162]

[0730]

[0731] [Chemistry 163]

[0732]

[0733] Furthermore, as a thermally active delayed phosphor, any compound represented by any of the following formulas (AD1), (AD2), and (AD3) may also be used.

[0734] [Chemistry 164]

[0735]

[0736] In the aforementioned formulas (AD1), (AD2), and (AD3),

[0737] M is independently a single bond, -O-, >N-Ar, or >CAr2, and from the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet and triplet energy levels, it is preferably a single bond, -O-, or >N-Ar. J is a spacer structure separating the donor and acceptor partial structures, and is independently an arylene group with 6 to 18 carbon atoms, and from the viewpoint of the magnitude of conjugation from the donor and acceptor partial structures, it is preferably an arylene group with 6 to 12 carbon atoms. More specifically, phenylene, methylphenylene, and dimethylphenylene can be listed. Q is independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the formed partial structure and the height of the excited singlet and triplet energy levels, =N- is preferred. Ar can be hydrogen, aryl (6-24 carbons), heteroaryl (2-24 carbons), alkyl (1-12 carbons), or cycloalkyl (3-18 carbons), respectively. From the viewpoint of the depth of the HOMO of the formed partial structure and the height of the excited singlet and triplet energy levels, it is preferred to be hydrogen, aryl (6-12 carbons), heteroaryl (2-14 carbons), alkyl (1-4 carbons), or cycloalkyl (6-10 carbons). More preferably, it is hydrogen, phenyl, tolyl, xylyl, mesitylelel, biphenyl, pyridyl, bipyridyl, triazine, carbazole, dimethylcarbazole, di-tert-butylcarbazole, benzimidazole, or phenylbenzimidazole. Hydrogen, phenyl, or carbazole is even more preferred. m is 1 or 2. n is an integer from 6 to (m), and from the viewpoint of steric hindrance, it is preferably an integer from 4 to (6 to (m)). Furthermore, at least one hydrogen atom in the compounds represented by the formulas may be substituted with halogen or deuterium.

[0738] More specifically, the compounds used as the second component in this embodiment are preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spirocyclic AC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0739] The compound used as the second component in this embodiment may be a donor-receptor type TADF compound represented by DA, in which an donor D is directly bonded to a receptor A or is bonded via a linker group. Compounds having a structure represented by the following formula (DAD1) with multiple donors D directly bonded to a receptor A or bonded via a linker group are preferred compounds that have better properties for organic electroluminescent elements.

[0740] (D1 -L 1 )nA 1 (DAD1)

[0741] Formula (DAD1) contains the compound represented by the following formula (DAD2).

[0742] D 2 -L 2 -A 2 -L 3 -D 3 (DAD2)

[0743] In equations (DAD1) and (DAD2), D 1 D 2 and D 3 Each donor base can be represented independently. The structure described above can be used as a donor base. A 1 and A 2 Each receptor group can be represented independently, and the structure described above can be used as the receptor group. L 1 L 2 and L 3 Each can be independently represented by a single bond or a conjugated linker. The conjugated linker is a spacer structure separating the donor and acceptor groups, preferably an arylene group with 6 to 18 carbon atoms, more preferably an arylene group with 6 to 12 carbon atoms. 1 L 2 and L 3 Preferably, each is independently phenylene, methylphenylene, or dimethylphenylene. In formula (DAD1), n ​​is 2 or more and represents an integer less than the maximum number of substitutions that Al can undergo. n can be selected, for example, in the range of 2 to 10, or in the range of 2 to 6. When n is 2, it represents the compound represented by formula (DAD2). n D 1 They can be the same or different, n L 1 They may be the same or different. As preferred examples of compounds represented by formulas (DAD1) and (DAD2), 2PXZ-TAZ or the following compounds can be listed, but the second component that may be used in this invention is not limited to these compounds.

[0744] [Chemistry 165]

[0745]

[0746] In this embodiment, the luminescent layer may be a single layer or may comprise multiple layers. Furthermore, the host compound, the thermally active delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained within the same layer, or each may be contained in at least one of multiple layers. The host compound, the thermally active delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the luminescent layer may each be one type, or a combination of multiple types; any of these are permissible. The auxiliary dopant and the emission dopant may be contained in the entire host compound serving as the matrix, or may be contained in a portion of the host compound serving as the matrix. The luminescent layer doped with the auxiliary dopant and the emission dopant may be formed by methods such as: a method of forming a film by a ternary co-evaporation method; a method of pre-mixing the host compound, the auxiliary dopant, and the emission dopant and then simultaneously evaporating; or a wet film-forming method by coating a composition (coating) for forming a luminescent layer prepared by dissolving the host compound, the auxiliary dopant, and the emission dopant in an organic solvent.

[0747] The amount of the host compound used varies depending on the type of host compound and can be determined based on its characteristics. The preferred amount of the host compound is 40% to 99.999% of the total mass of the material used in the luminescent layer, more preferably 50% to 99.99% of the total mass, and even more preferably 60% to 99.99% of the total mass. This range is preferred, for example, in terms of efficient charge transport and efficient energy movement toward the dopant.

[0748] The amount of auxiliary dopant (thermally active delayed phosphor) used varies depending on the type of auxiliary dopant, and can be determined based on the characteristics of the auxiliary dopant. The preferred basis for the amount of auxiliary dopant used is 1% to 60% of the total mass of the emitting layer material, more preferably 2% to 50% by mass, and even more preferably 5% to 30% by mass. If it falls within this range, it is preferred, for example, in terms of efficiently transferring energy to the emitting dopant.

[0749] The amount of emission dopant (a compound containing boron atoms) used varies depending on the type of emission dopant, and can be determined based on the characteristics of the emission dopant. The preferred amount of emission dopant used is 0.001% to 30% by mass of the total material used in the luminescent layer, more preferably 0.01% to 20% by mass, and even more preferably 0.1% to 10% by mass. Such a range is preferred, for example, in terms of preventing concentration quenching.

[0750] Regarding the prevention of concentration-induced extinction, it is preferable to use a low concentration of the emitting dopant. Regarding the efficiency of the thermally active delayed fluorescence mechanism, it is preferable to use a high concentration of the auxiliary dopant. Furthermore, regarding the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant, it is preferable that the concentration of the emitting dopant is low compared to the amount of the auxiliary dopant used.

[0751] 2-1-3. Substrate in organic electroluminescent devices

[0752] The substrate 101 is the support for the organic EL element 100, and can typically be made of quartz, glass, metal, plastic, etc. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and can be made of glass plates, metal plates, metal foils, plastic films, plastic sheets, etc. Preferably, it is made of glass plates or plates made of transparent synthetic resins such as polyester, polymethyl methacrylate, polycarbonate, or polysulfone. If it is a glass substrate, soda-lime glass or alkali-free glass can be used. Furthermore, the thickness only needs to be sufficient to maintain mechanical strength; for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, since the amount of dissolved ions from the glass should be minimal, alkali-free glass is preferred. Since soda-lime glass with a barrier coating such as SiO2 is also commercially available, soda-lime glass can be used. In addition, to improve gas barrier properties, a fine gas barrier film such as a silicon oxide film may be provided on at least one side of the substrate 101. When a plate, film or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101, it is particularly preferable to provide a gas barrier film.

[0753] 2-1-4. Anode in organic electroluminescent devices

[0754] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, when a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0755] Materials forming the anode 102 can include both inorganic and organic compounds. Examples of inorganic compounds include: metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (oxides of indium, oxides of tin, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, or NESA glass. Examples of organic compounds include: conductive polymers such as poly(3-methylthiophene), polypyrrole, and polyaniline. Furthermore, appropriate materials can be selected from those used as anodes in organic EL elements.

[0756] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of power consumption of the light-emitting element, low resistance is ideal. For example, if it is an ITO substrate with a resistance of 300Ω / □ or less, it functions as an electrode of the element, but nowadays substrates with a resistance of around 10Ω / □ are also available. Therefore, it is particularly ideal to use a low-resistance product, such as 100Ω / □ to 5Ω / □, preferably 50Ω / □ to 5Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50nm to 300nm.

[0757] 2-1-5. Hole injection layer and hole transport layer in organic electroluminescent devices

[0758] Hole injection layer 103 efficiently injects holes migrating from anode 102 into light-emitting layer 105 or hole transport layer 104. Hole transport layer 104 efficiently transports holes injected from anode 102, or holes injected from anode 102 via hole injection layer 103, to light-emitting layer 105. Hole injection layer 103 and hole transport layer 104 are formed by layering or mixing one or more hole injection / transport materials, or by a mixture of hole injection / transport materials and polymer binders. Alternatively, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[0759] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied. Ideally, it should have high hole injection efficiency and efficient transport of the injected holes. Therefore, a material with a low ionization potential, high hole mobility, and thus excellent stability, and which is less likely to generate impurities that could become traps during manufacturing and use, is preferred.

[0760] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from those compounds commonly used as hole charge transport materials in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples of these compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives, triarylamine derivatives (4,4′,4″-tris(N-carbazole)triphenylamine, polymers having aromatic tertiary amino groups on the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N′-diphenyl-N,N′-di(3-methylphenyl)-4,4′-diaminobiphenyl, N,N′-diphenyl-N,N′-dinaphthyl-4,4′-diaminobiphenyl, N,N′-diphenyl-N,N′-di(3-methylphenyl)-4,4′-diphenyl-1,1′-diamine, N,N′-dinaphthyl-N,N′-diphenyl-4,4′-diphenyl-1,1′-diamine, N 4 N 4′ -diphenyl-N 4 N 4′ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]-4,4′-diamine, N 4 N 4 N 4′ N 4′ -Tetra[1,1′-biphenyl]-4-yl-[1,1′-biphenyl]-4,4′-diamine, 4,4′,4″-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, 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 (e.g., 1,4,5,8,9,12-hexaazatriphenyl-2,3,6,7,10,11-hexacarbononitriles, etc.), porphyrin derivatives and other heterocyclic compounds, polysilanes, etc. In polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilanes having the aforementioned monomers on the side chains are preferred, but there is no particular limitation as long as the compound is a thin film required for the fabrication of the light-emitting element and can inject holes from the anode and thus transport holes.

[0761] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by their doping. The matrix material of such organic semiconductors contains compounds with good electron-donating or electron-accepting properties. For doping with electron-donating materials, strong electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (see, for example, the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo"). Beyer, T. Fritz, K. Leo, Appl. Phys. Letters, 73(22), 3202-3204 (1998) and the literature J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Letters, 73(6), 729-731 (1998)). They generate so-called holes through electron migration processes in electron-donating basic matter (hole-transporting matter). The conductivity of the basic matter varies considerably depending on the number and mobility of holes. As matrix materials with hole transport properties, such as benzidine derivatives (N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine, TPD, etc.) or starburst amine derivatives (4,4′,4″-tris(N,N-diphenylamino)triphenylamine, TDATA, etc.) or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc, etc.)) are known (Japanese Patent Application Publication No. 2005-167175).

[0762] The polycyclic aromatic compounds of the present invention can also be used as materials for forming hole injection layers or hole transport layers.

[0763] 2-1-6. The light-emitting layer in organic electroluminescent devices

[0764] An electron blocking layer can also be provided between the hole injection / transport layer and the light-emitting layer to prevent the diffusion of electrons from the light-emitting layer. The electron blocking layer can be formed using compounds represented by any of the formulas (H1), (H2), and (H3).

[0765] The polycyclic aromatic compounds of the present invention can be used as materials for forming electron blocking layers.

[0766] 2-1-7. Electron injection layer and electron transport layer in organic electroluminescent devices

[0767] The electron injection layer 107 efficiently injects electrons migrating from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 efficiently transports electrons injected from the cathode 108, or electrons injected from the cathode 108 via the electron injection layer 107, to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport / injection materials, or by forming a mixture of electron transport / injection materials and a polymer binder.

[0768] The electron injection / transport layer is a layer responsible for the injection and transport of electrons from the cathode. Ideally, it should have high electron injection efficiency and efficient transport of the injected electrons. Therefore, materials with high electron affinity and high electron mobility, resulting in excellent stability and minimizing the formation of impurities that could become traps during manufacturing and use, are preferred. However, considering the balance between hole and electron transport, when the primary function is to efficiently prevent unrecombined holes from the anode from flowing to the cathode, even materials with lower electron transport capabilities can achieve the same effect of improving luminous efficiency as materials with high electron transport capabilities. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that efficiently prevents hole migration.

[0769] The material (electron transport material) used to form the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds commonly used as electron transport compounds in photoconductive materials, and known compounds used in electron injection layers and electron transport layers of organic EL elements.

[0770] The materials used in the electron transport layer or electron injection layer are preferably compounds containing at least one of the following: compounds containing an aromatic ring or heteroaromatic ring comprising one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused-ring derivatives; and metal complexes with electron-accepting nitrogen. Specifically, examples include: fused-ring aromatic ring derivatives such as naphthalene and anthracene; styryl aromatic ring derivatives represented by 4,4′-bis(diphenylvinyl)biphenyl; violet ketone derivatives; coumarin derivatives; naphthalenedicarboximide derivatives; quinone derivatives such as anthraquinone or biphenylquinone; phosphorus oxide derivatives; aryl nitrile derivatives; and indole derivatives. Examples of metal complexes with electron-accepting nitrogen include: hydroxyazole complexes such as hydroxyphenyloxazole complexes; methylimine complexes; cycloheptatrienolone metal complexes; flavonol metal complexes; and benzoquinone metal complexes. These materials can be used alone or in combination with different materials.

[0771] In addition, specific examples of other electron-transfer compounds include: pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, phenanthroline derivatives, violacetone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]benzylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium complexes, pyrazole derivatives, and perfluorinated benzylene. Benzyl derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2′-bis(benzo[h]quinoline-2-yl)-9,9′-spirodifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4′-(2,2′:6′,2″-terpyridyl))benzene, naphthidine derivatives (bis(1-naphthyl)-4-(1,8-naphthidyl-2-yl)phenylphosphine oxide, etc.), aldehyde azo derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyrene derivatives, thiophene derivatives, and azoline derivatives, etc.

[0772] Alternatively, metal complexes with electron-accepting nitrogen can be used, such as hydroxyquinoline metal complexes or hydroxyphenyloxazole complexes, methylimine complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0773] The material can be used alone or in combination with different materials.

[0774] The preferred materials are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzo[a]thiazole derivatives, thiophene derivatives, and azoline derivatives.

[0775] The polycyclic aromatic compounds of the present invention can also be used as materials for forming electron injection layers or electron transport layers.

[0776] The electron transport layer or electron injection layer may also contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. The reducing substance can be any substance possessing a certain reducing property, and for example, preferably at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[0777] Preferred reducing agents include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV–2.5 eV), or Ba (work function 2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Among these, K, Rb, or Cs are more preferred as alkali metals, Rb or Cs are more preferred, and Cs is most preferred. These alkali metals have particularly high reducing power, and by adding a relatively small amount of these alkali metals to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved. Furthermore, combinations of two or more of these alkali metals are preferred as reducing agents with a work function of 2.9 eV or less, and combinations containing Cs are particularly preferred, such as Cs with Na, Cs with K, Cs with Rb, or Cs with Na and K. By including Cs, the reducing ability can be effectively utilized, and by adding it to the material forming the electron transport layer or electron injection layer, the luminous brightness or lifetime of organic EL devices can be improved.

[0778] 2-1-8. Cathode in Organic Electroluminescent Devices

[0779] The cathode 108 functions to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0780] The material forming the cathode 108 is not particularly limited if it is a substance capable of efficiently injecting electrons into the organic layer, and the same material as the material forming the anode 102 can be used. Preferred materials include 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 alloys, magnesium-indium alloys, lithium fluoride / aluminum and other aluminum-lithium alloys, etc.). To improve electron injection efficiency and thus enhance device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, generally, these low work function metals are unstable in the atmosphere in most cases. To improve this, methods such as doping the organic layer with trace amounts of lithium, cesium, or magnesium and using a highly stable electrode are known. Inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used as other dopants. However, these are not the only options.

[0781] Furthermore, the following are preferred examples: To protect the electrodes, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys of these metals, as well as inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers are layered. There are no particular restrictions on the methods used to fabricate these electrodes, as long as they are methods that achieve conductivity, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0782] 2-1-9. Adhesives that can be used in each layer

[0783] The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer can be formed individually or dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate resins, acrylonitrile butadiene styrene (ABS) resins, and polyurethane resins, or curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins.

[0784] 2-1-10. Fabrication method of organic electroluminescent elements

[0785] The layers constituting an organic electroluminescent (EL) element can be formed by depositing thin films of the materials to be constituting each layer using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, inkjet printing, spin coating, casting, and coating. The film thickness of each layer formed by these methods is not particularly limited and can be appropriately set according to the properties of the material, but is typically in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a crystal oscillating film thickness measuring device. When using vapor deposition for thin film formation, the vapor deposition conditions vary depending on the type of material, the target crystalline structure of the film, and the association structure. The preferred vapor deposition conditions are typically a boat heating temperature of +50°C to +400°C and a vacuum degree of 10... -6 Pa~10 -3 The Pa, evaporation rate (0.01 nm / s to 50 nm / s), substrate temperature (-150℃ to +300℃), and film thickness (2 nm to 5 μm) are appropriately set within the range.

[0786] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer containing a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. On a suitable substrate, an anode is fabricated by forming a thin film of an anode material using a vapor deposition method or the like. Then, thin films of a hole injection layer and a hole transport layer are formed on the anode. A thin film containing a host material and a dopant material is co-deposited on the thin film to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on the light-emitting layer. Finally, a thin film containing a cathode material is formed using a vapor deposition method or the like to form a cathode, thereby obtaining the target organic EL device. Alternatively, in the fabrication of the organic EL device, the fabrication order can be reversed, and the device can be fabricated in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0787] When a DC voltage is applied to the organic EL element obtained in the manner described above, it is sufficient to apply the voltage with the anode as the positive polarity and the cathode as the negative polarity. If a voltage of approximately 2V to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, the organic EL element also emits light when a pulsed current or alternating current is applied. Moreover, the waveform of the applied alternating current can be arbitrary.

[0788] 2-1-11. Examples of applications of organic electroluminescent elements

[0789] Organic EL elements can also be used in display devices or lighting devices.

[0790] Display devices or lighting devices including organic EL elements can be manufactured by known methods such as connecting organic EL elements with known driving devices, and can be driven by known driving methods such as DC driving, pulse driving, AC driving, etc.

[0791] Examples of display devices include: panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Application Publication No. 10-335066, Japanese Patent Application Publication No. 2003-321546, and Japanese Patent Application Publication No. 2004-281086). Furthermore, examples of display methods include matrix and / or segmented display methods. Moreover, matrix display and segmented display can coexist on the same panel.

[0792] In a matrix, pixels for display are arranged two-dimensionally in a grid or mosaic pattern, so that text or images are displayed by the collection of pixels. The shape or size of the pixels is determined by the application. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with one side less than 300μm are usually used. In the case of large displays such as display panels, pixels with one side in the millimeter range are used. In the case of monochrome display, pixels of the same color are simply arranged. In the case of color display, red, green, and blue pixels are displayed side by side. Typical patterns in these cases are triangular and striped. Moreover, the driving method of the matrix can be either a linear-sequential driving method or an active matrix. Linear driving has the advantage of simple structure, but when considering operating characteristics, sometimes an active matrix is ​​superior. Therefore, the driving method also needs to be selected according to the application.

[0793] In the segmented method (type), a pattern is formed to display pre-determined information, and the determined area is illuminated. Examples include: time or temperature displays in digital clocks or thermometers, operating status displays in audio equipment or induction cookers, and panel displays in automobiles.

[0794] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Application Publication Nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are primarily used to improve the visibility of display devices that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs. In particular, for backlights used in personal computers where thinning is becoming a problem in liquid crystal displays, backlights using organic EL elements are thin and lightweight, considering that existing methods are difficult to make thin due to the inclusion of fluorescent lamps or light guide plates.

[0795] 2-2. Other organic devices

[0796] In addition to being used in the aforementioned organic electroluminescent elements, the polycyclic aromatic compounds of the present invention can also be used in the fabrication of organic electroluminescent transistors or organic thin-film solar cells.

[0797] An organic field-effect transistor (FET) is a transistor that controls current by using an electric field generated by a voltage input. In addition to source and drain electrodes, it also has a gate electrode. An organic field-effect transistor works as follows: when a voltage is applied to the gate electrode, an electric field is generated, which can arbitrarily block the flow of electrons (or holes) between the source and drain electrodes to control the current. Compared to a single transistor (bipolar transistor), FETs are easier to miniaturize and are commonly used as components in integrated circuits.

[0798] Regarding the structure of an organic field-effective transistor, generally, the source electrode and drain electrode are simply provided in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and the gate electrode is provided in contact with an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following.

[0799] (1) Substrate / Gate electrode / Insulator layer / Source electrode and drain electrode / Organic semiconductor active layer

[0800] (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode and drain electrode

[0801] (3) Substrate / Organic semiconductor active layer / Source electrode and drain electrode / Insulator layer / Gate electrode

[0802] (4) Substrate / Source and Drain Electrodes / Organic Semiconductor Active Layer / Insulator Layer / Gate Electrode

[0803] The organic field-active transistor constructed in the manner described above can be used as a pixel driving switching element in an active matrix driven liquid crystal display or an organic electroluminescent display.

[0804] Organic thin-film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode, such as ITO, are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention, depending on their physical properties, can be used as materials for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer. In organic thin-film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the aforementioned layers, organic thin-film solar cells may also appropriately include hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. In organic thin-film solar cells, known materials used in organic thin-film solar cells can be appropriately selected and combined.

[0805] 3. Wavelength conversion materials

[0806] The polycyclic aromatic compounds of this invention can be used as wavelength conversion materials.

[0807] Currently, research is actively underway to apply multicolor technology based on color conversion to liquid crystal displays (LCDs), organic EL displays, and lighting. Color conversion refers to converting light emitted from a light source into light with longer wavelengths, such as converting ultraviolet or blue light into green or red light. By film-coating a wavelength conversion material with this color conversion function, for example, and combining it with a blue light source, it is possible to extract the three primary colors—blue, green, and red—from the blue light source, i.e., extract white light. Using this white light source, which combines a blue light source with a wavelength conversion film with color conversion function, as a light source unit, and combining it with a liquid crystal driving section and a color filter, a full-color display can be fabricated. Alternatively, without a liquid crystal driving section, it can be used directly as a white light source, for example, as a white light source for light-emitting diode (LED) lighting. Furthermore, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green and red light, a full-color organic EL display without a metal mask can be fabricated. Furthermore, by using blue microLEDs as a light source and combining them with wavelength conversion films that convert blue light into green and red light, it is possible to produce low-cost full-color microLED displays.

[0808] The polycyclic aromatic compounds of the present invention can be used as the wavelength conversion material. Wavelength conversion materials containing the polycyclic aromatic compounds of the present invention can be used to convert ultraviolet light or light from light sources or light-emitting elements that generate shorter wavelength blue light into blue or green light with high color purity suitable for use in display devices (display devices utilizing organic EL elements or liquid crystal display devices). The converted color can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compounds of the present invention, the adhesive resin used in the wavelength conversion composition described later, etc. The wavelength conversion material is prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, the wavelength conversion composition can also be used to form a wavelength conversion film.

[0809] In addition to the polycyclic aromatic compounds of the present invention, the wavelength conversion composition may also contain a binder resin, other additives, and a solvent. As a binder resin, for example, the resin described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 may be used. As other additives, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 may be used. As a solvent, refer to the description of the solvent contained in the composition for forming the light-emitting layer.

[0810] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for producing the wavelength conversion layer from the wavelength conversion composition, known film formation methods can be referenced. The wavelength conversion film may contain only a wavelength conversion layer formed from a composition comprising the polycyclic aromatic compounds of the present invention, or it may contain other wavelength conversion layers (e.g., a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may also include a substrate layer or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0811] [Example]

[0812] The present invention will be described in more detail below through embodiments, but the present invention is not limited to these embodiments.

[0813] Furthermore, in the reaction formulas of the examples, Me represents methyl, Et represents ethyl, tBu represents tert-butyl, and iPr represents isopropyl.

[0814] Synthesis example (1):

[0815] Synthesis of compound (1-1)

[0816] [Chemistry 166]

[0817]

[0818] First process

[0819] Under nitrogen atmosphere, compound (T-1) (13.0 g), compound (T-2) (17.8 g), sodium tert-butoxy (NaOtBu, 4.8 g), Pd-132 (trade name: dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium, 0.41 g), and xylene (140 ml) were placed in a reactor and heated to reflux. After cooling the reaction mixture to room temperature, the aqueous layer was extracted with toluene. The mixed organic layers were washed with water and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to obtain compound (T-3) (25.6 g).

[0820] Synthesis of compound (1-1)

[0821] Under nitrogen atmosphere and at -30°C, a 1.6M solution of tert-butyllithium pentane (tBuLi, 10ml) was added to a flask containing compound (T-3) (8.0g) and tert-butylbenzene (tBu-benzene, 60ml). After the addition was complete, the temperature was raised to 60°C and stirred for 2 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -30°C and boron tribromide (4.0g) was added. The temperature was raised to room temperature and stirred for 0.5 hours. Subsequently, the mixture was cooled again to 0°C and N,N-diisopropylethylamine (EtN(iPr)2, 2.8ml) was added. The mixture was stirred at room temperature until heating was complete, then the temperature was raised to 120°C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and sodium acetate aqueous solution cooled in an ice bath and heptane were added sequentially for separation. Next, after purification using a silica gel short-path column (developing solvent: toluene), the solid obtained by vacuum distillation of the solvent is dissolved in toluene, and heptane is added for reprecipitation to obtain the compound represented by formula (1-1).

[0822] 1 H-NMR (CDCl3): δ=9.04 (s, 1H), 8.99 (s, 1H), 7.66 (d, 2H), 7.53 (d, 1H), 7.48 (dd , 1H), 7.35(d, 2H), 7.29(t, 1H), 7.27-7.25(m, 2H), 7.02(d, 2H), 7.00(d, 2H), 6 .93(dd, 1H), 6.65(d, 1H), 5.91(s, 1H), 5.89(s, 1H), 5.73(s, 2H), 2.09(s, 3H), 1.90(s, 6H), 1.51(s, 9H), 1.46(s, 9H), 1.38(s, 9H), 1.30(s, 9H), 1.26(s, 18H).

[0823] Synthesis Example (2): Synthesis of compounds (1-7)

[0824] Except for changing compound (T-3) to compound (T-3-7), compounds (1-7) were obtained using the same sequence as in Synthesis Example 1.

[0825] The m / z (M+H) was determined by mass spectrometry (MS) using matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOFMS) and was found to be 940.67.

[0826] [Chemistry 167]

[0827]

[0828] Synthesis Example (3): Synthesis of compounds (1-10)

[0829] Except that compound (T-3) was changed to compound (T-3-10), compound (1-10) was obtained using the same sequence as in Synthesis Example 1.

[0830] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1072.76.

[0831] [Chemistry 168]

[0832]

[0833] Synthesis Example (4): Synthesis of Compounds (1-42)

[0834] Except for changing compound (T-3) to compound (T-3-42), compound (1-42) was obtained using the same sequence as in Synthesis Example 1.

[0835] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1054.72.

[0836] [Chemistry 169]

[0837]

[0838] Synthesis Example (5): Synthesis of Compound (1-350)

[0839] Except for changing compound (T-3) to compound (T-3-350), compound (1-350) was obtained using the same sequence as in Synthesis Example 1.

[0840] The m / z(M+H) value was obtained using MS (MALDI-TOFMS) = 1152.73.

[0841] 1H-NMR (CDCl3): δ = 8.7 (s, 1H), 7.9 (d, 1H), 7.7 (d, 2H), 7.5 (d, 1H), 7.5 ~ 7.4 (m , 7H), 7.1~7.0(m, 2H), 7.0(m, 3H), 7.0(dd, 1H), 6.9~6.8(m, 2H), 6.6(d, 1H), 6 .2(d,1H),6.0(d,1H),6.0(d,1H),5.9(s,1H),1.9(s,3H),1.9(s,3H),1.5(s , 9H), 1.4(s, 9H), 1.4(s, 9H), 1.3(s, 9H), 1.1(s, 9H), 1.1(s, 9H), 1.0(s, 9H).

[0842] [Chemistry 170]

[0843]

[0844] Synthesis Example (6): Synthesis of Compound (1-365)

[0845] Except that compound (T-3) was changed to compound (T-3-365), compound (1-365) was obtained using the same sequence as in Synthesis Example 1.

[0846] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1148.79.

[0847] [Chemistry 171]

[0848]

[0849] Synthesis Example (7): Synthesis of Compound (1-367)

[0850] Except for changing compound (T-3) to compound (T-3-367), compound (1-367) was obtained using the same sequence as in Synthesis Example 1.

[0851] The m / z (M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1038.68.

[0852] [Chemistry 172]

[0853]

[0854] Synthesis Example (8): Synthesis of Compound (1-369)

[0855] Except for changing compound (T-3) to compound (T-3-369), compound (1-369) was obtained using the same sequence as in Synthesis Example 1.

[0856] 1 H-NMR (CDCl3): δ = 9.00 (br, 1H), 8.89 (br, 1H), 7.60-7.50 (m, 2H), 7.39 (d, 1H), 7.37 (d, 1H) ), 7.33-7.27(m, 2H), 7.11(d, 2H), 7.07(d, 1H), 6.99(br, 2H), 6.96-6.89(m, 2H), 6.60(br, 1H), 6.23(dd, 1H), 6.09(br, 1H), 5.87(br, 1H), 5.48(br, 1H), 2.21-2.15(m, 3H), 1.97(dd, 6H), 1.91-1.68(m, 26H), 1.53(s, 6H), 1.40(s, 6H), 1.25(s, 6H), 1.09(s, 6H), 0.93(s, 9H).

[0857] [Chemistry 173]

[0858]

[0859] Synthesis Example (9): Synthesis of Compound (1-370)

[0860] Except for changing compound (T-3) to compound (T-3-370), compound (1-370) was obtained using the same sequence as in Synthesis Example 1.

[0861] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1148.79.

[0862] [Chemistry 174]

[0863]

[0864] Synthetic Example (10): Synthesis of Compound (1-374)

[0865] Except for changing compound (T-3) to compound (T-3-374), compound (1-374) was obtained using the same sequence as in Synthesis Example 1.

[0866] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1116.73.

[0867] 1H-NMR (CDCl3): δ=8.97 (br, 1H), 8.79 (br, 1H), 7.70 (br, 1H), 7.61-7.48 (m, 2H), 7 .42~7.26(m,5H),7.17(d,1H),7.14-7.08(m,4H),7.05-6.96(m,4H),6.95-6.88(m , 2H), 6.61 (br, 1H), 6.26-5.47 (m, 4H), 2.22-2.16 (m, 3H), 1.97 (d, 6H), 1.91-1.61 (m, 16H), 1.48-1.42 (m, 15H), 1.11 (s, 9H), 1.09 (s, 3H), 1.07 (s, 3H), 0.92 (s, 9H).

[0868] [Chemistry 175]

[0869]

[0870] Synthetic Example (11): Synthesis of Compound (1-380)

[0871] Except that compound (T-3) was changed to compound (T-3-380), compound (1-380) was obtained using the same sequence as in Synthesis Example 1.

[0872] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1128.82.

[0873] [Chemistry 176]

[0874]

[0875] Synthesis Example (12): Synthesis of Compound (1-381)

[0876] Except for changing compound (T-3) to compound (T-3-381), compound (1-381) was obtained using the same sequence as in Synthesis Example 1.

[0877] The m / z(M+H) value was obtained by MS measurement (MALDI-TOF MS) = 960.64.

[0878] 1H-NMR (CDCl3): δ=9.00 (br, 1H), 8.89 (br, 1H), 7.64-7.49 (m, 2H), 7.44-7.32 ( m, 4H), 7.31-7.27 (m, 2H), 7.14 (d, 2H), 7.06 (d, 1H), 7.01 (d, 2H), 6.96-6.89 (m , 2H), 6.60 (br, 1H), 6.26-5.50 (m, 4H), 1.87 (br, 6H), 1.82-1.68 (m, 8H), 1.57- 1.47(m, 6H), 1.40(s, 9H), 1.40(s, 6H), 1.24(s, 6H), 1.10(s, 6H), 0.93(s, 9H).

[0879] [Chemistry 177]

[0880]

[0881] Synthetic Example (13): Synthesis of Compound (1-382)

[0882] Except for changing compound (T-3) to compound (T-3-382), compound (1-382) was obtained using the same sequence as in Synthesis Example 1.

[0883] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1092.73.

[0884] 1 H-NMR (CDCl3): δ = 8.87 (br, 1H), 8.82 (br, 1H), 7.57 (d, 1H), 7.51 (m, 1H), 7.47-7.40 (m, 3H), 7 .38-7.32(m,2H),7.29(br,1H),7.15(dd,2H),7.07(br,1H),7.01(d,1H),6.99-6.87(m,6H), 6.61 (br, 1H), 6.22-6.17 (m, 1H), 6.01 (br, 2H), 5.59 (br, 1H), 1.92-1.64 (m, 14H), 1.53 (s, 6H ), 1.42(s, 9H), 1.40(s, 6H), 1.25(s, 6H), 1.11(s, 9H), 1.10(s, 3H), 1.09(s, 3H), 0.94(s, 9H).

[0885] [Chemistry 178]

[0886]

[0887] Synthetic Example (14): Synthesis of Compound (1-383)

[0888] Except for changing compound (T-3) to compound (T-3-383), compound (1-383) was obtained using the same sequence as in Synthesis Example 1.

[0889] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1128.82.

[0890] [Chemistry 179]

[0891]

[0892] Synthetic Example (15): Synthesis of Compound (1-386)

[0893] Except for changing compound (T-3) to compound (T-3-386), compound (1-386) was obtained using the same sequence as in Synthesis Example 1.

[0894] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1062.68.

[0895] [Chemistry 180]

[0896]

[0897] Synthetic Example (16): Synthesis of Compound (1-435)

[0898] Except that compound (T-3) was changed to compound (T-3-435), compound (1-435) was obtained using the same sequence as in Synthesis Example 1.

[0899] The m / z(M+H) value was obtained by MS measurement (MALDI-TOF MS) = 991.54.

[0900] [Chemistry 181]

[0901]

[0902] Synthesis Example (17): Synthesis of Compound (1-436)

[0903] Except that compound (T-3) was changed to compound (T-3-436), compound (1-436) was obtained using the same sequence as in Synthesis Example 1.

[0904] 1H-NMR (CDCl3): δ=8.85 (s, 1H), 8.19 (d, 1H), 8.07 (t, 1H), 7.95 (d, 1H), 7.67 (dd, 1H), 7. 56(dq, 2H), 7.49(d, 1H), 7.45(dd, 1H), 7.38-7.36(m, 3H), 7.24(q, 1H), 7.15(dd, 1H), 6 .82(d,1H),6.76(s,1H),6.31(s,1H),6.27(s,1H),6.15(s,1H),1.89(dd,6H),1.83(d, 4H), 1.48(s, 9H), 1.44(d, 6H), 1.33(s, 9H), 1.30-1.27(m, 6H), 1.13(s, 9H), 0.90(s, 9H)

[0905] [Chemistry 182]

[0906]

[0907] Synthetic Example (18): Synthesis of Compound (1-450)

[0908] Except for changing compound (T-3) to compound (T-3-450), compound (1-450) was obtained using the same sequence as in Synthesis Example 1.

[0909] The m / z(M+H) value was obtained by MS determination (MALDI-TOF MS) = 961.53.

[0910] [Chemistry 183]

[0911]

[0912] Synthetic Example (19): Synthesis of Compound (1-456)

[0913] Except that compound (T-3) was changed to compound (T-3-456), compound (1-456) was obtained using the same sequence as in Synthesis Example 1.

[0914] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1017.59.

[0915] [Chemistry 184]

[0916]

[0917] Synthetic Example (20): Synthesis of Compound (1-465)

[0918] Except that compound (T-3) was changed to compound (T-3-465), compound (1-465) was obtained using the same sequence as in Synthesis Example 1.

[0919] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1289.88.

[0920] [Chemistry 185]

[0921]

[0922] Synthetic Example (21): Synthesis of Compound (1-466)

[0923] Except that compound (T-3) was changed to compound (T-3-466), compound (1-466) was obtained using the same sequence as in Synthesis Example 1.

[0924] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1315.90.

[0925] [Chemistry 186]

[0926]

[0927] Synthesis Example (22): Synthesis of Compound (1-467)

[0928] Except that compound (T-3) was changed to compound (T-3-467), compound (1-467) was obtained using the same sequence as in Synthesis Example 1.

[0929] The m / z(M+H) value was obtained by MS measurement (MALDI-TOF MS) = 1341.91.

[0930] [Chemistry 187]

[0931]

[0932] Synthetic Example (23): Synthesis of Compound (1-480)

[0933] Except for changing compound (T-3) to compound (T-3-480), compound (1-480) was obtained using the same sequence as in Synthesis Example 1.

[0934] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1080.60.

[0935] [Chemistry 188]

[0936]

[0937] Other compounds of the present invention can be synthesized by appropriately changing the compounds of the raw materials and by using the method according to the synthesis example described above.

[0938] <Evaluation Methods for Basic Physical Properties>

[0939] Sample preparation

[0940] When evaluating the absorption and luminescence properties (fluorescence and phosphorescence) of a compound, there are cases where the compound is dissolved in a solvent and the evaluation is performed in the solvent, and cases where the evaluation is performed in a thin film state. Furthermore, when evaluating in a thin film state, there are cases where the compound is thin-filmed only to correspond to its intended use in an organic EL element, and cases where the compound is dispersed in a suitable matrix material and thin-filmed for evaluation. Here, a thin film obtained by vapor deposition of only the compound is called a "separate film," and a thin film obtained by coating a solution containing the compound and the matrix material and then drying it is called a "coating film."

[0941] Commercially available PMMA (polymethyl methacrylate) or similar materials can be used as the matrix material. In this embodiment, PMMA and the compound being evaluated are dissolved in toluene, and a thin film is formed on a transparent quartz substrate (10 mm × 10 mm) using spin coating to prepare a sample.

[0942] Fluorescence spectroscopy measurements were performed on compounds represented by formulas (1-1), (1-7), (1-10), (1-350), (1-369), and (1-380). Each compound (1% by mass relative to PMMA) and PMMA were dissolved in toluene, then spin-coated onto a substrate (quartz substrate, 10 mm × 10 mm), dried, and a thin film substrate was formed. Excitation was performed at an excitation wavelength of 380 nm, and the emission wavelength and the half-width at half-maximum (WHM) of the emission spectrum were measured (calculated as the width between wavelengths above and below the maximum emission wavelength where its intensity is 50%). The results are shown in Table 1 below.

[0943] [Table 1]

[0944]

[0945] As can be seen from the results in Table 1, the compounds of the present invention have a small half-width, enabling them to emit light with high color purity.

[0946] In addition, thin film samples with the matrix material as the main compound were prepared in the following manner.

[0947] A transparent quartz support substrate (10mm × 10mm × 1.0mm) is fixed onto the substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.). After mounting a molybdenum vapor deposition boat containing the main compound and a molybdenum vapor deposition boat containing the dopant material, the vacuum chamber is reduced to 5 × 10⁻⁶ mm. -4 Next, a vapor deposition boat containing the host compound and a vapor deposition boat containing the dopant material are simultaneously heated to perform co-deposition, thereby achieving an appropriate film thickness for both the host compound and the dopant material, to form a mixed thin film (sample) of the host compound and the dopant material. Here, the vapor deposition rate is controlled according to the set mass ratio of the host compound to the dopant material.

[0948] Evaluation of absorption and luminescence properties

[0949] The absorption spectra of the samples were measured using a UV-Vis-NIR spectrophotometer (Shimadzu Corporation, UV-2600). Additionally, the fluorescence or phosphorescence spectra of the samples were measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0950] For fluorescence spectroscopy measurements, photoluminescence is measured by excitation at room temperature with an appropriate excitation wavelength. For phosphorescence spectroscopy measurements, measurements are performed using the accompanying cooling unit while the sample is immersed in liquid nitrogen (temperature 77 K). To observe the phosphorescence spectrum, an optical chopper is used to adjust the delay time from the start of excitation light irradiation until the start of the measurement. Regarding the sample, photoluminescence is measured by excitation at an appropriate excitation wavelength.

[0951] In addition, the luminescent quantum yield (PLQY) was measured using an absolute PL quantum yield measurement device (manufactured by Hamamatsu Photonics Co., Ltd., C9920-02G).

[0952] Next, the basic physical property evaluation of the polycyclic aromatic compounds of the present invention will be described.

[0953] Evaluation of fluorescence lifetime (delayed fluorescence)

[0954] Fluorescence lifetime was measured at 300 K using a fluorescence lifetime measurement apparatus (manufactured by Hamamatsu Photonics, Inc., C11367-01). Specifically, the fast-emission and slow-emission components at the maximum emission wavelength measured with an appropriate excitation wavelength were observed. In the fluorescence lifetime measurement of general organic EL materials emitting fluorescence at room temperature, the triplet component is deactivated by heat, and thus the slow-emission component involving the phosphorescent triplet component is hardly observed. The observation of a slow-emission component in the evaluated compound indicates that the triplet energy with a long excitation lifetime is transferred to a singlet energy through thermal activation and is thus observed in the form of delayed fluorescence.

[0955] Calculation of bandgap (Eg)

[0956] The value is calculated using Eg = 1240 / A based on the long wavelength end A (nm) of the absorption spectrum obtained by the method described above.

[0957] Measurement of ionization potential (Ip)

[0958] A transparent support substrate (28mm × 26mm × 0.7mm) coated with ITO (indium tin oxide) was fixed onto the substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.). After mounting a molybdenum vapor deposition boat containing the target compound, the vacuum chamber was depressurized to 5 × 10⁻⁵. -4 Pa. Next, the vapor deposition vessel is heated to evaporate the target compound, forming a single film of the target compound (undoped film).

[0959] Using the obtained individual membranes as samples, the ionization potential of the target compounds was determined using a photoelectron spectrometer (Sumitomo Heavy Industries PYS-201).

[0960] Calculation of electron affinity (Ea)

[0961] Electron affinity can be estimated based on the difference between the ionization potential measured using the method and the bandgap calculated using the method.

[0962] Determination of excited singlet level E(S, Sh) and excited triplet level E(T, Sh)

[0963] For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77 K using the second absorption peak on the long wavelength side of the self-absorption spectrum as the excitation light, and the excited singlet energy level E(S, Sh) is determined based on the shoulder peak on the short wavelength side of the fluorescence spectrum peak.

[0964] In addition, for a single film of the target compound formed on a glass substrate, the phosphorescence spectrum was observed at 77 K using the second absorption peak on the long wavelength side of the self-absorption spectrum as the excitation light, and the excited triplet energy level E(T, Sh) was determined based on the shoulder peak on the short wavelength side of the peak of the phosphorescence spectrum.

[0965] <Evaluation of Organic EL Components>

[0966] The compounds of this invention possess a suitable band gap (Eg), a high triplet excitation energy (ET), and a small ΔE. ST Therefore, it is expected to be applied, for example, to light-emitting layers and charge transport layers, especially to light-emitting layers.

[0967] Evaluation items and evaluation methods

[0968] The evaluation parameters include driving voltage (V), emission wavelength (nm), International Commission on Illumination (CIE) chromaticity (x, y), external quantum efficiency (%), maximum wavelength of the emission spectrum (nm), and full width at half maximum (FWHM) (nm). These evaluation parameters can be values ​​obtained at appropriate luminous intensity.

[0969] The quantum efficiency of a light-emitting element has internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the proportion of external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element that is purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. Some of the photons generated in the light-emitting layer are absorbed internally by the light-emitting element or continuously reflected without being released to the outside of the light-emitting element. Therefore, external quantum efficiency is lower than internal quantum efficiency.

[0970] The methods for measuring spectroradiometer (emission spectrum) and external quantum efficiency are as follows. A voltage / current generator R6144 (Advantest) was used to apply a voltage, causing the element to emit light. A spectroradiometer SR-3AR (TOPCON) was used to measure the spectroradiometer in the visible light region from a direction perpendicular to the emitting surface. Assuming the emitting surface is a perfectly diffused surface, the number of photons at each wavelength was obtained by dividing the measured spectroradiometer value of each wavelength component by the wavelength energy and multiplying by π. The number of photons was then accumulated over the observed entire wavelength region and set as the total number of photons emitted from the element. The number of carriers injected into the element was obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency was obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. Furthermore, the full width at half maximum (FWHM) of the emission spectrum was calculated as the width between wavelengths above and below the maximum emission wavelength where its intensity is 50%.

[0971] Next, the fabrication and evaluation of organic EL elements using the polycyclic aromatic compounds of the present invention will be described.

[0972] Composition of organic EL elements

[0973] Using the polycyclic aromatic compounds of the present invention, an organic EL element comprising the following element component A and element composition B is manufactured.

[0974] <Component Composition A>

[0975] The material composition of each layer in the organic EL element of Examples (A-1) to Examples (A-23) and Comparative Example (1) is shown in Table 2 below.

[0976] [Table 2]

[0977]

[0978] In Table 2, “HI” represents N. 4 N 4′ -diphenyl-N 4 N 4′-bis(9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl]-4,4′-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylhexacarbononitrile, "HT-1" is N-([1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine, "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′: 4′,1″-[triphenyl]-4-amine, “BH” is 2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan, “ET-1” is 9,9′-(5-(6-(1,1′-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole), and “ET-2” is 4,4′-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))dipyridine. The chemical structures are shown below together with “Liq” and “Comparative Compound 1”.

[0979] [Chemistry 189]

[0980]

[0981] Fabrication of the organic EL element in Example (A-1)

[0982] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Opto Science, Inc.) with an ITO film thickness of 180nm ground to 150nm was used as a transparent support substrate. The transparent support substrate was fixed on the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum, Inc.), and a molybdenum vapor deposition boat containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, and an aluminum nitride vapor deposition boat containing Liq, LiF, and aluminum were respectively installed.

[0983] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4First, HI is heated and vapor-deposited to a thickness of 40 nm. Next, HAT-CN is heated and vapor-deposited to a thickness of 5 nm. Then, HT-1 is heated and vapor-deposited to a thickness of 45 nm. Finally, HT-2 is heated and vapor-deposited to a thickness of 10 nm to form a hole layer comprising four layers. Next, BH and compound (1-1) are simultaneously heated and vapor-deposited to a thickness of 25 nm to form a light-emitting layer. The vapor deposition rate is adjusted to maintain a BH to compound (1-1) mass ratio of approximately 97:3. Then, ET-1 is heated and vapor-deposited to a thickness of 5 nm. Next, ET-2 and Liq are simultaneously heated and vapor-deposited to a thickness of 25 nm to form an electron layer comprising two layers. The vapor deposition rate is adjusted to maintain an ET-2 to Liq mass ratio of approximately 50:50. The evaporation rate of each layer is 0.01 nm / s to 1 nm / s. Subsequently, LiF is heated and evaporation is performed at a evaporation rate of 0.01 nm / s to 0.1 nm / s to achieve a film thickness of 1 nm. Then, aluminum is heated and evaporation is performed to achieve a film thickness of 100 nm to form a cathode, thereby obtaining the organic EL device of Example (A-1).

[0984] Fabrication of organic EL elements in Examples (A-2) to (A-23) and Comparative Example (1)

[0985] Except for replacing compound (1-1) with the compounds listed in Table 2, the organic EL elements of Examples (A-2) to (A-23) and Comparative Example (1) were prepared in the same order as in Example (A-1).

[0986] Evaluation items and evaluation methods

[0987] Evaluation parameters include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of the emission spectrum (nm), and half-width (nm). These evaluation parameters can be, for example, based on a 1000 cd / m² emission density. 2 The value when it emits light.

[0988] The quantum efficiency of a light-emitting element (LED) has internal and external quantum efficiencies. Internal quantum efficiency represents the proportion of external energy injected into the LED layer as electrons (or holes) that is purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons released to the outside of the LED. Since some photons generated in the LED layer are absorbed internally or continuously reflected without being released to the outside, external quantum efficiency is lower than internal quantum efficiency.

[0989] The methods for measuring spectroradiance (emission spectrum) and external quantum efficiency are described below. Using an Advantest voltage / current generator R6144, the applied element's luminance reached 1000 cd / m². 2 The element emits light due to the voltage applied. Using a Topcon SR-3AR spectroradiometer, the spectroradiance in the visible light region was measured vertically from the emitting surface. Assuming the emitting surface is a perfectly diffused surface, the number of photons at each wavelength was obtained by dividing the measured spectroradiance value of each wavelength component by the wavelength energy and multiplying by π. Then, the number of photons was accumulated over the entire observed wavelength region and set as the total number of photons emitted from the element. The number of carriers injected into the element was determined by dividing the applied current value by the elementary charge, and the external quantum efficiency was obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. Furthermore, the full width at half maximum (FWHM) of the emission spectrum was calculated as the width between wavelengths above and below the maximum emission wavelength where its intensity is 50%.

[0990] For each of the fabricated organic EL elements, an ITO electrode was used as the anode and a LiF / aluminum electrode as the cathode to apply a DC voltage, and a voltage of 1000 cd / m was measured. 2 The driving voltage and external quantum efficiency during light emission. Additionally, utilizing 1000 cd / m²... 2 The voltage during emission was continuously applied, and the time it took to maintain more than 95% of the initial brightness was measured. The results are shown in Table 3.

[0991] [Table 3]

[0992]

[0993] <Component Composition B>

[0994] The material composition of each layer in the organic EL element of Example (B-1) is shown in Table 4 below.

[0995] [Table 4]

[0996]

[0997] In Table 4, “NPD” stands for N,N′-diphenyl-N,N′-dinathyl-4,4′-diaminobiphenyl, “TcTa” stands for 4,4′,4″-tris(N-carbazolyl)triphenylamine, “mCP” stands for 1,3-bis(N-carbazolyl)benzene, “mCBP” stands for 3,3′-bis(N-carbazolyl)-1,1′-biphenyl, “TSPO1” stands for diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide, and “2PXZ-TAZ” stands for 10,10′-((4-phenyl-4H-1,2,4-triazol-3,5-diyl)bis(4,1-phenylene))bis(10H-phenoxazine). The chemical structures are shown below.

[0998] [Chemistry 190]

[0999]

[1000] [Component B: A component with the host compound set to mCBP, the auxiliary dopant set to 2PXZ-TAZ, and the emission dopant set to compound (1-1)]

[1001] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Opto Science, Inc.) with ITO film of 200nm thickness ground down to 50nm was used as a transparent support substrate. The transparent support substrate was fixed on the substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo, Inc.), and tantalum vapor deposition boats containing NPD, TcTa, mCP, mCBP, 2PXZ-TAZ, compound (1-1), and TSPO1 were installed, as well as aluminum nitride vapor deposition boats containing LiF and aluminum.

[1002] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4First, NPD is heated and vapor-deposited to a thickness of 40 nm. Next, TcTa is heated and vapor-deposited to a thickness of 15 nm to form a two-layer hole injection transport layer. Then, mCP is heated and vapor-deposited to a thickness of 15 nm to form an electron blocking layer. Next, mCBP (the host), 2PXZ-TAZ (the auxiliary dopant), and compound (1-1) (the emission dopant) are simultaneously heated and co-deposited to a thickness of 20 nm to form a light-emitting layer. The deposition rate is adjusted to a mass ratio of approximately 90:9:1 for the host, auxiliary dopant, and emission dopant. Next, TSPO1 is heated and vapor-deposited to a thickness of 30 nm to form electron transport layer 1. The deposition rates for all the above layers are set to 0.01 nm / s to 1 nm / s. Subsequently, LiF is heated and vapor deposition is performed at a rate of 0.01 nm / s to 0.1 nm / s to achieve a film thickness of 1 nm. Then, aluminum is heated and vapor deposition is performed at a rate of 100 nm to form a cathode, thereby obtaining an organic EL device. The aluminum vapor deposition rate is adjusted to be between 1 nm / s and 10 nm / s.

[1003] Regarding the organic EL element of Example (B-1), a DC voltage was applied with an ITO electrode as the anode and a LiF / aluminum electrode as the cathode, and the voltage was measured at 100 cd / m². 2 When observing the luminescence characteristics, the external quantum efficiency is 25.3%. Additionally, utilizing 100 cd / m²... 2 The voltage during emission was continuously driven, and the time it took to maintain more than 90% of the initial brightness was measured, which was 72 hours.

[1004] Element structure A is characterized by maintaining brightness for a long time under high brightness, while element structure B is characterized by achieving high external quantum efficiency. In element structure A, in the example where the compound of the present invention is used as a dopant in the light-emitting layer, an element with higher external quantum efficiency and longer retention time compared to the comparative example can be obtained.

Claims

1. A polycyclic aromatic compound, represented by the following formula (1-b); Formula (1-b) contains at least one substituent selected from tertiary alkyl, neopentyl, and adamantyl groups represented by formula (tR). In equation (tR), R a R b and R c Each is an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is... The hydrogen atom is substituted with at least one hydrogen atom in formula (1-b), and Z in each of rings a, b11, and b13 is CR. Z The CR Z R Z Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group, and the two aryl groups of the diarylboryl group may be linked by a single bond or a linker group, and the two adjacent C and D groups are... Z R Z They can bond together to form a ring, which can be substituted with hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen can be substituted with an alkyl, cycloalkyl, or substituted silyl, and the two aryl groups of the diarylboryl group can be bonded via a single bond or a linker group. In the c-ring, Z is always CR. Z Or, one Z = Z is greater than 0, and the remaining Z is CR. Z R Z A benzene ring is formed by mutual bonding. The formed benzene ring can be substituted with hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. At least one hydrogen atom can be substituted with an alkyl, cycloalkyl, or substituted silyl group. The two aryl groups of the diarylboryl group can be bonded via single bonds or linker groups. When Z in the c-ring is CR... Z At that time, the R Z Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheterarylamino, arylheterarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen atom may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group, and the two aryl groups of the diarylboryl group may be linked by a single bond or a linker group. 1 For B, X 1 and X 2 Each is independently designated as >NR, wherein the R in >NR is an alkyl or cycloalkyl-substituted or unsubstituted aryl, an alkyl or cycloalkyl-substituted or unsubstituted heteroaryl, an unsubstituted alkyl, or an alkyl-substituted or unsubstituted cycloalkyl, and the R in >NR can be linked by a linking group or a single bond to a CR. Z R in Z Z One or two bonds, X 3 For >NR, where R is an alkyl-substituted or unsubstituted aryl group, X 4 The R in the >C(-R)2 group is either >O or >C(-R)2, where all R groups are methyl groups or two R groups can bond together to form a ring. The resulting ring is... Or a cycloalkanes having 3 to 24 carbon atoms, wherein at least one of the aryl rings or heteroaryl rings in the compound represented by formula (1-b) may be condensed from at least one cycloalkanes, wherein at least one hydrogen atom in the cycloalkanes may be substituted, wherein at least one -CH2- in the cycloalkanes may be substituted by -O-, wherein at least one hydrogen atom in the compound represented by formula (1-b) may be substituted by a cyano, a halogen, or a deuterium, wherein the aryl group is an aryl group having 6 to 30 carbon atoms, and the alkyl group is a straight-chain alkyl group having 1 to 24 carbon atoms or a cycloalkanes having 3 to 24 carbon atoms. The 24-branched alkyl group, wherein the heteroaryl group is a heteroaryl group with 2 to 30 carbon atoms, the cycloalkyl group is a cycloalkyl group with 3 to 24 carbon atoms, the alkoxy group is a straight-chain alkoxy group with 1 to 24 carbon atoms or a branched-chain alkoxy group with 3 to 24 carbon atoms, the aryloxy group is a group in which the hydrogen of the -OH group is replaced by an aryl group with 6 to 30 carbon atoms, and the substituted silyl group is a silyl group substituted by three substituents selected from the group consisting of alkyl groups with 1 to 5 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, and aryl groups with 6 to 30 carbon atoms.

2. The polycyclic aromatic compound according to claim 1, wherein, Z is CR Z .

3. The polycyclic aromatic compound according to claim 1, wherein X is... 3 The R in >NR is a phenyl group substituted with a tertiary alkyl group.

4. The polycyclic aromatic compound according to claim 1, represented by any of the following formulas, In the formula, Me represents methyl and tBu represents tert-butyl.

5. The polycyclic aromatic compound according to claim 1, represented by any of the following formulas, In the formula, Me represents methyl and tBu represents tert-butyl.

6. A polycyclic aromatic compound, represented by any of the following formulas, In the formula, Me represents methyl and tBu represents tert-butyl.

7. The polycyclic aromatic compound according to claim 6, represented by any of the following formulas, In the formula, Me represents methyl and tBu represents tert-butyl.

8. A material for organic devices, comprising a polycyclic aromatic compound as described in any one of claims 1 to 7.

9. An organic electroluminescent element comprising: a pair of electrodes, including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, wherein, The luminescent layer contains a polycyclic aromatic compound as described in any one of claims 1 to 7.

10. The organic electroluminescent element according to claim 9, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

11. The organic electroluminescent element according to claim 10, wherein the main body is an anthracene compound, a fluorene compound, or a dibenzo[a]pyrene compound.

12. A display device comprising an organic electroluminescent element as claimed in any one of claims 9 to 11.

13. A lighting device comprising an organic electroluminescent element as claimed in any one of claims 9 to 11.

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