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Being the first hyperconjugation-induced multiple-resonance (MR) emitters with the \u03c33-endo, \u03c3n-exo P-center, AP-PAHs exhibited thermally activated delayed fluorescence (TADF) with a narrow band (full width at half-maximum: 20 nm) and high photoluminescence quantum yields (PLQYs: 72% in CH2Cl2, 99% in doped films). Driven by the P-hybridization and P-hyperconjugation effects, the theoretical computations revealed that P(III)\/PB-PAHs demonstrated excited-state symmetry breaking (ESSB) characters, which induced a strong structural relaxation or a reduced transition overlap integral, thus decreasing the PLQYs. Such EESB is distinct from the symmetrical excited-state structure of the classical BN MR emitters. Switching to the strong PO\/PMe-induced \u03c0\u2013\u03c3(P\u2013O\/Me)* coupling enabled more symmetric excited-state structures and large transition overlap integrals and kRISCs, consequently boosting the PLQYs from 2% to 72% (99% in the 1% doped film). Leveraging on the cis-\/trans-hyperconjugation effects, emission ranges of the double PO-derivatives were efficiently extended to 477 nm for the cis-isomer and 620 nm for the trans-isomer. Although having suppressed TADF via the double PO-induced backbone twisting, the cis-isomer maintained PLQYs as high as 73% in CH2Cl2 and 99% in the 1% doped film. As a proof of concept, two narrow-emitting AP-PAHs were applied in organic lighting-emitting diodes that showed narrow-band blue-violet and deep-blue emission with an EQE as high as 10%. This study revealed a new P-hyperconjugation-induced EESB mechanism for PN-type MR emitters, which opens an avenue for designing new efficient light-emitting materials.<\/jats:p>","DOI":"10.1021\/jacs.6c14360","type":"journal-article","created":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T15:01:27Z","timestamp":1787151687000},"page":"37545-37556","source":"Crossref","is-referenced-by-count":0,"title":["\u03c33-Endo 1,4-Azaphosphinine-Embedded\nPolycyclic Aromatic Hydrocarbons: P-Hyperconjugation-Regulated\nExcited-State Symmetry and Thermally Activated Delayed Fluorescence"],"prefix":"10.1021","volume":"148","author":[{"given":"Ji","family":"Zhang","sequence":"first","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4571-394X","authenticated-orcid":true,"given":"Lingqiang","family":"Meng","sequence":"additional","affiliation":[{"name":"Henan University , , ,","place":["Zhengzhou, P. 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