Polycyclic aromatic compound, material for organic device, organic electroluminescent element, display device, and lighting device

Abstract

Provided are: a polycyclic aromatic compound which is improved as a material for an organic device; a material for an organic device; an organic electroluminescent element; a display device; the polycyclic aromatic compound has a structure containing a structural unit represented by formula (1); at least one of A ring, B ring, and C is a ring represented by formula (Az), the others are optionally substituted aryl rings or heteroaryl rings, Y1 is B, X1 is > O, > N-R, or > C (-Me) 2, two or three consecutive Z in any one group are carbon atoms directly bonded to Y1 and N-RNY1 and / or N-RNY2, the others are N or C-RZ, RZ is hydrogen or a substituent, at least one of RNY1, RNY2, and RNY3 is a group selected from the group consisting of formulas (RNY-a) to (RNY-d), at least one of the aryl ring or heteroaryl ring in the structure may be condensed from at least one cycloalkane.

Description

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, this invention relates to organic device materials comprising said polycyclic aromatic compounds, organic electroluminescent elements, and display and lighting devices. 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 and scaling. In particular, the development of organic materials with luminescent properties such as blue (one of the three primary colors of light) and organic materials possessing charge transport capabilities such as holes and electrons (potentially becoming semiconductors or superconductors) has been actively pursued to date, with both high-molecular-weight and low-molecular-weight compounds being actively studied.

[0003] Organic electroluminescent devices have a structure comprising: a pair of electrodes including an anode and a cathode; and one or more layers containing an organic compound disposed between the pair of electrodes. 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 boron-containing polycyclic aromatic compounds as materials that can be effectively used in organic electroluminescent elements. Organic electroluminescent elements containing these polycyclic aromatic compounds are reported to have good external quantum efficiency. Patent Document 3 discloses a polycyclic aromatic compound in which at least one of the rings in a boron-containing basic framework forms a tricyclic condensation structure; organic electroluminescent elements containing this polycyclic aromatic compound 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

[0009] [Patent Document 3] Korean Patent Publication No. 10-2022-0021418 Summary of the Invention

[0010] [The problem the invention aims to solve]

[0011] As mentioned above, various materials have been developed for use in organic electroluminescence (EL) devices, but further improvements in materials for organic EL devices are required.

[0012] The objective of this invention is to provide a compound that improves organic device materials such as organic EL elements.

[0013] [Technical means to solve the problem]

[0014] The inventors conducted diligent research to solve the aforementioned problem and discovered that, when the compound described in Patent Document 3 has a specific substitution structure, a polycyclic aromatic compound with superior luminescent properties can be obtained. Furthermore, they discovered that by configuring a layer containing the aforementioned polycyclic aromatic compound between a pair of electrodes to construct an organic EL element, an excellent organic EL element can be obtained, thus completing the present invention. That is, the present invention provides a polycyclic aromatic compound as described below, and further provides materials for organic devices containing such polycyclic aromatic compounds.

[0015] <1> A polycyclic aromatic compound having one or more structures comprising the structural unit represented by the following formula (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 (Az).

[0019] Y 1 For B, P, P=O, P=S, Al, Ga, As, Si-R S , or Ge-R Ge The Si-R S R S and Ge-R Ge R Ge Each can be independently substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0020] In formula (Az),

[0021] X 1 >C(-R) c )2、>C=C(-R c 2. >C(-OR) O )2、>Si(-R Si)2, or >C=O, wherein >C(-R c )2 and >C=C(-R c )2 of R c >C(-OR) O )2, and >Si(-R Si )2 of R Si Each of the two Rs 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. c They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring; in addition, the >C(-R) c )2 of R c It can be linked to one or two Z bonds via a linker base or a single bond.

[0022] Any two or three consecutive Z's are respectively related to Y's 1 and NR NY1 and / or NR NY2 The N atom is directly bonded to the carbon atom, and the other Z atoms are independently N or C. Z The CR Z R Z For hydrogen or substituents, two adjacent CR 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 set to >0 and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se, wherein >NR NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Each of the following 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, wherein the >C(-R CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring.

[0024] In equations (1) and (Az),

[0025] R NY1 R NY2 and R NY3 It 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, wherein at least one is selected from the following formula (R NY -a)~Formula (R) NY The base in -d),

[0026]

[0027] R NY1 Or R NY2 It can be bonded to A-rings and / or B-rings, or A-rings and / or C-rings, via linker bases or single bonds.

[0028] Formula (R) NY -a)~Form (R) NY In -d),

[0029] * indicates the bond position with N.

[0030] R a R b R c R d1 R d2 and R d3 Each of the following 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.

[0031] R b1 R b2 and R c1 Each is independently a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, wherein R b1 and R b2 They will not all become methyl groups.

[0032] a and b are independent integers from 0 to 5.

[0033] c is an integer between 0 and 3.

[0034] D stands for deuterium.

[0035] At least one aryl or heteroaryl ring in the structure may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted.

[0036] At least one hydrogen atom in the structure may be substituted with a cyano group or a halogen.

[0037] At least one -CH2- in the structure may be substituted with -O-.

[0038] In the structure, at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13 C) substitution, at least one boron can be replaced by boron-11( 11 B) Replace.

[0039] <2> The polycyclic aromatic compounds according to <1> are composed of the following formulas: (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b... 1) Equations (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8) represent the following:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048] Equation (1-a1), Equation (1-b1), Equation (1-c1), Equation (1-d1), Equation (1-e1), Equation (1-f1), Equation (1-a2), Equation (1-b2), Equation (1-c2), Equation (1-d2), Equation (1-e2), Equation (1-f2), Equation (1-d3), Equation (1-e3), Equation (2-a1), Equation (2-a2), Equation (2-b1), Equation (2-b2), Equation In equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8),

[0049] Z, Y 1 X 1 R NY1 R NY2 R NY3 Z and Z = Z are respectively related to Z and Y in equation (1). 1 X 1 R NY1 R NY2 R NY3 、 and Z=Z have the same meaning.

[0050] X 2 >C(-R) c )2、>C=C(-R c 2. C(-OR) O )2、>Si(-R Si )2, or >C=O, wherein >C(-R c )2 and >C=C(-R c )2 of R c C(-OR) O )2 of R O and >Si(-R Si )2 of R Si Each of the two Rs 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. c They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring; in addition, the >C(-R) c )2 of R c It can be linked to one or two Z bonds via a linker base or a single bond.

[0051] X 11and X 22 Independently defined as >O and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se, as X 11 or X 22 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0052] At least one aryl ring or heteroaryl ring may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted.

[0053] At least one hydrogen atom may be substituted with a cyano group or a halogen group.

[0054] At least one -CH2- can be substituted via -O-.

[0055] At least one hydrogen atom can be substituted with deuterium, and at least one nitrogen atom can be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13 C) substitution, at least one boron can be replaced by boron-11( 11 B) Replace.

[0056] <3> According to the polycyclic aromatic compound described in <1>, wherein R NY1 R NY2 and R NY3 At least one of them is selected from the following formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R)NY -c-20), and formula (R) NY -d-1)~Formula (R) NY The base in -d-25);

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] Formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R) NY In -d-25),

[0064] X Y For >O, >NR Nzy >C(-R) Czy )2、>Si(-R Sizy 2. or >S, as X Y >NR Nzy R Nzy >C(-R) Czy )2 of R Czy 、>Si(-R Sizy )2 of R Sizy Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0065] Ak is a substituted or unsubstituted alkyl group.

[0066] <4> The polycyclic aromatic compounds according to <2> are represented by the formula (1-b1), formula (1-d1), formula (2-b1) or formula (2-b2).

[0067] <5> According to the polycyclic aromatic compounds described in <4>, where Z is always CR Z .

[0068] <6> A polycyclic aromatic compound according to any one of <1> to <5>, wherein X 1 >C(-R) c )2, R c For substituted or unsubstituted alkyl groups, the two Rs c They can bond together to form a ring.

[0069] <7> A polycyclic aromatic compound according to any one of <1> to <5>, wherein X 1 >Si(-R) Si )2, R Si For substituted or unsubstituted alkyl groups, the two Rs Si They can bond together to form a ring.

[0070] <8> A polycyclic aromatic compound according to any one of <1> to <5>, wherein X 1 The value is >C=O.

[0071] <9> A polycyclic aromatic compound according to any one of <1> to <8>, wherein Y 1 The answer is B.

[0072] <10> A polycyclic aromatic compound according to any one of <1> to <9>, wherein R NY1 R NY2 and R NY3 At least one of them is the formula (R) NY -a).

[0073] <11> A polycyclic aromatic compound according to any one of <1> to <9>, wherein R NY1 R NY2 and R NY3 At least two of them are selected from formula (R) NY -a)~Form (R) NY The base in -d).

[0074] <12> A polycyclic aromatic compound according to any one of <2> to <11>, wherein X 1 and X 2 Each independently is >C(-R) c )2, R c It can be a substituted or unsubstituted alkyl group.

[0075] <13> The polycyclic aromatic compounds according to <4> are represented by the following formula (1-b1-Z), formula (2-b1-Z) or formula (2-b2-Z);

[0076]

[0077] In equations (1-b1-Z), (2-b1-Z), and (2-b2-Z),

[0078] R NY1 R NY2 and R NY3 Independently with R in equation (1) NY1 R NY2 and R NY3 They have the same meaning.

[0079] R Z4 Each is an unsubstituted alkyl group, and the two Rs are independent. Z4 They can bond together to form a ring.

[0080] R Z1 It is an unsubstituted alkyl group.

[0081] R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2.

[0082] R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2.

[0083] X 11 For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se,

[0084] As X 11 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0085] In the structures represented by formula (1-b1-Z), formula (2-b1-Z), or formula (2-b2-Z), at least one of the aryl rings or heteroaryl rings can be a structure formed by bonding a portion of the structure represented by formula (B) with an adjacent carbon atom.

[0086]

[0087] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0088] At least one hydrogen atom in the structure represented by formula (1-b1-Z), formula (2-b1-Z), or formula (2-b2-Z) may be substituted with a cyano group, a halogen, or a deuterium.

[0089] <14> The polycyclic aromatic compounds according to <4> are represented by formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T);

[0090]

[0091] In equations (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T),

[0092] X a For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, or >S, the >NR NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0093] R NY1 R NY2 and R NY3 Independently with R in equation (1) NY1 R NY2 and R NY3 They have the same meaning.

[0094] R Z4 Each is an unsubstituted alkyl group, and the two Rs are independent. Z4They can bond together to form a ring.

[0095] R Z1 It is an unsubstituted alkyl group.

[0096] R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2.

[0097] R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2.

[0098] X 11 For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se,

[0099] As X 11 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0100] In the structures represented by formulas (1-b1-T1), (1-b1-T2), (2-b1-T), or (2-b2-T), at least one of the aryl rings or heteroaryl rings can be a structure formed by bonding a portion of the structure represented by formula (B) with an adjacent carbon atom.

[0101]

[0102] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0103] At least one hydrogen atom in the structure represented by formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T) may be substituted with a cyano group, a halogen, or a deuterium.

[0104] <15> According to <1>, the polycyclic aromatic compound wherein at least one hydrogen in the formula (1) is substituted with a group represented by the following formula (Cz);

[0105]

[0106] In formula (Cz),

[0107] *a indicates the bond position.

[0108] Z y Each independently represents N or CR. ZY The CR ZY R ZY For hydrogen or substituents, two adjacent CR ZY R ZY They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0109] <16> The polycyclic aromatic compounds according to <1> are represented by any of the following formulas;

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] In the formula, Me is methyl and tBu is tert-butyl.

[0148] <17> A material for an organic device, comprising a polycyclic aromatic compound according to any one of <1> to <16>.

[0149] <18> An organic electroluminescent element includes: a pair of electrodes, comprising an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes.

[0150] The luminescent layer contains a polycyclic aromatic compound according to any one of <1> to <16>.

[0151] <19> The organic electroluminescent element according to <18>, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

[0152] <20> The organic electroluminescent element according to <19>, wherein the host is anthracene compound, fluorene compound, or dibenzo[a]benzene compound. These are compounds, or pyrene compounds.

[0153] <21> A display device or lighting device comprising an organic electroluminescent element according to any one of <18> to <20>.

[0154] [The effects of the invention]

[0155] This invention provides polycyclic aromatic compounds that exhibit superior light-emitting properties as materials for organic devices such as organic electroluminescent elements. These polycyclic aromatic compounds can be used to manufacture organic devices such as organic electroluminescent elements. Attached Figure Description

[0156] Figure 1 This is a schematic cross-sectional view showing an example of an organic electroluminescent element.

[0157] Explanation of icon numbers

[0158] 100: Organic electroluminescent element

[0159] 101: Substrate

[0160] 102: Anode

[0161] 103: Hole Injection Layer

[0162] 104: Hole Transport Layer

[0163] 105: Emissive layer

[0164] 106: Electron Transport Layer

[0165] 107: Electron Injection Layer

[0166] 108: Cathode Detailed Implementation

[0167] The present invention will now be described in detail. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, the numerical range indicated by “~” in this specification 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)”.

[0168] In this specification, organic electroluminescent elements are sometimes referred to as organic EL elements.

[0169] 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 substituted 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 substituted 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.

[0170] 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, for a single substance, there are actually multiple equivalent resonance structures, such as alternating double and single bonds. In this specification, only one resonance structural formula is described for each substance, but unless otherwise specified, other equivalent resonance structural formulas 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 structure represented as "Z=Z" in the described structure but also the structure represented as "ZZ" in the resonance structure. For example, regarding "Z=Z" in formula (1-b) described later, examples are shown as follows. This is not a limitation; it applies not only to the single described resonance structural formula but also to other considered equivalent resonance structural formulas.

[0171]

[0172] In this specification, "adjacent" means that atoms on the same ring are directly bonded to each other unless otherwise specified. "Adjacent base" refers to the bases that are directly bonded to atoms on the same ring.

[0173] 1. Polycyclic aromatic compounds

[0174] The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having a structure comprising one or more structural units represented by formula (1). The polycyclic aromatic compounds of the present invention have at least one ring represented by formula (Az) as ring A, ring B, or ring C in formula (1). When used as a light-emitting layer material for organic electroluminescent devices, the polycyclic aromatic compounds of the present invention can improve the external quantum efficiency and photoluminescence quantum yield (PLQY) of the device, and while reducing the half-width of the light emission, can also improve the device lifetime. Furthermore, the lower sublimation temperature can suppress the occurrence of defects in the device manufacturing process, particularly in the vapor deposition process.

[0175]

[0176] At least one ring selected from the group consisting of rings A, B, and C in one or more structures containing the structural unit represented by equation (1) is represented by equation (Az).

[0177] In a structure that includes the 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 (Az). When one ring is the ring represented by equation (Az), the ring is not particularly limited, but ring B or ring C is preferred. When two rings are the rings represented by equation (Az), these rings are not particularly limited, but rings B and C are preferred. In a structure that includes the structural unit represented by equation (1), it is more preferable to have one ring represented by equation (Az).

[0178] 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 (Az), or may not include any. That is, when there are two or more of rings A, B, or C, it is sufficient that at least one ring in the two or more structures that include the structural unit represented by equation (1) is the ring represented by equation (Az).

[0179] In formula (Az), X 1 >C(-R) C )2、>C=C(-R c 2. >C(-OR) O )2、>Si(-R Si 2. Or >C=O. As X 1 >C(-R) C )2 and >C=C(-R c )2 of R C >C(-OR) O)2, and >Si(-R Si )2 of R Si Each of the two Rs 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. C They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring. Two Rs C For example, they can bond with each other to form cycloalkanes.

[0180] In equation (Az), X 1 Preferably >C(-R) C )2、>Si(-R Si )2, or >C=O, more preferably >C(-R) C )2.

[0181] As X 1 >C(-R) C )2 and >Si(-R Si R in )2 C and R Si Preferably, all of them are substituted alkyl or substituted aryl groups, more preferably all of them are substituted alkyl groups, and even more preferably all of them are unsubstituted alkyl groups, and particularly preferably all of them are unsubstituted methyl groups.

[0182] In formula (Az), NR NY3 R NY3 The substituent 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. Here, the substituent 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. R NY3 Ideally, the aryl group is substituted or unsubstituted; more preferably, it is substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. Examples of substituted or unsubstituted aryl groups can be listed from the formulas (R) described below. NY -a)~Form (R) NY The bases in -d) can be more specifically listed from the formulas (R) described later. NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R)NY The base in -d-25).

[0183] In equation (Az), any two or three consecutive groups in Z are respectively related to Y. 1 and NR NY1 and / or NR NY2 The N atom is directly bonded to the C (carbon atom). That is, when the B ring is the ring represented by formula (Az), any two consecutive rings in any group are respectively bonded to Y. 1 and NR NY1 For N directly bonded to C, when the C ring is the ring represented by equation (Az), any two consecutive bonds in any group are respectively connected to Y. 1 and NR NY2 For the N-directly bonded C, when the A ring is the ring represented by equation (Az), any three consecutive bonds in any group are respectively bonded to Y. 1 NR NY1 N and NR NY2 The N-C is directly bonded. The other Z-Cs 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.

[0184] For details regarding these substituents, please refer to the descriptions of the first and second substituents described later.

[0185] Furthermore, in equation (Az), Z = Z can be independently set to >0 and >NR respectively. NX>C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se. Among these, >O and >NR are preferred. NX >C(-R) CX )2, or >S. The >NR mentioned above. NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Each of the following 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, wherein the >C(-R CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring. For a single ring (a single ring) in equation (Az), the following shows a Z = Z > NR. NX Examples of Z > O or > S where the rest of Z is CH, and an example of Z = Z being > NR. NX >O or >S and all other Z-adjacent unions are CR Z And these R Z Examples of benzene rings formed by mutual bonding.

[0186]

[0187] In equation (Az), X is included. 1 Of the two rings other than N, at least one is preferably a six-membered ring. Additionally, with Y... 1 and NR NY1 and / or NR NY2 The preferred ring for the bonding is a six-membered ring.

[0188] In formula (Az), the number of rings (single rings) containing Z as N is zero to two, more preferably zero to one. In formula (Az), it is also preferable to have a ring with Y... 1 and NR NY1 and / or NR NY2 All Z atoms except Z in the C (carbon atom) bond are CR. Z .

[0189] In formula (Az), among the rings (monocyclic rings) containing Z as N, it is preferable that one or two of the plurality of Zs is N, and when two are N, the two Ns are preferably 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.

[0190] As a set, Z = Z is >0, >NR NX >C(-R) CX )2、>Si(-R SiX )2. Examples of five-membered rings containing Z as N in the form of >S or >Se include thiazole rings and oxazole rings.

[0191] The explanations regarding Z = Z and Z in equation (Az) also apply to equations (1-a1), (1-b1), (1-c1), (1-d1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (2- c1), Equations (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8) contain Z=Z in single rings (e.g., ring a, ring c, etc.).

[0192] In equation (Az), NR NY3 R NY3 and / or X 1 >C(-R) CX >C(-R) at time 2 CX )2 of R CX It can be bonded to one or two Z bonds via a linker base or a single bond. The preferred Z bond for bonding is with an X bond. 1 Or the Z atom adjacent to the N atom. Furthermore, the Z atom undergoing the bonding only needs to be a carbon atom with a bonding bond. As such a linker, refer to the section on NR described later. NY1 NR NY2 Examples of linker bases with B-ring and C-ring bonds. As NR NY3 R NY3 Examples of structures that form such bonds can be listed by the structures represented by the following formulas.

[0193]

[0194] In the formula, Me is a methyl group, and it is associated with NR at the positions of the two *. NY3 or X 1 One of the two loops is bonded to the other loop at the ** position.

[0195] In one or more structures containing the structural unit represented by formula (1), the rings other than the rings that are rings A, B, and C and are the rings represented by formula (Az) are independently substituted aryl rings or substituted heteroaryl rings.

[0196] 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 NR NY1 and / or NR NY2 Bonding. The so-called "bonding with a pentagonal or hexacyclic ring and Y..." 1 and NR NY1 and / or NR NY2 "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... 1 and NR NY1 and / or NR NY2 Bonding. In the aryl or heteroaryl rings of rings A, B, and C, two or three consecutive ring-constituting atoms (carbon atoms) bond with Y. 1 and NR NY1 and / or NR NY2 Direct bonding is sufficient. That is, two consecutive ring-forming atoms (carbon atoms) in either the aryl or heteroaryl rings within the B ring bond with Y. 1 and NR NY1 Direct bonding, in any group of consecutive rings (carbon atoms) within the C ring, consisting of two atoms connected to the Y group. 1 and NR NY2 Direct bonding, where three consecutive rings (carbon atoms) in either the aryl or heteroaryl rings of ring A are bonded to Y. 1 NR NY1 and NR NY2 Direct bonding.

[0197] As the "aryl ring" in ring A, ring B and ring 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.

[0198] Specific examples of "aryl rings" include: monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings, 5,6,7,8-tetrahydronaphthalene rings, and indene rings, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), condensed tricyclic acenaphthene rings, fluorene rings, phenanthene rings, and anthracene rings, and condensed tetracyclic triphenylene rings, pyrene rings, and terephthalene rings. The ring is a perylene ring or a pentane-benzene ring, which are condensed pentacyclic rings. Additionally, fluorene rings, benzo[a]fluorene rings, and indene rings also contain structures with fluorene rings, benzo[a]fluorene rings, cyclopentane rings, etc., linked by spiral bonds. Furthermore, tetrahydronaphthalene rings, fluorene rings, benzo[a]fluorene rings, and indene rings also contain rings in which two of the two hydrogens of the methylene group are replaced by alkyl groups such as methyl groups (described later as first substituents), resulting in rings such as 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene rings, dimethylfluorene rings, dimethylbenzo[a]fluorene rings, and dimethyl indene rings.

[0199] Regarding the "heteroaryl ring" that is ring A, ring B, and ring C in formula (1), examples include heteroaryl rings with 2 to 30 carbon atoms, preferably heteroaryl rings with 2 to 25 carbon atoms, more preferably heteroaryl rings with 2 to 20 carbon atoms, and even more preferably heteroaryl rings with 2 to 15 carbon atoms, and particularly preferably heteroaryl rings with 2 to 10 carbon atoms. In addition, examples of "heteroaryl rings" include heterocycles that contain one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon atoms.

[0200] 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, quinazolinoline ring, quinoxaline ring, phthalazine ring, and naphthidine ring. Purine rings, pteridine rings, carbazole rings, acridine rings, phenothiazine rings, phenazine rings, phenazasiline rings, indazine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazan rings, thiathracene rings, indolocarbazole rings, benzoindolocarbazole rings, benzobenzoindolocarbazole rings, naphthobenzofuran rings, dioxin rings, dihydroacrylidine rings, xanthonium rings, thioxanthonium rings, dibenzodioxin rings, etc. Furthermore, in dihydroacrylidine rings, xanthonium rings, and thioxanthonium rings, it is also preferable that two of the two hydrogens of the methylene group are respectively replaced by alkyl groups such as methyl groups described later as first substituents to form dimethyldihydroacrylidine rings, dimethylxanthonium rings, dimethylthioxanthonium rings, etc. In addition, bipyridine rings, phenylpyridine rings, and pyridylphenyl rings (which are bicyclic systems), and tricyclic rings, terpyridine rings, bispyridylphenyl rings, and pyridylbiphenyl rings (which are tricyclic systems) can also be listed as "heteroaryl rings". Furthermore, "heteroaryl rings" also include pyran rings.

[0201] Alternatively, rings represented by the following formula (BO) can also be listed as heteroaryl rings.

[0202]

[0203] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be replaced by 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 via a single bond or a linking group)", a substituted or unsubstituted "alkyl", or a group that has undergone substitution. The substitution may be a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl" but with respect to "aryl" or "heteroaryl", "aryl of "diarylamino", "heteroaryl of "diheteroarylamino", "aryl and heteroaryl of "arylheteroarylamino", "aryl of "diarylboryl", and "aryloxy", the monovalent groups of the "aryl ring" or "heteroaryl ring" may be listed.

[0204] 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.

[0205] Specific examples of aryl groups include: phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl, (1-, 2-)5,6,7,8-tetrahydronaphthyl, and (2-, 3-, 4-, 5-, 6-, 7-)indenyl as condensed dicyclic aryl groups; and terphenyl (meta-terphenyl-2'-yl, meta-terphenyl) as a tricyclic aryl group. Benzene-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), as condensed tricyclic compounds. Aryl 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, (1-, 2-, 3-, 4-, 9-)phenanthrene, as tetracyclic aryl tetraphenyl(5'-phenyl-m-terphenyl-2-) 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.

[0206] 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 one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms, in addition to carbon atoms.

[0207] Specific heteroaryl groups include, for example: furanyl, thiopheneyl, pyrroleyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazoleyl, pyrazolyl, oxadiazolyl, furazolyl, thiazolyl, triazolyl, tetrazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thiopheneyl, dibenzothiopheneyl, indolyl, isoindolyl, 1H-indazoleyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphthidyl, purineyl, pteridinyl, carbazolyl, acridineyl, phenoxazinyl, phenthiazolyl, phenoxazinyl, thiazolyl, thiazolyl, indazinyl, etc.

[0208] Furthermore, the "alkyl" group used as the first substituent can be either straight-chain or branched-chain, for example, straight-chain alkyl groups having 1 to 24 carbon atoms or branched-chain alkyl groups having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (branched-chain alkyl groups having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched-chain alkyl groups having 3 to 12 carbon atoms), even more preferably an alkyl group having 1 to 8 carbon atoms (branched-chain alkyl groups having 3 to 8 carbon atoms), particularly preferably an alkyl group having 1 to 6 carbon atoms (branched-chain alkyl groups having 3 to 6 carbon atoms), and most preferably an alkyl group having 1 to 5 carbon atoms (branched-chain alkyl groups having 3 to 5 carbon atoms).

[0209] 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.

[0210] Other 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.

[0211] 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 in the aryl ring or heteroaryl ring is substituted 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 to use the tertiary alkyl group represented by formula (tR) as a second substituent to substitute for other substituents. Specifically, examples include diarylamino groups substituted with tertiary alkyl groups represented by formula (tR), carbazolyl groups substituted with tertiary alkyl groups represented by formula (tR) (preferably N-carbazolyl), or benzo[a]carbazolyl groups substituted with tertiary alkyl groups represented by formula (tR) (preferably N-benzo[a]carbazolyl). 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).

[0212]

[0213] In equation (tR), R a R b and R c Each is an alkyl group having 1 to 24 carbon atoms, wherein any -CH2- group 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).

[0214] As R a R b and R cThe term "alkyl group having 1 to 24 carbon atoms" can be either straight-chain or branched-chain. Examples include: straight-chain alkyl groups having 1 to 24 carbon atoms or branched-chain alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched-chain alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched-chain alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched-chain alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched-chain alkyl groups having 3 to 4 carbon atoms).

[0215] 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.

[0216] As R a R b and R c Specific 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.

[0217] 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.

[0218] In addition, examples of "cycloalkyl" as the first substituent include: 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, and cycloalkyl with 5 carbon atoms.

[0219] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) 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.

[0220] Furthermore, regarding the "alkoxy group" as the first substituent, examples 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).

[0221] Specific alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-pentoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0222] Furthermore, regarding "substituted silyl" as the first substituent, examples include 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.

[0223] As "trialkylsilyl", a group in which the three hydrogens of a silyl group are each independently substituted 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.

[0224] 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.

[0225] As "tricycloalkylsilyl", a group in which the three hydrogens of the silyl group are each independently substituted 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.

[0226] Specific examples of tricycloalkylsilyl groups include tricyclopentylsilyl and tricyclohexylsilyl.

[0227] 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.

[0228] 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.

[0229] Additionally, the "aryl" in "diarylboryl" as the first substituent can be referenced from the description of the aryl group. Furthermore, the two aryl groups can be bonded 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), and the first substituent 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.

[0230] As a first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboroyl" (the two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl" may, as described in the description of substituted or unsubstituted, have at least one hydrogen atom that 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", or the "alkyl" or "cycloalkyl" as the first substituent. Furthermore, in the case of an aryl or heteroaryl group as a second substituent, a structure in which at least one hydrogen atom is substituted by an aryl group such as phenyl (specifically, the group described above), an alkyl group such as methyl, tert-butyl (specifically, the group described above), or a cycloalkyl group such as cyclohexyl (specifically, the group described above) is also included in the aryl or heteroaryl group as a second substituent. 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 substituted 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 as a second substituent.

[0231] The description of the second substituent also applies to substituents referred to as "substituted or unsubstituted" that are not separately described in this specification.

[0232] The emission wavelength can be adjusted according to 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-trimethylyl, 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.

[0233] 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.

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] 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 alkyl 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.

[0246] In equation (1), Y 1 Independently, B, P, P=O, P=S, Al, Ga, As, and Si-R S , or Ge-R Ge The Si-R S R S and Ge-R Ge R Ge It can be a substituted or unsubstituted aryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. Examples of the aryl, alkyl, or cycloalkyl groups are listed below. 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 Preferred materials are B, P, P=O, P=S, or Si-R. S B is particularly preferred. Y in equation (1) 1 The relevant explanations also apply to the following formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), and (2-a2) as described below. -b2), Equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and Y in Equations (3-e1) to (3-e8) 1 .

[0247] NR NY1 or NR NY2 R NY1 Or R NY2It can be hydrogen, a substituted aryl group, a substituted heteroaryl group, a substituted alkyl group, or a substituted cycloalkyl group. Regarding NR... NY1 or NR NY2 R NY1 Or R NY2 The aryl, heteroaryl, alkyl, and cycloalkyl groups mentioned can be referred to the description of these as the first substituents.

[0248] NR NY1 or NR NY2 R NY1 Or R NY2 Preferably, the alkyl group is a substituted aryl group, a substituted heteroaryl group, or a substituted cycloalkyl group, more preferably a substituted aryl group or a substituted heteroaryl group. Examples of cycloalkyl groups can be listed 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.), dibenzodioxinyl, 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 zero to two, more preferably one or two, and even more preferably one. It is also preferable that the aryl ring in the aryl group is condensed from a substituted cycloalkanes, as described later. Specific cycloalkanes can be referred to those described later.

[0249] Regarding NR NY1 or NR NY2 R NY1 Or R NY2 Particularly preferred examples include: substituted phenyl groups, substituted 2-biphenyl groups, substituted terphenyl-2'-yl groups, substituted terphenyl-4'-yl groups, and aryl groups condensed from cycloalkanes (substitutable). As substituted phenyl groups, substituted 2-biphenyl groups, substituted terphenyl-2'-yl groups, and substituted terphenyl-4'-yl groups, the form with one to three tert-butyl substitutions is preferred. As aryl groups condensed from cycloalkanes, the following are particularly preferred.

[0250]

[0251] (In the formula, Me represents methyl, tBu represents tert-butyl, and * represents the bond position)

[0252] In equations (1) and (Az), R NY1 R NY2and R NY3 In, at least one is selected from the following formula (R) NY -a)~Form (R) NY The base in -d).

[0253]

[0254] Formula (R) NY -a)~Form (R) NY In -d),

[0255] * indicates the bond position with N.

[0256] R a R b R c R d1 R d2 and R d3 It is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

[0257] R b1 R b2 and R c1 Each is independently a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, wherein R b1 and R b2 They will not all become methyl groups.

[0258] a and b are independent integers from 0 to 5, and c is an integer from 0 to 3.

[0259] D stands for deuterium.

[0260] R NY1 R NY2 and R NY3 At least two of them are preferably selected from formula (R) NY -a)~Form (R) NY The base in -d).

[0261] R NY1 R NY2 and R NY3 At least one of them is preferably the formula (R) NY -a), or the specific base described later.

[0262] More specifically, R NY1 R NY2 and R NY3 At least one of them can be selected from the following formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY-b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R) NY The base representation in -d-25).

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269] Formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R) NY In -d-25),

[0270] X Y For >O, >NR Nzy >C(-R) Czy )2、>Si(-R Sizy 2. or >S, as X Y >NR Nzy R Nzy >C(-R) Czy )2 of R Czy 、>Si(-R Sizy )2 of R Sizy Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 has the same meaning.

[0271] Ak is a substituted or unsubstituted alkyl group.

[0272] NR NY1 RNY1 or NR NY2 R NY2 It can be bonded to A-rings and / or B-rings, or A-rings and / or C-rings, via linker bases or single bonds. That is, NR NY1 R NY1 NR can be bonded to A-rings and / or B-rings via linker bases or single bonds. NY2 R in NY2 It 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 expressed by compounds represented by the following formula (1-3-1) and having NR. NY1 or NR NY2 The ring structure introduced into condensation rings B' and C'. That is, for example, a ring structure with other rings to introduce NR. NY1 (or NR) NY2 Compounds that form a B' ring (or C' ring) by condensation of the B ring (or C ring) which is a benzene ring. The condensed ring B' (or condensed ring C') that can be formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0273] Alternatively, the specification can also be expressed by a compound represented by formula (1-3-2) or formula (1-3-3) and having NR. NY1 and / or NR NY2 The ring structure is introduced into the condensation ring A'. That is, for example, a ring with other rings to introduce NR. NY1 (and / or NR) NY2 Compounds with an A' ring formed by condensation of the A ring, which is a benzene ring, in a manner that allows for the formation of an A' ring.

[0274] The condensation ring A' that can be formed can be, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0275]

[0276] As an example, the NR is also preferred. NY1 R NY1 or NR NY2 R NY2 It is a substituted cycloalkyl group that is bonded to ring A, ring B, or ring C via a single bond. Preferably, it is a substituted cyclopentyl or a substituted cyclohexyl group.

[0277] As a particularly preferred example, the structure represented by enumeration (A11) can be used.

[0278]

[0279] In formula (A11), Me is a methyl group, and it is associated with NR at the positions of the two asterisks. NY1 or NR NY2 One of the two loops is bonded to the other loop at the ** position.

[0280] By using R with the preferred range NY1 Or R NY2 The compounds of the present invention, when used as luminescent materials, can further improve luminous efficiency or device lifespan.

[0281] As NR in equation (1) NY1 NR NY2 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).

[0282] The above NR with equation (1) NY1 NR NY2 The relevant explanations also apply to the following formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), and (2- b2), Equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and NR in Equations (3-e1) to (3-e8). NY1 NR NY2 .

[0283] 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). Examples of polycyclic aromatic compounds having one of the structural units include those represented by the formula described herein, which are structural units represented by formula (1). Examples of polycyclic aromatic compounds having two or more structural units comprising the structural unit represented by formula (1) include compounds that are polymers equivalent to the polycyclic aromatic compounds represented by the formula described herein, which are structural units represented by formula (1). 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 compound having multiple structural units, and can be any ring (A ring, B ring, or C ring) contained in the structural unit bonded in a manner common to multiple structural units, or any ring (A ring, B ring, or C ring) contained in the structural unit bonded to each other in a condensed manner. Alternatively, the structural unit may be configured to be linked by multiple bonds through single bonds, alkylene groups with 1 to 3 carbon atoms, phenylene groups, naphthylene groups, etc. Among these, the configuration of bonding in the form of a common ring is preferred.

[0284] A polycyclic aromatic compound having a structure containing one or more structural units represented by formula (1) may be condensed by at least one cycloalkane from the group consisting of aryl rings and heteroaryl rings. The same applies to the polycyclic aromatic compounds represented by formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), and (1-e3) described below. The following description also applies to the polycyclic aromatic compounds represented by formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), and (1-e3).

[0285] 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.

[0286] In the case where at least one of the structures comprising one or more 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 at least one hydrogen atom in the cycloalkane may be a cycloalkane substituted with 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.

[0287] As for "cycloalkanes", cycloalkanes with 3 to 24 carbon atoms are preferred. Further preferred examples include, in order: 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.

[0288] 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, and their alkyl (especially methyl) substituted derivatives, halogen (especially fluorine) substituted derivatives, and deuterium substituted derivatives, etc., having carbon numbers of 1 to 5.

[0289] Among these, a preferred structure is one in which at least one hydrogen atom of 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 atom of the condensation site) is substituted, as shown in the following structural formula. More preferably, a structure in which two hydrogen atoms of the α-carbon are substituted, and even more preferably, a structure in which a total of four hydrogen atoms of the two α-carbons are substituted. Examples of substituents include alkyl (especially methyl) substituents with 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents. A structure in which a portion of the structure represented by formula (B) is bonded to adjacent carbon atoms in the aryl ring or heteroaryl ring is particularly preferred.

[0290]

[0291] In formula (B), Me represents a methyl group, and * represents the bond position.

[0292] Examples of this structure include equations (1-1) to (1-10), (1-14), (1-17), (1-18), (1-21) to (1-24), (1-26), (1-31), (1-35), (1-37), (1-38), (1-40), (1-41), (1-44), (1-47), (1-49) to (1-52), (1-61), (1-63) to (1-64), (1-68), (1-69), (1-75), (1-76), (1-81) to (1-84), (1-105) to (1-108), (1-110), and (1-1... 12) The structure of a compound represented by any one of the following formulas: (1-115) to (1-118), (1-120), (1-121), (1-123) to (1-128), (1-132), (1-137) to (1-142), (1-145), (1-151), (1-164), (1-199), (1-202), (1-204) to (1-206), (1-209), (1-212), (1-215), (1-218), (1-283), (1-285), (1-290), (1-293), (1-295), (1-297), and (1-304).

[0293] The number of cycloalkanes condensed on an aryl ring or heteroaryl ring is preferably one to three, more preferably one or two, and even more preferably one. For example, the following shows an example in which one or more cycloalkanes are condensed on a benzene ring (phenyl). * indicates the bonding position, which can be any carbon that constitutes the benzene ring and does not constitute a cycloalkane. Cycloalkanes condensed as in formulas (Cy-1-4) and (Cy-2-4) can also condense with each other. This is true 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.

[0294]

[0295] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows examples of one or more -CH2- substituents of a cycloalkane condensed on a benzene ring (phenyl) with -O- substitution. This is true whether the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or whether the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0296]

[0297] 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 bonded via a single bond or a linking group), 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 also preferred. Furthermore, when cycloalkyl is substituted, a spirostructure may be formed, examples of which are shown below.

[0298]

[0299] As a form of cycloalkane condensation, firstly, one or more of the aryl or heteroaryl rings of the A, B, and C rings of polycyclic aromatic compounds having one or more structural units represented by formula (1) can be listed as (hereinafter referred to as formula (1-a1), formula (1-b1), formula (1-c1), formula (1-d1), formula (1-e1), formula (1-f1), formula (1-a2), formula (1-b2), formula (1-c2), formula (1-d2), formula (1-e2), formula (1-f2), formula (1-d3), formula (1-e3), formula (2-a1), formula (2-a2), formula (2-b1), formula (2-b2), formula (2- c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), wherein any one or more of the aryl ring, heteroaryl ring, or condensed ring in the formula (3-e1) to (3-e8) are formed by the condensation of cycloalkanes. Examples of condensed rings in these formulas include the tetrahydronaphthiophene ring or the tetrahydronaphthothiophene ring.

[0300] Other forms of cycloalkane condensation include polycyclic aromatic compounds having one or more structural units represented by formula (1), or formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), and (2-b2). Polycyclic aromatic compounds represented by formulas (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8) have a form in which an aryl group condensed from a cycloalkane or a heteroaryl group condensed from a cycloalkane is a substituent, or is part of a substituent. For example, R can be listed. NY1 ~R NY3 Any of them is in the form of an aryl group condensed from a cycloalkane or a heteroaryl group condensed from a cycloalkane. Other examples include: a diarylamino group condensed from a cycloalkane (condensed into the aryl moiety), an arylheteroarylamino group condensed from a cycloalkane (condensed into the aryl moiety and / or the heteroaryl moiety), a diarylamino group condensed from a cycloalkane (condensed into the heteroaryl moiety), a carbazole group condensed from a cycloalkane (condensed into the benzene ring moiety), or a benzo[a]carbazole group condensed from a cycloalkane (condensed into the benzene ring moiety), and other examples of aryl groups condensed from cycloalkane, or heteroaryl groups condensed from cycloalkane, or partial structures of a substituent (e.g., the aryl portion of an aryloxy group, etc.) having an aryl group condensed from a cycloalkane, or a heteroaryl group condensed from a cycloalkane. Regarding "diarylamino," examples of groups described as the "first substituent" can be cited.

[0301] Furthermore, as more concrete examples, equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (1-a1) can be listed. In polycyclic aromatic compounds represented by formulas (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8), the a ring located in the Y ring is... 1 The opposite R Z Examples include a diarylamino group condensed from a cycloalkane (condensed toward the aryl moiety) or a carbazole group condensed from a cycloalkane (condensed toward the benzene ring moiety).

[0302] In polycyclic aromatic compounds containing the structural unit represented by formula (1), each element contains multiple naturally occurring isotopes in a naturally occurring ratio, unless otherwise specified. Furthermore, all or some of the elements in each structural formula may exceed the naturally occurring ratio (e.g., in boron-11...). 11 B) contains 90% or more of a heavy stable isotope. In this specification, this is simply referred to as "substitution" or "heavy stable isotope". More specifically, at least one hydrogen atom may be substituted for deuterium, and at least one nitrogen atom may be substituted for nitrogen-15 (…). 15 N), at least one sulfur can be substituted with sulfur-33 (N), 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be substituted with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be substituted with carbon-13 (O), 13 C), at least one boron can be processed via boron-11 ( 11B) Substitution. The following formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (2-c1) are replaced. The structures represented by equations (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8) are also the same, and the description is the same. The sample plots are applicable to the following formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (…). Polycyclic aromatic compounds represented by formulas (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8). These compounds are obtained by substituting at least a portion of the elements with heavier stable isotopes, particularly by using at least one boron via boron-11 (…). 11 B) Substitution can achieve long lifetimes for organic electroluminescent elements that use polycyclic aromatic compounds containing the structural units represented by formula (1) as dopants.

[0303] In structures containing one or more structural units represented by formula (1), all or part of the hydrogen atoms may be substituted with deuterium, cyano, or halogen. The formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (2-c1) described below... The same applies to polycyclic aromatic compounds represented by formulas (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8). The same explanation applies to equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (2-b2). Polycyclic aromatic compounds represented by formulas (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8).

[0304] 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 For Si-R S or Ge-R Ge R at that time S Or R Ge (R S Or R Ge (including alkyl, cycloalkyl, or aryl groups), and NR NY1 R NY1 and NR NY2 R NY2 (R NY1 and R NY2The hydrogen in the alkyl, cycloalkyl, or aryl group can be substituted with deuterium, cyano, or halogen. Examples of such substitutions include the substitution of all or part of the hydrogen in the aryl or heteroaryl group with 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 of the structural units represented by formula (1) is deuterated, but more preferably that all hydrogens directly bonded to the aromatic ring are deuterated, or that all hydrogens are deuterated, and most preferably that all hydrogens directly bonded to the aromatic ring are deuterated.

[0305] At least one -CH2- of one or more structures containing the structural unit represented by formula (1) may also be replaced by -O-.

[0306] At least one hydrogen atom in one or more of the structures containing the structural unit represented by formula (1) may also be substituted by the base represented by the following formula (Cz).

[0307]

[0308] In formula (Cz),

[0309] *a indicates the bond position.

[0310] Z y Each independently represents N or CR. ZY The CR ZY R ZY For hydrogen or substituents, two adjacent CR ZY R ZY They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

[0311] As the R ZY The substituents may be subject to the provisions for the first substituent as described in formula (1), or may be further substituted on the second substituent as described in formula (1).

[0312] The basis represented by formula (Cz) ideally refers to at least one of the rings A to C in formula (1) that is not represented by formula (Az). For example, if ring A in formula (1) is represented by formula (Az), the basis represented by formula (Cz) ideally refers to ring B and / or ring C that is substituted.

[0313] Two adjacent CRs ZY R ZY The heteroaryl rings formed by mutual bonding can be governed by the definition of heteroaryl rings described in formula (1), and may also contain Se as a heteroatom. For example, two adjacent CRs ZY RZY They can bond with each other to form a benzo[selenyl]phene ring. Two adjacent CRs ZY R ZY The heteroaryl rings formed by mutual bonding can also be further substituted, and the substituents here can be subject to the provisions for the second substituent in the description of formula (1).

[0314] At least one hydrogen in formula (Cz) can be substituted with deuterium.

[0315] In a structure comprising one or more structural units represented by formula (1), at least one hydrogen-substituted polycyclic aromatic compound or polymer thereof, represented by formula (Cz), as described below, exhibits desirable properties as an emission dopant in a light-emitting layer comprising an emission dopant and an auxiliary dopant.

[0316] Preferred examples of polycyclic aromatic compounds having one or more structural units comprising the structural unit represented by formula (1) include the following formulas: (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), and (2-a2). Polycyclic aromatic compounds represented by any one of the formulas (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8). Furthermore, regarding equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), and (2-c2)... The structure and preferred range of the substituents or rings contained in formulas (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8) can be referred to the descriptions of the corresponding formulas (1).

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325] Equation (1-a1), Equation (1-b1), Equation (1-c1), Equation (1-d1), Equation (1-e1), Equation (1-f1), Equation (1-a2), Equation (1-b2), Equation (1-c2), Equation (1-d2), Equation (1-e2), Equation (1-f2), Equation (1-d3), Equation (1-e3), Equation (2-a1), Equation (2-a2), Equation (2-b1), Equation (2-b2), Equation In equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), Y 1 NR NY1 and NR NY2 respectively with Y in equation (1) 1 NR NY1 and NR NY2For the same meaning, the preferred range is also the same. Additionally, equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), and (2-b2) are also considered. X in equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8) 1 and R NY3 respectively with X in equation (Az) 1 and R NY3 For the same meaning, the preferred range is also the same.

[0326] Furthermore, X in equations (1-d1), (1-e1), (1-d2), (1-e2), (1-d3), (1-e3), (2-d1) to (2-d5), (2-e1) to (2-e5), (3-d1) to (3-d5), and (3-e1) to (3-e8) 2 With X in equation (Az) 1 For the same meaning, the preferred range is also the same. That is, X 2 >C(-R) C )2、>C=C(-R c 2. C(-OR) O )2、>Si(-R Si 2. Or >C=O. As X 2 >C(-R) C )2 and >C=C(-R c )2 of R C C(-OR) O )2 of R O and >Si(-R Si )2 of R Si Each of the two Rs 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. C They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring. X 2Ideally, it should be >C(-R) C )2, at this time, R c Ideally, the alkyl group may be substituted or unsubstituted. In formulas (1-d1), (1-e1), (1-d2), (1-e2), (1-d3), and (1-e3), X 1 With X 2 Each independently is >C(-R) C )2, R here C Ideally, it should be a substituted or unsubstituted alkyl group.

[0327] In equations (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), X 11 and X 22 Independently defined as >O and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se, as X 11 or X 22 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0328] Here, R in equation (1) NY1 and NR NY2 Related "R" NY1 or NR NY2The definition of "bonding to ring A and / or ring B, or ring A and / or ring C by linking bases or single bonds" corresponds to equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), and (2-a2). Equations (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8) contain “R”. NY1 or NR NY2 Through -O-, -S-, -C(-R)2- or a single bond, and associated with CR Z R in Z Z The specification of "one or two bonds". Specifically, the R NY1 or NR NY2 The one that is spatially closest to each of the rings shown below can be taken as CR. Z Z-bonds.

[0329] Equations (1-a1), (1-a2), (2-a1), (2-a2), (3-a1), and (3-a2): R NY1 For ring a, R NY2 For ring a and / or ring c.

[0330] Equations (1-b1), (1-b2), (2-b1), (2-b2), (3-b1), and (3-b2): R NY1 For ring a and / or ring b11, R NY2 For ring a and / or ring c.

[0331] Equations (1-c1), (1-c2), (2-c1), (2-c2), (3-c1), and (3-c2): R NY1 For ring a and / or ring b11, R NY2 For ring a and / or ring c.

[0332] Equations (1-d1), (1-d2), (1-d3), (2-d1) to (2-d5), (3-d1) to (3-d5): R NY1 For ring a and / or ring b11, R NY2 For ring a and / or ring c11.

[0333] Equations (1-e1), (1-e2), (1-e3), (2-e1) to (2-e5), (3-e1) to (3-e8): R NY1 For ring a, R NY2 It is ring a.

[0334] Equations (1-f1), (1-f2), (2-f1), and (2-f2): R NY1 For a11 ring and / or b ring, R NY2 It is ring c.

[0335] Equation (1-a1), Equation (1-b1), Equation (1-c1), Equation (1-d1), Equation (1-e1), Equation (1-f1), Equation (1-a2), Equation (1-b2), Equation (1-c2), Equation (1-d2), Equation (1-e2), Equation (1-f2), Equation (1-d3), Equation (1-e3), Equation (2-a1), Equation (2-a2), Equation (2-b1), Equation (2-b2), Equation (2-c1) In equations (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), Z is independently N or CR. Z As the CR Z R Z Refer to R in the above formula (Az). Z Explanation. Z is preferably CR. Z The form of R. Multiple R in each formula. Z They can be the same or different.

[0336] Furthermore, Z = Z can be independently set to >0 and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se. Among these, >O and >NR are preferred. NX >C(-R) CX )2, or >S. The >NR mentioned above. NX The >C(-R) CX )2 and the above >Si(-R SiX The R in )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, wherein the >C(-R CX)2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can be bonded together to form a loop. For example, when Z = Z is > NR NX When >O, or >S, pyrrole rings, furan rings, or thiophene rings can be formed similarly to those described with respect to one ring (monocyclic ring) in formula (Az). In the remaining Z adjacent rings and all being CR... Z In the case of these R Z If a benzene ring is formed by bonding, it can form an indole ring, a benzofuran ring, or a benzothiophene ring, similar to the ring (monocyclic ring) described with respect to formula (Az).

[0337] In equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2 In each of the formulas (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), the number of rings (single rings) containing Z as N is zero to four, preferably zero to three, more preferably zero to two, and particularly preferably zero to one. In equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), and (2-c1) In each of the following formulas, Z is preferably all of CR: (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8). Z .

[0338] Equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) ~ Equations ( In formulas (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), in the ring (monocyclic ring) containing Z as N, it is preferable that one or two of the plurality of Zs is N, and 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.

[0339] Equation (1-a1), Equation (1-b1), Equation (1-c1), Equation (1-d1), Equation (1-e1), Equation (1-f1), Equation (1-a2), Equation (1-b2), Equation (1-c2), Equation (1-d2), Equation (1-e2), Equation (1-f2), Equation (1-d3), Equation (1-e3), Equation (2-a1), Equation (2-a2), Equation (2-b1), Equation (2-b2), Equation In equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), Preferred formulas are (1-a1), (1-b1), (1-c1), or (1-d1), (1-a2), (1-b2), (1-d2), (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (3-a1), (3-a2), (3-b 1) Formula (3-b2), Formula (3-c1), Formula (3-c2), or Formula (3-d1) to Formula (3-d5), more preferably Formula (1-b1), Formula (1-d1), Formula (1-b2), Formula (1-d2), Formula (2-b1), Formula (2-b2), Formula (2-d1) to Formula (2-d5), Formula (3-b1), Formula (3-b2), or Formula (3-d1) to Formula (3-d5).

[0340] Equations (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), Equations In formulas (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), the preferred Z for each of the following rings is CR: a11 ring, a13 ring (or a14 ring), b ring, b11 ring, b13 ring (or b14 ring), c11 ring, and c13 ring (or c14 ring). Z Furthermore, in the c-ring, it is preferable that Z is always CR.Z Or, a Z = Z is greater than 0 or greater than NR. NX >C(-R) CX )2、>Si(-R SiX )2, >S, or >Se (for examples of their morphology and preferred forms, please refer to the specification), and the remaining Z are 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.

[0341] The polycyclic aromatic compounds represented by formula (1-b1), formula (2-b1), or formula (2-b2) are particularly preferred, especially those represented by formula (1-b1-Z), formula (2-b1-Z), formula (2-b2-Z), formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T).

[0342]

[0343]

[0344] In equations (1-b1-Z), (2-b1-Z), (2-b2-Z), (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T),

[0345] R NY1 R NY2 and R NY3 Independently with R in equation (1) NY1 R NY2 and R NY3 They have the same meaning.

[0346] R Z4 Each is an unsubstituted alkyl group, and the two Rs are independent. Z4 They can bond together to form a ring.

[0347] R Z1 Each is an unsubstituted alkyl group,

[0348] R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2.

[0349] R Z3 Each is an unsubstituted alkyl group, and n is an integer from 0 to 2.

[0350] In the structures represented by formulas (1-b1-Z), (2-b1-Z), (2-b2-Z), (1-b1-T1), (1-b1-T2), (2-b1-T), or (2-b2-T), at least one of the aryl rings or heteroaryl rings can be a structure formed by bonding a partial structure represented by formula (B) to an adjacent carbon atom.

[0351]

[0352] In formula (B), Me represents a methyl group, and * indicates the bond position.

[0353] At least one hydrogen atom in the structure represented by formula (1-b1-Z), formula (2-b1-Z), formula (2-b2-Z), formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T) may be substituted with a cyano group, a halogen, or a deuterium.

[0354] In equations (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T), X a For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, or >S, the >NR NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0355] In equations (2-b1-Z), (2-b2-Z), (2-b1-T), and (2-b2-T), X 11 For >O, >NR NX >C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se, as X 11 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX)2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning.

[0356] In equations (1-b1-Z), (2-b1-Z), (2-b2-Z), (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T), R NY1 and R NY2 Preferably, all are substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or the structure represented by formula (A11) is used as NR. NY1 or NR NY2 Regarding R NY1 and R NY2 The preferred range can be referred to R in equation (1). NY1 Or R NY2 The preferred range is recorded.

[0357] R NY3 Preferably, it is 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).

[0358] R Z4 Preferably, all of them are methyl.

[0359] 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, R Z3 Preferably relative to NR NY3 N is located in the opposite position.

[0360] Furthermore, in the structures represented by formulas (1-b1-Z), (2-b1-Z), (2-b2-Z), (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T), zero to two of the aryl rings or heteroaryl rings are preferably bonds between the partial structure represented by formula (B) and adjacent carbon atoms in the ring. When the structures represented by formulas (1-b1-Z), (2-b1-Z), (2-b2-Z), (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T) include the partial structure represented by formula (B), the ring bonded by the partial structure represented by formula (B) is preferably R. Z2 The bonded benzene ring or R NY1 Or R NY2 Any of the aryl rings on it.

[0361] As a further 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 formula, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, and "D" represents deuterium. In addition, the following structure is an example.

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399] Depending on the type of substituent, the polycyclic aromatic compounds of the present invention may contain enantiomers or diastereomers. However, 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.

[0400] Polycyclic aromatic compounds having one or more structural units represented by formula (1) can also be used as polymers (the monomers used to obtain the polymers have polymerizable substituents) or crosslinkers (the polymers used to obtain the crosslinkers have crosslinking substituents), or suspended polymers (the reactive compounds used to obtain the suspended polymers have reactive substituents) or crosslinkers (the suspended polymers used to obtain the crosslinkers have crosslinking substituents) for use in... In materials for mechanical devices, such as materials for organic electroluminescent elements, materials for organic field-effective transistors, or materials for organic thin-film solar cells, the polymer compound is polymerized by replacing a reactive substituent in a polycyclic aromatic compound having one or more structural units represented by formula (1) as a monomer; the polymer crosslinker is formed by further crosslinking the polymer compound; the suspended polymer compound is formed by reacting a main-chain polymer with the reactive compound; and the suspended polymer crosslinker is formed by further crosslinking the suspended polymer compound.

[0401] 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 group of cycloalkyl (e.g., epoxy group), unsaturated forms of condensed cycloalkanes (e.g., condensed cyclobutenyl), etc., preferably substituents with the following structures. * in each structural formula indicates a bond position.

[0402]

[0403] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group having 1 to 12 carbon atoms, alkylene group having 1 to 12 carbon atoms, or polyalkylene group having 1 to 12 carbon atoms. Among the substituents, those represented by formulas (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and those represented by formulas (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0404] 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.

[0405] Methods for manufacturing polycyclic aromatic compounds

[0406] Regarding polycyclic aromatic compounds having one or more structural units represented by formula (1) or formulas (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b1), and (1-a2) Polycyclic aromatic compounds represented by formulas (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8) are basically first utilized using bonding groups (including NR). NY1 or NR NY2 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), and then using the bonding group (containing Y) 1The 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 general reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used; if it is an amination reaction, a general 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, as follows) can be used. By using a starting material having the desired condensed ring at some point in the reaction steps or by adding a step to condense the ring, a compound of which at least one ring selected from the group consisting of the A ring, B ring, and C ring is represented by the ring (Az) can be produced.

[0407] Manufacturing method via intermediate-1

[0408] The polycyclic aromatic compounds of the present invention can be manufactured using a manufacturing method comprising the following steps. Reference can be made to International Publication No. 2015 / 102118 for details of these steps.

[0409] The manufacturing method includes the following reaction steps: using an organic base compound to react NR in intermediate-1 below. NY1 With NR NY2 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 The exchange is performed; and the Y is utilized via a series of aromatic electrophilic substitution reactions using a Bronsted base. 1 This allows the B ring to bond with the C ring.

[0410]

[0411] Manufacturing method via intermediate-2

[0412] The polycyclic aromatic compounds of the present invention are preferably manufactured using a manufacturing method that includes 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.

[0413]

[0414] (In intermediate-2, Z is esterifiable -B(OH)2)

[0415] In intermediate-2, Z is esterifiable -B(OH)2. Preferred Y... 1 It is an esterified group of -B(OH)2.

[0416] The group that is esterified from -B(OH)2 (-B(OR)2) is not particularly limited; for example, groups obtained by reacting an alcohol containing a diol or a carboxylic acid with boric acid can be listed. 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), and the R groups can bond to each other to form a ring. Additionally, 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.

[0417]

[0418] 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.

[0419] 2. Organic devices

[0420] 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.

[0421] 2-1. Organic electroluminescent element

[0422] 2-1-1. Structure of Organic Electroluminescent Element

[0423] Figure 1 This is a schematic cross-sectional view showing an example of an organic EL element.

[0424] Figure 1 The organic EL element 100 shown 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.

[0425] Furthermore, the organic EL element 100 can also be formed by reversing the fabrication order to form, for example, the following structure: 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.

[0426] Not all of the layers are indispensable. The smallest constituent unit is designed 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.

[0427] 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 layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode". The structural forms of “electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode”, “substrate / anode / light-emitting layer / electron transport layer / cathode”.

[0428] 2-1-2. The light-emitting layer in organic electroluminescent devices

[0429] 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.

[0430] 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 by being excited through 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.

[0431] The light-emitting layer can be a single layer or multiple layers, either of which is acceptable, and each layer is formed from a light-emitting layer material (a host material and a dopant material). The host material and the 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 for the 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.

[0432] The amount of main material used varies depending on the type of main material, and can be determined in accordance with 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 mass, and even more preferably 90% to 99.9% of the mass. When the main material is a combination of hole-transporting and electron-transporting main materials, the amount of main material used is the sum of the mass of the hole-transporting and electron-transporting main materials. The mass ratio of the hole-transporting to the electron-transporting main material is 1:9 to 9:1, preferably 4:6 to 6:4, and more preferably approximately 1:1.

[0433] 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 material used is 0.001% to 50% of the total mass of the material used in the luminescent layer, more preferably 0.05% to 20% of the total mass, and even more preferably 0.1% to 10% of the total mass. Within this range, for example, concentration quenching can be prevented, and this is preferable in this respect.

[0434] As dopant materials, both emitting dopant and auxiliary dopant materials can be used. As auxiliary dopant materials, either thermally active delayed fluorescence materials or phosphorescent materials are preferably used. In organic electroluminescent devices using auxiliary dopant materials, it is preferable to use a low concentration of emitting dopant material to prevent concentration quenching. Regarding the efficiency of the thermally active delayed fluorescence mechanism, it is preferable to use a high concentration of auxiliary dopant material. Furthermore, in organic electroluminescent devices using thermally active delayed fluorescence auxiliary dopant materials, regarding the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant material, it is preferable that the concentration of emitting dopant material is low compared to the amount of auxiliary dopant material used.

[0435] When using auxiliary dopant materials, the base amounts of the main material, auxiliary dopant material, and emission dopant material relative to the total mass of the material used in the light-emitting layer are 40% to 99% by mass, 59% to 1% by mass, and 20% to 0.001% by mass, respectively; preferably 60% to 95% by mass, 39% to 5% by mass, and 10% to 0.01% by mass, respectively; and more preferably 70% to 90% by mass, 29% to 10% by mass, and 5% to 0.05% by mass, respectively.

[0436] The polycyclic aromatic compounds of the present invention are preferably used as materials for forming the light-emitting layer, and more preferably as dopants.

[0437] Polycyclic aromatic compounds containing the structural unit represented by formula (1) can be used as emission dopants for TTF elements that utilize the phenomenon of generating singlet excitons from multiple triplet excitons (Triplet-Triplet Fusion (TTF)).

[0438] Furthermore, the polycyclic aromatic compounds of the present invention can also be used as "thermally activated delayed phosphors" as emission dopants in organic EL elements (hereinafter, sometimes referred to as "TADF elements") that exhibit thermally activated delayed fluorescence (TADF). In a "thermally activated delayed phosphor," by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem transitions from the lowest excited triplet state to the lowest excited singlet state, which typically have low transition probabilities, are generated efficiently, thereby exhibiting emission from the singlet state (thermally activated delayed fluorescence, TADF). In conventional fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal inactivation path and therefore cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, enabling highly efficient organic EL elements.

[0439] The polycyclic aromatic compounds of the present invention can be used as emission dopants for "TADF elements," emission dopants for TADF elements using two substrates, emission dopants for organic electroluminescent elements (TAF elements) using other thermally active delayed phosphors as auxiliary dopants, and emission dopants for organic electroluminescent elements (phosphorescent auxiliary elements) using phosphorescent materials as auxiliary dopants. From the viewpoint that less material is used in the element makes it easier to manufacture, it is preferable to use it as an emission dopant for TADF elements or as an emission dopant for TADF elements using two substrates, and more preferably the former. From the viewpoint of efficiency, it is preferable to use it as an emission dopant for both TAF elements and phosphorescent auxiliary elements, and more preferably as an emission dopant for TAF elements.

[0440] It is generally believed that fast delayed fluorescence exhibits excellent TADF properties. Specifically, when luminescent materials with a delayed fluorescence lifetime of 20 μsec or less are used as emitting dopants in light-emitting elements, high device efficiency and long device lifetime can be provided. The delayed fluorescence lifetime is preferably less than 20 μsec, more preferably less than 10 μsec, and most preferably less than 5 μsec.

[0441] In addition, generally speaking, ΔE S1T1 The smaller the value, the better the TADF property. Furthermore, ΔE S1T1 It is the lowest excited singlet state energy level (E S1 ) and the lowest excited triplet energy level (E T1 The energy difference. Specifically, ΔE S1T1 The value is preferably 0.20 eV or less, more preferably 0.15 eV or less, and particularly preferably 0.10 eV or less.

[0442] <Main Material>

[0443] As the main material, examples include condensed ring derivatives such as anthracene or pyrene, bis(styrene) derivatives such as bis(styrene)-anthracene derivatives or styrene-based benzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo[a]fluorene derivatives, N-phenylcarbazole derivatives, carbazole nitrile derivatives, and dibenzo[a]fluorene derivatives. Derivatives, etc. Furthermore, from the viewpoint of durability, it is preferable that some or all of the hydrogen atoms in the host material are deuterated. Moreover, it is also preferable to form the light-emitting layer by combining a host compound with some or all of its hydrogen atoms deuterated, and a dopant compound with some or all of its hydrogen atoms deuterated.

[0444] From the perspective of promoting rather than hindering the generation of TADF within the emissive layer, the lowest excited triplet energy level (E) of the host material T1Preferably, it has the highest E within the light-emitting layer. T1 E of dopants or auxiliary dopants T1 High, specifically, the E of the main material T1 Preferably, the E of the dopant or auxiliary dopant is greater than that of the dopant or auxiliary dopant. T1 The voltage is 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Additionally, the E of the main material... T1 Preferably, it is 2.70 eV or higher, more preferably 2.73 eV or higher, and even more preferably 2.80 eV or higher.

[0445] TADF-active compounds can also be used in the host material.

[0446] The host material can be a single material or a combination of multiple materials. In the case of multiple combinations, a combination of a hole-transporting host material and an electron-transporting host material is preferred.

[0447] The hole transport host material (HH) and electron transport host material (EH) satisfy the following relationship regarding the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

[0448] The HOMO of the hole transport host material (HH) is shallower than that of the electron transport host material (EH), and the LUMO of the electron transport host material (EH) is deeper than that of the hole transport host material (HH).

[0449] In addition, it is preferable that the HOMO of the emission dopant is shallower than that of the hole transport host material (HH), or that the LUMO of the emission dopant is deeper than that of the electron transport host material (EH).

[0450] Furthermore, from the viewpoint of promoting rather than hindering the generation of TADF within the emissive layer, the lowest excited triplet energy level (E) of the hole transport host material (HH) and the electron transport host material (EH) T1 Preferably, it has the highest E within the light-emitting layer. T1 E emission dopants or auxiliary dopants T1 High, specifically, the E of the main material T1 Preferably, the E of the emission dopant or auxiliary dopant is greater than that of the emission dopant or auxiliary dopant. T1 The voltage is 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. Additionally, the E of the main material... T1Preferably, it is 2.47 eV or higher, more preferably 2.49 eV or higher, and even more preferably 2.56 eV or higher.

[0451] Furthermore, it is preferable to use a hole-transporting host material in the hole transport layer adjacent to the light-emitting layer, and an electron-transporting host material in the electron transport layer adjacent to the light-emitting layer. This is because it reduces the likelihood of carrier leakage and energy leakage from the self-emissive layer to the adjacent layer, resulting in a high-efficiency organic EL device. The host material (hole-transporting host material) in the light-emitting layer can be the same as or different from the material of the hole transport layer. Similarly, the host material (electron-transporting host material) in the light-emitting layer can be the same as or different from the material of the electron transport layer.

[0452] [Hole transport host material (HH)]

[0453] Examples of preferred hole transport host materials (HH) include compounds represented by formula (HH-1) or having a partial structure represented by formula (HH-1) and having a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The compounds preferably do not contain an imine structure (-N=C-; a ​​partial structure containing a heteroaryl ring), boron (>B-), or cyano (CN).

[0454]

[0455] In equation (HH-1),

[0456] Q is>O,>S, or>NA H ,

[0457] In formula (HH-1), the carbon atom adjacent to the carbon atom bonded to Q in each of the two phenyl groups can be bonded to each other through L.

[0458] L represents a single bond, >O, >S, or >C(-A). H )2,

[0459] A H It is hydrogen, aryl, or heteroaryl, >C(-A H The two A's in )2 H They can be bonded together.

[0460] When the hole-transporting host material includes the structure represented by formula (HH-1) as a partial structure, it may include one of the partial structures, but preferably two or more. In the case of two or more partial structures, the two or more partial structures may be identical or different from each other. The two or more partial structures may be bonded to each other by single bonds, or by sharing any ring contained in the partial structure, or by condensation of any ring contained in the partial structure with each other. The partial structure may also have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy groups.

[0461] Compounds represented by formula (HH-1) or having a partial structure represented by formula (HH-1) have a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings is preferably 6 or more, more preferably 8 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings; with respect to condensed rings, it is defined as the number obtained by counting the single rings constituting the condensed ring.

[0462] The hole-transporting host material is preferably a compound comprising one or more partial structures selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a condensed polycyclic ring containing a phenothiazine or phenothiazine. The hole-transporting host material may comprise one such partial structure, but is preferably comprising two or more. In the case of comprising two or more partial structures, the two or more partial structures may be identical or different from each other.

[0463] Specific examples of materials that serve as host materials for hole transport include the following compounds.

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477] Among the above, HH-1-1, HH-1-2, HH-1-4~HH-1-12, HH-1-17, HH-1-18, HH-1-20~HH-1-24, HH-1 are preferred -82, HH-1-84~HH-1-89, HH-1-91, HH-1-92, HH-1-106~HH-1-108, and HH-1-109~HH-1-115.

[0478] [Electron transport host material (EH)]

[0479] Examples of electron transport host materials (EH) include compounds represented by formulas (EH-1A) to (EH-1D) or having partial structures represented by formulas (EH-1A) to (EH-1D) and having a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings.

[0480]

[0481] In equations (EH-1A) to (EH-1D),

[0482] Ar is a heteroaryl ring containing N=C as part of the ring structure.

[0483] Z represents a single bond, -O-, -S-, or -N (-A). E )-,

[0484] The carbon atom adjacent to the carbon atom bonded to Z and the A atom bonded to Z E They can be bonded to each other through L.

[0485] L represents a single bond, >O, >S, or >C(-A) E )2,

[0486] A E It is an aryl, heteroaryl, or triarylsilyl group, and any one of the A atoms in formula (EH-1C) is... E It can be a diarylamino group.

[0487] Two A atoms with the same atomic bond E They can be bonded to each other through L.

[0488] X is C, P, or S.

[0489] When X is C, n = 2, m = 1.

[0490] When X is P, n = 3, m = 1.

[0491] When X is S, n = 2, m = 1 to 2.

[0492] Compounds represented by formulas (EH-1A) to (EH-1D), or having a partial structure represented by formulas (EH-1A) to (EH-1D), have a structure comprising at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. Furthermore, it is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings; for condensed rings, it is defined as the number obtained by counting the single rings constituting the condensed ring.

[0493] When the electron transport host material comprises the structures represented by formulas (EH-1A) to (EH-1D) as partial structures, it may include one of the partial structures, but preferably two or more. In the case of two or more partial structures, the two or more partial structures may be identical or different from each other. The two or more partial structures may be bonded to each other by single bonds, or by sharing any ring contained in the partial structure, or by condensation of any ring contained in the partial structure with each other. The partial structure may also have substituents selected from aryl, heteroaryl, diarylamino, or aryloxy groups.

[0494] The following compounds can be cited as specific examples of electron transport host materials.

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503] Other preferred examples of electron transport host materials (compounds having a partial structure represented by formula (EH-1)) include polycyclic aromatic compounds represented by formula (EH-1b) below, or polymers of polycyclic aromatic compounds having a plurality of structures represented by formula (EH-1b) below.

[0504]

[0505] In equation (EH-1b),

[0506] R 1 R 2 R 3 R 4 and R 5 (Hereafter referred to as "R") 1 Each of the substituents ("etc.") can be hydrogen or a substituent independently. The substituents need only be selected from the substituent group Z.

[0507] In equation (EH-1b), X 1 and X 2 X can be independently classified as >NR (amine nitrogen), >O, >C(-R)2, >S, or >Se. 1 and X 2 It cannot be >C(-R)2 at the same time.

[0508] The R in >NR and >C(-R)2 is independently hydrogen or a substituent selected from substituent group Z, and may be further substituted by aryl, heteroaryl, alkyl or cycloalkyl (the above are second substituents). The R in >NR and >C(-R)2 may be independently bonded to at least one of the a ring, b ring and c ring through a linking group or a single bond.

[0509] Y 1 Y 2 Y 3 Y 4 Y 5 and Y 6 (Hereafter referred to as "Y") 1 Each of these terms is independently =C(-R)- or =N- (pyridine nitrogen), and at least one is =N- (pyridine nitrogen).

[0510] In the case of =C(-R)-, R is independently hydrogen or a substituent selected from the substituent group Z.

[0511] The R 1 R 2 R 3 R 4 and R 5 and as Y 1 ~Y6 The adjacent groups in the =C(-R)- of the R can be bonded to each other and together with at least one of the rings a, b and c to form an aryl ring or a heteroaryl ring. At least one hydrogen in the formed ring can be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups can be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (the above are the first substituents), and at least one of these hydrogens can be further substituted by an aryl, heteroaryl, alkyl or cycloalkyl (the above are the second substituents).

[0512] In the compound and structure represented by formula (EH-1b), at least one hydrogen atom may be substituted by a cyano group, a halogen, or a deuterium.

[0513] In formula (EH-1b), R is preferred. 1 R 2 R 3 R 4 and R 5 All are hydrogen, or R 3 and R 4 All are hydrogen, and are chosen freely from R 1 R 2 and R 5 One or more of the groups consist of substituents other than hydrogen, while the others are hydrogen. Preferred substituents are alkyl, aryl groups substituted with alkyl or heteroaryl groups, heteroaryl groups substituted with alkyl or aryl groups, or diarylamino groups substituted with alkyl or aryl groups. In this case, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms (methyl, tert-butyl, etc.), the aryl group is preferably phenyl or biphenyl, and the heteroaryl group is preferably triazine, carbazole (2-carbazole, 3-carbazole, 9-carbazole, etc.), pyrimidinyl, pyridinyl, dibenzofuranyl, or dibenzothiophene. Specific examples include: phenyl, biphenyl, diphenyltriazine, carbazoletriazine, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazoletriazine, pyridinyl, dibenzofuranyl, and dibenzothiophene.

[0514] Y 1 Each of them is independently equal to either =C(-R)- or =N-, with at least one being =N-. Y 1 ~Y 6 Either of them can be =N-. Preferably, it is Y. 1 and Y 6 =N-(a ring is a pyrimidine ring), Y 1 Or Y 6 =N-(a ring is a pyridine ring), Y 2 and Y 5 =N-(b- and c-rings are pyridine rings), Y 3 and Y 4=N-(b- and c-rings are pyridine rings), Y 2 ~Y 5 =N-(ring b and ring c are pyrimidine rings), Y 1 Y 3 Y 4 and Y 6 =N-(ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 Y 2 Y 5 and Y 6 =N-(ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 ~Y 6 =N- (a, b, and c rings are pyrimidine rings), Y 2 Or Y 5 =N-(b ring or c ring is a pyridine ring).

[0515] In addition to the above =N- configuration relationship, X is preferred. 1 and X 2 It is >0, and preferably a polycyclic aromatic compound containing a partial structure represented by any of the following formulas.

[0516]

[0517] In particular, polycyclic aromatic compounds with partial structures represented by the inclusion formula (EH-1b-N1) have higher E values ​​compared to structures without nitrogen. S1 High E T1 Small ΔE S1T1 .

[0518] The following are specific examples of polycyclic aromatic compounds represented by formula (EH-1b).

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525] Among the above, preferred ones are EH-1-1 to EH-1-4, EH-1-10, EH-1-21 to EH-1-25, EH-1-32, EH-1-33, EH-1-51 to EH-1-59, EH-1-61, EH-1-66, EH-1-68, EH-1-71, and EH-1-7. 2. EH-1-90, EH-1-94~EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1- 115. EH-1-117, EH-1-120, EH-1-122, EH-1-123, EH-1-127~EH-1-130.

[0526] [A combination of hole-transporting host materials and electron-transporting host materials]

[0527] The combination of hole transport host materials and electron transport host materials is based on the HOMO, LUMO, and lowest excited triplet energy level (E) of the hole transport host material, electron transport host material, and dopant material. T1 Use ) to choose.

[0528] Regarding HOMO and LUMO, a combination is selected where the HOMO(HH) of the hole transport host material is shallower than the HOMO(EH) of the electron transport host material, and the LUMO(EH) of the electron transport host material is deeper than the LUMO(HH) of the hole transport host material. More specifically, a combination in which HOMO(HH) is at least 0.10 eV shallower than HOMO(EH) and LUMO(HH) is at least 0.10 eV deeper than HOMO(EH) is preferred. A combination in which HOMO(HH) is at least 0.20 eV shallower than HOMO(EH) and LUMO(HH) is at least 0.20 eV deeper than HOMO(EH) is preferred. A combination in which HOMO(HH) is at least 0.25 eV shallower than HOMO(EH) and LUMO(HH) is at least 0.25 eV deeper than HOMO(EH) is preferred.

[0529] Hole-transporting host materials and electron-transporting host materials can be combinations that form an associative complex called an exciplex. It is generally known that exciplexes readily form between materials with a relatively deep LUMO level and materials with a shallow HOMO level. The interaction between the hole-transporting host materials and the electron-transporting host materials, specifically whether an exciplex forms, can be determined as follows: A monolayer film containing only the hole-transporting host material and the electron-transporting host material is formed under the same conditions as the formation of the emitting layer. The emission spectra (fluorescence and phosphorescence spectra) are measured, and the obtained emission spectra are compared with the emission spectra exhibited by the hole-transporting host material and the electron-transporting host material individually. It can also be determined as follows: the spectrum of the mixed film containing the hole-transporting host material and the electron-transporting host material shows emission wavelengths that are different from the spectra of both the film containing the hole-transporting host material and the film containing the electron-transporting host material. Specifically, a difference of more than 10 nm in the peak wavelength of the spectrum is sufficient as an indicator.

[0530] Specific examples of combinations of hole-transporting host materials and electron-transporting host materials that do not form excimer complexes include the following combinations. To satisfy the aforementioned HOMO, LUMO, and E... T1 Regarding the physical properties, in hole transport host materials, compounds having carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole, and benzoxazinophenazozine as partial structures are preferred; compounds having carbazole, dibenzofuran, and dibenzothiophene as partial structures are more preferred; and compounds having carbazole as a partial structure are even more preferred. Similarly, in electron transport host materials, compounds having pyridine, triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxazinophenaline as partial structures are preferred; compounds having triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxazinophenaline as partial structures are even more preferred; and compounds having triazine are even more preferred.

[0531] More specifically, the hole transport host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-4 to HH-1-12, HH-1-17, HH-1-18, HH-1-20 to HH-1-24, HH-1-82, HH-1-84 to HH-1-89, HH-1-91, HH-1-92 and HH-1-106 to HH-1-108, and the electron transport host material is preferably selected from EH-1-1 to EH-1-4. EH-1-10, EH-1-21~EH-1-25, EH-1-32, EH-1-33, EH-1-51~EH-1-59, EH-1-61, EH-1-71, EH-1-72, EH-1-90, In the group consisting of EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127~EH-1-130. Examples of preferred combinations include: compounds HH-1-1 and EH-1-22, compounds HH-1-1 and EH-1-23, compounds HH-1-1 and EH-1-24, compounds HH-1-2 and EH-1-22, compounds HH-1-2 and EH-1-23, compounds HH-1-2 and EH-1-24, or compounds HH-1-1 and EH-1-128.

[0532] Specific examples of combinations of hole-transporting host materials and electron-transporting host materials for forming excimer complexes include the following combinations. To satisfy the aforementioned HOMO, LUMO, and E... T1 Regarding the physical properties, in hole transport host materials, compounds having carbazole, triarylamine, indolocarbazole, and benzoxazinophenazine as partial structures are preferred, more preferably compounds having triarylamine, indolocarbazole, and benzoxazinophenazine as partial structures are even more preferred, and compounds having triarylamine as a partial structure are even more preferred. Similarly, in electron transport host materials, compounds having pyridine, triazine, phosphine oxide, and benzofuran-pyridine as partial structures are preferred, more preferably compounds having triazine, phosphine oxide, benzofuran-pyridine, and dibenzoxadiazine as partial structures are even more preferred, and compounds having phosphine oxide and triazine are even more preferred.

[0533] More specifically, the hole transport host material is preferably selected from the group consisting of HH-1-1, HH-1-2, HH-1-11, HH-1-12, HH-1-17, HH-1-18, HH-1-23, HH-1-24, and HH-1-115, and the electron transport host material is preferably selected from EH-1-1 to EH-1-4, EH-1-21 to EH-1-25, and EH-1 The group consisting of -51 to EH-1-57, EH-1-59, EH-1-66, EH-1-68, EH-1-90, EH-1-94, EH-1-99, EH-1-100, EH-1-101, EH-1-104, EH-1-117, EH-1-120, EH-1-122, EH-1-123, and EH-1-127 to EH-1-130. Examples of preferred combinations include: compounds HH-1-1 and EH-1-21, compounds HH-1-2 and EH-1-21, compounds HH-1-12 and EH-1-94, compounds HH-1-12 and EH-1-117, compounds HH-1-1 and EH-1-130, compounds HH-1-33 and EH-1-117, compounds HH-1-48 and EH-1-117, compounds HH-1-49 and EH-1-117, or compounds HH-1-115 and EH-1-99.

[0534] Furthermore, for specific combinations of hole-transporting host materials and electron-transporting host materials, please refer to: *Organic Electronics* (66(2019) 227-24), *Advanced Functional Materials* (25(2015) 361-366), *Advanced Materials* (26(2014) 4730-4734), *ACS Applied Materials and Interfaces* (8(2016) 32984-32991), *ACS Applied Materials and Interfaces* (2016, 8, 9806-9810), *ACS Applied Materials and Interfaces* (2016, 8, 32984-32991), and *Journal of Materials Chemistry*. The records are found in publications such as Materials Chemistry (C, 2018, 6, 8784-8792), Angewante Chemie International Edition (2018, 57, 12380-12384), Advanced Functional Materials (24, 2014, 3970), Advanced Materials (26, 2014, 5684), Synthetic Metals (201, 2015, 49), and Nature Photonics (16, 212-218 (2022)).

[0535] <Anthracene compounds>

[0536] Regarding the anthracene compounds that are the main components, examples include compounds represented by formula (3-H) and compounds represented by formula (3-H2).

[0537]

[0538] In equation (3-H),

[0539] X and Ar 4Each 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, and all of X and Ar. 4 It cannot be hydrogen at the same time.

[0540] At least one hydrogen atom in the compound represented by formula (3-H) may be substituted by halogen, cyano, deuterium or a substituted heteroaryl group.

[0541] Alternatively, the structure represented by formula (3-H) can be used as a structural unit to form a polymer (preferably a dimer). In this case, examples of structural units represented by formula (3-H) bonded to each other via X can be listed, where X can be listed as: 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., having divalent bonding valences).

[0542] Details of the groups 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.

[0543] The preferred forms of the anthracene compounds are described below. The symbols in the following structures have the same definitions as those described above.

[0544]

[0545] 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, neither of the two X's is simultaneously a base represented by formula (3-X3). More preferably, neither of the two X's is simultaneously a base represented by formula (3-X2).

[0546] Alternatively, the structure represented by formula (3-H) can be used as a structural unit to form a polymer (preferably a dimer). In this case, examples of structural units represented by formula (3-H) bonded to each other via X can be listed, where X can be listed as: 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., having divalent bonding valences).

[0547] The naphthyl group in formulas (3-X1) and (3-X2) can be condensed from a benzene ring. The structure formed by condensation in this manner is as follows.

[0548]

[0549] 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.

[0550] Ar 3 It is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorene, benzo[a]fluorene, 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).

[0551] Additionally, Ar 3 It can have substituents, Ar 3 At least one hydrogen atom in the form can then be annealed via 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.

[0552] Ar 4 The silane is independently substituted with hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or alkyl with 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and / or cycloalkyl with 5 to 10 carbon atoms.

[0553] Examples of alkyl groups with 1 to 4 carbon atoms that can be substituted on a silane include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclobutyl, etc., in which the three hydrogens in the silane are independently substituted by these alkyl groups.

[0554] 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.

[0555] Examples of cycloalkyl groups with 5 to 10 carbon atoms that are substituted on a silane group 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 group are independently substituted by these cycloalkyl groups.

[0556] Specific examples of "silyl groups substituted with cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilane and tricyclohexylsilane.

[0557] 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. Specific examples of substituted alkyl and cycloalkyl groups can be listed as described.

[0558] 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).

[0559] 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.

[0560]

[0561] 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.

[0562] In formula (A), Y is preferably -O-.

[0563] As R 21 ~R 28 The "alkyl" in "substitutable alkyl" can be either straight-chain or branched-chain, for example, straight-chain alkyl with 1 to 24 carbon atoms or branched-chain alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched-chain alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched-chain alkyl with 3 to 12 carbon atoms), even more preferably an alkyl with 1 to 6 carbon atoms (branched-chain alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 4 carbon atoms (branched-chain alkyl with 3 to 4 carbon atoms).

[0564] 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.

[0565] 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.

[0566] Specific examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) 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, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0567] 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.

[0568] Specific examples of "aryl" groups include: phenyl (monocyclic), biphenyl (bicyclic), naphthyl (condensed bicyclic), terphenyl (tricyclic) (m-terphenyl, o-terphenyl, p-terphenyl), acenaphthene, fluorenyl, phenatenyl, phenanthrene, tricyclic, triphenylene, pyrene, tetraphenyl, perylene, pentaphenyl, etc. (condensed tricyclic).

[0569] 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 one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring-forming atoms in addition to carbon atoms.

[0570] 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. , ...

[0571] 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).

[0572] Specific examples of alkoxy groups include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, octoxy, etc.

[0573] As R 21 ~R 28 The "aryloxy group" in "substitutable aryloxy group" refers to a group in which the hydrogen of the -OH group is aryl-substituted, and the aryl group can be used as the R group. 21 ~R 28 The "aryl" in the text refers to the base.

[0574] As R 21 ~R 28 The "arylthio" in "substitutable arylthio" refers to a group in which the hydrogen of the -SH group is aryl-substituted, and the aryl group can be referenced as the R. 21 ~R 28 The "aryl" in the text refers to the base.

[0575] 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 substituted 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.

[0576] 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.

[0577] As R 21 ~R 28 The term "tricycloalkylsilyl" can be used to refer to groups in which the three hydrogens of a silyl group are independently substituted by a cycloalkyl group, and the cycloalkyl group can be used as the 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.

[0578] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

[0579] 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.

[0580] As R 21 ~R 28 The term "substituted amino group" in the phrase "substituteable amino group" can include, for example, amino groups with two hydrogen atoms substituted by an aryl or heteroaryl group. An amino group with two hydrogen atoms substituted by an aryl group is a diaryl-substituted amino group, an amino group with two hydrogen atoms substituted by a heteroaryl group is a dihexanel-substituted amino group, and an amino group with two hydrogen atoms substituted by both 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.

[0581] Specific examples of "substituted amino groups" include: diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

[0582] As R 21 ~R 28 The "halogens" mentioned include: fluorine, chlorine, bromine, and iodine.

[0583] As R 21 ~R 28 Among the groups described, several groups may also be substituted as 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".

[0584] 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.

[0585] R 21 ~R 28 The adjacent groups can bond with each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. The group represented by formula (A-1) below does not form a ring; for example, the groups represented by formulas (A-2) to (A-14) below can be used to form a ring. Furthermore, at least one hydrogen atom in any of the groups represented by formulas (A-1) to (A-14) can be substituted with 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.

[0586]

[0587] 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 28 The ring structures described in “aryl” or “heteroaryl” are formed by condensation with one or both benzene rings of formula (A-1).

[0588] The base represented by formula (A) is obtained by removing a hydrogen atom from any position in formula (A), where * indicates the position. That is, the base represented by formula (A) can have any position as a bonding position. 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 Atoms on any ring formed by the mutual bonding of adjacent bases, or ">NR" in the structure of formula (A) as Y 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).

[0589] As a basis represented by formula (A), for example, any of the bases represented by formulas (A-1) to (A-14) can be listed, preferably any of the bases represented by formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably any of the bases represented by formulas (A-1) to (A-4), and even more preferably any of the bases represented by formulas (A-1), (A-3) and (A-4), and particularly preferably the base represented by formula (A-1).

[0590] As a basis represented by equation (A), the following bases can be listed for example. Y and * in the equation have the same definitions as described above.

[0591]

[0592] 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.

[0593] In addition, all or part of the hydrogen in the chemical structure of the anthracene compounds represented by formula (3-H) can be deuterium.

[0594] The main anthracene compounds can also be, for example, compounds represented by the following formula (3-H2).

[0595]

[0596] 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 Ar13 Ar 14 Ar 15 Ar 16 Ar 17 and Ar 18 The hydrogen atom in the compound represented by formula (3-H2) may be substituted with halogen, cyano, or deuterium, and may be substituted with 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.

[0597] 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 from the description in formula (1).

[0598] As a "substitutable aryl group", it is also preferred to be a group represented by any one of the following formulas (3-H2-X1) to (3-H2-X7).

[0599]

[0600] In equations (3-H2-X1) to (3-H2-X7), * indicates the location of the bond.

[0601] In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 and Ar 23 Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, The radical, triphenylene, pyrene, anthracene, or the radical represented by formula (A). Furthermore, in the description of formula (3-H2), the radical represented by formula (A) is the same as that described in the anthracene compounds represented by formula (3-H).

[0602] In equations (3-H2-X4) to (3-H2-X7), Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, and fluorene. The radical, triphenylene, pyrene, or the radical represented by formula (A).

[0603] In addition, any one or more hydrogens in each of the groups represented by formulas (3-H2-X1) to (3-H2-X7) may be substituted by an alkyl group having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

[0604] Furthermore, preferred examples of "substituted aryl groups" include those selected from phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, and others. Triphenylene (especially meta-terphenyl-5'-yl) is a terphenyl group substituted with one or more of the substituents in the group consisting of methyl, triphenylene, pyrene, and methyl group represented by formula (A).

[0605] As a “substitutable heteroaryl group”, the group represented by formula (A) can also be listed.

[0606] In addition, specific examples of "substituted aryl" and "substituted heteroaryl" include: dibenzofuranyl, naphthobenzofuranyl, phenyl-substituted dibenzofuranyl, etc.

[0607] At least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with a halogen, a cyano group, or a deuterium group. Examples of "halogen" in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms in the compound represented by formula (3-H2) are substituted with deuterium are particularly preferred.

[0608] In equation (3-H2), R c It is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or tert-butyl, and more preferably hydrogen.

[0609] In formula (3-H2), Ar is preferred. 11 ~Ar 18 At 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.

[0610] The anthracene compounds represented by formula (3-H2) are more preferably Ar. 11 ~Ar 18Two 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.

[0611] The anthracene compounds represented by formula (3-H2) are more preferably Ar. 11 ~Ar 18 Any two of them are substituted aryl or substituted heteroaryl groups, and the other six are hydrogen, methyl, or tert-butyl.

[0612] Therefore, in equation (3-H2), R is preferred. c It is hydrogen, and Ar 11 ~Ar 18 Any six of them are hydrogen.

[0613] 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).

[0614]

[0615] 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 contain phenyl, triphenyl, pyrene, or a group represented by formula (A), wherein at least one hydrogen atom of these groups may be substituted with phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, or phenyl[b]fluorenyl. Substitution with methyl, triphenyl, pyrene, or the methyl 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 through single bonds. In Ar c' Ar 11' Ar 12' Ar 13' Ar 14' Ar 15' Ar 17'and Ar 18' The carbon atoms of unbonded anthracene rings can be bonded with methyl or tert-butyl groups in place of hydrogen atoms.

[0616] 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 represented by any one of the formulas (3-H2-X1) to (3-H2-X7).

[0617] 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), wherein at least one hydrogen 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).

[0618] 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 halogen, cyano, or deuterium.

[0619] As particularly preferred anthracene compounds represented by formula (3-H2), examples include anthracene compounds represented by formula (3-H2-Aa).

[0620]

[0621] 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 contain a group consisting of a phenyl group, a triphenylene group, a pyrene group, or a group represented by any of the formulas (A-1) to (A-11), wherein at least one hydrogen atom of these groups may be derived from 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 represented by a phenyl group, a triphenylene group, a naphthyl group, a phenanthryl group, a fluorene group, a benzo[a]fluorene group, a phenyl group, a phenylene ... 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 the fluorenyl and benzo[a]fluorenyl groups are both substituted with phenyl groups, these phenyl groups can be bonded to each other through single bonds. Additionally, in Ar... c' Ar 14' and Ar 15' The carbon atom on the unbonded 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.

[0622] 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).

[0623] 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 of the bonded carbon is substituted 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 the position is at least deuterium, and any one or more of the other hydrogens in formula (3-H2-Aa) can be deuterium at the same time. Preferably, all hydrogens in formula (3-H2-Aa) are also deuterium.

[0624]

[0625] 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.

[0626]

[0627]

[0628]

[0629]

[0630]

[0631]

[0632]

[0633] 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), (3-255-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), (3-255-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 same definition applies as described above) or >C(-R) 30 )2(R 30 R is any one of the connectable aryl or alkyl groups. 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).

[0634]

[0635]

[0636]

[0637]

[0638]

[0639]

[0640]

[0641]

[0642]

[0643]

[0644]

[0645]

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652] Among these compounds, 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) are preferred. 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-.

[0653] 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. 4Compounds with reactive groups in the structure of formula (A) or other parts thereof are used as starting materials and manufactured by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens or boric acids. For specific manufacturing methods, for example, the synthesis methods described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725 can be referred to.

[0654] <Fluorene compounds>

[0655] The compound represented by formula (4-H) essentially functions as the main component.

[0656]

[0657] In equation (4-H),

[0658] 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.

[0659] 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 condensation rings or spiro rings, and at least one hydrogen in the formed ring can be substituted by an aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a linker), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, where at least one hydrogen can be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0660] At least one hydrogen atom in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0661] For details of the groups in the definition of formula (4-H), please refer to the description of polycyclic aromatic compounds of formula (1).

[0662] As R 1 To R10 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.

[0663] 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).

[0664]

[0665] In equations (4-Ar1) to (4-Ar5), Y 1 Each can be independently O, S, or NR, where R is phenyl, biphenyl, naphthyl, anthracene, or hydrogen.

[0666] At least one hydrogen atom in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0667] 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-, etc.

[0668] 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 to form condensation rings, R 9 With R 10 They can be bonded to form a helical ring. (From R) 1 To R 8The resulting condensation 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 including 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.

[0669] 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), respectively, where R in formula (4-H) is a compound that represents R. 1 With R 2 Compounds formed by the condensation of benzene rings formed by bonding, where R in formula (4-H) 3 With R 4 Compounds formed by the condensation of benzene rings formed by bonding, where R in formula (4-H) 1 To R 8 Compounds in which neither of the elements is bonded.

[0670]

[0671] 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-H) 1 To R 10 same.

[0672] 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 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.

[0673]

[0674] R in equations (4-H-1A), (4-H-2A), and (4-H-3A) 2 To R 7 The definition of R in equations (4-H-1), (4-H-2), and (4-H-3) is the same as that in other equations. 2 To R7 Similarly, R in equations (4-H-1A) and (4-H-2A) 11 To R 14 The definition is also the same as R in equations (4-H-1) and (4-H-2). 11 To R 14 same.

[0675] In addition, all or part of the hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0676] More specific examples of fluorene compounds as the main component can be listed in the following structural formulas. Furthermore, "Me" indicates methyl.

[0677]

[0678] <Dibenzo-p-ethyl System compounds >

[0679] dibenzo[a] as the main component The compounds are, for example, those represented by the following formula (5-H).

[0680]

[0681] In equation (5-H),

[0682] 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.

[0683] Additionally, R 1 To R 16 The adjacent groups can bond to each other to form a condensation ring, and at least one hydrogen in the formed ring can be substituted by an aryl, heteroaryl (the heteroaryl can be bonded to the formed ring via a linker), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, where at least one hydrogen can be substituted by an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0684] At least one hydrogen atom in the compound represented by formula (5-H) may be substituted with halogen, cyano or deuterium.

[0685] For details of the groups in the definition of formula (5-H), please refer to the description of polycyclic aromatic compounds of formula (1).

[0686] As an alkenyl group defined in 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.

[0687] 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).

[0688]

[0689] 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.

[0690] At least one hydrogen atom in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0691] 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 to each other via a linker group. Examples of such linker groups include: phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc.

[0692] 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 10 R 11 R 14and R 15 Preferably, the monovalent group 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.

[0693] 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 and R 14 At least one (preferably one or two, more preferably one) is a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0694] The least one other (i.e., other than the position after the monovalent group of the structure is substituted) is hydrogen, phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl, or butyl, wherein at least one of these hydrogens may be substituted by phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl, or butyl.

[0695] Furthermore, by selecting a monovalent base having the structure represented by equations (5-Ar1) to (5-Ar5) as R in equation (5-H), 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15 In the case where at least one hydrogen in the structure can react with R in formula (5-H) 1To R 16 A single bond is formed by bonding between any two elements.

[0696] Regarding dibenzo[a] as the main component More specific examples of compounds can be listed by the following structural formulas. Furthermore, "tBu" represents tert-butyl.

[0697]

[0698]

[0699] <Pyrene compounds>

[0700] Examples of pyrene compounds include those described in International Publication Nos. 2021 / 210304, 2021 / 210305, or 2021 / 049659.

[0701] The following compounds can be listed as specific examples of pyrene compounds.

[0702]

[0703] <Doped Materials>

[0704] In addition to the polycyclic aromatic compounds of the present invention, known compounds can be used as dopant materials, and can be selected from a variety of materials according to the desired luminescence color. Specifically, examples include: phenanthrene, anthracene, pyrene, tetraphenylene, pentaphenylene, perylene, naphthylpyrene, dibenzopyrene, rubrene, and others. Condensation ring derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis(styrene)-anthracene derivatives, or stilbene-based benzene derivatives, etc. (Japanese Patent Application Publication No. 1-245087), bis(styrene)-arylene derivatives (Japanese Patent Application Publication No. 2-247278), diazabenzodiindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, di-trimethylmethylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trimethylphenyl)isobenzofuran, di(2-trimethylphenyl)isobenzofuran, etc. Fiberglass isobenzofuran, phenylisobenzofuran and other isobenzofuran derivatives, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinylcoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzooxazolylcoumarin derivatives and other coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiaran derivatives, polymethimide derivatives, anthocyanin derivatives, oxobenzanthracene derivatives, xanthones derivatives, rhodamine derivatives, fluorescein derivatives, pyranonium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene ethers. Derivatives of oxides, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furanopyridine derivatives, 1,2,5-thiadiazolpyrene derivatives, pyrrole methylene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violantrone derivatives, phenazine derivatives, acridinone derivatives, deazaflavin derivatives, fluorene derivatives, and benzo[a]fluorene derivatives, etc.

[0705] As a dopant material, boron-containing polycyclic aromatic compounds described in International Publication No. 2015 / 102118, International Publication No. 2020 / 162600, and Japanese Patent Application Publication No. 2021-077890, specifically paragraphs 0097 to 0269, are preferred.

[0706] <Auxiliary dopants (thermally active delayed phosphors or phosphorescent materials)>

[0707] The emitting layer preferably comprises an emitting dopant, a host material, and an auxiliary dopant. As an auxiliary dopant, a thermally active delayed phosphor or a phosphorescent material is preferred. The polycyclic aromatic compounds of the present invention can preferably be used as emitting dopants in TAF or PSF elements.

[0708] In this formulation, known compounds can be used as the host 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. Specific examples include mCP (1,3-bis(N-carbazole-9-yl)benzene) or mCBP (3,3'-bis(9H-carbazole-9-yl)-1,1'-biphenyl). Alternatively, TADF-active compounds can be used as the host compound.

[0709] In this embodiment, it is also preferable to use a combination of hole-transporting host materials and electron-transporting host materials (e.g., compounds HH-1-115 and EH-1-99) as the host.

[0710] From the viewpoint of promoting rather than hindering the generation of TADF within the emissive layer, the lowest excited triplet energy level E(1, T, Sh) of the host compound, determined from the shoulder peak on the short wavelength side of the phosphorescence spectrum peak, is preferably higher than the lowest excited triplet energy levels E(2, T, Sh) and E(3, T, Sh) of the emitting dopant or auxiliary dopant that have the highest lowest excited triplet energy level within the emissive layer. Specifically, compared to E(2, T, Sh) and E(3, T, Sh), the lowest excited triplet energy level E(1, T, Sh) of the host compound is preferably 0.01 eV higher, more preferably 0.03 eV higher, and even more preferably 0.1 eV higher. Furthermore, the lowest excited triplet energy level E of the host material is preferably 2.70 eV or higher, more preferably 2.73 eV or higher, and even more preferably 2.80 eV or higher.

[0711] [Thermoactive Delayed Fluorescent Electron]

[0712] A "thermally active delayed fluorescence" refers to a compound that absorbs thermal energy, undergoes a reverse intersystem transition from the lowest excited triplet state to the lowest excited singlet state, and is radioactively inactivated from the lowest excited singlet state, thereby emitting delayed fluorescence. "Thermally active delayed fluorescence" also includes cases where the excitation process from the lowest excited triplet state to the lowest excited singlet state involves a higher-order triplet state. For example, examples include the paper by Monkman et al. from Durham University (Nature Communications (7:13680, Digital Object Identifier, DOI: 10.1038 / ncomms13680)), the paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (SIST) (Science Advances, 2017; 3: e1603282)), and the paper by Sato et al. from Kyoto University (Scientific Reports). Reports (7:4820, DOI: 10.1038 / s41598-017-05007-7) and a similar academic presentation by Sato et al. from 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 a Luminescent Molecule," Graduate School of Engineering, Kyoto University) Comments published by Bui et al. (DOI: 10.3762 / bjoc.14.18), Duan et al. (DOI: 10.1063 / 1.5143501), Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201), and Xie et al. (DOI: 10.1002 / adom.202002204), etc., are cited in this invention. In this invention, a sample containing 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, a slow fluorescence component refers to a component with a fluorescence lifetime of 0.1 μsec or more. Fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01).

[0713] In the luminescent layer that further includes a "thermally active delayed phosphor" as an auxiliary dopant, the polycyclic aromatic compound of the present invention can function as an emission dopant. That is, the "thermally active delayed phosphor" can function as an auxiliary dopant to assist the luminescence of the polycyclic aromatic compound of the present invention.

[0714] In this specification, organic electroluminescent elements that use thermally active delayed phosphors as auxiliary dopants are sometimes referred to as "TAF elements" (TADF Assisting Fluorescence elements).

[0715] The so-called "host compound" in a TAF element refers to a compound whose lowest excited singlet state energy level, determined by the shoulder peak on the short wavelength side of the fluorescence spectrum peak, is higher than that of the lowest excited singlet state energy level of the thermally active delayed phosphor and the emission dopant used as auxiliary dopants.

[0716] 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.

[0717] In this specification, the term "electron-donating substituent" (donor) refers to the substituent and part of the structure that is locally present in the HOMO of a thermally active delayed fluorophore molecule, and the term "electron-accepting substituent" (acceptor) refers to the substituent and part of the structure that is locally present in the LUMO of a thermally active delayed fluorophore molecule.

[0718] Generally, thermally active delayed fluorescent phosphors using donors or acceptors have high spin-orbit coupling (SOC) and low exchange interaction between HOMO and LUMO due to their structure, resulting in low ΔE. S1T1The small size allows for a very fast reverse intersystem crossing speed. By using the polycyclic aromatic compound of the present invention as the emission dopant and a thermally active delayed phosphor (TADF material) as an auxiliary dopant, devices that satisfy one or all of the following can be provided: high efficiency, high color purity, and long lifetime. The thermally active delayed phosphor is any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound and the TADF compound of the present invention can be contained in the same layer, or in adjacent layers or other close layers.

[0719] 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-butylphenyl)amine, 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, dibenzoquinoxaline, heptaazafinaene, thioxanone dioxide, dimethylanthrone, anthrone, 5H-cyclohepta[1,2-b:5,4-b']bipyridine, fluorenedicarbonyl, triphenyltriazine, pyrazinedicarbonyl, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonyl, dibenzoquinoxalinedicarbonyl, 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.

[0720] The compound used as the auxiliary dopant for the emitting layer in the TAF element is a thermally active delayed phosphor, and preferably a compound whose emission spectrum overlaps at least partially with the absorption peak of the emission dopant.

[0721] [Phosphorescent materials]

[0722] In the luminescent layer, phosphorescent materials can be used as auxiliary dopants. In this specification, organic electroluminescent elements using phosphorescent materials as auxiliary dopants are sometimes referred to as phosphorescent auxiliary elements: phosphor-sensitized fluorescent elements, PSF elements. Phosphorescent materials utilize intramolecular spin-orbit interactions (heavy atom effect) caused by metal atoms to obtain luminescence from the excited triplet state. For example, luminescent metal complexes can be used as such phosphorescent materials. Examples of luminescent metal complexes include compounds represented by formulas (B-1) and (B-2) below.

[0723]

[0724] In formula (B-1), M is selected from at least one of the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag and Cu, n is an integer from 1 to 3, and "XY" are independently bidentate ligands.

[0725] In formula (B-2), M is selected from at least one of the group consisting of Pt, Re and Cu, and "WXYZ" is a tetradentate ligand.

[0726] In equation (B-1), from the viewpoint of efficiency and lifespan, M is preferably Ir, and n is preferably 3.

[0727] In equation (B-2), from the viewpoint of efficiency and lifespan, M is preferably Pt.

[0728] The ligand (XY) in formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (WXYZ) in formula (B-2) has at least one ligand selected from the group consisting of the following as a part.

[0729]

[0730] In the formula,

[0731] It bonds to the central metal M at ---.

[0732] Y is independently BR e NR e PR e ,O,S,Se,C=O,S=O,SO2,CRe R f SiR e R f Or GeR e R f ,

[0733] The aromatic carbons CH in the ring can be independently substituted to N.

[0734] R e and R f They can be arbitrarily condensed or bonded to form rings.

[0735] R a R b R c and R d Each can be independently represented as either unsubstituted or substituted up to 1, or the largest number that can be substituted.

[0736] R a R b R c R d R e and R f Each of these can be independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, mercapto, or a combination thereof.

[0737] Among them, R a R b R c and R d Any two adjacent substituents can condense or bond to form a ring, or they can form a polydentate ligand.

[0738] Examples of compounds represented by formula (B-1) include: Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq)3, Ir(fbi)2(acac), and fac-Tris(2-(3-p-xylyl)phenyl)pyridine. iridium(III)(fac-tris(2-(3-p-xylyl)phenyl)pyridinium(III)), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq )2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir( BT)2(acac), Ir(DMP)3, Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)( Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0739] In addition to the compounds represented by formula (B-1), the following compounds may be listed as examples.

[0740]

[0741]

[0742] Alternatively, iridium complexes described in Japanese Patent Application Publication No. 2006-089398, Japanese Patent Application Publication No. 2006-080419, Japanese Patent Application Publication No. 2005-298483, Japanese Patent Application Publication No. 2005-097263, and Japanese Patent Application Publication No. 2004-111379, U.S. Patent Application Publication No. 2019 / 0051845, or those described in *Advanced Materials* (26: 7116-7121), *NPG AsiaMaterials* (13, 53 (2021)), *Applied Physics Letters* (117, 253301 (2020)), and *Light-Emitting Diode: An Outlook On the Empirical Features and Its Recent Technological Advances* may be used. The platinum complex described in Chapter 5 of Technological Advancements.

[0743] 2-1-3. Substrate in organic electroluminescent devices

[0744] 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. The thickness is only required to maintain sufficient mechanical strength, for example, 0.2 mm or more. The upper limit for the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, the fewer leached ions from the glass, the better; therefore, alkali-free glass is preferred. Since soda-lime glass with a barrier coating such as SiO2 is also commercially available, it 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. In particular, when a plate, film or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0745] 2-1-4. Anode in organic electroluminescent devices

[0746] The anode 102 functions to inject holes into the light-emitting layer 105. Furthermore, if 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.

[0747] 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, suitable materials that can be used as the anode of organic EL elements can be selected for use.

[0748] 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. However, from the viewpoint of power consumption of the light-emitting element, low resistance is ideal. For example, if the ITO substrate is 300Ω / □ or less, it functions as an electrode for the element. However, substrates with a resistance of around 10Ω / □ are also available now. 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 in most cases it is usually used between 50nm and 300nm.

[0749] 2-1-5. Hole injection layer and hole transport layer in organic electroluminescent devices

[0750] 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.

[0751] 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.

[0752] 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 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 with 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-hexacarboxynitrile, etc.), porphyrin derivatives and other heterocyclic compounds, polysilanes, etc. In polymer systems, polycarbonate or styrene derivatives, polyvinylcarbazole and polysilanes having the monomers on the side chains are preferred, but there is no particular limitation as long as it is a thin film required for the fabrication of the light-emitting element, and a compound that can inject holes from the anode and transport holes.

[0753] 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 properties or good electron-accepting properties. For doping with electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (e.g., see the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo"). A. 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)"). These holes are generated 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.) (Japanese Patent Application Publication No. 2005-167175).

[0754] The polycyclic aromatic compounds of the present invention can also be used as materials for forming hole injection layers or hole transport layers.

[0755] 2-1-6. Electron blocking layer in organic electroluminescent devices

[0756] 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 a compound represented by any of the formulas (H1), (H2), and (H3).

[0757] The polycyclic aromatic compounds of the present invention can be used as materials for forming electron blocking layers.

[0758] 2-1-7. Electron injection layer and electron transport layer in organic electroluminescent devices

[0759] 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.

[0760] 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, materials that effectively prevent unrecombined holes from the anode from flowing to the cathode can achieve the same effect of improving luminous efficiency as materials with high electron transport capabilities, even if their electron transport capability is not very high. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that effectively prevents hole migration.

[0761] 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.

[0762] 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 condensed ring derivatives; and metal complexes with electron-accepting nitrogen. Specifically, examples include: condensed 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; azomethyl base complexes; cycloheptatrienolone metal complexes; flavonol metal complexes; and benzoquinone metal complexes. These materials can be used alone or in combination with different materials.

[0763] In addition, specific examples of other electron-transfer compounds include: pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, phenanthroline derivatives, violet ketone derivatives, coumarin derivatives, naphthalenediamine derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, etc. Biological 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, phosphorus oxide derivatives, bisstyrene derivatives, thiophene derivatives, and azoline derivatives, etc.

[0764] Alternatively, metal complexes with electron-accepting nitrogen can be used, such as hydroxyquinoline metal complexes or hydroxyphenyloxazole complexes, azomethyl base complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0765] The material can be used alone or in combination with different materials.

[0766] 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.

[0767] The polycyclic aromatic compounds of the present invention can be used as materials for forming electron injection layers or electron transport layers.

[0768] The electron transport layer or electron injection layer may also contain a substance that can reduce the material forming the electron transport layer or electron injection layer. The reducing substance can be any substance with 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.

[0769] 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, alkali metals such as K, Rb, or Cs are more preferred, 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 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 combinations of 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.

[0770] 2-1-8. Cathode in Organic Electroluminescent Devices

[0771] 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.

[0772] The material forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject 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 the electron injection efficiency and thus enhance the 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 limited to these.

[0773] 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.

[0774] 2-1-9. Adhesives that can be used in each layer

[0775] 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.

[0776] 2-1-10. Fabrication method of organic electroluminescent elements

[0777] 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 in 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 quartz 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 crystal structure of the target film, and the associated structure. Generally, the preferred vapor deposition conditions are a boat heating temperature of +50°C to +400°C and a vacuum degree of 10... -6 Pa~10 -3 The appropriate settings are as follows: Pa, evaporation rate (0.01 nm / s to 50 nm / s), substrate temperature (-150℃ to +300℃), and film thickness (2 nm to 5 μm).

[0778] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device including 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. Furthermore, in the fabrication of the organic EL device, the fabrication order can also be reversed, fabricating the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0779] 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.

[0780] 2-1-11. Examples of applications of organic electroluminescent elements

[0781] Organic EL elements can also be used in display devices or lighting devices.

[0782] Display devices or lighting devices including organic EL elements can be manufactured by known methods such as connecting organic EL elements to known driving devices, and can be driven by known driving methods such as DC driving, pulse driving, AC driving, etc.

[0783] Examples of display devices include panel displays such as color flat panel displays and 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, display methods for the display include, for example, matrix display and / or segmented display. Moreover, matrix display and segmented display can coexist on the same panel.

[0784] 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 screens, 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. In these cases, triangular and striped patterns are typical. Moreover, the driving method of the matrix can be either a line-sequential driving method or an active matrix. Line-sequential 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.

[0785] 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.

[0786] 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 displays that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs. In particular, backlights for personal computers, where thinning is becoming a key issue in liquid crystal displays, offer advantages such as thinness and light weight, considering that previous methods were difficult to make thinner due to the inclusion of fluorescent lamps or light guide plates.

[0787] 2-2. Other organic devices

[0788] The polycyclic aromatic compounds of the present invention can be used not only in the fabrication of the organic electroluminescent elements, but also in the fabrication of organic field-effective transistors or organic thin-film solar cells.

[0789] An organic field-effect transistor (FET) is a transistor that controls current by using an electric field generated by a voltage input. It has not only source and drain electrodes but also a gate electrode. Specifically, 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.

[0790] The structure of an organic effective transistor typically involves simply placing the source and drain electrodes in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and then placing the gate electrode through an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such element structures include the following.

[0791] (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer

[0792] (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode

[0793] (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode

[0794] (4) Substrate / Source electrode, Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode

[0795] Organic field-active transistors constructed in the manner described above can be used as pixel driving conversion elements in liquid crystal displays or organic electroluminescent displays with active matrix driving.

[0796] Organic thin-film solar cells have a structure in which an anode (such as ITO), a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are 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, based 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 above, organic thin-film solar cells may also suitably include hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. In organic thin-film solar cells, known materials for organic thin-film solar cells can be suitably selected and used in combination.

[0797] 3. Wavelength conversion materials

[0798] The polycyclic aromatic compounds of this invention can be used as wavelength conversion materials.

[0799] 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 the wavelength of light emitted from a light source into 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, the three primary colors—blue, green, and red—can be extracted from the blue light source, resulting in white light. Using this white light source, formed by combining 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 color filters, 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.

[0800] 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 light from a light source or light-emitting element that generates ultraviolet light or blue light of shorter wavelengths 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 adjusted color can be achieved by appropriately selecting substituents of the polycyclic aromatic compounds of the present invention, adhesive resins used in the wavelength conversion compositions described later. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, the wavelength conversion composition can be used to form a wavelength conversion film.

[0801] 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.

[0802] The wavelength conversion film comprises 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 comprise only a wavelength conversion layer formed from a composition containing the polycyclic aromatic compounds of the present invention, or it may comprise 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 comprise a substrate layer, or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0803] [Example]

[0804] The present invention will be described in more detail below through embodiments, but the present invention is not limited thereto.

[0805] Furthermore, in the reaction formulas of the examples, Me represents methyl, Et represents ethyl, tBu represents tert-butyl, and iPr represents isopropyl.

[0806] Additionally, "APCI-MS" refers to atmospheric pressure chemical ionization mass spectrometry, while "MALDI-TOFMS (Matrix-assisted laser desorption / ionization-time of flight mass spectrometry)" refers to matrix-assisted laser desorption / ionization-time of flight mass spectrometry.

[0807] Synthesis example (1):

[0808] Synthesis of compound (1-1)

[0809]

[0810] First process

[0811] Under nitrogen atmosphere, compound (T-1) (10.0 g), compound (T-2) (15.2 g), sodium tert-butoxy (NaOtBu, 3.9 g), Pd-132 (trade name: dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium, 0.58 g), and xylene (100 ml) were placed in a reactor and heated under reflux for 2 hours. 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) (21.6 g).

[0812] Synthesis of compound (1-1)

[0813] Compound (T-3) (20.0 g) and tert-butylbenzene (T-3) were placed in a nitrogen atmosphere at -30°C. t A 1.6 M solution of tert-butyllithium pentane (tBuLi, 10 ml) was added to a flask containing 200 ml of Bu-benzene. 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 removed by vacuum distillation. The solution was cooled to -30 °C and boron tribromide (8.4 g) was added. The temperature was raised to room temperature and stirred for 0.5 hours. Then, the solution was cooled again to 0 °C and N,N-diisopropylethylamine (EtN(iPr)2, 7.6 ml) was added. The solution was stirred at room temperature until heating was complete, then the temperature was raised to 120 °C and stirred for 3 hours. The reaction solution was cooled to room temperature, and sodium acetate aqueous solution cooled in an ice bath and heptane were added sequentially for separation. The solution was then purified using a silica gel short-path column (developing solvent: toluene). The solid obtained by vacuum distillation to remove the solvent was dissolved in toluene, and heptane was added to precipitate it again, thus obtaining the compound represented by formula (1-1).

[0814] 1 H-NMR (CD2Cl2): δ=9.01(s,1H),8.85(s,1H),7.77(d,1H),7.55(d,1H),7.43(dd,1H),7.27 (t,1H),7.02(s,2H),6.94(d,2H),6.92(dd,1H),6.89(d,1H),6.51(s,1H),6.10(d,1H),5.9 7(s,1H),5.56(s,1H),5.53(s,1H),2.01(s,3H),1.81(s,4H),1.60(s,3H),1.50(s,3H),1.4 2(s,12H),1.32(s,9H),1.29(s,9H),1.26(s,18H),1.10(s,3H),1.05(s,12H),0.86(s,9H).

[0815] Synthesis Example (2): Synthesis of compounds (1-8)

[0816] Compound (T-3) was changed to compound (T-3-8), and otherwise compound (1-8) was obtained using the same procedure as in Synthesis Example 1.

[0817] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 995.71.

[0818]

[0819] Synthesis Example (3): Synthesis of Compounds (1-21)

[0820] Compound (T-3) was changed to compound (T-3-21), and otherwise compound (1-21) was obtained using the same procedure as in Synthesis Example 1.

[0821] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1107.84.

[0822]

[0823] Synthesis Example (4): Synthesis of Compounds (1-34)

[0824] Compound (T-3) was changed to compound (T-3-34), and otherwise compound (1-34) was obtained using the same procedure as in Synthesis Example 1.

[0825] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1037.67.

[0826]

[0827] Synthesis Example (5): Synthesis of Compounds (1-39)

[0828] Compound (T-3) was changed to compound (T-3-39), and otherwise compound (1-39) was obtained using the same procedure as in Synthesis Example 1.

[0829] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 919.67.

[0830]

[0831] Synthesis Example (6): Synthesis of Compounds (1-63)

[0832] Compound (T-3) was changed to compound (T-3-63), and otherwise compound (1-63) was obtained using the same procedure as in Synthesis Example 1.

[0833] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1213.90.

[0834]

[0835] Synthesis Example (7): Synthesis of Compounds (1-15)

[0836] Compound (T-3) was changed to compound (T-3-15), and otherwise compound (1-15) was obtained using the same procedure as in Synthesis Example 1.

[0837] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1187.90.

[0838]

[0839] Synthesis Example (8): Synthesis of Compounds (1-32)

[0840] Compound (T-3) was changed to compound (T-3-32), and otherwise compound (1-32) was obtained using the same procedure as in Synthesis Example 1.

[0841] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 940.67.

[0842]

[0843] Synthesis Example (9): Synthesis of Compounds (1-47)

[0844] Compound (T-3) was changed to compound (T-3-47), and otherwise compound (1-47) was obtained using the same procedure as in Synthesis Example 1.

[0845] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1243.78.

[0846]

[0847] Synthetic Example (10): Synthesis of Compounds (1-59)

[0848] Compound (T-3) was changed to compound (T-3-59), and otherwise compound (1-59) was obtained using the same procedure as in Synthesis Example 1.

[0849] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1202.72.

[0850]

[0851] Synthetic Example (11): Synthesis of Compounds (1-69)

[0852] Compound (T-3) was changed to compound (T-3-69), and otherwise compound (1-69) was obtained using the same procedure as in Synthesis Example 1.

[0853] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1179.88.

[0854]

[0855] Synthetic Example (12): Synthesis of Compounds (1-74)

[0856] Compound (T-3) was changed to compound (T-3-74), and otherwise compound (1-74) was obtained using the same procedure as in Synthesis Example 1.

[0857] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1062.68.

[0858]

[0859] Synthetic Example (13): Synthesis of Compounds (1-78)

[0860] Compound (T-3) was changed to compound (T-3-78), and otherwise compound (1-78) was obtained using the same procedure as in Synthesis Example 1.

[0861] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 926.61.

[0862]

[0863] Synthetic Example (14): Synthesis of Compounds (1-79)

[0864] Compound (T-3) was changed to compound (T-3-79), and otherwise compound (1-79) was obtained using the same procedure as in Synthesis Example 1.

[0865] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1053.70.

[0866]

[0867] Synthetic Example (15): Synthesis of Compounds (1-80)

[0868] Compound (T-3) was changed to compound (T-3-80), and otherwise compound (1-80) was obtained using the same procedure as in Synthesis Example 1.

[0869] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1036.72.

[0870]

[0871] Synthetic Example (16): Synthesis of Compounds (1-84)

[0872] Compound (T-3) was changed to compound (T-3-84), and otherwise compound (1-84) was obtained using the same procedure as in Synthesis Example 1.

[0873] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1215.78.

[0874]

[0875] Synthetic Example (17): Synthesis of Compounds (1-88)

[0876] Compound (T-3) was changed to compound (T-3-88), and otherwise compound (1-88) was obtained using the same procedure as in Synthesis Example 1.

[0877] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1245.85.

[0878]

[0879] Synthetic Example (18): Synthesis of Compounds (1-97)

[0880] Compound (T-3) was changed to compound (T-3-97), and otherwise compound (1-97) was obtained using the same procedure as in Synthesis Example 1.

[0881] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1138.85.

[0882]

[0883] Synthetic Example (19): Synthesis of Compound (1-103)

[0884] Compound (T-3) was changed to compound (T-3-103), and compound (1-103) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0885] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1373.84.

[0886]

[0887] Synthetic Example (20): Synthesis of Compounds (1-5)

[0888] Compound (T-3) was changed to compound (T-3-5), and otherwise compound (1-5) was obtained using the same procedure as in Synthesis Example 1.

[0889] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1029.78.

[0890]

[0891] Synthetic Example (21): Synthesis of Compounds (1-33)

[0892] Compound (T-3) was changed to compound (T-3-33), and otherwise compound (1-33) was obtained using the same procedure as in Synthesis Example 1.

[0893] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1261.92.

[0894]

[0895] Synthesis Example (22): Synthesis of Compounds (1-36)

[0896] Compound (T-3) was changed to compound (T-3-36), and otherwise compound (1-36) was obtained using the same procedure as in Synthesis Example 1.

[0897] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1133.67.

[0898]

[0899] Synthetic Example (23): Synthesis of Compounds (1-12)

[0900] Compound (T-3) was changed to compound (T-3-12), and otherwise compound (1-12) was obtained using the same procedure as in Synthesis Example 1.

[0901] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1053.79.

[0902]

[0903] Synthetic Example (24): Synthesis of Compounds (1-16)

[0904] Compound (T-3) was changed to compound (T-3-16), and otherwise compound (1-16) was obtained using the same procedure as in Synthesis Example 1.

[0905] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1187.90.

[0906]

[0907] Synthetic Example (25): Synthesis of Compounds (1-25)

[0908] Compound (T-3) was changed to compound (T-3-25), and otherwise compound (1-25) was obtained using the same procedure as in Synthesis Example 1.

[0909] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1215.93.

[0910]

[0911] Synthetic Example (26): Synthesis of Compounds (1-31)

[0912] Compound (T-3) was changed to compound (T-3-31), and otherwise compound (1-31) was obtained using the same procedure as in Synthesis Example 1.

[0913] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 995.71.

[0914]

[0915] Synthetic Example (27): Synthesis of Compounds (1-43)

[0916] Compound (T-3) was changed to compound (T-3-43), and otherwise compound (1-43) was obtained using the same procedure as in Synthesis Example 1.

[0917] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1052.68.

[0918]

[0919] Synthetic Example (28): Synthesis of Compounds (1-44)

[0920] Compound (T-3) was changed to compound (T-3-44), and otherwise compound (1-44) was obtained using the same procedure as in Synthesis Example 1.

[0921] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1106.72.

[0922]

[0923] Synthetic Example (29): Synthesis of Compounds (1-46)

[0924] Compound (T-3) was changed to compound (T-3-46), and otherwise compound (1-46) was obtained using the same procedure as in Synthesis Example 1.

[0925] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1031.68.

[0926]

[0927] Synthetic Example (30): Synthesis of Compounds (1-62)

[0928] Compound (T-3) was changed to compound (T-3-62), and compound (1-62) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0929] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1197.74.

[0930]

[0931] Synthetic Example (31): Synthesis of Compounds (1-70)

[0932] Compound (T-3) was changed to compound (T-3-70), and compound (1-70) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0933] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1081.67.

[0934]

[0935] Synthetic Example (32): Synthesis of Compounds (1-71)

[0936] Compound (T-3) was changed to compound (T-3-71), and otherwise compound (1-71) was obtained using the same procedure as in Synthesis Example 1.

[0937] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1079.81.

[0938]

[0939] Synthetic Example (33): Synthesis of Compounds (1-77)

[0940] Compound (T-3) was changed to compound (T-3-77), and otherwise compound (1-77) was obtained using the same procedure as in Synthesis Example 1.

[0941] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1079.66.

[0942]

[0943] Synthetic Example (34): Synthesis of Compounds (1-81)

[0944] Compound (T-3) was changed to compound (T-3-81), and otherwise compound (1-81) was obtained using the same procedure as in Synthesis Example 1.

[0945] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1106.82.

[0946]

[0947] Synthetic Example (35): Synthesis of Compounds (1-86)

[0948] Compound (T-3) was changed to compound (T-3-86), and otherwise compound (1-86) was obtained using the same procedure as in Synthesis Example 1.

[0949] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1105.73.

[0950]

[0951] Synthetic Example (36): Synthesis of Compounds (1-87)

[0952] Compound (T-3) was changed to compound (T-3-87), and otherwise compound (1-87) was obtained using the same procedure as in Synthesis Example 1.

[0953] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1261.83.

[0954]

[0955] Synthetic Example (37): Synthesis of Compounds (1-96)

[0956] Compound (T-3) was changed to compound (T-3-96), and otherwise compound (1-96) was obtained using the same procedure as in Synthesis Example 1.

[0957] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1196.86.

[0958]

[0959] Synthetic Example (38): Synthesis of Compounds (1-98)

[0960] Compound (T-3) was changed to compound (T-3-98), and otherwise compound (1-98) was obtained using the same procedure as in Synthesis Example 1.

[0961] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1256.88.

[0962]

[0963] Synthetic Example (39): Synthesis of Compounds (1-100)

[0964] Compound (T-3) was changed to compound (T-3-100), and compound (1-100) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0965] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1320.85.

[0966]

[0967] Synthetic Example (40): Synthesis of Compound (1-105)

[0968] Compound (T-3) was changed to compound (T-3-105), and compound (1-105) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0969] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1129.83.

[0970]

[0971] Synthetic Example (41): Synthesis of Compound (1-107)

[0972] Compound (T-3) was changed to compound (T-3-107), and compound (1-107) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0973] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1225.83.

[0974]

[0975] Synthetic Example (42): Synthesis of Compound (1-109)

[0976] Compound (T-3) was changed to compound (T-3-109), and otherwise compound (1-109) was obtained using the same procedure as in Synthesis Example 1.

[0977] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1152.53.

[0978]

[0979] Synthetic Example (43): Synthesis of Compound (1-111)

[0980] Compound (T-3) was changed to compound (T-3-111), and compound (1-111) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0981] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1042.53.

[0982]

[0983] Synthetic Example (44): Synthesis of Compound (1-112)

[0984] Compound (T-3) was changed to compound (T-3-112), and compound (1-112) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0985] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1097.58.

[0986]

[0987] Synthetic Example (45): Synthesis of Compound (1-114)

[0988] Compound (T-3) was changed to compound (T-3-114), and otherwise compound (1-114) was obtained using the same procedure as in Synthesis Example 1.

[0989] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1152.53.

[0990]

[0991] Synthetic Example (46): Synthesis of Compound (1-115)

[0992] Compound (T-3) was changed to compound (T-3-115), and otherwise compound (1-115) was obtained using the same procedure as in Synthesis Example 1.

[0993] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1100.48.

[0994]

[0995] Synthetic Example (47): Synthesis of Compounds (1-120)

[0996] Compound (T-3) was changed to compound (T-3-120), and compound (1-120) was otherwise obtained using the same procedure as in Synthesis Example 1.

[0997] The m / z(M+H) value was determined by MS measurement (MALDI-TOF MS) to be 1658.21.

[0998]

[0999] Synthetic Example (48): Synthesis of Compound (1-121)

[1000] Compound (T-3) was changed to compound (T-3-121), and compound (1-121) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1001] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1450.08.

[1002]

[1003] Synthetic Example (49): Synthesis of Compound (1-122)

[1004] Compound (T-3) was changed to compound (T-3-122), and compound (1-122) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1005] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1172.50.

[1006]

[1007] Synthetic Example (50): Synthesis of Compounds (1-126)

[1008] Compound (T-3) was changed to compound (T-3-126), and otherwise compound (1-126) was obtained using the same procedure as in Synthesis Example 1.

[1009] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1456.39.

[1010]

[1011] Synthetic Example (51): Synthesis of Compounds (1-129)

[1012] Compound (T-3) was changed to compound (T-3-129), and otherwise compound (1-129) was obtained using the same procedure as in Synthesis Example 1.

[1013] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1274.55.

[1014]

[1015] Synthetic Example (52): Synthesis of Compounds (1-130)

[1016] Compound (T-3) was changed to compound (T-3-130), and otherwise compound (1-130) was obtained using the same procedure as in Synthesis Example 1.

[1017] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1165.55.

[1018]

[1019] Synthetic Example (53): Synthesis of Compound (1-278)

[1020] Compound (T-3) was changed to compound (T-3-278), and otherwise compound (1-278) was obtained using the same procedure as in Synthesis Example 1.

[1021] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1190.50.

[1022]

[1023] Synthetic Example (54): Synthesis of Compound (1-281)

[1024] Compound (T-3) was changed to compound (T-3-281), and otherwise compound (1-281) was obtained using the same procedure as in Synthesis Example 1.

[1025] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1314.74.

[1026]

[1027] Synthetic Example (55): Synthesis of Compound (1-282)

[1028] Compound (T-3) was changed to compound (T-3-282), and compound (1-282) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1029] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1199.77.

[1030]

[1031] Synthetic Example (56): Synthesis of Compound (1-294)

[1032] Compound (T-3) was changed to compound (T-3-294), and otherwise compound (1-294) was obtained using the same procedure as in Synthesis Example 1.

[1033] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1304.76.

[1034]

[1035] Synthetic Example (57): Synthesis of Compound (1-296)

[1036] Compound (T-3) was changed to compound (T-3-296), and otherwise compound (1-296) was obtained using the same procedure as in Synthesis Example 1.

[1037] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1235.69.

[1038]

[1039] Synthetic Example (58): Synthesis of Compound (1-313)

[1040] Compound (T-3) was changed to compound (T-3-313), and otherwise compound (1-313) was obtained using the same procedure as in Synthesis Example 1.

[1041] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1058.65.

[1042]

[1043] Synthetic Example (59): Synthesis of Compound (1-314)

[1044] Compound (T-3) was changed to compound (T-3-314), and otherwise compound (1-314) was obtained using the same procedure as in Synthesis Example 1.

[1045] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1047.32.

[1046]

[1047] Synthetic Example (60): Synthesis of Compound (1-315)

[1048] Compound (T-3) was changed to compound (T-3-315), and compound (1-315) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1049] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1122.70.

[1050]

[1051] Synthetic Example (61): Synthesis of Compound (1-316)

[1052] Compound (T-3) was changed to compound (T-3-316), and compound (1-316) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1053] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1106.73.

[1054]

[1055] Synthetic Example (62): Synthesis of Compound (1-317)

[1056] Compound (T-3) was changed to compound (T-3-317), and otherwise compound (1-317) was obtained using the same procedure as in Synthesis Example 1.

[1057] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1162.72.

[1058]

[1059] Synthetic Example (63): Synthesis of Compound (1-318)

[1060] Compound (T-3) was changed to compound (T-3-318), and compound (1-318) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1061] The m / z(M+H) value was obtained by MS determination (APCI-MS) as 1169.76.

[1062]

[1063] Synthetic Example (64): Synthesis of Compound (1-319)

[1064] Compound (T-3) was changed to compound (T-3-319), and otherwise compound (1-319) was obtained using the same procedure as in Synthesis Example 1.

[1065] The m / z(M+H) value was obtained by MS determination (APCI-MS) = 1078.72.

[1066]

[1067] Synthetic Example (65): Synthesis of Compounds (1-143)

[1068] Compound (T-3) was changed to compound (T-3-143), and otherwise compound (1-143) was obtained using the same procedure as in Synthesis Example 1.

[1069] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1258.79.

[1070]

[1071] Synthetic Example (66): Synthesis of Compounds (1-144)

[1072] Compound (T-3) was changed to compound (T-3-144), and otherwise compound (1-144) was obtained using the same procedure as in Synthesis Example 1.

[1073] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1370.91.

[1074]

[1075] Synthetic Example (67): Synthesis of Compounds (1-145)

[1076] Compound (T-3) was changed to compound (T-3-145), and otherwise compound (1-145) was obtained using the same procedure as in Synthesis Example 1.

[1077] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1366.88.

[1078]

[1079] Synthetic Example (68): Synthesis of Compounds (1-146)

[1080] Compound (T-3) was changed to compound (T-3-146), and otherwise compound (1-146) was obtained using the same procedure as in Synthesis Example 1.

[1081] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1278.76.

[1082]

[1083] Synthetic Example (69): Synthesis of Compounds (1-147)

[1084] Compound (T-3) was changed to compound (T-3-147), and otherwise compound (1-147) was obtained using the same procedure as in Synthesis Example 1.

[1085] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1376.78.

[1086]

[1087] Synthetic Example (70): Synthesis of Compounds (1-148)

[1088] Compound (T-3) was changed to compound (T-3-148), and otherwise compound (1-148) was obtained using the same procedure as in Synthesis Example 1.

[1089] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1390.88.

[1090]

[1091] Synthetic Example (71): Synthesis of Compounds (1-149)

[1092] Compound (T-3) was changed to compound (T-3-149), and otherwise compound (1-149) was obtained using the same procedure as in Synthesis Example 1.

[1093] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1334.82.

[1094]

[1095] Synthetic Example (72): Synthesis of Compounds (1-150)

[1096] Compound (T-3) was changed to compound (T-3-150), and compound (1-150) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1097] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1324.56.

[1098]

[1099] Synthetic Example (73): Synthesis of Compound (1-151)

[1100] Compound (T-3) was changed to compound (T-3-151), and otherwise compound (1-151) was obtained using the same procedure as in Synthesis Example 1.

[1101] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1240.65.

[1102]

[1103] Synthetic Example (74): Synthesis of Compounds (1-152)

[1104] Compound (T-3) was changed to compound (T-3-152), and otherwise compound (1-152) was obtained using the same procedure as in Synthesis Example 1.

[1105] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1416.72.

[1106]

[1107] Synthetic Example (75): Synthesis of Compounds (1-153)

[1108] Compound (T-3) was changed to compound (T-3-153), and otherwise compound (1-153) was obtained using the same procedure as in Synthesis Example 1.

[1109] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1295.59.

[1110]

[1111] Synthetic Example (76): Synthesis of Compounds (1-154)

[1112] Compound (T-3) was changed to compound (T-3-154), and otherwise compound (1-154) was obtained using the same procedure as in Synthesis Example 1.

[1113] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1367.78.

[1114]

[1115] Synthetic Example (77): Synthesis of Compounds (1-155)

[1116] Compound (T-3) was changed to compound (T-3-155), and compound (1-155) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1117] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1364.77.

[1118]

[1119] Synthetic Example (78): Synthesis of Compounds (1-156)

[1120] Compound (T-3) was changed to compound (T-3-156), and otherwise compound (1-156) was obtained using the same procedure as in Synthesis Example 1.

[1121] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1364.77.

[1122]

[1123] Synthetic Example (79): Synthesis of Compounds (1-157)

[1124] Compound (T-3) was changed to compound (T-3-157), and otherwise compound (1-157) was obtained using the same procedure as in Synthesis Example 1.

[1125] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1395.06.

[1126]

[1127] Synthetic Example (80): Synthesis of Compounds (1-158)

[1128] Compound (T-3) was changed to compound (T-3-158), and otherwise compound (1-158) was obtained using the same procedure as in Synthesis Example 1.

[1129] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1410.85.

[1130]

[1131] Synthetic Example (81): Synthesis of Compounds (1-159)

[1132] Compound (T-3) was changed to compound (T-3-159), and compound (1-159) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1133] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1314.85.

[1134]

[1135] Synthetic Example (82): Synthesis of Compounds (1-160)

[1136] Compound (T-3) was changed to compound (T-3-160), and compound (1-160) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1137] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1476.90.

[1138]

[1139] Synthetic Example (83): Synthesis of Compound (1-351)

[1140] Compound (T-3) was changed to compound (T-3-351), and compound (1-351) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1141] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1151.798.

[1142]

[1143] Synthetic Example (84): Synthesis of Compound (1-352)

[1144] Compound (T-3) was changed to compound (T-3-352), and compound (1-352) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1145] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1075.758.

[1146]

[1147] Synthetic Example (85): Synthesis of Compound (1-353)

[1148] Compound (T-3) was changed to compound (T-3-353), and compound (1-353) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1149] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1155.766.

[1150]

[1151] Synthetic Example (86): Synthesis of Compound (1-354)

[1152] Compound (T-3) was changed to compound (T-3-354), and otherwise compound (1-354) was obtained using the same procedure as in Synthesis Example 1.

[1153] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1139.789.

[1154]

[1155] Synthetic Example (87): Synthesis of Compound (1-355)

[1156] Compound (T-3) was changed to compound (T-3-355), and compound (1-355) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1157] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1029.782.

[1158]

[1159] Synthetic Example (88): Synthesis of Compound (1-356)

[1160] Compound (T-3) was changed to compound (T-3-356), and compound (1-356) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1161] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 975.536.

[1162]

[1163] Synthetic Example (89): Synthesis of Compound (1-357)

[1164] Compound (T-3) was changed to compound (T-3-357), and compound (1-357) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1165] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1015.767.

[1166]

[1167] Synthetic Example (90): Synthesis of Compound (1-358)

[1168] Compound (T-3) was changed to compound (T-3-358), and otherwise compound (1-358) was obtained using the same procedure as in Synthesis Example 1.

[1169] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1165.826.

[1170]

[1171] Synthetic Example (91): Synthesis of Compound (1-359)

[1172] Compound (T-3) was changed to compound (T-3-359), and otherwise compound (1-359) was obtained using the same procedure as in Synthesis Example 1.

[1173] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 993.652.

[1174]

[1175] Synthesis Example (92): Synthesis of Compounds (1-360)

[1176] Compound (T-3) was changed to compound (T-3-360), and compound (1-360) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1177] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1125.782.

[1178]

[1179] Synthetic Example (93): Synthesis of Compound (1-361)

[1180] Compound (T-3) was changed to compound (T-3-361), and compound (1-361) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1181] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1063.758.

[1182]

[1183] Synthesis Example (94): Synthesis of Compound (1-362)

[1184] Compound (T-3) was changed to compound (T-3-362), and compound (1-362) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1185] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1029.782.

[1186]

[1187] Synthetic Example (95): Synthesis of Compound (1-363)

[1188] Compound (T-3) was changed to compound (T-3-363), and compound (1-363) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1189] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1103.752.

[1190]

[1191] Synthetic Example (96): Synthesis of Compound (1-364)

[1192] Compound (T-3) was changed to compound (T-3-364), and compound (1-364) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1193] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1059.820.

[1194]

[1195] Synthesis Example (97): Synthesis of Compound (1-365)

[1196] Compound (T-3) was changed to compound (T-3-365), and otherwise compound (1-365) was obtained using the same procedure as in Synthesis Example 1.

[1197] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1123.851.

[1198]

[1199] Synthesis Example (98): Synthesis of Compound (1-321)

[1200] Compound (T-3) was changed to compound (T-3-321), and otherwise compound (1-321) was obtained using the same procedure as in Synthesis Example 1.

[1201] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1007.789.

[1202]

[1203] Synthetic Example (99): Synthesis of Compounds (1-330)

[1204] Compound (T-3) was changed to compound (T-3-330), and compound (1-330) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1205] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 993.773.

[1206]

[1207] Synthetic Example (100): Synthesis of Compound (1-331)

[1208] Compound (T-3) was changed to compound (T-3-331), and compound (1-331) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1209] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 953.742.

[1210]

[1211] Synthetic Example (101): Synthesis of Compound (1-366)

[1212] Compound (T-3) was changed to compound (T-3-366), and compound (1-366) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1213] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1099.851.

[1214]

[1215] Synthesis Example (102): Synthesis of Compound (1-368)

[1216] Compound (T-3) was changed to compound (T-3-368), and compound (1-368) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1217] The m / z(M+) value was obtained by MS measurement (MALDI-TOF MS) = 1099.851.

[1218]

[1219] Synthetic Example (103): Synthesis of Compound (1-378)

[1220] Compound (T-3) was changed to compound (T-3-378), and otherwise compound (1-378) was obtained using the same procedure as in Synthesis Example 1.

[1221] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1153.768.

[1222]

[1223] Synthetic Example (104): Synthesis of Compound (1-379)

[1224] Compound (T-3) was changed to compound (T-3-379), and compound (1-379) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1225] The m / z(M+) value was determined by MS measurement (MALDI-TOF MS) to be 1043.668.

[1226]

[1227] Synthetic Example (105): Synthesis of Compound (1-380)

[1228] Compound (T-3) was changed to compound (T-3-380), and compound (1-380) was otherwise obtained using the same procedure as in Synthesis Example 1.

[1229] The m / z(M+) value was obtained by MS determination (MALDI-TOF MS) = 1114.768.

[1230]

[1231] By appropriately changing the compounds used as raw materials, other compounds of the present invention can be synthesized using the method according to the described synthesis example.

[1232] <Manufacturing and Evaluation of Organic EL Components>

[1233] Using the compounds of the present invention and the comparative compounds synthesized therein, organic EL elements of TTF, TAF, and PSF are manufactured.

[1234] <TTF Structure: Examples 1-1-1 to 1-1-49, Comparative Example 1-1-1>

[1235] ITO (120nm) / HAT-CN (5nm) / HT-1 (90nm) / HT-2 (10nm) / BH: Compounds listed in Table 1 (97:3) (20nm) / ET-1 (20nm) / ET-2 (10nm) / LiF (1nm) / Al (100nm)

[1236] The chemical structures of the compounds used in the manufacture of the components are shown below.

[1237]

[1238] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Opto Science, Inc.) with an ITO film thickness of 180nm ground to 120nm 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 molybdenum vapor deposition boats containing HAT-CN, HT-1, HT-2, BH, the compounds listed in Table 1, ET-1, and ET-2, and aluminum nitride vapor deposition boats containing LiF and aluminum, respectively, were installed.

[1239] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4 Up to Pa, firstly, HAT-CN was heated and vapor-deposited to a thickness of 5 nm. Next, HT-1 was heated and vapor-deposited to a thickness of 90 nm. Then, HT-2 was heated and vapor-deposited to a thickness of 10 nm to form a hole layer. Next, BH and the compounds listed in Table 1 were simultaneously heated and vapor-deposited to a thickness of 20 nm to form a light-emitting layer. The vapor deposition rate was adjusted to approximately a 97:3 mass ratio of BH to the compounds listed in Table 1. Then, ET-1 was heated and vapor-deposited to a thickness of 20 nm. Next, ET-2 was heated and vapor-deposited to a thickness of 10 nm to form an electron transport layer. The vapor deposition rate for each layer was 0.01 nm / s to 1 nm / s. Subsequently, LiF is heated and vaporized 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 vaporized at a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[1240] Instead of the compounds listed in Table 1, the organic EL element of Comparative Example 1-1-1 was obtained using the following comparative compound 1.

[1241]

[1242] <TAF Structure: Examples 2-1-1 to 2-1-22, Comparative Examples 2-1-1 to 2-1-3>

[1243] ITO (50nm) / HAT-CN (10nm) / HT-1 (60nm) / SiCzCz (5nm) / SiCzCz:SiTrzCz2:TADF-1:The compounds listed in Table 2 (60:26:13:1) (35nm) / mSiTrz (5nm) / mSiTrz:Liq (1:1) (30nm) / LiF (1nm) / Al (100nm)

[1244] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Opto Science, Inc.) with an ITO film thickness of 200nm ground 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 Showa Vacuum, Inc.), and a molybdenum vapor deposition boat containing HAT-CN, HT-1, SiCzCz, SiTrzCz2, the compounds listed in Table 2, mSiTrz, and Liq, and a tungsten vapor deposition boat containing LiF and aluminum were installed.

[1245] 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, HAT-CN is heated and vapor-deposited to a thickness of 10 nm to form a hole injection layer. Next, HT-1 is heated and vapor-deposited to a thickness of 60 nm to form a hole transport layer 1. Then, SiCzCz is heated and vapor-deposited to a thickness of 5 nm to form a hole transport layer 2. Next, SiCzCz, SiTrzCz2, (TADF-1), and each compound listed in Table 2 are simultaneously heated and vapor-deposited to a thickness of 35 nm. The vapor deposition rate is adjusted so that the mass ratio of SiCzCz, SiTrzCz2, (TADF-1), and each compound listed in Table 2 is approximately 60:26:13:1. Next, mSiTrz is heated and vapor-deposited to a thickness of 5 nm to form an electron transport layer 1. Then, mSiTrz and Liq are heated and vapor-deposited to a thickness of 30 nm to form an electron transport layer 2. The deposition rate was adjusted to approximately a 1:1 mass ratio of mSiTrz to Liq. The deposition rate for each layer was 0.01 nm / s to 1 nm / s. Next, LiF was heated and deposited at a rate of 0.01 nm / s to 0.1 nm / s to achieve a film thickness of 1 nm. Then, aluminum was heated and deposited at a rate of 100 nm to form the cathode, thus obtaining the organic EL device. At this point, the deposition rate of aluminum was adjusted to 1 nm / s to 10 nm / s. Furthermore, the SiCzCz in the light-emitting layer acts as the host material for hole transport, and the SiTrzCz2 acts as the host material for electron transport.

[1246] <PSF Structure: Examples 3-1-1 to 3-1-22, Comparative Examples 3-1-1 to 3-1-3>

[1247] ITO(50nm) / HAT-CN(10nm) / HT-1(60nm) / SiCzCz(5nm) / SiCzCz: SiTrzCz2: PtON-TBBI: Table 2 Each compound contained (60:26:13:1)(35nm) / mSiTrz(5nm) / mSiTrz: Liq(1:1)(30nm) / LiF(1nm) / Al(100nm)

[1248] The TAF structure (TADF-1) is replaced with PtON-TBBI, and the element is fabricated in the same way.

[1249] The chemical structures of the compounds used in the manufacture of the aforementioned components are shown below.

[1250]

[1251] The comparative example components were prepared by using compounds TR1, TR2, and TR3 of the comparative examples in place of the compounds described in Table 2. Here, compounds (TR1) to (TR3) are the compounds described in Science Advances (8, eabq1641 (2022)), Korean Patent Application Publication No. 2022-0069866A, and Japanese Patent Application Publication No. 2022-32966, and were synthesized using the methods described in the literature.

[1252]

[1253] [evaluate]

[1254] Evaluation parameters include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), and half-width (nm). These evaluation parameters can be, for example, based on a 1000 cd / m² emission intensity level. 2 The value when it emits light.

[1255] 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.

[1256] The methods for measuring spectroradiance (emission spectrum) and external quantum efficiency are as follows. Using an Advantest voltage / current generator R6144, an application is made to achieve a brightness of 1000 cd / m². 2The element emits light due to the voltage applied. Using a Topcon SR-3AR spectroradiometer, the spectroradiance in the visible light region was measured 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 spectroradiance value of each wavelength component by the wavelength energy and multiplying by π. The number of photons was then accumulated across the entire observed wavelength range 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 half-width of the emission spectrum was calculated as the width between wavelengths above and below the maximum emission wavelength where its intensity is 50%.

[1257] A DC voltage was applied using the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, and the voltage was measured at 1000 cd / m². 2 The emission characteristics were assessed. Furthermore, for TTF structure elements, the time it took to maintain more than 90% of the initial brightness (lifetime) was measured; for TAF and PSF structure elements, the time it took to maintain more than 50% of the initial brightness (LT90, lifetime) was measured. In addition, the emission peak values ​​of the elements were all in the range of 450 nm to 470 nm. The emission spectrum half-width of the element in Example 1-1-3 using compound (1-1) of the present invention was 19 nm, and the half-width of the element in Comparative Example 1-1-1 was 23 nm.

[1258] [Table 1]

[1259]

[1260]

[1261] [Table 2]

[1262]

[1263]

[1264] In any element structure, the compounds of this application can produce elements with higher external quantum efficiency and longer lifetime compared to the compounds of the comparative examples.

Claims

1. A polycyclic aromatic compound having one or more structures comprising one or more structural units represented by the following formula (1); In equation (1), Rings A, B, and C are each independently a substituted aryl ring or a substituted heteroaryl ring, wherein... In the structure, at least one ring selected from the group consisting of rings A, B, and C is the ring represented by equation (Az). Y 1 For B, P, P=O, P=S, Al, Ga, As, Si-R S , or Ge-R Ge The Si-R S R S and Ge-R Ge R Ge Each can be independently substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. In formula (Az), X 1 >C(-R) c )2、>C=C(-R c 2. >C(-OR) O )2、>Si(-R Si )2, or >C=O, wherein >C(-R c )2 and >C=C(-R c )2 of R c >C(-OR) O )2, and >Si(-R Si )2 of R Si Each of the two Rs 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. c They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring; in addition, the >C(-R) c )2 of R c It can be linked to one or two Z bonds via a linker base or a single bond. Any two or three consecutive Z's are respectively related to Y's 1 and NR NY1 and / or NR NY2 The N atom is directly bonded to the carbon atom, and the other Z atoms are independently N or C. Z The CR Z R Z For hydrogen or substituents, two adjacent CR Z R Z They can bond with each other to form aryl rings or heteroaryl rings, and the formed rings can be substituted. Z = Z can be independently set to >0 and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se, wherein >NR NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Each of the following 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, wherein the >C(-R CX )2 two R CX and the aforementioned >Si(-R SiX )2 two R SiX They can bond together to form a ring. In equations (1) and (Az), R NY1 R NY2 and R NY3 It 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, wherein at least one is selected from the following formula (R NY -a)~Form (R) NY The base in -d), R NY1 Or R NY2 It can be bonded to A-rings and / or B-rings, or A-rings and / or C-rings, via linker bases or single bonds. Formula (R) NY -a)~Form (R) NY In -d), * indicates the bond position with N. R a R b R c R d1 R d2 and R d3 Each of the following 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. R b1 R b2 and R c1 Each is independently a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, wherein R b1 and R b2 They will not all become methyl groups. a and b are independent integers from 0 to 5. c is an integer between 0 and 3. D stands for deuterium. At least one aryl or heteroaryl ring in the structure may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted. At least one hydrogen atom in the structure may be substituted with a cyano group or a halogen. At least one -CH2- in the structure may be substituted with -O-. In the structure, at least one hydrogen may be substituted with deuterium, and at least one nitrogen may be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13 C) substitution, at least one boron can be replaced by boron-11( 11 B) Replace.

2. The polycyclic aromatic compound according to claim 1, comprising the following formulas: (1-a1), (1-b1), (1-c1), (1-d1), (1-e1), (1-f1), (1-a2), (1-b2), (1-c2), (1-d2), (1-e2), (1-f2), (1-d3), (1-e3), (2-a1), (2-a2), (2-b... 1) Equations (2-b2), (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), or (3-e1) to (3-e8) represent the following: Equation (1-a1), Equation (1-b1), Equation (1-c1), Equation (1-d1), Equation (1-e1), Equation (1-f1), Equation (1-a2), Equation (1-b2), Equation (1-c2), Equation (1-d2), Equation (1-e2), Equation (1-f2), Equation (1-d3), Equation (1-e3), Equation (2-a1), Equation (2-a2), Equation (2-b1), Equation (2-b2), Equation In equations (2-c1), (2-c2), (2-d1) to (2-d5), (2-e1) to (2-e5), (2-f1), (2-f2), (3-a1), (3-a2), (3-b1), (3-b2), (3-c1), (3-c2), (3-d1) to (3-d5), and (3-e1) to (3-e8), Z, Y 1 X 1 R NY1 R NY2 R NY3 Z and Z = Z are respectively related to Z and Y in equation (1). 1 X 1 R NY1 R NY2 R NY3 、 and Z=Z have the same meaning. X 2 >C(-R) c )2、>C=C(-R c 2. C(-OR) O )2、>Si(-R Si )2, or >C=O, wherein >C(-R c )2 and >C=C(-R c )2 of R c C(-OR) O )2 of R O and >Si(-R Si )2 of R Si Each of the two Rs 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. c They can bond together to form a ring, two R O They can bond together to form a ring, two R Si They can bond together to form a ring; in addition, the >C(-R) c )2 of R c It can be linked to one or two Z bonds via a linker base or a single bond. X 11 and X 22 Independently defined as >O and >NR respectively. NX >C(-R) CX )2、>Si(-R SiX 2. >S, >CO, >SO, >SO2, or >Se, as X 11 or X 22 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning. At least one aryl ring or heteroaryl ring may be condensed from at least one cycloalkane, wherein at least one hydrogen atom in the cycloalkane may be substituted. At least one hydrogen atom may be substituted with a cyano group or a halogen group. At least one -CH2- can be substituted via -O-. At least one hydrogen atom can be substituted with deuterium, and at least one nitrogen atom can be substituted with nitrogen-15 ( 15 N) substitution, at least one sulfur can be replaced by sulfur-33( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S) substitution, at least one oxygen can be replaced by oxygen-17( 17 O) or oxygen-18 ( 18 O) substitution, at least one carbon can be replaced by carbon-13 ( O) 13 C) substitution, at least one boron can be replaced by boron-11( 11 B) Replace.

3. The polycyclic aromatic compound according to claim 1, wherein R NY1 R NY2 and R NY3 At least one of them is selected from the following formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R) NY The base in -d-25); Formula (R) NY -a-1)~Formula (R) NY -a-37), Equation (R) NY -b-1)~Formula (R) NY -b-21), Equation (R) NY -c-1)~Formula (R) NY -c-20), and formula (R) NY -d-1)~Formula (R) NY In -d-25), X Y For >O, >NR Nzy >C(-R) Czy )2、>Si(-R Sizy 2. or >S, as X Y >NR Nzy R Nzy >C(-R) Czy )2 of R Czy 、>Si(-R Sizy )2 of R Sizy Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning. Ak is a substituted or unsubstituted alkyl group.

4. The polycyclic aromatic compound according to claim 2, wherein it is represented by formula (1-b1), formula (1-d1), formula (2-b1) or formula (2-b2).

5. The polycyclic aromatic compound according to claim 4, wherein Z is all CR Z .

6. The polycyclic aromatic compound according to claim 1, wherein X 1 >C(-R) c )2, R c For substituted or unsubstituted alkyl groups, the two Rs c They can bond together to form a ring.

7. The polycyclic aromatic compound according to claim 1, wherein X 1 >Si(-R) Si )2, R Si For substituted or unsubstituted alkyl groups, the two Rs Si They can bond together to form a ring.

8. The polycyclic aromatic compound according to claim 1, wherein X 1 The value is >C=O.

9. The polycyclic aromatic compound according to claim 1, wherein Y 1 The answer is B.

10. The polycyclic aromatic compound according to claim 1, wherein R NY1 R NY2 and R NY3 At least one of them is the formula (R) NY -a).

11. The polycyclic aromatic compound according to claim 1, wherein R NY1 R NY2 and R NY3 At least two of them are selected from formula (R) NY -a)~Form (R) NY The base in -d).

12. The polycyclic aromatic compound according to claim 2, wherein X 1 and X 2 Each independently is >C(-R) c )2, R c It can be a substituted or unsubstituted alkyl group.

13. The polycyclic aromatic compound according to claim 4, which is represented by the following formula (1-b1-Z), formula (2-b1-Z), or formula (2-b2-Z); In equations (1-b1-Z), (2-b1-Z), and (2-b2-Z), R NY1 R NY2 and R NY3 Independently with R in equation (1) NY1 R NY2 and R NY3 They have the same meaning. R Z4 Each is an unsubstituted alkyl group, and the two Rs are independent. Z4 They can bond together to form a ring. R Z1 It is an unsubstituted alkyl group. R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2. R Z3 Each is an independent unsubstituted alkyl group, and n is an integer from 0 to 2. X 11 For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se, As X 11 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning. In the structures represented by formula (1-b1-Z), formula (2-b1-Z), or formula (2-b2-Z), at least one of the aryl rings or heteroaryl rings can be a structure formed by bonding a portion of the structure represented by formula (B) with an adjacent carbon atom. In formula (B), Me represents a methyl group, and * indicates the bond position. At least one hydrogen atom in the structure represented by formula (1-b1-Z), formula (2-b1-Z), or formula (2-b2-Z) may be substituted with a cyano group, a halogen, or a deuterium.

14. The polycyclic aromatic compound according to claim 4, wherein it is represented by formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T); In equations (1-b1-T1), (1-b1-T2), (2-b1-T), and (2-b2-T), X a For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, or >S, the >NR NX R NX The >C(-R) CX )2 of R CX and the aforementioned >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning. R NY1 R NY2 and R NY3 Independently with R in equation (1) NY1 R NY2 and R NY3 They have the same meaning. R Z4 Each is an unsubstituted alkyl group, and the two Rs are independent. Z4 They can bond together to form a ring. R Z1 It is an unsubstituted alkyl group. R Z2 Each is an unsubstituted alkyl group, and m is an integer from 0 to 2. R Z3 Each is an independent unsubstituted alkyl group, and n is an integer from 0 to 2. X 11 For >O, >NR NX >C(-R) CX )2、>Si(-R SiX )2, >S, >CO, >SO, >SO2, or >Se, As X 11 >NR NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX Independently compared with >NR in equation (1) as Z = Z NX R NX >C(-R) CX )2 of R CX and >Si(-R SiX )2 of R SiX They have the same meaning. In the structures represented by formulas (1-b1-T1), (1-b1-T2), (2-b1-T), or (2-b2-T), at least one of the aryl rings or heteroaryl rings can be a structure formed by bonding a portion of the structure represented by formula (B) with an adjacent carbon atom. In formula (B), Me represents a methyl group, and * indicates the bond position. At least one hydrogen atom in the structure represented by formula (1-b1-T1), formula (1-b1-T2), formula (2-b1-T), or formula (2-b2-T) may be substituted with a cyano group, a halogen, or a deuterium.

15. The polycyclic aromatic compound according to claim 1, wherein at least one hydrogen in formula (1) is substituted with a group represented by the following formula (Cz); In formula (Cz), *a indicates the bond position. Z y Each independently represents N or CR. ZY The CR ZY R ZY For hydrogen or substituents, two adjacent CRs ZY R ZY They can bond together to form aryl rings or heteroaryl rings, and the formed rings can be substituted.

16. The polycyclic aromatic compound according to claim 1, wherein it is represented by any of the following formulas; In the formula, Me is methyl and tBu is tert-butyl.

17. A material for organic devices, comprising a polycyclic aromatic compound as described in any one of claims 1 to 16.

18. An organic electroluminescent element, comprising: A pair of electrodes, comprising an anode and a cathode; and a light-emitting layer, disposed between the pair of electrodes, The luminescent layer contains a polycyclic aromatic compound as described in any one of claims 1 to 16.

19. The organic electroluminescent element according to claim 18, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

20. The organic electroluminescent element according to claim 19, wherein the main component is anthracene compound, fluorene compound, or dibenzo[a]benzene compound. These are compounds, or pyrene compounds.

21. A display device or lighting device, comprising the organic electroluminescent element as described in claim 18.

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